CN116536788A - Antibacterial polyester fiber containing imidazole ring structure and preparation method thereof - Google Patents
Antibacterial polyester fiber containing imidazole ring structure and preparation method thereof Download PDFInfo
- Publication number
- CN116536788A CN116536788A CN202310374537.3A CN202310374537A CN116536788A CN 116536788 A CN116536788 A CN 116536788A CN 202310374537 A CN202310374537 A CN 202310374537A CN 116536788 A CN116536788 A CN 116536788A
- Authority
- CN
- China
- Prior art keywords
- antibacterial
- polyester
- ring structure
- imidazole ring
- polyester fiber
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 229920000728 polyester Polymers 0.000 title claims abstract description 177
- 230000000844 anti-bacterial effect Effects 0.000 title claims abstract description 156
- 239000000835 fiber Substances 0.000 title claims abstract description 104
- 125000002883 imidazolyl group Chemical group 0.000 title claims abstract description 61
- 238000002360 preparation method Methods 0.000 title claims abstract description 21
- 239000000178 monomer Substances 0.000 claims abstract description 62
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims abstract description 46
- 239000000463 material Substances 0.000 claims abstract description 28
- 238000006068 polycondensation reaction Methods 0.000 claims abstract description 22
- 150000002009 diols Chemical class 0.000 claims abstract description 21
- 238000009987 spinning Methods 0.000 claims abstract description 20
- 238000000034 method Methods 0.000 claims abstract description 13
- -1 imidazole compound Chemical class 0.000 claims abstract description 11
- 238000002074 melt spinning Methods 0.000 claims abstract description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 9
- 238000004519 manufacturing process Methods 0.000 claims abstract 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 21
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 14
- 238000002156 mixing Methods 0.000 claims description 9
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 6
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 6
- JTYMXXCJQKGGFG-UHFFFAOYSA-N 3-(imidazol-1-yl)lactic acid Chemical group OC(=O)C(O)CN1C=CN=C1 JTYMXXCJQKGGFG-UHFFFAOYSA-N 0.000 claims description 5
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 claims description 3
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims description 3
- 229940035437 1,3-propanediol Drugs 0.000 claims description 3
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 claims description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 3
- 239000001361 adipic acid Substances 0.000 claims description 3
- 235000011037 adipic acid Nutrition 0.000 claims description 3
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims description 3
- OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical compound CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 claims description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 3
- 239000011976 maleic acid Substances 0.000 claims description 3
- 229920000166 polytrimethylene carbonate Polymers 0.000 claims description 3
- 239000001384 succinic acid Substances 0.000 claims description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 3
- 230000000845 anti-microbial effect Effects 0.000 claims description 2
- 239000003242 anti bacterial agent Substances 0.000 abstract description 25
- 230000008569 process Effects 0.000 abstract description 8
- 238000006116 polymerization reaction Methods 0.000 abstract description 5
- 230000000052 comparative effect Effects 0.000 description 11
- 230000006872 improvement Effects 0.000 description 9
- 239000004744 fabric Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 239000013084 copper-based metal-organic framework Substances 0.000 description 5
- 238000009776 industrial production Methods 0.000 description 3
- 238000004321 preservation Methods 0.000 description 3
- 150000003384 small molecules Chemical class 0.000 description 3
- 239000004753 textile Substances 0.000 description 3
- 229920003043 Cellulose fiber Polymers 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000002688 persistence Effects 0.000 description 2
- 238000012643 polycondensation polymerization Methods 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229920002413 Polyhexanide Chemical group 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 239000002608 ionic liquid Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000010128 melt processing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 150000004714 phosphonium salts Chemical group 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Classifications
-
- 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
- D01F6/78—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from copolycondensation products
- D01F6/84—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from copolycondensation products from copolyesters
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
- C08G63/682—Polyesters containing atoms other than carbon, hydrogen and oxygen containing halogens
- C08G63/6824—Polyesters containing atoms other than carbon, hydrogen and oxygen containing halogens derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/6826—Dicarboxylic acids and dihydroxy compounds
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/78—Preparation processes
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Polyesters Or Polycarbonates (AREA)
Abstract
The invention provides an antibacterial polyester fiber containing an imidazole ring structure and a preparation method thereof, wherein diacid monomers and diol monomers are mixed and prepolymerized to obtain a polyester prepolymer; carrying out vacuum polycondensation on the polyester prepolymer and an antibacterial functional monomer to obtain an antibacterial polyester material; and finally, carrying out melt spinning on the antibacterial polyester material to obtain the antibacterial polyester fiber containing the imidazole ring structure. The invention connects the imidazole ring structure with antibacterial effect into the polyester molecular chain in a covalent bond way, thus solving the problem that the existing antibacterial agent is easy to fall off or dissolve out from the fiber; the antibacterial functional monomer is an imidazole compound containing hydroxyl and carboxyl, can be subjected to polycondensation reaction in the polymerization process of the polyester prepolymer, is polycondensed into a polyester molecular chain in a covalent bond mode, has little influence on the polycondensation process of the polyester, has little influence on the subsequent spinning process, and is suitable for industrialized production. The antibacterial polyester fiber has the advantages of good antibacterial effect, stable antibacterial performance, high safety and good market application prospect.
Description
Technical Field
The invention relates to the technical field of antibacterial material preparation, in particular to an antibacterial polyester fiber containing an imidazole ring structure and a preparation method thereof.
Background
Along with the rapid development of society and the improvement of people's safety and health consciousness, the pursuit of people on life quality is also continuously improved; the pursuit of healthy intelligent textiles is that the textiles are required to have certain antibacterial functions on the basis of meeting the requirements of durability, heat preservation and comfortableness of common textiles. At present, the antibacterial polyester fiber on the market mainly comprises antibacterial polyester fiber added with inorganic antibacterial agents of silver, copper and zinc series and antibacterial fiber added with organic antibacterial agents such as quaternary ammonium salt, quaternary phosphonium salt, polyhexamethylene biguanide hydrochloride and the like. However, polyester fibers added with inorganic antibacterial agents have certain biological safety toxicity and can affect the wearing performance of the fabric; the polyester fiber added with the organic antibacterial agent has the defects of difficult spinning, precipitation of the antibacterial agent solution and the like.
In the prior art, when an organic antibacterial agent is adopted to prepare the antibacterial polyester fiber, the antibacterial agent is generally blended into polyester to prepare the antibacterial fiber, or the antibacterial fiber is prepared by coating, soaking the antibacterial agent solution and the like. For example, the invention patent (application number is CN 2016610504987. X) discloses a copper-based metal organic framework antibacterial fiber and a preparation method thereof, the antibacterial fiber is prepared from polyester, copper-based metal organic framework material and antibacterial agent, specifically, polyester and copper-based metal organic framework material are melt-blended and spun to obtain copper-based metal organic framework polyester composite fiber, and then the copper-based metal organic framework polyester composite fiber is immersed in the antibacterial agent to obtain the antibacterial fiber. The invention patent (application number is CN 201811011918.0) discloses a preparation method of an antibacterial cellulose fiber, which comprises the steps of mixing a dispersing agent, an antibacterial agent and cellulose, dissolving the mixture in an ionic liquid aqueous solution to prepare a mixed spinning solution, and then carrying out a spinning process on the mixed spinning solution to obtain the antibacterial cellulose fiber.
In the above patent, the antibacterial fiber prepared by immersing the fiber in the antibacterial agent and blending the antibacterial agent with the fiber raw material is liable to fall off or dissolve out from the fiber, the safety to the human body is poor, the antibacterial function of the fabric is liable to decay, the problem of gradual decrease with the lapse of time occurs, and the fabric is unsuitable for long-term use.
In view of the above, there is a need to design an improved antibacterial polyester fiber containing imidazole ring structure and a preparation method thereof to solve the above problems.
Disclosure of Invention
The invention aims to provide an antibacterial polyester fiber containing an imidazole ring structure and a preparation method thereof, wherein the imidazole ring structure with an antibacterial effect is connected into a polyester molecular chain in a covalent bond manner, so that the problem that the existing antibacterial agent is easy to fall off or dissolve out of the fiber is solved, and the safety of the antibacterial polyester fiber is improved; the antibacterial polyester fiber containing the imidazole ring structure has the advantages of good antibacterial effect, long-acting antibacterial performance and good market application prospect.
In order to achieve the aim of the invention, the invention provides an antibacterial polyester fiber containing an imidazole ring structure, wherein the molecular chain of the antibacterial polyester fiber is a polyester molecular chain containing the imidazole ring structure, and the imidazole ring structure is connected into the polyester molecular chain in a covalent bond manner.
As a further improvement of the invention, the component of the imidazole ring structure in the molecular chain of the antibacterial polyester fiber is 1-15%.
The invention also provides a preparation method of the antibacterial polyester fiber containing the imidazole ring structure, which comprises the following steps:
s1, mixing diacid monomers and diol monomers according to a specific proportion, and carrying out prepolymerization, wherein the prepolymerization temperature is 240-260 ℃ and the pressure is 2-3 MPa, so as to obtain a polyester prepolymer;
s2, carrying out vacuum polycondensation on the polyester prepolymer obtained in the step S1 and an antibacterial functional monomer according to a proportion, wherein the temperature of the vacuum polycondensation is 245-275 ℃, the time is 60-100 min, and the vacuum degree is less than 100Pa, so as to obtain an antibacterial polyester material; the antibacterial functional monomer is an imidazole compound containing hydroxyl and carboxyl;
and S3, carrying out melt spinning on the antibacterial polyester material prepared in the step S2 to obtain the antibacterial polyester fiber containing the imidazole ring structure.
As a further improvement of the present invention, in the step S1, the specific ratio is that the molar ratio of the diacid monomer to the diol monomer is 1 (1.0-1.3), and the molar ratio of the diacid monomer to the diol monomer is preferably 1:1.18.
As a further improvement of the present invention, in the step S2, the molar ratio of the polyester prepolymer to the antibacterial functional monomer is 1 (0.05 to 0.2).
As a further improvement of the present invention, in step S2, the antibacterial functional monomer is 2-hydroxy-3-imidazol-1-yl-propionic acid.
As a further improvement of the present invention, in step S1, the time for the preliminary polymerization is 50 to 180 minutes.
As a further improvement of the invention, in the step S3, the spinning process temperature of the melt spinning is 270-290 ℃ and the spinning speed is 3500-5000 m/min.
As a further improvement of the present invention, in step S1, the diacid monomer includes one of terephthalic acid, adipic acid, maleic acid, glutaric acid, succinic acid; the diacid monomer is preferably terephthalic acid.
As a further improvement of the present invention, in step S1, the diol monomer includes one of ethylene glycol, 1, 3-propanediol, 2, 3-butanediol; the diol monomer is preferably ethylene glycol.
The beneficial effects of the invention are as follows:
1. the invention provides an antibacterial polyester fiber containing imidazole ring structure and a preparation method thereof, which comprises the steps of mixing diacid monomers and diol monomers according to a specific proportion, and carrying out prepolymerization to obtain a polyester prepolymer; vacuum polycondensation is carried out on the polyester prepolymer and the antibacterial functional monomer according to a proportion, so as to prepare an antibacterial polyester material; and finally, carrying out melt spinning on the antibacterial polyester material to obtain the antibacterial polyester fiber containing the imidazole ring structure. The invention connects the imidazole ring structure with antibacterial effect into the polyester molecular chain in a covalent bond way, so as to solve the problem that the existing antibacterial agent is easy to fall off or dissolve out of the fiber, and improve the safety of the antibacterial polyester fiber; the antibacterial polyester fiber containing the imidazole ring structure has good antibacterial effect, long-acting antibacterial performance and good market application prospect.
2. The antibacterial functional monomer is an imidazole compound containing hydroxyl and carboxyl, can be subjected to polycondensation reaction in the polymerization process of a polyester prepolymer, is polycondensed into a molecular chain of polyester in a covalent bond mode, has small influence on the polycondensation process of the polyester, ensures that a polycondensation product still has the characteristic of the polyester, can reach higher viscosity, has small influence on the subsequent spinning process of the polyester, is suitable for industrial production, and is used for preparing antibacterial polyester fibers in batches stably.
3. In the preparation process of the antibacterial polyester fiber containing the imidazole ring structure, the temperature, time and pressure for preparing the polyester prepolymer are controlled to control the prepolymerization process of the diacid monomer and the diol monomer, so that the continuous polycondensation or copolymerization is avoided, and the polyester prepolymer is successfully formed; and then the polyester prepolymer is continuously polycondensed with an imidazole compound containing hydroxyl and carboxyl, and the imidazole compound is connected into a polyester molecular chain in a covalent bond form to form the antibacterial polyester material with an integrated molecular chain structure. The antibacterial polyester material has good spinning performance, and the prepared antibacterial polyester fiber has good comprehensive performance, is finally used in the field of wearable fabrics, and does not influence the durability, heat preservation and comfort of the fabrics.
4. When the antibacterial polyester fiber containing the imidazole ring structure is applied, the molecular weight is large, the molecular chain length and the molecular structure are stable, the antibacterial polyester fiber is not easily influenced by temperature and humidity, and the antibacterial performance is stable; and because the antibacterial imidazole structure is bonded into the polyester molecular chain in a covalent bond mode, unlike the polyester fiber in which the common antibacterial agent is blended into polyester, the imidazole micromolecular antibacterial agent cannot fall off or dissolve out of the fiber, so that the attenuation of the antibacterial effect is not easy to occur, the service life of the antibacterial polyester fiber is long, the harm to human bodies is small, and the safety is high.
Drawings
FIG. 1 is a schematic flow chart of a preparation method of the antibacterial polyester fiber containing the imidazole ring structure.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention will be described in detail with reference to the accompanying drawings and specific embodiments.
It should be noted that, in order to avoid obscuring the present invention due to unnecessary details, only structures and/or processing steps closely related to aspects of the present invention are shown in the drawings, and other details not greatly related to the present invention are omitted.
In addition, it should be further noted that the terms "comprises," "comprising," or any other variation thereof, are intended to cover a non-exclusive inclusion, such that a process, method, article, or apparatus that comprises a list of elements does not include only those elements but may include other elements not expressly listed or inherent to such process, method, article, or apparatus.
An antibacterial polyester fiber containing an imidazole ring structure, wherein the molecular chain of the antibacterial polyester fiber is a polyester molecular chain containing the imidazole ring structure, and the imidazole ring structure is connected into the polyester molecular chain in a covalent bond manner. In the molecular chain of the antibacterial polyester fiber, the imidazole ring structure comprises 1-15%. The invention connects the imidazole ring structure with antibacterial effect into the polyester molecular chain in a covalent bond way, so as to solve the problem that the existing antibacterial agent is easy to fall off or dissolve out of the fiber, and improve the safety of the antibacterial polyester fiber. The component content of the imidazole ring structure in the polyester fiber is controlled, so that the influence on the performance of the polyester material is reduced, the polyester material is ensured to have better spinnability, and the antibacterial polyester fiber obtained by spinning has good comprehensive performance. The antibacterial polyester fiber containing the imidazole ring structure has good antibacterial effect, long-acting antibacterial performance and good market application prospect.
Referring to fig. 1, a preparation method of an antibacterial polyester fiber containing an imidazole ring structure comprises the following steps:
s1, mixing diacid monomers and diol monomers according to a specific proportion, and carrying out prepolymerization, wherein the prepolymerization temperature is 240-260 ℃, the pressure is 2-3 MPa, and the time is 50-180 min, so as to obtain a polyester prepolymer;
s2, carrying out vacuum polycondensation on the polyester prepolymer obtained in the step S1 and an antibacterial functional monomer in proportion, wherein the temperature of the vacuum polycondensation is 245-275 ℃, the time is 60-100 min, and the vacuum degree is less than 100Pa, so as to obtain the antibacterial polyester material; the antibacterial functional monomer is an imidazole compound containing hydroxyl and carboxyl;
s3, carrying out melt spinning on the antibacterial polyester material prepared in the step S2, wherein the spinning process temperature of the melt spinning is 270-290 ℃, and the spinning speed is 3500-5000 m/min, so as to obtain the antibacterial polyester fiber containing the imidazole ring structure.
Particularly, the antibacterial functional monomer is an imidazole compound containing hydroxyl and carboxyl, can be subjected to polycondensation reaction in the polymerization process of the polyester prepolymer, is polycondensed into a molecular chain of the polyester in a covalent bond mode, has small influence on the polycondensation process of the polyester, ensures that a polycondensation product still has the characteristic of the polyester, can reach higher viscosity, has small influence on the subsequent spinning process of the polyester, is suitable for industrial production, and is used for preparing antibacterial polyester fibers in batches stably.
In some specific embodiments, the antimicrobial functional monomer is 2-hydroxy-3-imidazol-1-yl-propionic acid.
Specifically, in step S1, the specific ratio is 1 (1.0 to 1.3) of the molar ratio of the diacid monomer to the diol monomer, and the molar ratio of the diacid monomer to the diol monomer is preferably 1:1.18. In the step S2, the molar ratio of the polyester prepolymer to the antibacterial functional monomer is 1 (0.05-0.2). The temperature, time and pressure for preparing the polyester prepolymer are controlled to control the prepolymerization process of the diacid monomer and the diol monomer, so that the continuous polycondensation or copolymerization of the diacid monomer and the diol monomer is avoided, and the polyester prepolymer is successfully formed; and then the polyester prepolymer is continuously polycondensed with an imidazole compound containing hydroxyl and carboxyl, and the imidazole compound is connected into a polyester molecular chain in a covalent bond form to form the antibacterial polyester material with an integrated molecular chain structure. The antibacterial polyester material has good spinning performance, and the prepared antibacterial polyester fiber has good comprehensive performance, is finally used in the field of wearable fabrics, and does not influence the durability, heat preservation and comfort of the fabrics.
In some specific embodiments, the diacid monomer comprises one of terephthalic acid, adipic acid, maleic acid, glutaric acid, succinic acid; the diacid monomer is preferably terephthalic acid.
In some embodiments, the diol monomer comprises one of ethylene glycol, 1, 3-propanediol, 2, 3-butanediol; the diol monomer is preferably ethylene glycol.
When the antibacterial polyester fiber containing the imidazole ring structure is applied, the molecular weight is large, the molecular chain length and the molecular structure are stable, the antibacterial polyester fiber is not easily influenced by temperature and humidity, and the antibacterial performance is stable; and because the antibacterial imidazole structure is bonded into the polyester molecular chain in a covalent bond mode, unlike the polyester fiber in which the common antibacterial agent is blended into polyester, the imidazole micromolecular antibacterial agent cannot fall off or dissolve out of the fiber, so that the attenuation of the antibacterial effect is not easy to occur, the service life of the antibacterial polyester fiber is long, the harm to human bodies is small, and the safety is high.
Example 1
The embodiment provides an antibacterial polyester fiber containing an imidazole ring structure and a preparation method thereof, wherein the preparation method specifically comprises the following steps:
s1, mixing terephthalic acid and ethylene glycol monomers according to a molar ratio of 1:1.18, and carrying out prepolymerization, wherein the prepolymerization temperature is 250 ℃, the pressure is 2.5MPa, and the time is 50min, so as to obtain a polyester prepolymer;
s2, carrying out vacuum polycondensation on the polyester prepolymer obtained in the step S1 and 2-hydroxy-3-imidazol-1-yl-propionic acid according to a molar ratio of 1:0.1, wherein the temperature of the vacuum polycondensation is 260 ℃, the time is 80min, and the vacuum degree is less than 100Pa, so as to obtain an antibacterial polyester material;
s3, carrying out melt spinning on the antibacterial polyester material prepared in the step S2, wherein the spinning process temperature of the melt spinning is 280 ℃, and the spinning speed is 4500m/min, so as to obtain the antibacterial polyester fiber containing the imidazole ring structure; the content of the imidazole ring structure component in the antibacterial polyester fiber is 1%.
Examples 2 to 4
Examples 2 to 4 provide an antibacterial polyester fiber containing an imidazole ring structure and a preparation method thereof, and compared with example 1, the difference is that the molar ratio of the polyester prepolymer to the 2-hydroxy-3-imidazole-1-yl-propionic acid is adjusted in examples 2 to 4, so that the component content of the imidazole ring structure in the antibacterial polyester fiber is 5%, 10% and 15% respectively; the remainder is substantially the same as that of example 1, and will not be described in detail here.
Comparative example 1
Comparative example 1 provides an antibacterial polyester fiber and a preparation method thereof, which is different from example 1 in that the comparative example 1 directly blends an imidazole antibacterial agent with polyester to prepare an antibacterial polyester material, and the content of the imidazole antibacterial agent is 5%; the remainder is substantially the same as that of example 1, and will not be described in detail here.
Comparative example 2
Comparative example 2 provides an antibacterial polyester fiber and a method for preparing the same, which is different from example 1 in that comparative example 2 first prepares a polyester fiber and impregnates the polyester fiber into an imidazole antibacterial agent to prepare the antibacterial polyester fiber.
The antibacterial polyester fibers prepared in examples 1 to 4 and comparative examples 1 to 2 were tested for the viscosity of antibacterial polyester material and the antibacterial property of the antibacterial polyester fibers, while the common polyester fibers were used as a control group; the results obtained are shown in the following table.
TABLE 1 Material Performance test results for examples 1-4, comparative examples 1-2, and control group
As can be seen from Table 1, the polyester fiber with good antibacterial performance is successfully prepared by the preparation method of the invention, the viscosity of the antibacterial polyester material and the antibacterial rate of the antibacterial polyester fiber are both related to the component content of the imidazole ring structure in the antibacterial polyester fiber, the higher the component content of the imidazole ring structure is, the higher the antibacterial rate of the prepared antibacterial polyester fiber is, the better the antibacterial persistence is, but the lower the viscosity of the antibacterial polyester is, so that the component content of the imidazole ring structure in the antibacterial polyester fiber is limited to be 1% -15% from the view of the comprehensive performance of the antibacterial polyester fiber. As can be seen from the data of comparative examples 1 to 2, the imidazole ring-structured small molecules in comparative example 1 are blended into the polyester fiber material in a melt processing manner, so that the imidazole ring-structured small molecules are easy to separate out, and the duration of the antibacterial effect is not long; in addition, the polyester is melt-modified in a blending mode, so that the viscosity of the polyester material is easy to be low, the subsequent spinning process is unstable, and the industrialization is not good. In comparative example 2, the imidazole ring-based antibacterial small molecules are compounded on the surface of the polyester fiber by a dipping coating, and the defect of poor antibacterial effect persistence exists.
In summary, the invention provides an antibacterial polyester fiber containing an imidazole ring structure and a preparation method thereof, which comprises the steps of mixing diacid monomers and diol monomers according to a specific proportion, and performing prepolymerization to obtain a polyester prepolymer; vacuum polycondensation is carried out on the polyester prepolymer and the antibacterial functional monomer according to a proportion, so as to prepare an antibacterial polyester material; and finally, carrying out melt spinning on the antibacterial polyester material to obtain the antibacterial polyester fiber containing the imidazole ring structure. The invention connects the imidazole ring structure with antibacterial effect into the polyester molecular chain in a covalent bond way, so as to solve the problem that the existing antibacterial agent is easy to fall off or dissolve out of the fiber, and improve the safety of the antibacterial polyester fiber. The antibacterial functional monomer is an imidazole compound containing hydroxyl and carboxyl, can be subjected to polycondensation reaction in the polymerization process of a polyester prepolymer, is polycondensed into a molecular chain of polyester in a covalent bond mode, has small influence on the polycondensation process of the polyester, ensures that a polycondensation product still has the characteristic of the polyester, can reach higher viscosity, has small influence on the subsequent spinning process of the polyester, is suitable for industrial production, and is used for preparing antibacterial polyester fibers in batches stably. The antibacterial polyester fiber containing the imidazole ring structure is not easy to attenuate antibacterial effect, has good antibacterial effect and long-acting antibacterial performance, and has small harm to human bodies, high safety and good market application prospect.
The above embodiments are only for illustrating the technical solution of the present invention and not for limiting the same, and although the present invention has been described in detail with reference to the preferred embodiments, it should be understood by those skilled in the art that modifications and equivalents may be made thereto without departing from the spirit and scope of the technical solution of the present invention.
Claims (10)
1. The antibacterial polyester fiber containing the imidazole ring structure is characterized in that the molecular chain of the antibacterial polyester fiber is a polyester molecular chain containing the imidazole ring structure, and the imidazole ring structure is connected into the polyester molecular chain in a covalent bond mode.
2. The antibacterial polyester fiber containing imidazole ring structure according to claim 1, wherein the component of the imidazole ring structure in the molecular chain of the antibacterial polyester fiber is 1% -15%.
3. The preparation method of the antibacterial polyester fiber containing the imidazole ring structure is characterized by comprising the following steps of:
s1, mixing diacid monomers and diol monomers according to a specific proportion, and carrying out prepolymerization, wherein the prepolymerization temperature is 240-260 ℃ and the pressure is 2-3 MPa, so as to obtain a polyester prepolymer;
s2, carrying out vacuum polycondensation on the polyester prepolymer obtained in the step S1 and an antibacterial functional monomer according to a proportion, wherein the temperature of the vacuum polycondensation is 245-275 ℃, the time is 60-100 min, and the vacuum degree is less than 100Pa, so as to obtain an antibacterial polyester material; the antibacterial functional monomer is an imidazole compound containing hydroxyl and carboxyl;
and S3, carrying out melt spinning on the antibacterial polyester material prepared in the step S2 to obtain the antibacterial polyester fiber containing the imidazole ring structure.
4. The method of producing an imidazole ring-structure-containing antimicrobial polyester fiber according to claim 3, wherein in the step S1, the specific ratio is that the molar ratio of the diacid monomer to the diol monomer is 1 (1.0 to 1.3), and the molar ratio of the diacid monomer to the diol monomer is preferably 1:1.18.
5. The method for producing an antibacterial polyester fiber having an imidazole ring structure according to claim 4, wherein in the step S2, the molar ratio of the polyester prepolymer to the antibacterial functional monomer is 1 (0.05 to 0.2).
6. The method for producing an antibacterial polyester fiber containing an imidazole ring structure according to claim 3, wherein in step S2, the antibacterial functional monomer is 2-hydroxy-3-imidazol-1-yl-propionic acid.
7. The method for producing an antibacterial polyester fiber containing an imidazole ring structure according to claim 3, wherein in the step S1, the time for the prepolymerization is 50 to 180min.
8. The method for producing an antibacterial polyester fiber containing an imidazole ring structure according to claim 3, wherein in the step S3, the spinning process temperature of the melt spinning is 270 to 290 ℃ and the spinning speed is 3500 to 5000m/min.
9. The method for producing an antibacterial polyester fiber containing an imidazole ring structure according to claim 3, wherein in step S1, the diacid monomer comprises one of terephthalic acid, adipic acid, maleic acid, glutaric acid, succinic acid; the diacid monomer is preferably terephthalic acid.
10. The method for preparing an antibacterial polyester fiber containing an imidazole ring structure according to claim 3, wherein in the step S1, the diol monomer comprises one of ethylene glycol, 1, 3-propanediol, and 2, 3-butanediol; the diol monomer is preferably ethylene glycol.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310374537.3A CN116536788A (en) | 2023-04-10 | 2023-04-10 | Antibacterial polyester fiber containing imidazole ring structure and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310374537.3A CN116536788A (en) | 2023-04-10 | 2023-04-10 | Antibacterial polyester fiber containing imidazole ring structure and preparation method thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN116536788A true CN116536788A (en) | 2023-08-04 |
Family
ID=87451410
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202310374537.3A Pending CN116536788A (en) | 2023-04-10 | 2023-04-10 | Antibacterial polyester fiber containing imidazole ring structure and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN116536788A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN117966296A (en) * | 2024-03-29 | 2024-05-03 | 浙江伊诺环保集团股份有限公司 | Water treatment filter material and preparation method thereof |
-
2023
- 2023-04-10 CN CN202310374537.3A patent/CN116536788A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN117966296A (en) * | 2024-03-29 | 2024-05-03 | 浙江伊诺环保集团股份有限公司 | Water treatment filter material and preparation method thereof |
| CN117966296B (en) * | 2024-03-29 | 2024-06-14 | 浙江伊诺环保集团股份有限公司 | Water treatment filter material and preparation method thereof |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US7052765B2 (en) | Method for manufacturing antibacterial polyester master batches and fibers both containing nano-silver particles | |
| CN116536788A (en) | Antibacterial polyester fiber containing imidazole ring structure and preparation method thereof | |
| CN105544222A (en) | Chitosan and polyester-polyether copolymer hydrophilic finishing method of dacron fabric | |
| CN111270335B (en) | Antibacterial polyester fiber and preparation method thereof | |
| CN112921440A (en) | Multifunctional civil antibacterial fabric and preparation method thereof | |
| CN111519278A (en) | Biodegradable antibacterial polyester fiber material and preparation method thereof | |
| CN114045673B (en) | Antibacterial polyester mixed fiber elastic yarn and preparation method thereof | |
| CN113122954B (en) | Sports fabric based on graphene polyamide 6 fibers and preparation method thereof | |
| JP2004131647A (en) | Composite of silk protein with chitosan and method for producing the same | |
| CN111253719B (en) | Organic zinc antibacterial PET granules and preparation method thereof | |
| CN116043544B (en) | Dip dyeing agent for improving cold feel and anti-ultraviolet function of fabric as well as preparation method and application thereof | |
| CN115961379B (en) | Sea-island fiber fabric and preparation method thereof | |
| CN113652768B (en) | Polyester network yarn and production process thereof | |
| CN111235676B (en) | Graphene-based pneumonia pathogen protection fabric and preparation method thereof | |
| CN111560170B (en) | Antibacterial polyamide and preparation method and application thereof | |
| CN118207651B (en) | Soft skin-friendly polypropylene fiber and preparation method thereof | |
| CN111364123B (en) | Polyester FDY (fully drawn yarn) easy to dye and degrade and processing technology thereof | |
| CN110846898A (en) | Preparation method of antibacterial degradable composite fiber | |
| CN115976681B (en) | Method for manufacturing antibacterial polyester fabric | |
| CN114457591B (en) | Antigen fibrillated cellulose fiber and preparation method thereof | |
| CN110052186B (en) | Mixed material for preparing polyether sulfone hollow fiber membrane and preparation method and application thereof | |
| CN112481764B (en) | Spandex core-spun yarn defect-free production process | |
| CN118773773A (en) | Composite chemical fiber fabric and preparation method thereof | |
| CN114921864B (en) | Humidity response guar gum fiber and preparation method thereof | |
| CN118581601A (en) | Preparation method of alginate fibers |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination |