WO2023216556A1 - Hydrophilic antibacterial finishing agent, antibacterial finishing method of fabric and antibacterial fabric - Google Patents

Hydrophilic antibacterial finishing agent, antibacterial finishing method of fabric and antibacterial fabric Download PDF

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Publication number
WO2023216556A1
WO2023216556A1 PCT/CN2022/134213 CN2022134213W WO2023216556A1 WO 2023216556 A1 WO2023216556 A1 WO 2023216556A1 CN 2022134213 W CN2022134213 W CN 2022134213W WO 2023216556 A1 WO2023216556 A1 WO 2023216556A1
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propyl
antibacterial
fabric
hydrophilic
triethoxysilyl
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PCT/CN2022/134213
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French (fr)
Inventor
Tao Long
Wei Wang
Xin Zhao
William KER
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Suzhou J&K Ultrafine Materials Co., Ltd.
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Publication of WO2023216556A1 publication Critical patent/WO2023216556A1/en

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    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/53Polyethers
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32Polymers modified by chemical after-treatment
    • C08G65/329Polymers modified by chemical after-treatment with organic compounds
    • C08G65/333Polymers modified by chemical after-treatment with organic compounds containing nitrogen
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32Polymers modified by chemical after-treatment
    • C08G65/329Polymers modified by chemical after-treatment with organic compounds
    • C08G65/333Polymers modified by chemical after-treatment with organic compounds containing nitrogen
    • C08G65/33303Polymers modified by chemical after-treatment with organic compounds containing nitrogen containing amino group
    • C08G65/33317Polymers modified by chemical after-treatment with organic compounds containing nitrogen containing amino group heterocyclic
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32Polymers modified by chemical after-treatment
    • C08G65/329Polymers modified by chemical after-treatment with organic compounds
    • C08G65/336Polymers modified by chemical after-treatment with organic compounds containing silicon
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32Polymers modified by chemical after-treatment
    • C08G65/329Polymers modified by chemical after-treatment with organic compounds
    • C08G65/337Polymers modified by chemical after-treatment with organic compounds containing other elements
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/244Treating 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 sulfur or phosphorus
    • D06M13/282Treating 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 sulfur or phosphorus with compounds containing phosphorus
    • D06M13/285Phosphines; Phosphine oxides; Phosphine sulfides; Phosphinic or phosphinous acids or derivatives thereof
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322Treating 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
    • D06M13/35Heterocyclic compounds
    • D06M13/352Heterocyclic compounds having five-membered heterocyclic rings
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322Treating 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
    • D06M13/44Treating 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 containing nitrogen and phosphorus
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322Treating 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
    • D06M13/46Compounds containing quaternary nitrogen atoms
    • D06M13/47Compounds containing quaternary nitrogen atoms derived from heterocyclic compounds
    • D06M13/473Compounds containing quaternary nitrogen atoms derived from heterocyclic compounds having five-membered heterocyclic rings
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/50Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with organometallic compounds; with organic compounds containing boron, silicon, selenium or tellurium atoms
    • D06M13/51Compounds with at least one carbon-metal or carbon-boron, carbon-silicon, carbon-selenium, or carbon-tellurium bond
    • D06M13/513Compounds with at least one carbon-metal or carbon-boron, carbon-silicon, carbon-selenium, or carbon-tellurium bond with at least one carbon-silicon bond
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/50Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with organometallic compounds; with organic compounds containing boron, silicon, selenium or tellurium atoms
    • D06M13/51Compounds with at least one carbon-metal or carbon-boron, carbon-silicon, carbon-selenium, or carbon-tellurium bond
    • D06M13/513Compounds with at least one carbon-metal or carbon-boron, carbon-silicon, carbon-selenium, or carbon-tellurium bond with at least one carbon-silicon bond
    • D06M13/5135Unsaturated compounds containing silicon atoms
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M16/00Biochemical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. enzymatic
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2101/00Chemical constitution of the fibres, threads, yarns, fabrics or fibrous goods made from such materials, to be treated
    • D06M2101/02Natural fibres, other than mineral fibres
    • D06M2101/04Vegetal fibres
    • D06M2101/06Vegetal fibres cellulosic
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02ATECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

Definitions

  • the present invention relates to the technical field of antibacterial finishing agents for textiles, and relates to a hydrophilic antibacterial finishing agent, a method for conducting antibacterial finishing of a fabrics, and an antibacterial fabric.
  • Antibacterial sanitary finishing of the textiles is a processing technology that employs an antibacterial or bacteriostatic agent to treat a fabric, so as to obtain an antibacterial, mildew-proof, and odor-proof textile that keeps clean and sanitary. Its purpose is not only to prevent the textile from being contaminated by microorganisms, but more importantly to prevent infectious diseases, ensure the safety, health and wearing comfort of human body, and reduce the cross-infection rate of public environment, so that the textile can acquire a new function of health care and meet people's demands for hygiene and health.
  • Quaternary ammonium salt antibacterial agents have been widely studied and utilized because of their low price and fast sterilization speed. 4 generations of quaternary ammonium salt antibacterial agents of typical significance have been developed internationally; among them, DC-5700, an antibacterial agent of silicone quaternary ammonium salt developed by Dow Corning is the most representative. Since the antibacterial agent of silicone quaternary ammonium salt combines a quaternary ammonium salt with a silane coupling agent in its structure, this product has accepted washing resistance and an excellent antibacterial effect at the same time. However, DC-5700 has an obvious defect in that a fabric subjected to antibacterial finishing with it is extremely hydrophobic, which limits its application scenarios. It severely limits its application in fabrics that contact with skin, such as an underwear.
  • the present invention has developed a hydrophilic antibacterial finishing agent for post finishing of a fabric.
  • An antibacterial fabric made by this antibacterial finishing method not only has an excellent antibacterial performance, but also has good hydrophilicity.
  • hydrophilic antibacterial finishing agent including the following components in parts by weight:
  • silicone hydrophilic antibacterial agent has a chemical structure as shown in the formula I below,
  • R is selected from methyl, ethyl, C 3 -C 6 alkyl, vinyl, allyl or an aromatic ring substituent;
  • X 1 is selected from chlorine, bromine, iodine, p-toluenesulfonyloxy, benzenesulfonyloxy or methanesulfonyloxy;
  • X 2 is selected from chlorine, bromine, iodine, p-toluenesulfonyloxy, benzenesulfonyloxy or methanesulfonyloxy;
  • the r, s, t, m and n satisfy that the sum of r + s + t + 3 (m + n) is greater than or equal to 40 and less than or equal to 80.
  • the aforementioned silicone coupling antibacterial agent is at least one of dimethylhexadecyl [3- (trimethoxysilyl) propyl] ammonium chloride, dimethylhexadecyl [3- (triethoxysilyl) propyl] ammonium chloride, dimethyloctadecyl [3- (trimethoxysilyl) propyl] ammonium chloride, dimethyloctadecyl [3- (triethoxysilyl) propyl] ammonium chloride, dimethyleicosanyl [3- (trimethoxysilyl) propyl] ammonium chloride, dimethyleicosanyl [3- (triethoxysilyl) propyl] ammonium chloride, dimethylhexadecyl [3- (trimethoxysilyl) propyl] ammonium bromide, dimethylhexadecyl [3- (trimethoxysilyl) propy
  • it further includes 0.001-0.1 part of a pH regulator.
  • the aforementioned pH regulator is at least one of hydrochloric acid, phosphoric acid, acetic acid, lactic acid, hydroxyacetic acid, citric acid or sulfuric acid.
  • the second one of the technical solutions of the present invention is to provide a method for conducting antibacterial finishing of a fabric, which includes the following steps:
  • formulation of an antibacterial finishing solution formulating a hydrophilic antibacterial finishing agent according to the aforementioned weight parts and components of the hydrophilic antibacterial finishing agent;
  • the aforementioned step (1) further includes adding 0.001-0.1 part of a pH regulator to adjust the pH to 3-6.
  • the third one of the technical solutions of the present invention is to provide an antibacterial fabric prepared by the aforementioned finishing method.
  • the fabric prepared by soaking and finishing with the antibacterial finishing agent of the present invention has an excellent antibacterial performance and a high bacteriostasis rate against Escherichia coli.
  • the bacteriostasis rate remains at the level of 99.9%after 50 times of washing, and thus the bacteriostasis performance is lasting; and meanwhile, its hydrophilic performance remains at a very high level after 50 times of washing, which thus can keep the health level of human body for a long time and maintain the wearing performance of clothes.
  • the fabric material is used as the substrate, and the antibacterial finishing solution is applied onto the surface of the fabric in a soaking manner to form the hydrophilic antibacterial composite layer.
  • the present invention provides a hydrophilic antibacterial finishing agent including the following components in parts by weight:
  • silicone hydrophilic antibacterial agent has a chemical structure as shown in the formula I below,
  • R is selected from methyl, ethyl, C 3 -C 6 alkyl, vinyl, allyl, phenyl, benzyl or an aromatic ring substituent;
  • X 1 is selected from chlorine, bromine, iodine, p-toluenesulfonyloxy, benzenesulfonyloxy or methanesulfonyloxy;
  • X 2 is selected from chlorine, bromine, iodine, p-toluenesulfonyloxy, benzenesulfonyloxy or methanesulfonyloxy;
  • the aforementioned silicone hydrophilic antibacterial agent is a main active ingredient of the hydrophilic antibacterial finishing agent of the present invention, and there is no ready-made product on the market currently, so it is prepared by our in the present invention.
  • a method for preparing the silicone hydrophilic antibacterial agent of the present invention is as follows:
  • the first reaction solvent can be at least one of xylene, p-xylene, toluene, ethylene glycol diethyl ether or DMF
  • the second reaction solvent can be at least one of xylene, p-xylene, toluene, ethylene glycol diethyl ether or DMF
  • the aforementioned r, s, t, m and n satisfy that the sum of r + s + t + 3 (m + n) is greater than or equal to 40 and less than or equal to 80.
  • a method for preparing a compound of formula I-1 as a silicone hydrophilic antibacterial agent is as follows.
  • reaction solution is cooled to room temperature, added with a proper amount of petroleum ether, cooled to 0°C to precipitate a large amount of solid, and filtered.
  • the filter cake is collected to obtain 0.959 mol of a product as a white solid.
  • the yield is 95.9%, and the titration purity of the product is 99.4%.
  • the reaction solution is cooled to room temperature, added with a proper amount of petroleum ether, cooled to -20°C to precipitate a large amount of solid, and filtered.
  • the filter cake is collected to obtain 0.911 mol of a product as a white solid.
  • the yield is 95.0%
  • the total yield of reaction of the two steps is 91.1%, and the titration purity of the product is 99.3%.
  • Examples 2-7 a compound of formula I-2, a compound of formula I-3, a compound of formula I-4, a compound of formula I-5, a compound of formula I-6 and a compound of formula I-7 are respectively used as silicone hydrophilic antibacterial agents.
  • Their preparation methods refer to that of the compound of formula I-1, and their structures are confirmed by nuclear magnetic data.
  • a cotton fabric was soaked in the finishing agent solution at a bath ratio of 1: 10 for 10 minutes, and then passed through a pressing roll at a rolling over rate of 80%. Subsequently, the fabric was placed into a drying room at 150°C and baked for 5 minutes, and then the fabric was taken out of the drying room, and naturally cooled to room temperature to obtain a washing-resistant hydrophilic antibacterial fabric.
  • a cotton fabric was soaked in the finishing agent solution at a bath ratio of 1: 20 for 15 minutes, and then passed through a pressing roll at a rolling over rate of 90%. Subsequently, the fabric was placed into a drying room at 160°C and baked for 4 minutes, and then the fabric was taken out of the drying room, and naturally cooled to room temperature to obtain a washing-resistant hydrophilic antibacterial fabric.
  • a polyester-cotton blended fabric was soaked in the finishing agent solution at a bath ratio of 1: 5 for 60 minutes, and then passed through a pressing roll at a rolling over rate of 100%. Subsequently, the fabric was placed into a drying room at 170°C and baked for 3 minutes, and then the fabric was taken out of the drying room, and naturally cooled to room temperature to obtain a washing-resistant hydrophilic antibacterial fabric.
  • a cotton fabric was soaked in the finishing agent solution at a bath ratio of 1: 30 for 10 minutes, and then passed through a pressing roll at a rolling over rate of 60%. Subsequently, the fabric was placed into a drying room at 160°C and baked for 4 minutes, and then the fabric was taken out of the drying room, and naturally cooled to room temperature to obtain a washing-resistant hydrophilic antibacterial fabric.
  • a cotton fabric was soaked in the finishing agent solution at a bath ratio of 1: 15 for 10 minutes, and then passed through a pressing roll at a rolling over rate of 80%. Subsequently, the fabric was placed into a drying room at 80°C and baked for 10 minutes, and then the fabric was taken out of the drying room, and naturally cooled to room temperature to obtain a washing-resistant hydrophilic antibacterial fabric.
  • a cotton fabric was soaked in the finishing solution at a bath ratio of 1: 10 for 10 minutes, and then passed through a pressing roll at a rolling over rate of 100%. Subsequently, the fabric was placed into a drying room at 180°C and baked for 1 minutes, and then the fabric was taken out of the drying room, and naturally cooled to room temperature to obtain a washing-resistant hydrophilic antibacterial fabric.
  • a cotton fabric was soaked in the finishing agent solution at a bath ratio of 1: 20 for 10 minutes, and then passed through a pressing roll at a rolling over rate of 50%. Subsequently, the fabric was placed into a drying room at 150°C and baked for 5 minutes, and then the fabric was taken out of the drying room, and naturally cooled to room temperature to obtain a washing-resistant hydrophilic antibacterial fabric.
  • Hydrophilicity a wetting time determination method was adopted: in an environment with an average temperature of 25°C and an average relative humidity of 60%, a fabric to be tested was laid flat and tightened on a beaker, and a drop of water was dripped with a rubber-tipped dropper at a distance of about 3 cm from a cloth surface, and the time was counted until the water droplet was diffused on the cloth surface until there was no mirror emission. This time was the time for diffusion of the water droplet. The hydrophilicity is better when the spreading time is shorter. The specific results were as shown in Table 1.
  • the fabric prepared by soaking and finishing with the antibacterial finishing agent of the present invention had an excellent antibacterial performance and a high bacteriostasis rate against Escherichia coli.
  • the bacteriostasis rate remained at the level of 99.9%after 50 times of washing, and thus the bacteriostasis performance was lasting; and meanwhile, its hydrophilic performance remained at a very high level after 50 times of washing, which thus could keep the health level of human body for a long time and maintain the wearing performance of clothes.

Abstract

A hydrophilic antibacterial finishing agent including the following components in parts by weight: 0.01-1 part of a silicone hydrophilic antibacterial agent; 1-5 parts of a silicone coupling antibacterial agent; and 94-98.99 parts of water; wherein the silicone hydrophilic antibacterial agent has a chemical structure as shown in formula I. A fabric prepared by antibacterial finishing with the antibacterial finishing agent has an excellent antibacterial performance and a lasting bacteriostatic performance; and meanwhile, its hydrophilic performance remains at a very high level after 50 times of washing, which thus can keep the health level of human body for a long time and maintain the wearing performance of clothes.

Description

HYDROPHILIC ANTIBACTERIAL FINISHING AGENT, ANTIBACTERIAL FINISHING METHOD OF FABRIC AND ANTIBACTERIAL FABRIC
FIELD OF TECHNOLOGY/Technical Field
The present invention relates to the technical field of antibacterial finishing agents for textiles, and relates to a hydrophilic antibacterial finishing agent, a method for conducting antibacterial finishing of a fabrics, and an antibacterial fabric.
BACKGROUND
In recent years, with the improvement of living standards, people's awareness of health and environmental protection has been continuously strengthened. While the beauty and comfort of textiles and clothing are gained attention, higher requirements are put forward for their health care functions. Producing textiles with antibacterial functions is one of the effective ways to protect people from or be less affected by bacteria, and thus the textiles with antibacterial functions are more and more favored by people.
Antibacterial sanitary finishing of the textiles is a processing technology that employs an antibacterial or bacteriostatic agent to treat a fabric, so as to obtain an antibacterial, mildew-proof, and odor-proof textile that keeps clean and sanitary. Its purpose is not only to prevent the textile from being contaminated by microorganisms, but more importantly to prevent infectious diseases, ensure the safety, health and wearing comfort of human body, and reduce the cross-infection rate of public environment, so that the textile can acquire a new function of health care and meet people's demands for hygiene and health.
With the improvement of living standards, people's understanding of the living environment and requirements for the quality of life are constantly improving, especially their awareness of health is constantly increasing. Since harmful bacteria are distributed very widely in nature, of many kinds and in a huge number, they seriously threaten human health. Diseases caused by infections transmitted by bacteria have become a major social problem, which causes widespread concern. An organic antibacterial agent has the characteristics of a fast sterilization speed, high  antibacterial efficiency, convenient processing, a stable color and the like. They have a long history of use and play an irreplaceable role in some fields. Producing a textile with an antibacterial function by using an antibacterial finishing agent is one of the effective ways to prevent people from or be less attacked by bacteria, and thus the textiles with antibacterial functions are more and more favored by people.
Quaternary ammonium salt antibacterial agents have been widely studied and utilized because of their low price and fast sterilization speed. 4 generations of quaternary ammonium salt antibacterial agents of typical significance have been developed internationally; among them, DC-5700, an antibacterial agent of silicone quaternary ammonium salt developed by Dow Corning is the most representative. Since the antibacterial agent of silicone quaternary ammonium salt combines a quaternary ammonium salt with a silane coupling agent in its structure, this product has accepted washing resistance and an excellent antibacterial effect at the same time. However, DC-5700 has an obvious defect in that a fabric subjected to antibacterial finishing with it is extremely hydrophobic, which limits its application scenarios. It severely limits its application in fabrics that contact with skin, such as an underwear.
It is necessary to develop an antibacterial agent not only with good antibacterial property, but also with good hydrophilicity.
SUMMARY
In view of the problems existed in the prior art, the present invention has developed a hydrophilic antibacterial finishing agent for post finishing of a fabric. An antibacterial fabric made by this antibacterial finishing method not only has an excellent antibacterial performance, but also has good hydrophilicity.
One of the technical solutions of the present invention is to provide a hydrophilic antibacterial finishing agent including the following components in parts by weight:
0.01-1 part of a silicone hydrophilic antibacterial agent;
1-5 parts of a silicone coupling antibacterial agent; and
94-98.99 parts of water;
wherein the silicone hydrophilic antibacterial agent has a chemical structure as shown in the formula I below,
Figure PCTCN2022134213-appb-000001
wherein R is selected from methyl, ethyl, C 3-C 6 alkyl, vinyl, allyl or an aromatic ring substituent; X 1 is selected from chlorine, bromine, iodine, p-toluenesulfonyloxy, benzenesulfonyloxy or methanesulfonyloxy; X 2 is selected from chlorine, bromine, iodine, p-toluenesulfonyloxy, benzenesulfonyloxy or methanesulfonyloxy; r = 1-100; s = 1-100; t = 1-100; m = 1-100; and n = 1-100.
In a preferred embodiment of the present invention, the r, s, t, m and n satisfy that the sum of r + s + t + 3 (m + n) is greater than or equal to 40 and less than or equal to 80.
In a preferred embodiment of the present invention, the aforementioned silicone coupling antibacterial agent is at least one of dimethylhexadecyl [3- (trimethoxysilyl) propyl] ammonium chloride, dimethylhexadecyl [3- (triethoxysilyl) propyl] ammonium chloride, dimethyloctadecyl [3- (trimethoxysilyl) propyl] ammonium chloride, dimethyloctadecyl [3- (triethoxysilyl) propyl] ammonium chloride, dimethyleicosanyl [3- (trimethoxysilyl) propyl] ammonium chloride, dimethyleicosanyl [3- (triethoxysilyl) propyl] ammonium chloride, dimethylhexadecyl [3- (trimethoxysilyl) propyl] ammonium bromide, dimethylhexadecyl [3- (triethoxysilyl) propyl] ammonium bromide, dimethyloctadecyl [3- (trimethoxysilyl) propyl] ammonium bromide, dimethyloctadecyl [3- (triethoxysilyl) propyl] ammonium bromide, dimethyleicosanyl [3- (trimethoxysilyl) propyl] ammonium bromide, dimethyleicosanyl [3- (triethoxysilyl) propyl] ammonium bromide, dimethylhexadecyl [3- (trimethoxysilyl) propyl] ammonium iodide,  dimethylhexadecyl [3- (triethoxysilyl) propyl] ammonium iodide, dimethyloctadecyl [3- (trimethoxysilyl) propyl] ammonium iodide, dimethyloctadecyl [3- (triethoxysilyl) propyl] ammonium iodide, dimethyleicosanyl [3- (trimethoxysilyl) propyl] ammonium iodide, and dimethyleicosanyl [3- (triethoxysilyl) propyl] ammonium iodide.
In a preferred embodiment of the present invention, it further includes 0.001-0.1 part of a pH regulator.
In a preferred embodiment of the present invention, the aforementioned pH regulator is at least one of hydrochloric acid, phosphoric acid, acetic acid, lactic acid, hydroxyacetic acid, citric acid or sulfuric acid.
The second one of the technical solutions of the present invention is to provide a method for conducting antibacterial finishing of a fabric, which includes the following steps:
(1) formulation of an antibacterial finishing solution: formulating a hydrophilic antibacterial finishing agent according to the aforementioned weight parts and components of the hydrophilic antibacterial finishing agent;
(2) taking a fabric material as a substrate, and applying the antibacterial finishing solution to a surface of the fabric in a soaking manner to form a hydrophilic antibacterial composite layer, wherein a soaking bath ratio is 1: 5-1: 30, a soaking time is 3-60 minutes, and a rolling over rate of a pressing roll is 50-100%; and
(3) baking the fabric at 80-180℃ for 3-10 minutes, and naturally cooling it to room temperature.
In a preferred embodiment of the present invention, the aforementioned step (1) further includes adding 0.001-0.1 part of a pH regulator to adjust the pH to 3-6.
The third one of the technical solutions of the present invention is to provide an antibacterial fabric prepared by the aforementioned finishing method.
Beneficial effects
The fabric prepared by soaking and finishing with the antibacterial finishing agent of the present invention has an excellent antibacterial performance and a high bacteriostasis rate against Escherichia coli., the bacteriostasis rate remains at the level of 99.9%after 50 times of washing, and thus the bacteriostasis performance is lasting; and meanwhile, its hydrophilic performance remains at a very high level after 50 times of washing, which thus can keep the health level of human body for a long time and maintain the wearing performance of clothes. Furthermore, in the present  invention, the fabric material is used as the substrate, and the antibacterial finishing solution is applied onto the surface of the fabric in a soaking manner to form the hydrophilic antibacterial composite layer. Other manners, such as padding, spraying and spin coating, can also used similarly for preparation, and the substrate and the hydrophilic antibacterial composite layer are connected by covalent bonds, electrostatic forces and Van der Waals forces. The scope of the present invention is expanded to include these similar methods.
DETAILED DESCRIPTION OF THE EMBODIMENTS
The following clearly and completely describes the technical solutions in the embodiments of the present invention. Apparently, the described embodiments are merely a part rather than all of the embodiments of the present invention. Based on the embodiments of the present invention, all other embodiments obtained by those skilled in the art without involving any inventive effort fall within the claimed scope of the present invention.
The materials, reagents, etc. used in the following embodiments are all commercially available, unless otherwise specified.
The present invention provides a hydrophilic antibacterial finishing agent including the following components in parts by weight:
0.01-1 part of a silicone hydrophilic antibacterial agent;
1-5 parts of a silicone coupling antibacterial agent; and
94-98.99 parts of water;
wherein the silicone hydrophilic antibacterial agent has a chemical structure as shown in the formula I below,
Figure PCTCN2022134213-appb-000002
wherein R is selected from methyl, ethyl, C 3-C 6 alkyl, vinyl, allyl, phenyl, benzyl or an aromatic ring substituent; X 1 is selected from chlorine, bromine, iodine, p-toluenesulfonyloxy, benzenesulfonyloxy or methanesulfonyloxy; X 2 is selected from chlorine, bromine, iodine, p-toluenesulfonyloxy, benzenesulfonyloxy or methanesulfonyloxy; r = 1-100; s = 1-100; t = 1-100; m = 1-100; and n = 1-100.
In the present invention, the aforementioned silicone hydrophilic antibacterial agent is a main active ingredient of the hydrophilic antibacterial finishing agent of the present invention, and there is no ready-made product on the market currently, so it is prepared by ourselves in the present invention.
Specifically, a method for preparing the silicone hydrophilic antibacterial agent of the present invention is as follows:
Figure PCTCN2022134213-appb-000003
Figure PCTCN2022134213-appb-000004
step (a) . a compound of formula 1 and a compound of formula 2 are reacted in a second reaction solvent at a reaction temperature of 100-200℃ for a reaction time of 12-72 hours to prepare a compound of formula 3, wherein R is selected from methyl, ethyl, C 3-C 6 alkyl, vinyl, allyl, phenyl, benzyl or an aromatic ring substituent; X 1 is selected from chlorine, bromine, iodine, p-toluenesulfonyloxy, benzenesulfonyloxy or methanesulfonyloxy; X 2 is selected from chlorine, bromine, iodine, p-toluenesulfonyloxy, benzenesulfonyloxy or methanesulfonyloxy; r = 1-100; s =1-100; t = 1-100; m = 1-100; and n = 1-100; and
step (b) . under a condition of isolation from air, a compound of formula 3 and a compound of formula 4 are reacted in a first reaction solvent at a reaction temperature of 100-200℃ for a reaction time of 10-200 hours to obtain a hydrophilic antibacterial finishing agent with a chemical structure as shown in formula 5, wherein R is selected from methyl, ethyl, C 3-C 6 alkyl, vinyl, allyl, phenyl, benzyl or an aromatic ring substituent; X 1 is selected from chlorine, bromine, iodine, p-toluenesulfonyloxy, benzenesulfonyloxy or methanesulfonyloxy; X 2 is selected from chlorine, bromine, iodine, p-toluenesulfonyloxy, benzenesulfonyloxy or methanesulfonyloxy; r = 1-100; s = 1-100; t = 1-100; m = 1-100; and n = 1-100,
wherein, the first reaction solvent can be at least one of xylene, p-xylene, toluene, ethylene glycol diethyl ether or DMF, the second reaction solvent can be at least one of xylene, p-xylene, toluene, ethylene glycol diethyl ether or DMF, and the aforementioned r, s, t, m and n satisfy that the sum of r + s + t + 3 (m + n) is greater than or equal to 40 and less than or equal to 80.
A method for preparing a compound of formula I-1 as a silicone hydrophilic antibacterial agent is as follows.
Figure PCTCN2022134213-appb-000005
Step (a) : preparation of compound of formula 3-1
Under an N2 atm, into a 20 L reaction flask are sequentially added 5 L of xylene,  1.0 mol of a compound of formula 1-1 and 3.0 mol of a compound of formula 2-1, and stirred evenly after the addition; and the reaction solution is heated to 100℃ for reaction. The temperature is kept for 72 hours to complete the reaction.
The reaction solution is cooled to room temperature, added with a proper amount of petroleum ether, cooled to 0℃ to precipitate a large amount of solid, and filtered. The filter cake is collected to obtain 0.959 mol of a product as a white solid.
The yield is 95.9%, and the titration purity of the product is 99.4%.
1H NMR (400 MHz, CDCl 3) : δ2.65 (t, 6H) , 3.42 (t, 12H) , 3.51-3.87 (m, 172H) , 4.02 (t, 12H) , 4.42 (t, 6H) , 4.52 (s, 6H) , 4.57 (s, 6H) , 7.73-7.83 (m, 90H) .
Step (b) : preparation of compound of formula I-1
Under an N2 atm, into a 20 L reaction flask are sequentially added 5 L of xylene, 0.959 mol of a compound of formula 3-1, and 1.0 mol of a compound of formula 4-1, i.e., chloropropyl trimethoxysilane, and stirred evenly after the addition; and the reaction solution is heated to 120℃ for reaction. The temperature is kept for 48 hours to complete the reaction.
The reaction solution is cooled to room temperature, added with a proper amount of petroleum ether, cooled to -20℃ to precipitate a large amount of solid, and filtered. The filter cake is collected to obtain 0.911 mol of a product as a white solid. The yield is 95.0%,
the total yield of reaction of the two steps is 91.1%, and the titration purity of the product is 99.3%.
1H NMR (400MHz, CDCl 3) : δ0.63 (t, 2H) , 1.76 (m, 2H) , 3.28 (t, 6H) , 3.37 (t, 2H) , 3.42 (t, 12H) , 3.51-3.87 (m, 181H) , 4.02 (t, 12H) , 4.42 (t, 6H) , 4.52 (s, 6H) , 4.57 (s, 6H) , 7.73-7.83 (m, 90H) .
In Examples 2-7, a compound of formula I-2, a compound of formula I-3, a compound of formula I-4, a compound of formula I-5, a compound of formula I-6 and a compound of formula I-7 are respectively used as silicone hydrophilic antibacterial agents. Their preparation methods refer to that of the compound of formula I-1, and their structures are confirmed by nuclear magnetic data.
Example 1
The structure of a silicone hydrophilic antibacterial agent (I-1) was as follows:
Figure PCTCN2022134213-appb-000006
0.1 part of a compound of formula I-1, 3 parts of dimethylhexadecyl [3- (trimethoxysilyl) propyl] ammonium chloride and 98.9 parts of water, were added with 0.1 part of hydroxyacetic acid to adjust the pH of the system to 3-6, so as to obtain a hydrophilic antibacterial finishing agent.
A cotton fabric was soaked in the finishing agent solution at a bath ratio of 1: 10 for 10 minutes, and then passed through a pressing roll at a rolling over rate of 80%. Subsequently, the fabric was placed into a drying room at 150℃ and baked for 5 minutes, and then the fabric was taken out of the drying room, and naturally cooled to room temperature to obtain a washing-resistant hydrophilic antibacterial fabric.
Example 2
The structure of a silicone hydrophilic antibacterial agent (I-2) was as follows:
Figure PCTCN2022134213-appb-000007
0.3 part of a compound of formula I-2, 2.8 parts of dimethylhexadecyl [3- (triethoxysilyl) propyl] ammonium chloride and 98.5 parts of water, were added with 0.08 part of acetic acid to adjust the pH of the system to 3-6, so as to obtain a hydrophilic antibacterial finishing agent.
A cotton fabric was soaked in the finishing agent solution at a bath ratio of 1: 20 for 15 minutes, and then passed through a pressing roll at a rolling over rate of 90%. Subsequently, the fabric was placed into a drying room at 160℃ and baked for 4 minutes, and then the fabric was taken out of the drying room, and naturally cooled to room temperature to obtain a washing-resistant hydrophilic antibacterial fabric.
Example 3
The structure of a silicone hydrophilic antibacterial agent (I-3) was as follows:
Figure PCTCN2022134213-appb-000008
0.5 part of a compound of formula I-3, 2.5 parts of dimethyloctadecyl [3- (trimethoxysilyl) propyl] ammonium chloride and 98 parts of water, were added with 0.05 part of phosphoric acid to adjust the pH of the system to 3-6, so as to obtain a hydrophilic antibacterial finishing agent.
A polyester-cotton blended fabric was soaked in the finishing agent solution at a bath ratio of 1: 5 for 60 minutes, and then passed through a pressing roll at a rolling over rate of 100%. Subsequently, the fabric was placed into a drying room at 170℃ and baked for 3 minutes, and then the fabric was taken out of the drying room, and naturally cooled to room temperature to obtain a washing-resistant hydrophilic antibacterial fabric.
Example 4
The structure of a silicone hydrophilic antibacterial agent (I-4) was as follows:
Figure PCTCN2022134213-appb-000009
0.01 part of a compound of formula I-4, 2 parts of dimethyloctadecyl [3- (triethoxysilyl) propyl] ammonium chloride and 97 parts of water, were added with 0.04 part of citric acid to adjust the pH of the system to 3-6, so as to obtain a hydrophilic antibacterial finishing agent.
A cotton fabric was soaked in the finishing agent solution at a bath ratio of 1: 30 for 10 minutes, and then passed through a pressing roll at a rolling over rate of 60%. Subsequently, the fabric was placed into a drying room at 160℃ and baked for 4 minutes, and then the fabric was taken out of the drying room, and naturally cooled to room temperature to obtain a washing-resistant hydrophilic antibacterial fabric.
Example 5
The structure of a silicone hydrophilic antibacterial agent (I-5) was as follows:
Figure PCTCN2022134213-appb-000010
0.8 part of a compound of formula I-5, 1.5 parts of dimethyleicosanyl [3- (trimethoxysilyl) propyl] ammonium chloride and 96.5 parts of water, were added with 0.01 part of lactic acid to adjust the pH of the system to 3-6, so as to obtain a hydrophilic antibacterial finishing agent.
A cotton fabric was soaked in the finishing agent solution at a bath ratio of 1: 15 for 10 minutes, and then passed through a pressing roll at a rolling over rate of 80%. Subsequently, the fabric was placed into a drying room at 80℃ and baked for 10 minutes, and then the fabric was taken out of the drying room, and naturally cooled to room temperature to obtain a washing-resistant hydrophilic antibacterial fabric.
Example 6
The structure of a silicone hydrophilic antibacterial agent (I-6) was as follows:
Figure PCTCN2022134213-appb-000011
0.1 part of a compound of formula I-6, 1 part of dimethyleicosanyl [3- (triethoxysilyl) propyl] ammonium bromide and 98.99 parts of water, were added with 0.005 part of hydrochloric acid to adjust the pH of the system to 3-6, so as to obtain a hydrophilic antibacterial finishing agent.
A cotton fabric was soaked in the finishing solution at a bath ratio of 1: 10 for 10 minutes, and then passed through a pressing roll at a rolling over rate of 100%. Subsequently, the fabric was placed into a drying room at 180℃ and baked for 1 minutes, and then the fabric was taken out of the drying room, and naturally cooled to room temperature to obtain a washing-resistant hydrophilic antibacterial fabric.
Example 7
The structure of a silicone hydrophilic antibacterial agent (I-7) was as follows:
Figure PCTCN2022134213-appb-000012
1 part of a compound of formula 1-7, 5 parts of dimethyleicosanyl [3- (triethoxysilyl) propyl] ammonium iodide and 94 parts of water were utilized to obtain a hydrophilic antibacterial finishing agent.
A cotton fabric was soaked in the finishing agent solution at a bath ratio of 1: 20 for 10 minutes, and then passed through a pressing roll at a rolling over rate of 50%. Subsequently, the fabric was placed into a drying room at 150℃ and baked for 5 minutes, and then the fabric was taken out of the drying room, and naturally cooled to room temperature to obtain a washing-resistant hydrophilic antibacterial fabric.
Comparative Example 1:
1 part of DC5700 and 99 parts of water were formulated into a solution of silicone antibacterial finishing agent, and added with hydroxyacetic acid to adjust the pH of the system to 6. A cotton fabric was soaked in the finishing solution at a bath ratio of 1: 15 for 10 minutes, and then passed through a pressing roll at a rolling over rate of 80%. Subsequently, the fabric was placed into a drying room at 150℃ and baked for 5 minutes, and then the fabric was taken out of the drying room to obtain an antibacterial fabric.
Comparative Example 2:
3 parts of DC5700 and 97 parts of water were formulated into a solution of silicone antibacterial finishing agent, and added with phosphoric acid to adjust the pH of the system to 5. A polyester-cotton blended fabric was soaked in the finishing solution at a bath ratio of 1: 20 for 60 minutes, and then passed through a pressing roll at a rolling over rate of 100%, that was, the increase in wet weight of the fabric was 100%. Subsequently, the fabric was placed into a drying room at 170℃ and baked for 2 minutes, and then the fabric was taken out of the drying room to obtain an antibacterial fabric.
Performance Test
Antibacterial property: With reference to “Textiles -Evaluation for antibacterial activity -Part 3: Shake flask method” in GB/120944.3-2008, Escherichia coli. Was selected as the strain, and the specific results were as shown in Table 1.
Hydrophilicity: a wetting time determination method was adopted: in an environment with an average temperature of 25℃ and an average relative humidity of 60%, a fabric to be tested was laid flat and tightened on a beaker, and a drop of water was dripped with a rubber-tipped dropper at a distance of about 3 cm from a cloth surface, and the time was counted until the water droplet was diffused on the cloth surface until there was no mirror emission. This time was the time for diffusion of the water droplet. The hydrophilicity is better when the spreading time is shorter. The specific results were as shown in Table 1.
Table 1 Data collation of Examples 1-7 and Comparative Examples 1-2
Figure PCTCN2022134213-appb-000013
Figure PCTCN2022134213-appb-000014
Therefore, It could be concluded that the fabric prepared by soaking and finishing with the antibacterial finishing agent of the present invention had an excellent antibacterial performance and a high bacteriostasis rate against Escherichia coli., the bacteriostasis rate remained at the level of 99.9%after 50 times of washing, and thus the bacteriostasis performance was lasting; and meanwhile, its hydrophilic performance remained at a very high level after 50 times of washing, which thus could keep the health level of human body for a long time and maintain the wearing performance of clothes.
Those of ordinary skills in the art can make various forms under the inspiration of this specification and without departing from the claimed scope of the claims of the present invention, and these forms are all within the claimed scope of the present invention.

Claims (8)

  1. A hydrophilic antibacterial finishing agent comprising the following components in parts by weight:
    0.01-1 part of a silicone hydrophilic antibacterial agent;
    1-5 parts of a silicone coupling antibacterial agent; and
    94-98.99 parts of water;
    wherein the silicone hydrophilic antibacterial agent has a chemical structure as shown in the formula I below,
    Figure PCTCN2022134213-appb-100001
    wherein R is selected from methyl, ethyl, C 3-C 6 alkyl, vinyl, allyl or an aromatic ring substituent; X 1 is selected from chlorine, bromine, iodine, p-toluenesulfonyloxy, benzenesulfonyloxy or methanesulfonyloxy; X 2 is selected from chlorine, bromine, iodine, p-toluenesulfonyloxy, benzenesulfonyloxy or methanesulfonyloxy; r = 1-100; s = 1-100; t = 1-100; m = 1-100; and n = 1-100.
  2. The hydrophilic antibacterial finishing agent according to claim 1, wherein the r, s, t, m and n satisfy that the sum of r + s + t + 3 (m + n) is greater than or equal to 40 and less than or equal to 80.
  3. The hydrophilic antibacterial finishing agent according to claim 1, wherein the silicone coupling antibacterial agent is at least one of dimethylhexadecyl [3- (trimethoxysilyl) propyl] ammonium chloride, dimethylhexadecyl [3- (triethoxysilyl) propyl] ammonium chloride, dimethyloctadecyl [3- (trimethoxysilyl) propyl] ammonium chloride,  dimethyloctadecyl [3- (triethoxysilyl) propyl] ammonium chloride, dimethyleicosanyl [3- (trimethoxysilyl) propyl] ammonium chloride, dimethyleicosanyl [3- (triethoxysilyl) propyl] ammonium chloride, dimethylhexadecyl [3- (trimethoxysilyl) propyl] ammonium bromide, dimethylhexadecyl [3- (triethoxysilyl) propyl] ammonium bromide, dimethyloctadecyl [3- (trimethoxysilyl) propyl] ammonium bromide, dimethyloctadecyl [3- (triethoxysilyl) propyl] ammonium bromide, dimethyleicosanyl [3- (trimethoxysilyl) propyl] ammonium bromide, dimethyleicosanyl [3- (triethoxysilyl) propyl] ammonium bromide, dimethylhexadecyl [3- (trimethoxysilyl) propyl] ammonium iodide, dimethylhexadecyl [3- (triethoxysilyl) propyl] ammonium iodide, dimethyloctadecyl [3- (trimethoxysilyl) propyl] ammonium iodide, dimethyloctadecyl [3- (triethoxysilyl) propyl] ammonium iodide, dimethyleicosanyl [3- (trimethoxysilyl) propyl] ammonium iodide, and dimethyleicosanyl [3- (triethoxysilyl) propyl] ammonium iodide.
  4. The hydrophilic antibacterial finishing agent according to claim 1, further comprising 0.001-0.1 part of a pH regulator.
  5. The hydrophilic antibacterial finishing agent according to claim 4, wherein the pH regulator is at least one of hydrochloric acid, phosphoric acid, acetic acid, lactic acid, hydroxyacetic acid, citric acid or sulfuric acid.
  6. A method for conducting antibacterial finishing of a fabric, comprising the following steps:
    (1) formulation of an antibacterial finishing solution: formulating a hydrophilic antibacterial finishing agent according to the weight parts and components of the hydrophilic antibacterial finishing agent according to claim 1;
    (2) taking a fabric material as a substrate, and applying the antibacterial finishing solution to a surface of the fabric in a soaking manner to form a hydrophilic antibacterial composite layer, wherein a soaking bath ratio is 1: 5-1: 30, a soaking time is 3-60 minutes, and a rolling over rate of a pressing roll is 50-100%; and
    (3) baking the fabric at 80-180℃ for 3-10 minutes, and naturally cooling it to room temperature.
  7. The method for conducting antibacterial finishing of a fabric according to claim 6, wherein the formulation of the antibacterial finishing solution in the step (1) further comprises adding 0.001-0.1 part of a pH regulator to adjust the pH to 3-6.
  8. An antibacterial fabric prepared by employing the finishing method of claim 6 or 7.
PCT/CN2022/134213 2022-05-10 2022-11-25 Hydrophilic antibacterial finishing agent, antibacterial finishing method of fabric and antibacterial fabric WO2023216556A1 (en)

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CN114592352B (en) * 2022-05-10 2022-08-16 苏州百灵威超精细材料有限公司 Hydrophilic antibacterial finishing agent and preparation method and application thereof
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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103924444A (en) * 2014-04-24 2014-07-16 南雄鼎成化工有限公司 Preparation method and application of hydrophilic anti-bacteria conditioner for fabric
WO2018095004A1 (en) * 2016-11-24 2018-05-31 包磊 Medical antibacterial fabric and preparation method therefor
US20190203409A1 (en) * 2016-09-19 2019-07-04 Grasim Industries Limited Antibacterial regenerated cellulosic fibers and process of preparation thereof
CN111235884A (en) * 2020-02-28 2020-06-05 稳健医疗(黄冈)有限公司 Antibacterial finishing agent, antibacterial all-cotton spunlace non-woven fabric and product thereof
CN114592348A (en) * 2022-05-10 2022-06-07 苏州百灵威超精细材料有限公司 Hydrophilic antibacterial finishing agent, antibacterial finishing method of fabric and antibacterial fabric

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8252778B2 (en) * 2006-03-24 2012-08-28 University Of Utah Research Foundation Highly fluorinated oils and surfactants and methods of making and using same
CN106491633A (en) * 2016-10-21 2017-03-15 克灵美(天津)生物科技有限公司 A kind of good antimicrobial disinfectant of biocompatibility
US11541120B2 (en) * 2017-12-05 2023-01-03 Anthos Partners, Lp Phosphonium-based ionic drug conjugates
CN113429559A (en) * 2020-03-23 2021-09-24 厦门赛诺邦格生物科技股份有限公司 Six-arm polyethylene glycol derivative with end hetero-functionalized and preparation method thereof
CN112142947A (en) * 2020-09-29 2020-12-29 广州恩沣新材料科技有限公司 Preparation method and application of multifunctional moisture-absorbing quick-drying type water-based antibacterial polyurethane finishing agent
CN113801123B (en) * 2021-10-18 2022-12-09 苏州百灵威超精细材料有限公司 Preparation method of 1,4,8, 11-tetraazacyclotetradecane compound and intermediate thereof

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103924444A (en) * 2014-04-24 2014-07-16 南雄鼎成化工有限公司 Preparation method and application of hydrophilic anti-bacteria conditioner for fabric
US20190203409A1 (en) * 2016-09-19 2019-07-04 Grasim Industries Limited Antibacterial regenerated cellulosic fibers and process of preparation thereof
WO2018095004A1 (en) * 2016-11-24 2018-05-31 包磊 Medical antibacterial fabric and preparation method therefor
CN111235884A (en) * 2020-02-28 2020-06-05 稳健医疗(黄冈)有限公司 Antibacterial finishing agent, antibacterial all-cotton spunlace non-woven fabric and product thereof
CN114592348A (en) * 2022-05-10 2022-06-07 苏州百灵威超精细材料有限公司 Hydrophilic antibacterial finishing agent, antibacterial finishing method of fabric and antibacterial fabric

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