CN113403845A - Production process of antibacterial yarn - Google Patents
Production process of antibacterial yarn Download PDFInfo
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- CN113403845A CN113403845A CN202110717575.5A CN202110717575A CN113403845A CN 113403845 A CN113403845 A CN 113403845A CN 202110717575 A CN202110717575 A CN 202110717575A CN 113403845 A CN113403845 A CN 113403845A
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/01—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with natural macromolecular compounds or derivatives thereof
- D06M15/03—Polysaccharides or derivatives thereof
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- D—TEXTILES; PAPER
- D02—YARNS; MECHANICAL FINISHING OF YARNS OR ROPES; WARPING OR BEAMING
- D02G—CRIMPING OR CURLING FIBRES, FILAMENTS, THREADS, OR YARNS; YARNS OR THREADS
- D02G3/00—Yarns or threads, e.g. fancy yarns; Processes or apparatus for the production thereof, not otherwise provided for
- D02G3/44—Yarns or threads characterised by the purpose for which they are designed
- D02G3/449—Yarns or threads with antibacterial properties
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/368—Hydroxyalkylamines; Derivatives thereof, e.g. Kritchevsky bases
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/01—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with natural macromolecular compounds or derivatives thereof
- D06M15/15—Proteins or derivatives thereof
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M16/00—Biochemical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. enzymatic
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M23/00—Treatment of fibres, threads, yarns, fabrics or fibrous goods made from such materials, characterised by the process
- D06M23/12—Processes in which the treating agent is incorporated in microcapsules
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- D—TEXTILES; PAPER
- D10—INDEXING SCHEME ASSOCIATED WITH SUBLASSES OF SECTION D, RELATING TO TEXTILES
- D10B—INDEXING SCHEME ASSOCIATED WITH SUBLASSES OF SECTION D, RELATING TO TEXTILES
- D10B2401/00—Physical properties
- D10B2401/13—Physical properties anti-allergenic or anti-bacterial
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Abstract
The invention discloses a production process of antibacterial yarns, which comprises the steps of treating yarns with a dopamine solution, and then treating the yarns with a sodium hydroxide solution dispersed with an antibacterial additive to obtain the antibacterial yarns, wherein the antibacterial additive contains a quaternary ammonium salt structure and can react with a head group of acidic phospholipid in a bacterial cell membrane to reduce the permeability of the cell membrane and cause bacterial cell liquid leakage to cause bacterial cell death, and meanwhile, an epoxy group on the surface of the antibacterial additive can react with a phenolic hydroxyl group on the surface of the yarns to firmly fix the antibacterial additive on the surfaces of the yarns, so that clothes prepared from the yarns still have a good antibacterial effect after being washed for multiple times.
Description
Technical Field
The invention relates to the technical field of spinning, in particular to a production process of antibacterial yarns.
Background
The yarn is a soft and slender fiber aggregate which is formed by gathering textile fibers along the length direction and has certain mechanical property, is divided into filament yarn, short fiber yarn and special yarn according to the structure and the appearance, is divided into pure yarn, blended yarn, polyester/cotton yarn, CVC yarn and the like according to the types of fibers forming the yarn, and provides more diversified requirements for the performance and the like of the yarn along with the change of market requirements and the continuous progress of technology;
however, the existing antibacterial yarns have common self antibacterial effect, a large amount of bacteria still breed in the use process, the antibacterial effect is obviously reduced after the existing antibacterial yarns are washed for many times, and the antibacterial effect of the surfaces of part of the yarns can be directly contacted with skin, so that the health of a user is influenced;
in view of the above technical drawbacks, a solution is proposed.
Disclosure of Invention
The invention aims to provide a production process of antibacterial yarn.
The technical problems to be solved by the invention are as follows:
the existing antibacterial yarn has a common self antibacterial effect, a large amount of bacteria can still be bred in the using process, the antibacterial effect is obviously reduced after washing for many times, and the antibacterial effect on the surface of part of the yarn can be in direct contact with skin, so that the health of a user is influenced.
The purpose of the invention can be realized by the following technical scheme:
the production process of the antibacterial yarn comprises the following steps:
step S1: ultrasonically cleaning the yarn for 2-3h by using absolute ethyl alcohol, cleaning the yarn for 2-3 times by using deionized water, wherein the cleaning time is 3-5min each time, and drying the yarn at the temperature of 50 ℃;
step S2: soaking the yarn in a dopamine aqueous solution with the mass fraction of 20%, adding a Tris reagent until the pH value is 8.5, soaking for 20-25h, taking out the yarn and drying;
step S3: dispersing the antibacterial additive in a sodium hydroxide solution, soaking the yarn for 5-8h at the temperature of 120-150 ℃, taking out the yarn and drying.
Further, the antibacterial additive is prepared by the following steps:
step A1: adding deionized water, sodium hydroxide and 3, 5-dinitrotoluene into a reaction kettle, stirring for 10-15min under the condition that the rotation speed is 200-300r/min, adding raney nickel, adding hydrazine hydrate under the condition that the temperature is 90-95 ℃ to react for 2-3h to obtain an intermediate 1, adding the intermediate 1 and the deionized water into the reaction kettle, stirring and dropwise adding a sulfuric acid solution and methyl isobutyl ketone under the conditions that the rotation speed is 150-200r/min and the temperature is 25-30 ℃, cooling to 0 ℃ after the addition is finished, dropwise adding a sodium nitrite solution for 1-1.5h, heating to 50-55 ℃ after the dropwise addition is finished, and reacting for 2-3h to obtain an intermediate 2;
the reaction process is as follows:
step A2: adding 4-methylpyridine and deionized water into a reaction kettle, refluxing and adding potassium permanganate under the conditions of a rotation speed of 200-phase-change at 300r/min and a temperature of 110-phase-change at 120 ℃ to react for 4-5h to obtain an intermediate 3, adding the intermediate 3, 2, 6, 6-tetramethylpiperidinol and concentrated sulfuric acid into the reaction kettle, reacting for 3-5h under the conditions of a rotation speed of 150-phase-change at 200r/min and a temperature of 80-90 ℃ to obtain an intermediate 4, adding the intermediate 4, sodium hypochlorite and dilute sulfuric acid into the reaction kettle, and stirring for 1-3h under the conditions of a rotation speed of 200-phase-change at 300r/min to obtain an intermediate 5;
the reaction process is as follows:
step A3: adding 5, 5-dimethyl hydantoin, potassium carbonate and acetone into a reaction kettle, refluxing and adding dibromoethane under the conditions of the rotation speed of 150-200r/min and the temperature of 60-70 ℃, performing reflux reaction for 3-5h to obtain an intermediate 6, adding the intermediate 6, the intermediate 5 and acetonitrile into the reaction kettle, performing reflux reaction for 10-15h under the condition of the temperature of 90-100 ℃ to obtain an intermediate 7, adding the intermediate 7, tert-butyl alcohol and butyl hypochlorite into the reaction kettle, and performing light-resistant reaction for 20-25h under the conditions of the rotation speed of 200-300r/min and the temperature of 20-25 ℃ to obtain an intermediate 8;
the reaction process is as follows:
step A4: adding the intermediate 2, the intermediate 8, sodium hydride and toluene into a reaction kettle, stirring for 3-5h at the rotation speed of 150-200r/min to obtain an intermediate 9, adding the intermediate 9, nitrogen-bromosuccinimide, benzoyl peroxide and carbon tetrachloride into the reaction kettle, reacting for 8-10h at the temperature of 80-90 ℃ to obtain an intermediate 10, adding the intermediate 10, potassium carbonate, deionized water and tetraethylammonium bromide into the reaction kettle, performing reflux reaction for 2-3h to obtain an intermediate 11, adding the intermediate 11, N-dimethylglycine and concentrated sulfuric acid into the reaction kettle, reacting for 3-5h at the rotation speed of 150-200r/min and the temperature of 80-90 ℃ to obtain an intermediate 12, adding the intermediate 12, stirring for 3-5h at the rotation speed of 150-200r/min, and the temperature of 80-90 ℃ to obtain an intermediate 12, Adding acetonitrile and hydroquinone into a reaction kettle, stirring and adding bromohexadecane under the conditions that the rotating speed is 150-200r/min and the temperature is 45-50 ℃, and reacting for 10-15h to obtain an intermediate 13;
the reaction process is as follows:
step A5: adding chitosan, epoxy chloropropane and isopropanol into a reaction kettle, stirring and adding triethylamine under the conditions that the rotation speed is 150-40 ℃ and the temperature is 35-40 ℃, removing the isopropanol to prepare modified chitosan, dissolving the modified chitosan into the isopropanol, adding an intermediate 13 and gelatin solution, stirring and uniformly mixing under the conditions that the rotation speed is 300-500r/min, adding deionized water, reacting for 30-40min under the conditions that the temperature is 50-55 ℃ and the pH value is 6-6.5, cooling to 20-25 ℃, adding glutaraldehyde, reacting for 40-50min under the temperature of 30-35 ℃, filtering to remove filtrate, and drying filter cakes to prepare the antibacterial additive.
Further, the dosage ratio of the deionized water, the sodium hydroxide, the 3, 5-dinitrotoluene, the raney nickel and the hydrazine hydrate in the step A1 is 100 mL: 4.3 g: 1.5 g: 30g of hydrazine hydrate, wherein the mass fraction of the hydrazine hydrate is 30%, and the dosage ratio of the intermediate 1, deionized water, sulfuric acid solution, methyl isobutyl ketone and sodium nitrite solution is 3.5 g: 30mL of: 8mL of: 5.5 g: 10mL, 65 percent of sulfuric acid solution and 25 percent of sodium nitrite solution.
Further, the dosage ratio of the 4-methylpyridine, the deionized water and the potassium permanganate in the step A2 is 1.2 g: 50mL of: 4.3g, the dosage ratio of the intermediate 3, the 2, 2, 6, 6-tetramethyl piperidinol and the concentrated sulfuric acid is 0.01 mol: 0.01 mol: 20mL, the mass fraction of concentrated sulfuric acid is 96%, and the dosage ratio of the intermediate 4, sodium hypochlorite and dilute sulfuric acid is 0.01 mol: 0.012 mol: 30mL, and the mass fraction of the dilute sulfuric acid is 50%.
Further, the amount of the 5, 5-dimethylhydantoin, the potassium carbonate, the acetone and the dibromoethane in the step A3 is 3.2 g: 12.5 g: 200mL of: 13.8g, the dosage ratio of the intermediate 6, the intermediate 5 and the acetonitrile is 12 mmol: 50mL of: 30mmol, the dosage ratio of the intermediate 7, the tert-butyl alcohol and the butyl hypochlorite is 1 mmol: 20mL of: 4 mmol.
Further, the dosage ratio of the intermediate 2, the intermediate 8, the sodium hydride and the toluene in the step A4 is 0.01 mol: 0.01 mol: 0.015 mol: 30mL, wherein the dosage ratio of the intermediate 9, the nitrogen-bromosuccinimide, the benzoyl peroxide and the carbon tetrachloride is 0.1 mol: 0.1 mol: 0.15 g: 200mL, intermediate 10, potassium carbonate, deionized water, tetraethylammonium bromide 6 g: 11.6 g: 100mL of: 4mL, wherein the dosage ratio of the intermediate 11, the N, N-dimethylglycine and the concentrated sulfuric acid is 0.01 mol: 0.01 mol: 25mL, wherein the concentrated sulfuric acid is the same as the concentrated sulfuric acid described in the step A2, and the using amount ratio of the intermediate 12, the acetonitrile, the hydroquinone and the bromohexadecane is 0.01 mol: 30mL of: 0.01 mol: 0.01 mol.
Further, the dosage ratio of the chitosan, the epichlorohydrin, the isopropanol and the triethylamine in the step A5 is 3 g: 1.5 g: 50mL of: 2g, the use amount ratio of the modified chitosan, the isopropanol, the intermediate 13, the gelatin solution, the deionized water and the glutaraldehyde is 5 g: 30mL of: 3.2 g: 20mL of: 120mL of: 10 mL.
The invention has the beneficial effects that:
the invention prepares an antibacterial additive in the process of preparing antibacterial yarns, the antibacterial additive is prepared by treating 3, 5-dinitrotoluene with raney nickel to prepare an intermediate 1, further treating the intermediate 1 to prepare an intermediate 2, oxidizing 4-methylpyridine with potassium permanganate to prepare an intermediate 3, carrying out esterification reaction on the intermediate 3 and 2, 2, 6, 6-tetramethylpiperidinol to prepare an intermediate 4, treating the intermediate 4 with sodium hypochlorite to prepare an intermediate 5, reacting the 5, 5-dimethylhydantoin with dibromoethane to prepare an intermediate 6, reacting the intermediate 5 and the intermediate 6 to prepare an intermediate 7, treating the intermediate 7 with butyl hypochlorite to prepare an intermediate 8, reacting the intermediate 8 with the intermediate 2 to prepare an intermediate 9, treating the intermediate 9 with nitrogen-bromosuccinimide to obtain an intermediate 10, further treating the intermediate 10 to obtain an intermediate 11, performing esterification reaction on the intermediate 11 and N, N-dimethylglycine to obtain an intermediate 12, reacting the intermediate 12 with bromohexadecane to obtain an intermediate 13, modifying chitosan with epichlorohydrin to react amino groups on the chitosan with chlorine atom sites of the epichlorohydrin to obtain modified chitosan, and microencapsulating the intermediate 12 to obtain the antibacterial additive, wherein the antibacterial additive contains a quaternary ammonium salt structure which can act with head groups of acidic phospholipids in bacterial cell membranes to reduce the permeability of the cell membranes and cause bacterial cell sap leakage to cause bacterial cell death, and epoxy groups on the surfaces of the antibacterial additive can react with phenolic hydroxyl groups on the surfaces of yarns, and the antibacterial additive is firmly fixed on the surface of the yarn, so that clothes prepared from the yarn still have a good antibacterial effect after being washed for many times, and meanwhile, the antibacterial component cannot be in direct contact with the skin of a human body and cannot cause damage to the human body due to microencapsulation treatment.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1:
the production process of the antibacterial yarn comprises the following steps:
step S1: ultrasonically cleaning the yarn for 2h by using absolute ethyl alcohol, cleaning the yarn for 2 times by using deionized water, wherein the cleaning time is 3min each time, and drying the yarn at the temperature of 50 ℃;
step S2: soaking the yarn in dopamine aqueous solution, adding a Tris reagent until the pH value is 8.5, soaking for 20 hours, taking out the yarn and drying;
step S3: dispersing the antibacterial additive in a sodium hydroxide solution with the mass fraction of 20%, soaking the yarn for 5 hours at the temperature of 120 ℃, taking out the yarn and drying.
The antibacterial additive is prepared by the following steps:
step A1: adding deionized water, sodium hydroxide and 3, 5-dinitrotoluene into a reaction kettle, stirring for 10min at the rotation speed of 200r/min, adding raney nickel, adding hydrazine hydrate at the temperature of 90 ℃ to react for 2h to obtain an intermediate 1, adding the intermediate 1 and the deionized water into the reaction kettle, stirring and dropwise adding a sulfuric acid solution and methyl isobutyl ketone at the rotation speed of 150r/min and the temperature of 25 ℃, cooling to 0 ℃ after the addition is finished, dropwise adding a sodium nitrite solution for 1h, heating to 50 ℃ after the dropwise addition is finished, and reacting for 2h to obtain an intermediate 2;
step A2: adding 4-methylpyridine and deionized water into a reaction kettle, refluxing and adding potassium permanganate under the conditions of a rotating speed of 200r/min and a temperature of 110 ℃ for reaction for 4 hours to obtain an intermediate 3, adding the intermediate 3, 2, 6, 6-tetramethylpiperidinol and concentrated sulfuric acid into the reaction kettle, reacting for 3 hours under the conditions of a rotating speed of 150r/min and a temperature of 80 ℃ to obtain an intermediate 4, adding the intermediate 4, sodium hypochlorite and dilute sulfuric acid into the reaction kettle, and stirring for 1 hour under the condition of a rotating speed of 200r/min to obtain an intermediate 5;
step A3: adding 5, 5-dimethylhydantoin, potassium carbonate and acetone into a reaction kettle, refluxing and adding dibromoethane under the conditions of the rotating speed of 150r/min and the temperature of 60 ℃, performing reflux reaction for 3 hours to prepare an intermediate 6, adding the intermediate 6, the intermediate 5 and acetonitrile into the reaction kettle, performing reflux reaction for 10 hours under the condition of the temperature of 90 ℃ to prepare an intermediate 7, adding the intermediate 7, tert-butyl alcohol and butyl hypochlorite into the reaction kettle, and performing light-resistant reaction for 20 hours under the conditions of the rotating speed of 200r/min and the temperature of 20 ℃ to prepare an intermediate 8;
step A4: adding the intermediate 2, the intermediate 8, sodium hydride and toluene into a reaction kettle, stirring for 3h at the rotation speed of 150r/min to obtain an intermediate 9, adding the intermediate 9, nitrogen-bromosuccinimide, benzoyl peroxide and carbon tetrachloride into the reaction kettle, reacting for 8h at the temperature of 80 ℃ to obtain an intermediate 10, adding the intermediate 10, potassium carbonate, deionized water and tetraethylammonium bromide into the reaction kettle, performing reflux reaction for 2h to obtain an intermediate 11, adding the intermediate 11, N-dimethylglycine and concentrated sulfuric acid into the reaction kettle, reacting for 3h at the rotation speed of 150r/min and the temperature of 80 ℃ to obtain an intermediate 12, adding the intermediate 12, acetonitrile and hydroquinone into the reaction kettle, reacting at the rotation speed of 150r/min and the temperature of 45 ℃, stirring and adding bromohexadecane to react for 10h to obtain an intermediate 13;
step A5: adding chitosan, epoxy chloropropane and isopropanol into a reaction kettle, stirring and adding triethylamine under the conditions of the rotating speed of 150r/min and the temperature of 35 ℃, removing the isopropanol after reacting for 1h to prepare modified chitosan, dissolving the modified chitosan into the isopropanol, adding an intermediate 13 and gelatin solution, stirring to mix uniformly under the conditions of the rotating speed of 300r/min, adding deionized water, reacting for 30min under the conditions of the temperature of 50 ℃ and the pH value of 6, cooling to 20 ℃, adding glutaraldehyde, reacting for 40min under the temperature of 30 ℃, filtering to remove filtrate, drying filter cakes, and preparing the antibacterial additive.
Example 2:
the production process of the antibacterial yarn comprises the following steps:
step S1: ultrasonically cleaning the yarn for 2h by using absolute ethyl alcohol, cleaning the yarn for 3 times by using deionized water, wherein the cleaning time is 3min each time, and drying the yarn at the temperature of 50 ℃;
step S2: soaking the yarn in a dopamine aqueous solution with the mass fraction of 20%, adding a Tris reagent until the pH value is 8.5, soaking for 25h, taking out the yarn and drying;
step S3: dispersing the antibacterial additive in a sodium hydroxide solution, soaking the yarn for 8 hours at the temperature of 120 ℃, taking out the yarn and drying.
The antibacterial additive is prepared by the following steps:
step A1: adding deionized water, sodium hydroxide and 3, 5-dinitrotoluene into a reaction kettle, stirring for 15min at the rotation speed of 200r/min, adding raney nickel, adding hydrazine hydrate at the temperature of 90 ℃ to react for 3h to obtain an intermediate 1, adding the intermediate 1 and the deionized water into the reaction kettle, stirring and dropwise adding a sulfuric acid solution and methyl isobutyl ketone at the rotation speed of 150r/min and the temperature of 30 ℃, cooling to 0 ℃ after the addition is finished, dropwise adding a sodium nitrite solution for 1h, heating to 55 ℃ after the dropwise addition is finished, and reacting for 2h to obtain an intermediate 2;
step A2: adding 4-methylpyridine and deionized water into a reaction kettle, refluxing and adding potassium permanganate under the conditions of a rotating speed of 300r/min and a temperature of 110 ℃ for 5 hours to prepare an intermediate 3, adding the intermediate 3, 2, 6, 6-tetramethylpiperidinol and concentrated sulfuric acid into the reaction kettle, reacting for 3 hours under the conditions of a rotating speed of 150r/min and a temperature of 90 ℃ to prepare an intermediate 4, adding the intermediate 4, sodium hypochlorite and dilute sulfuric acid into the reaction kettle, and stirring for 1 hour under the condition of a rotating speed of 300r/min to prepare an intermediate 5;
step A3: adding 5, 5-dimethylhydantoin, potassium carbonate and acetone into a reaction kettle, refluxing and adding dibromoethane under the conditions of the rotating speed of 200r/min and the temperature of 60 ℃, performing reflux reaction for 5 hours to prepare an intermediate 6, adding the intermediate 6, the intermediate 5 and acetonitrile into the reaction kettle, performing reflux reaction for 15 hours under the condition of the temperature of 90 ℃ to prepare an intermediate 7, adding the intermediate 7, tert-butyl alcohol and butyl hypochlorite into the reaction kettle, and performing light-resistant reaction for 20 hours under the conditions of the rotating speed of 200r/min and the temperature of 25 ℃ to prepare an intermediate 8;
step A4: adding the intermediate 2, the intermediate 8, sodium hydride and toluene into a reaction kettle, stirring for 3h at the rotation speed of 200r/min to obtain an intermediate 9, adding the intermediate 9, nitrogen-bromosuccinimide, benzoyl peroxide and carbon tetrachloride into the reaction kettle, reacting for 8h at the temperature of 90 ℃ to obtain an intermediate 10, adding the intermediate 10, potassium carbonate, deionized water and tetraethylammonium bromide into the reaction kettle, performing reflux reaction for 3h to obtain an intermediate 11, adding the intermediate 11, N-dimethylglycine and concentrated sulfuric acid into the reaction kettle, reacting for 3h at the rotation speed of 150r/min and the temperature of 90 ℃ to obtain an intermediate 12, adding the intermediate 12, acetonitrile and hydroquinone into the reaction kettle, reacting at the rotation speed of 200r/min and the temperature of 45 ℃, stirring and adding bromohexadecane to react for 15h to obtain an intermediate 13;
step A5: adding chitosan, epoxy chloropropane and isopropanol into a reaction kettle, stirring and adding triethylamine under the conditions of the rotating speed of 150r/min and the temperature of 40 ℃, removing the isopropanol after reacting for 1h to prepare modified chitosan, dissolving the modified chitosan into the isopropanol, adding an intermediate 13 and gelatin solution, stirring to mix uniformly under the conditions of the rotating speed of 500r/min, adding deionized water, reacting for 30min under the conditions of the temperature of 50 ℃ and the pH value of 6.5, cooling to 25 ℃, adding glutaraldehyde, reacting for 50min under the temperature of 30 ℃, filtering to remove filtrate, and drying filter cakes to prepare the antibacterial additive.
Example 3:
the production process of the antibacterial yarn comprises the following steps:
step S1: ultrasonically cleaning the yarn for 3h by using absolute ethyl alcohol, cleaning the yarn for 3 times by using deionized water, wherein the cleaning time is 5min each time, and drying the yarn at the temperature of 50 ℃;
step S2: soaking the yarn in a dopamine aqueous solution with the mass fraction of 20%, adding a Tris reagent until the pH value is 8.5, soaking for 25h, taking out the yarn and drying;
step S3: dispersing the antibacterial additive in a sodium hydroxide solution, soaking the yarn for 8 hours at the temperature of 150 ℃, taking out the yarn and drying.
The antibacterial additive is prepared by the following steps:
step A1: adding deionized water, sodium hydroxide and 3, 5-dinitrotoluene into a reaction kettle, stirring for 15min at the rotation speed of 300r/min, adding raney nickel, adding hydrazine hydrate at the temperature of 95 ℃ to react for 3h to obtain an intermediate 1, adding the intermediate 1 and the deionized water into the reaction kettle, stirring and dropwise adding a sulfuric acid solution and methyl isobutyl ketone at the rotation speed of 200r/min and the temperature of 30 ℃, cooling to 0 ℃ after the addition is finished, dropwise adding a sodium nitrite solution for 1.5h, heating to 55 ℃ after the dropwise addition is finished, and reacting for 3h to obtain an intermediate 2;
step A2: adding 4-methylpyridine and deionized water into a reaction kettle, refluxing and adding potassium permanganate under the conditions of a rotating speed of 300r/min and a temperature of 120 ℃ to react for 5 hours to prepare an intermediate 3, adding the intermediate 3, 2, 6, 6-tetramethylpiperidinol and concentrated sulfuric acid into the reaction kettle, reacting for 5 hours under the conditions of a rotating speed of 200r/min and a temperature of 90 ℃ to prepare an intermediate 4, adding the intermediate 4, sodium hypochlorite and dilute sulfuric acid into the reaction kettle, and stirring for 3 hours under the conditions of a rotating speed of 300r/min to prepare an intermediate 5;
step A3: adding 5, 5-dimethylhydantoin, potassium carbonate and acetone into a reaction kettle, refluxing and adding dibromoethane under the conditions of the rotating speed of 200r/min and the temperature of 70 ℃, performing reflux reaction for 5 hours to prepare an intermediate 6, adding the intermediate 6, the intermediate 5 and acetonitrile into the reaction kettle, performing reflux reaction for 15 hours under the condition of the temperature of 100 ℃ to prepare an intermediate 7, adding the intermediate 7, tert-butyl alcohol and butyl hypochlorite into the reaction kettle, and performing light-resistant reaction for 25 hours under the conditions of the rotating speed of 300r/min and the temperature of 25 ℃ to prepare an intermediate 8;
step A4: adding the intermediate 2, the intermediate 8, sodium hydride and toluene into a reaction kettle, stirring for 5 hours at the rotation speed of 200r/min to obtain an intermediate 9, adding the intermediate 9, nitrogen-bromosuccinimide, benzoyl peroxide and carbon tetrachloride into the reaction kettle, reacting for 10 hours at the temperature of 90 ℃ to obtain an intermediate 10, adding the intermediate 10, potassium carbonate, deionized water and tetraethylammonium bromide into the reaction kettle, performing reflux reaction for 3 hours to obtain an intermediate 11, adding the intermediate 11, N-dimethylglycine and concentrated sulfuric acid into the reaction kettle, reacting for 5 hours at the rotation speed of 200r/min and the temperature of 90 ℃ to obtain an intermediate 12, adding the intermediate 12, acetonitrile and hydroquinone into the reaction kettle, reacting at the rotation speed of 200r/min and the temperature of 45-50 ℃, stirring and adding bromohexadecane to react for 15h to obtain an intermediate 13;
step A5: adding chitosan, epoxy chloropropane and isopropanol into a reaction kettle, stirring and adding triethylamine under the conditions of the rotating speed of 200r/min and the temperature of 40 ℃, removing the isopropanol after reacting for 1.5h to prepare modified chitosan, dissolving the modified chitosan into the isopropanol, adding an intermediate 13 and gelatin solution, stirring to mix uniformly under the conditions of the rotating speed of 500r/min, adding deionized water, reacting for 40min under the conditions of the temperature of 55 ℃ and the pH value of 6.5, cooling to 25 ℃, adding glutaraldehyde, reacting for 50min under the temperature of 35 ℃, filtering to remove filtrate, and drying a filter cake to prepare the antibacterial additive.
Comparative example 1:
in this comparative example, the yarn was not treated with an aqueous dopamine solution, but was directly immersed in an aqueous dispersion of an antimicrobial additive, as compared to example 1.
Comparative example 2:
this comparative example compares with example 1 without replacing the antimicrobial additive with p-nitrophenol and the rest of the procedure is the same.
The antibacterial yarns prepared in examples 1 to 3 and comparative examples 1 to 2 were subjected to the performance test, and the test results are shown in the following table 1:
TABLE 1
As can be seen from table 1 above, the antibacterial yarns prepared in examples 1 to 3 have an escherichia coli inhibition rate of 99.23 to 99.28%, an candida albicans inhibition rate of 99.45 to 99.47%, an aspergillus niger inhibition rate of 99.37 to 99.40%, the antibacterial yarn prepared in comparative example 1 has the same antibacterial effect as the antibacterial yarns prepared in examples 1 to 3, the antibacterial yarn prepared in comparative example 2 has a poorer antibacterial effect than the antibacterial yarns prepared in examples 1 to 3, and after 20 times of washing, the antibacterial ability of the antibacterial yarns prepared in examples 1 to 3 is not reduced, while the antibacterial ability of the antibacterial yarns prepared in comparative examples 1 to 2 is greatly reduced.
The foregoing is merely exemplary and illustrative of the principles of the present invention and various modifications, additions and substitutions of the specific embodiments described herein may be made by those skilled in the art without departing from the principles of the present invention or exceeding the scope of the claims set forth herein.
Claims (7)
1. The production process of the antibacterial yarn is characterized by comprising the following steps: the method comprises the following steps:
step S1: ultrasonically cleaning the yarn for 2-3h by using absolute ethyl alcohol, cleaning the yarn for 2-3 times by using deionized water, wherein the cleaning time is 3-5min each time, and drying the yarn at the temperature of 50 ℃;
step S2: soaking the yarn in dopamine aqueous solution, adding a Tris reagent until the pH value is 8.5, soaking for 20-25h, taking out the yarn and drying;
step S3: dispersing the antibacterial additive in a sodium hydroxide solution with the mass fraction of 20%, soaking the yarn for 5-8h at the temperature of 120-150 ℃, taking out the yarn and drying.
2. The process for producing an antimicrobial yarn according to claim 1, wherein: the antibacterial additive is prepared by the following steps:
step A1: adding deionized water, sodium hydroxide and 3, 5-dinitrotoluene into a reaction kettle, stirring for 10-15min under the condition that the rotation speed is 200-300r/min, adding raney nickel, adding hydrazine hydrate under the condition that the temperature is 90-95 ℃ to react for 2-3h to obtain an intermediate 1, adding the intermediate 1 and the deionized water into the reaction kettle, stirring and dropwise adding a sulfuric acid solution and methyl isobutyl ketone under the conditions that the rotation speed is 150-200r/min and the temperature is 25-30 ℃, cooling to 0 ℃ after the addition is finished, dropwise adding a sodium nitrite solution for 1-1.5h, heating to 50-55 ℃ after the dropwise addition is finished, and reacting for 2-3h to obtain an intermediate 2;
step A2: adding 4-methylpyridine and deionized water into a reaction kettle, refluxing and adding potassium permanganate under the conditions of a rotation speed of 200-phase-change at 300r/min and a temperature of 110-phase-change at 120 ℃ to react for 4-5h to obtain an intermediate 3, adding the intermediate 3, 2, 6, 6-tetramethylpiperidinol and concentrated sulfuric acid into the reaction kettle, reacting for 3-5h under the conditions of a rotation speed of 150-phase-change at 200r/min and a temperature of 80-90 ℃ to obtain an intermediate 4, adding the intermediate 4, sodium hypochlorite and dilute sulfuric acid into the reaction kettle, and stirring for 1-3h under the conditions of a rotation speed of 200-phase-change at 300r/min to obtain an intermediate 5;
step A3: adding 5, 5-dimethyl hydantoin, potassium carbonate and acetone into a reaction kettle, refluxing and adding dibromoethane under the conditions of the rotation speed of 150-200r/min and the temperature of 60-70 ℃, performing reflux reaction for 3-5h to obtain an intermediate 6, adding the intermediate 6, the intermediate 5 and acetonitrile into the reaction kettle, performing reflux reaction for 10-15h under the condition of the temperature of 90-100 ℃ to obtain an intermediate 7, adding the intermediate 7, tert-butyl alcohol and butyl hypochlorite into the reaction kettle, and performing light-resistant reaction for 20-25h under the conditions of the rotation speed of 200-300r/min and the temperature of 20-25 ℃ to obtain an intermediate 8;
step A4: adding the intermediate 2, the intermediate 8, sodium hydride and toluene into a reaction kettle, stirring for 3-5h at the rotation speed of 150-200r/min to obtain an intermediate 9, adding the intermediate 9, nitrogen-bromosuccinimide, benzoyl peroxide and carbon tetrachloride into the reaction kettle, reacting for 8-10h at the temperature of 80-90 ℃ to obtain an intermediate 10, adding the intermediate 10, potassium carbonate, deionized water and tetraethylammonium bromide into the reaction kettle, performing reflux reaction for 2-3h to obtain an intermediate 11, adding the intermediate 11, N-dimethylglycine and concentrated sulfuric acid into the reaction kettle, reacting for 3-5h at the rotation speed of 150-200r/min and the temperature of 80-90 ℃ to obtain an intermediate 12, adding the intermediate 12, stirring for 3-5h at the rotation speed of 150-200r/min, and the temperature of 80-90 ℃ to obtain an intermediate 12, Adding acetonitrile and hydroquinone into a reaction kettle, stirring and adding bromohexadecane under the conditions that the rotating speed is 150-200r/min and the temperature is 45-50 ℃, and reacting for 10-15h to obtain an intermediate 13;
step A5: adding chitosan, epoxy chloropropane and isopropanol into a reaction kettle, stirring and adding triethylamine under the conditions that the rotation speed is 150-40 ℃ and the temperature is 35-40 ℃, removing the isopropanol to prepare modified chitosan, dissolving the modified chitosan into the isopropanol, adding an intermediate 13 and gelatin solution, stirring and uniformly mixing under the conditions that the rotation speed is 300-500r/min, adding deionized water, reacting for 30-40min under the conditions that the temperature is 50-55 ℃ and the pH value is 6-6.5, cooling to 20-25 ℃, adding glutaraldehyde, reacting for 40-50min under the temperature of 30-35 ℃, filtering to remove filtrate, and drying filter cakes to prepare the antibacterial additive.
3. The process for producing an antimicrobial yarn according to claim 2, wherein: the dosage ratio of the deionized water, the sodium hydroxide, the 3, 5-dinitrotoluene, the raney nickel and the hydrazine hydrate in the step A1 is 100 mL: 4.3 g: 1.5 g: 30g of hydrazine hydrate, wherein the mass fraction of the hydrazine hydrate is 30%, and the dosage ratio of the intermediate 1, deionized water, sulfuric acid solution, methyl isobutyl ketone and sodium nitrite solution is 3.5 g: 30mL of: 8mL of: 5.5 g: 10mL, 65 percent of sulfuric acid solution and 25 percent of sodium nitrite solution.
4. The process for producing an antimicrobial yarn according to claim 2, wherein: the dosage ratio of the 4-methylpyridine, the deionized water and the potassium permanganate in the step A2 is 1.2 g: 50mL of: 4.3g, the dosage ratio of the intermediate 3, the 2, 2, 6, 6-tetramethyl piperidinol and the concentrated sulfuric acid is 0.01 mol: 0.01 mol: 20mL, the mass fraction of concentrated sulfuric acid is 96%, and the dosage ratio of the intermediate 4, sodium hypochlorite and dilute sulfuric acid is 0.01 mol: 0.012 mol: 30mL, and the mass fraction of the dilute sulfuric acid is 50%.
5. The process for producing an antimicrobial yarn according to claim 2, wherein: the using amount ratio of the 5, 5-dimethylhydantoin, the potassium carbonate, the acetone and the dibromoethane in the step A3 is 3.2 g: 12.5 g: 200mL of: 13.8g, the dosage ratio of the intermediate 6, the intermediate 5 and the acetonitrile is 12 mmol: 50mL of: 30mmol, the dosage ratio of the intermediate 7, the tert-butyl alcohol and the butyl hypochlorite is 1 mmol: 20mL of: 4 mmol.
6. The process for producing an antimicrobial yarn according to claim 2, wherein: the dosage ratio of the intermediate 2, the intermediate 8, the sodium hydride and the toluene in the step A4 is 0.01 mol: 0.01 mol: 0.015 mol: 30mL, wherein the dosage ratio of the intermediate 9, the nitrogen-bromosuccinimide, the benzoyl peroxide and the carbon tetrachloride is 0.1 mol: 0.1 mol: 0.15 g: 200mL, intermediate 10, potassium carbonate, deionized water, tetraethylammonium bromide 6 g: 11.6 g: 100mL of: 4mL, wherein the dosage ratio of the intermediate 11, the N, N-dimethylglycine and the concentrated sulfuric acid is 0.01 mol: 0.01 mol: 25mL, wherein the concentrated sulfuric acid is the same as the concentrated sulfuric acid described in the step A2, and the using amount ratio of the intermediate 12, the acetonitrile, the hydroquinone and the bromohexadecane is 0.01 mol: 30mL of: 0.01 mol: 0.01 mol.
7. The process for producing an antimicrobial yarn according to claim 2, wherein: the dosage ratio of the chitosan, the epichlorohydrin, the isopropanol and the triethylamine in the step A5 is 3 g: 1.5 g: 50mL of: 2g, the use amount ratio of the modified chitosan, the isopropanol, the intermediate 13, the gelatin solution, the deionized water and the glutaraldehyde is 5 g: 30mL of: 3.2 g: 20mL of: 120mL of: 10 mL.
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