CN107522621B - Preparation method of photo-induced antibacterial finishing agent benzophenone tetraformate - Google Patents
Preparation method of photo-induced antibacterial finishing agent benzophenone tetraformate Download PDFInfo
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- CN107522621B CN107522621B CN201710936337.7A CN201710936337A CN107522621B CN 107522621 B CN107522621 B CN 107522621B CN 201710936337 A CN201710936337 A CN 201710936337A CN 107522621 B CN107522621 B CN 107522621B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/42—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing within the same carbon skeleton a carboxylic group or a thio analogue, or a derivative thereof, and a carbon atom having only two bonds to hetero atoms with at the most one bond to halogen, e.g. keto-carboxylic acids
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/56—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
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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
- D06M13/10—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 oxygen
- D06M13/224—Esters of carboxylic acids; Esters of carbonic acid
-
- 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
- D06M16/006—Biochemical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. enzymatic with wool-protecting agents; with anti-moth agents
Abstract
The invention relates to a preparation method of a photoinduction antibacterial finishing agent benzophenone tetracarboxylic acid ester, which comprises the steps of adding 3,3',4,4' -benzophenone tetracarboxylic dianhydride and alcohol into a reaction bottle provided with a water separator, stirring, slowly dropwise adding concentrated sulfuric acid for reaction, cooling to room temperature, washing, drying, filtering and separating to obtain the photoinduction antibacterial finishing agent benzophenone tetracarboxylic acid ester. The method is simple, easy to operate, mild in reaction condition and low in cost; the prepared benzophenone tetracarboxylic acid ester has high-efficiency, lasting and broad-spectrum antibacterial performance and strong affinity with polyester fibers, is used for finishing polyester fabrics, and the finished fabrics have high-efficiency and lasting antibacterial performance to staphylococcus aureus and escherichia coli.
Description
Technical Field
The invention belongs to the field of textile antibiosis, and particularly relates to a preparation method of a light-induced antibacterial finishing agent benzophenone tetraformate.
Background
In the last two decades, the chemical fiber industry in our country has been rapidly developed, wherein the yield of polyester fibers accounts for three quarters of the total yield of chemical fibers, and the polyester fibers are widely used in the fields of clothing, medical treatment and the like due to excellent performance.
Because the polyester fabric has high hydrophobicity and compact structure and does not have reactive active groups, compared with natural fibers, the polyester fabric has poor antibacterial finishing durability and small affinity between most antibacterial agents and polyester macromolecules. At present, the antibacterial modification of polyester is mainly realized by a blending method, for example, patent CN200510012956 discloses a blending high-speed spinning method of nano composite antibacterial polyester POY, which adopts 20-60 nm silver, zinc and silicon-based oxide composite antibacterial powder to prepare polyester master batches, and then the master batches are added into spinning polyester resin by 3-7% of the addition amount to carry out melt spinning to prepare the antibacterial polyester fiber. However, the high-temperature melting conditions during modification by the blending method tend to deactivate the antibacterial agent, and the antibacterial powder is difficult to uniformly disperse in the polyester fiber, which tends to cause poor spinnability.
At present, antibacterial agents for antibacterial finishing of polyester fabrics are mainly inorganic nanoparticles, quaternary ammonium salts, halogen amines and the like. However, these terylene antibacterial agents have disadvantages, such as poor affinity between inorganic nano-particle antibacterial agents and terylene fibers, small particle size, easy penetration into skin and harm to skin; quaternary ammonium salt antibacterial agents are less active and less durable; the synthesis of the haloamine has the disadvantages of expensive raw materials, harsh reaction conditions, complex production process and low yield. Therefore, the development of the antibacterial agent for after-finishing, which has high affinity with the polyester fiber and high antibacterial activity, is of great significance.
Disclosure of Invention
The invention aims to solve the technical problem of providing a preparation method of a light-induced antibacterial finishing agent benzophenone tetracarboxylic acid ester, the method is simple and easy to operate, the reaction conditions are mild, and the prepared benzophenone tetracarboxylic acid ester has high-efficiency, lasting and broad-spectrum antibacterial performance.
The invention relates to a preparation method of a light-induced antibacterial finishing agent benzophenone tetraformate, which comprises the following specific steps:
adding 3,3',4,4' -benzophenone tetracarboxylic dianhydride and alcohol into a reaction bottle with a water separator according to a molar ratio of 1: 4-8, stirring, dropwise adding concentrated sulfuric acid for reaction, cooling to room temperature, washing, drying, filtering, and separating to obtain the light-induced antibacterial finishing agent benzophenone tetracarboxylic acid ester, wherein the volume ratio of the alcohol to the concentrated sulfuric acid is 50: 1-175: 1.
The reaction temperature is 100-160 ℃, and the reaction time is 6-8 h.
The washing is carried out by using 15-30 percent of Na2CO3Washing the solution to be neutral; dried over anhydrous sodium sulfate.
The separation is that reduced pressure distillation is firstly carried out and then column chromatography separation is carried out.
The eluent for the column chromatography is a mixed solution of dichloromethane and methanol.
The chemical structure of the light-induced antibacterial finishing agent benzophenone tetraformate is shown as follows:
in the formula (I), the compound is shown in the specification,
n＝1～11。
the light-induced antibacterial finishing agent benzophenone tetraformate is used for finishing polyester fabrics and comprises the following specific steps:
(1) dissolving an emulsifier in a solvent, stirring to obtain an emulsifier solution, adding a light-induced antibacterial finishing agent benzophenone tetraformate, and continuously stirring to obtain a finishing working solution, wherein the mass ratio of the benzophenone tetraformate to the emulsifier is 1: 5-10, and the effective concentration of the benzophenone tetraformate in the finishing working solution is 10-110 g/L;
(2) and (2) immersing the non-finished polyester fabric into the finishing working solution in the step (1), soaking twice, rolling twice, pre-drying, and baking to obtain the antibacterial polyester fabric.
The emulsifier in the step (1) comprises one or more of Tween emulsifier, sodium dodecyl sulfate, span emulsifier, TX emulsifier and OP emulsifier.
The solvent in the step (1) is distilled water; stirring for 30 min; the continuous stirring time is 0.5-3 h.
The liquid carrying rate of the second soaking and the second rolling in the step (2) is 80-100 percent; the pre-drying temperature is 80 ℃, and the pre-drying time is 3 min.
And (3) in the step (2), the baking temperature is 160-200 ℃, and the baking time is 1-4 min.
The invention relates to a preparation method of a photoinduction antibacterial finishing agent benzophenone tetracarboxylate, which is characterized in that a complete esterification reaction is carried out on an optically active compound 3,3',4,4' -benzophenone tetracarboxylic dianhydride and corresponding alcohol under the catalysis of concentrated sulfuric acid, and the photoinduction antibacterial finishing agent benzophenone tetracarboxylate is obtained.
Advantageous effects
(1) The method is simple, easy to operate, mild in reaction condition, free of special requirements on reaction conditions such as temperature, air pressure and pH value and reaction equipment, easy to meet the requirements of industrial production, and raw materials adopted in the preparation process are all conventional, can be directly purchased from the market, are not treated at all, and are low in cost;
(2) the benzophenone tetracarboxylic acid ester prepared by the invention has high-efficiency, lasting and broad-spectrum antibacterial performance;
(3) the application of the prepared benzophenone tetraformate to the polyester fabric can be realized by adopting a conventional process flow;
(4) the benzophenone tetracarboxylate prepared by the method has stronger affinity with polyester fibers, and the finished fabric has high-efficiency and lasting antibacterial property on staphylococcus aureus and escherichia coli.
Drawings
FIG. 1 is a scheme showing the synthesis of benzophenone tetracarboxylates of the present invention;
FIG. 2 is a UV-VIS absorption spectrum of butyl 3,3',4,4' -benzophenone tetracarboxylic acid in example 1;
FIG. 3 is an infrared spectrum of butyl 3,3',4,4' -benzophenonetetracarboxylate of example 1;
FIG. 4 is a nuclear magnetic resonance spectrum of butyl 3,3',4,4' -benzophenone tetracarboxylic acid in example 1;
FIG. 5 is a UV-VIS absorption spectrum of ethyl 3,3',4,4' -benzophenonetetracarboxylate of example 2;
FIG. 6 is an IR spectrum of ethyl 3,3',4,4' -benzophenonetetracarboxylate of example 2;
FIG. 7 shows the NMR spectrum of ethyl 3,3',4,4' -benzophenonetetracarboxylate in example 2.
Detailed Description
The invention will be further illustrated with reference to the following specific examples. It should be understood that these examples are for illustrative purposes only and are not intended to limit the scope of the present invention. Further, it should be understood that various changes or modifications of the present invention may be made by those skilled in the art after reading the teaching of the present invention, and such equivalents may fall within the scope of the present invention as defined in the appended claims.
Example 1
Adding 10.00g of 3,3',4,4' -benzophenone tetracarboxylic dianhydride and 15.00mL of n-butyl alcohol into a 100mL three-neck flask provided with a reflux condenser, a water separator and a thermometer in sequence, slowly dropwise adding 0.27mL of concentrated sulfuric acid under the stirring condition, continuously stirring, heating to 120 ℃ for reaction, observing the reaction completion by using thin layer chromatography, cooling the system to room temperature, and adding 20% of Na2CO3The solution is washed to be neutral, organic phases are combined, anhydrous sodium sulfate is used for drying and filtering, the filtrate is subjected to reduced pressure distillation to obtain crude butyl 3,3',4,4' -benzophenone tetracarboxylic acid, the crude product is subjected to column chromatography separation and purification by using a mixed solution of dichloromethane and methanol with a volume ratio of 7:1 as an eluent to obtain 16.72g of pure butyl 3,3',4,4' -benzophenone tetracarboxylic acid with the yield of 92.45%. The nuclear magnetism of the product 3,3',4,4' -butyl benzophenone tetracarboxylic acid (shown in figure 4) is as follows:1H NMR(400MHz，DMSO)δ8.09(s，2H)，7.90～8.00(m，4H)，4.30(t，8H)，1.60～1.67(m，8H)，1.33～1.38(m，8H)，0.92(t，12H)。
example 2
In the presence of reflux condensationAdding 10.00g of 3,3',4,4' -benzophenone tetracarboxylic dianhydride and 8.70mL of ethanol into a 100mL three-neck flask of a pipe, a water separator and a thermometer in sequence, slowly dripping 0.05mL of concentrated sulfuric acid under the stirring condition, continuously stirring, heating to 150 ℃ for reaction, observing the reaction completion by using thin layer chromatography, cooling the system to room temperature, and adding 15% of Na2CO3The solution is washed to be neutral, organic phases are combined, anhydrous sodium sulfate is used for drying and filtering, the filtrate is subjected to reduced pressure distillation to obtain crude 3,3',4,4' -benzophenone tetracarboxylic acid ethyl ester, the crude product is subjected to column chromatography separation and purification by using a mixed solution of dichloromethane and methanol in a volume ratio of 7:1 as an eluent to obtain a pure product of benzophenone tetracarboxylic acid ethyl ester 13.12g, and the yield is 90%. The nuclear magnetism of the product 3,3',4,4' -ethyl benzophenone tetracarboxylic acid (as shown in figure 7) is as follows:1H NMR(400MHz，DMSO)δ8.11(s，2H)，7.80～8.00(m，4H)，4.34(t，8H)，1.28(t，12H)。
example 3
The 3,3',4,4' -benzophenone tetracarboxylic acid butyl ester obtained in the example 1 is used for finishing the polyester fabric, and the specific method is as follows:
(1) adding 1.5g of emulsifier Tween 80 into 150mL of distilled water, stirring for 30min to obtain an emulsifier solution, then slowly adding 15g of 3,3',4,4' -benzophenone butyl tetracarboxylic acid ester in example 1, and stirring for 1h to obtain a finishing working solution with the effective concentration of the antibacterial agent of 100 g/L.
(2) And (2) immersing the unfinished polyester fabric into the finishing working solution in the step (1), performing two-immersion and two-rolling (the liquid carrying rate is 90%), pre-drying at 80 ℃ for 3min, and baking at 180 ℃ for 2.5min to obtain the antibacterial polyester fabric. And (3) taking the antibacterial polyester fabric, and washing the antibacterial polyester fabric for 30 times according to a washing procedure of FZ/T73023-2006 antibacterial knitwear appendix C antibacterial fabric sample washing test method.
Example 4
The antibacterial polyester fabric prepared in example 3 and the antibacterial polyester fabric washed 30 times were subjected to an antibacterial test. The bacteria for detection are staphylococcus aureus and escherichia coli. In this example, the antibacterial properties of the fabric against staphylococcus aureus and escherichia coli were tested with reference to the test standard of AATCC 100-2004-. The specific method is as followsThe following: sterilizing two pieces of antibacterial polyester fabric (3.5 cm × 3.5 cm) and washed with water 30 times at 121 deg.C for 15min, placing in sterilized culture medium, and dripping 300 μ L10 onto the fabric5Irradiating the CFU/mL bacterial solution for 60min under the condition of ultraviolet light (365nm), taking out the irradiated fabric, soaking the fabric in 30mL PBS sterile buffer solution, and uniformly oscillating for 3 min. Diluting the bacteria liquid to 10 in sequence after the oscillation is finished3、102、101、100CFU/mL, 100. mu.L of each dilution was dropped to 4 zones of sterile medium, and the medium was incubated in a 37 ℃ incubator for a period of time and then taken out to calculate the bacteriostatic rate. The results are shown in the following table:
example 5
The ethyl 3,3',4,4' -benzophenonetetracarboxylate obtained in example 2 was used for finishing polyester fabrics. The specific method comprises the following steps:
(1) adding 1.5g of emulsifier Tween 80 into 150mL of distilled water, stirring for 30min to obtain an emulsifier solution, then slowly adding 15g of 3,3',4,4' -benzophenone tetracarboxylic acid ethyl ester in example 2, and stirring for 1h to obtain a finishing working solution with the effective concentration of the antibacterial agent of 100 g/L.
(2) And (2) immersing the unfinished polyester fabric into the finishing working solution in the step (1), performing two-immersion and two-rolling (the liquid carrying rate is 90%), pre-drying at 80 ℃ for 3min, and baking at 180 ℃ for 2.5min to obtain the antibacterial polyester fabric. And (3) taking the antibacterial polyester fabric, and washing the antibacterial polyester fabric for 30 times according to a washing procedure of FZ/T73023-2006 antibacterial knitwear appendix C antibacterial fabric sample washing test method.
Example 6
The antibacterial polyester fabric prepared in example 5 and the antibacterial polyester fabric washed 30 times were subjected to an antibacterial test. The bacteria for detection are staphylococcus aureus and escherichia coli. In the experiment, the antibacterial property of the fabric to staphylococcus aureus and escherichia coli is tested according to the test standard of AATCC 100-2004 & evaluation on antibacterial finishing of textile materials. In particular toThe method comprises the following steps: sterilizing two pieces of antibacterial polyester fabric (3.5 cm × 3.5 cm) and washed with water 30 times at 121 deg.C for 15min, placing in sterilized culture medium, and dripping 300 μ L10 onto the fabric5Irradiating CFU/mL bacterial solution under ultraviolet light (365nm) for 60min, taking out the irradiated fabric, soaking the fabric in 30mL PBS sterile buffer solution, uniformly oscillating for 3min, and sequentially diluting the bacterial solution to 10 after oscillation is finished3、102、101、100CFU/mL, 100. mu.L of each dilution was dropped to 4 zones of sterile medium, and the medium was incubated in a 37 ℃ incubator for a period of time and then taken out to calculate the bacteriostatic rate. The results are shown in the following table:
Claims (7)
1. a method for finishing polyester fabric by using a photoinduced antibacterial finishing agent benzophenone tetracarboxylic acid ester comprises the following specific steps:
(1) adding 3,3',4,4' -benzophenone tetracarboxylic dianhydride and alcohol into a reaction bottle with a water separator in a molar ratio of 1: 4-8, stirring, dropwise adding concentrated sulfuric acid for reaction, cooling to room temperature, washing, drying, filtering, and separating to obtain a light-induced antibacterial finishing agent benzophenone tetracarboxylate, wherein the volume ratio of the alcohol to the concentrated sulfuric acid is 50: 1-175: 1; the chemical structure of the light-induced antibacterial finishing agent benzophenone tetraformate is shown as follows:
(2) dissolving an emulsifier in a solvent, stirring to obtain an emulsifier solution, adding a light-induced antibacterial finishing agent benzophenone tetraformate, and continuously stirring to obtain a finishing working solution, wherein the mass ratio of the benzophenone tetraformate to the emulsifier is 1: 5-10, and the effective concentration of the benzophenone tetraformate in the finishing working solution is 10-110 g/L;
(3) and (2) immersing the non-finished polyester fabric into the finishing working solution in the step (1), soaking twice, rolling twice, pre-drying, and baking to obtain the antibacterial polyester fabric.
2. The method for finishing polyester fabrics with the photo-induced antibacterial finishing agent benzophenone tetracarboxylic acid ester according to claim 1, wherein the reaction temperature in the step (1) is 100 to 160 ℃ and the reaction time is 6 to 8 hours.
3. The method for finishing polyester fabrics with photo-induced antibacterial finishing agent benzophenone tetracarboxylic acid ester according to claim 1, wherein the washing in the step (1) is 15-30% of Na2CO3Washing the solution to be neutral; anhydrous sodium sulfate for drying; the separation is carried out by vacuum distillation and then column chromatography.
4. The method for finishing polyester fabrics with the photoinduced antibacterial finishing agent benzophenone tetracarboxylic acid ester according to claim 3, wherein the eluent for the column chromatography is a mixed solution of dichloromethane and methanol.
5. The method for finishing polyester fabrics with the photo-induced antibacterial finishing agent benzophenone tetracarboxylic acid ester according to claim 1, wherein the emulsifier in the step (2) comprises one or more of tween emulsifier, sodium dodecyl sulfate, span emulsifier, TX emulsifier and OP emulsifier.
6. The method for finishing polyester fabrics with the photo-induced antibacterial finishing agent benzophenone tetracarboxylic acid ester according to claim 1, wherein the solvent in the step (2) is distilled water; stirring for 30 min; the continuous stirring time is 0.5-3 h.
7. The method for finishing polyester fabrics with the photoinduced antibacterial finishing agent benzophenone tetracarboxylic acid ester according to the claim 1, characterized in that the liquid carrying rate of the second dipping and the second rolling in the step (3) is 80-100%; the pre-drying temperature is 80 ℃, and the pre-drying time is 3 min; the baking temperature is 160-200 ℃, and the baking time is 1-4 min.
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| CN110037040B (en) * | 2019-05-22 | 2021-07-30 | 浙江养生堂天然药物研究所有限公司 | Method for preventing pathogen from infecting plant |
| CN110283524B (en) * | 2019-07-08 | 2021-07-02 | 东华大学 | Polycarboxylate photocatalytic self-cleaning waterborne polyurethane coating and preparation and application thereof |
| CN110402931A (en) * | 2019-07-31 | 2019-11-05 | 东华大学 | A kind of antibacterial agent, antibacterial wool fabric and its preparation and application |
| CN110725128B (en) * | 2019-09-29 | 2022-03-25 | 嘉兴市特欣织造有限公司 | Preparation method and application of anti-ultraviolet and antibacterial biomass fiber PA56 fabric |
| CN111379159B (en) * | 2020-05-22 | 2022-09-02 | 无锡浦惠恒业纺织科技有限公司 | Hydrogen peroxide catalytic system based on polycarboxylic acid or anhydride compound and application of hydrogen peroxide catalytic system in low-temperature pretreatment of textiles |
| CN112646144A (en) * | 2020-12-18 | 2021-04-13 | 东华大学 | Heat-storage temperature-regulating cellulose liquid crystal composite fabric based on covalent grafting and preparation method thereof |
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Application publication date: 20171229 Assignee: LUOLAI LIFESTYLE TECHNOLOGY Co.,Ltd. Assignor: DONGHUA University Contract record no.: X2021310000044 Denomination of invention: A preparation method of light induced antibacterial finishing agent benzophenone tetraformate Granted publication date: 20210402 License type: Common License Record date: 20211129 |
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