Compound capable of being used for resisting bacteria of textiles as well as preparation method and application of compound

By developing a compound with a structure such as Formula I for the immersion of textiles, the problem of poor effect of textile antibacterial materials on drug-resistant bacteria in the prior art is solved, and effective antibacterial against Gram-positive and negative bacteria is achieved. It has an effect and enhances antibacterial ability under light conditions, and is suitable for antibacterial treatment of a variety of textiles.

CN119219552AActive Publication Date: 2024-12-31NORTH SICHUAN MEDICAL COLLEGE
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Patent Information

Application Number
CN202411272615.X
Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
Filing Date
2024-09-11
Publication Date
2024-12-31
Estimated Expiration
2044-09-11

AI Technical Summary

Technical Problem

Existing textile antibacterial materials cannot effectively fight drug-resistant bacteria, and lack photosensitizers with strong Type I and Type II photosensitivity, making it impossible to achieve safe, efficient and broad-spectrum antibacterial effects.

Method used

A compound of structure such as formula I was developed, prepared by reacting with anion exchanger, for textile impregnation, with high photosensitive and biocompatible, capable of effectively adsorbing bacteria or viruses, binding to cell membranes or DNA, and achieving broad-spectrum antibacterials. Effect.

Benefits of technology

This compound can be effectively antibacterial without light treatment, and exhibits stronger antibacterial effects under light conditions. It is effective against Gram-positive and negative bacteria. It is hydrophobic and inhibits bacterial adhesion. It is suitable for many Antibacterial treatment of textiles is simple to operate and low cost.

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Abstract

The invention provides an antibacterial compound for textiles as well as a preparation method and application of the antibacterial compound, and belongs to the technical field of medical materials. The invention develops a compound with high photosensitivity, and the structure of the compound is shown as a formula I. The compound has the advantages of good modification property, good biological compatibility, strong biological adhesion and adsorption capacity, easiness in combination with cell membranes and the like, can effectively adsorb nucleic acid or protein of bacteria or viruses, can effectively resist bacteria without light treatment, has a better antibacterial effect after light treatment, and can be applied to the field of biological treatment. In addition, the compound shows an excellent antibacterial effect on gram-positive bacteria and gram-negative bacteria. The textile subjected to dip dyeing treatment by the compound has certain hydrophobicity, can inhibit bacterial adhesion and play an excellent antibacterial role, and is simple to operate, low in cost, suitable for antibacterial treatment of various textiles and wide in application prospect. # imgabs0 #
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Description

Technical Field

[0001] The invention belongs to the technical field of medical materials, and in particular relates to a class of compounds that can be used for antibacterial textiles, and a preparation method and use thereof. Background Art

[0002] The close contact between textile materials and skin provides an attachment basis for microorganisms to transfer from human skin to textiles. Similarly, external microorganisms can also transfer to the skin surface by adhering to the surface of textile materials, causing skin inflammation, infection or allergic reactions. In addition, the growth of microorganisms on textiles will destroy the fiber structure or dyes of textiles, resulting in a decrease in the strength, color fastness or appearance quality of textiles. Microorganisms will also decompose sweat, grease or other organic matter on textiles, producing unpleasant odors. Therefore, the antibacterial properties of textile materials have received widespread attention. In practical applications, textile materials are easily wetted by water and provide a breeding ground for bacteria. Dyeing with hydrophobic dyes can usually inhibit the growth and adhesion of bacteria on textile materials, but it cannot effectively kill bacteria.

[0003] Since the advent of penicillin, antibiotics have been regarded as the golden drug for clinical prevention and treatment of bacterial infections. However, with the increasing abuse of antibiotics, the problem of clinical bacterial resistance has become increasingly serious, especially the emergence and spread of super bacteria, which makes antibiotic treatment ineffective. Although great efforts have been made to combat bacterial resistance, there is still a big gap between the sustainable emergence of resistant bacteria and the development of new antibiotics. Therefore, it is urgent to seek to develop new antibacterial means to inactivate bacteria and curb the growth of multidrug-resistant bacteria.

[0004] Antibacterial photodynamic therapy (APDT) is a new method of antibacterial treatment that uses the principle of photodynamic therapy. Under the irradiation of laser light of a specific wavelength, the photosensitizer is excited, and the excited photosensitizer transfers energy to the surrounding oxygen, generating highly active reactive oxygen species (ROS) and singlet oxygen, which can then inactivate surrounding bacteria to resist bacterial infection. The reaction of APDT is mainly divided into type II and type I mechanisms. Most of the existing ones are type II photodynamic systems, which are based on the reaction of triple ground state molecular oxygen ( 3 O 2 ) undergoes energy transfer to convert it into highly reactive singlet oxygen ( 1 O 2) to exert therapeutic effects. The high dependence and large consumption of oxygen by type II photosensitizers limit their efficacy against anaerobic bacteria. Different from the energy transfer mechanism of type II, type I produces free radical ions or free radicals through electron transfer, which can effectively treat hypoxia. Different bacteria have different sensitivities to type I and type II. For example, Gram-negative bacteria are more sensitive to hydroxyl radicals, while Gram-positive bacteria are more sensitive to singlet oxygen. At present, the bacterial lethal mechanism of APDT includes two aspects: (1) Membrane damage: Due to the large differences in the structural composition of cell walls and cell membranes, APDT is generally more effective in damaging the membrane of Gram-positive bacteria than that of Gram-negative bacteria. (2) DNA damage: In APDT, photosensitizers interfere with the replication and transcription process of bacteria by inhibiting DNA synthesis and combining with DNA to form complexes. In addition, the ROS generated during the APDT process can irreversibly damage bases and ribose, thereby destroying the DNA structure of bacteria. Combining photodynamic antimicrobial therapy with textile materials and applying it to textile materials can not only kill bacteria and fungi, reduce odors and stains, but also prevent the growth of bacteria and fungi, keep textiles clean and hygienic, and isolate bacteria and viruses from the human body to prevent cross infection. Therefore, although APDT shows good efficacy for infections caused by bacteria, fungi and viruses, especially for infections caused by drug-resistant bacteria, it is still necessary to develop photosensitizers with strong type I and type II photosensitivity at the same time, so as to achieve safe, efficient and broad-spectrum antibacterial effects on textile antimicrobial materials. However, there are few reports on textile antimicrobial materials that can meet the above requirements. Summary of the invention

[0005] In view of the deficiencies of the prior art, the object of the present invention is to provide a class of compounds that can be used for antibacterial textiles, and a preparation method and use thereof.

[0006] The present invention provides a compound, the structure of which is shown in Formula I: Where R is C 1-15 Alkyl, X is halogen.

[0007] Furthermore, R is C 1-12 Alkyl, X is selected from chlorine, bromine, and iodine.

[0008] Further, R is -CH 3 、-CH 2 CH 3 、-CH 2 CH 2 CH 3 、-CH(CH 3 )CH 3 、-CH 2 (CH2 ) 2 CH 3 、-CH(CH 3 )CH 2 CH 3 、-CH 2 (CH 2 ) 3 CH 3 、-CH 2 CH(CH 3 )CH 2 CH 3 、-CH 2 CH 2 CH(CH 3 ) 2 、-CH 2 (CH 2 ) 4 CH 3 、-CH 2 (CH 2 ) 2 CH(CH 3 ) 2 、-CH 2 CH 2 C(CH 3 ) 3 、-CH 2 (CH 2 ) 5 CH 3 、-CH 2 (CH 2 ) 3 CH(CH 3 ) 2 、-CH 2 (CH 2 ) 2 C(CH 3 ) 3 、-CH 2 (CH 2 ) 6 CH 3 、-CH 2 (CH 2 ) 4 CH(CH 3 ) 2 、-CH 2 (CH 2 ) 3 C(CH 3 ) 3 、-CH 2 (CH 2 ) 7 CH 3 、-CH2 (CH 2 ) 5 CH(CH 3 ) 2 、-CH 2 (CH 2 ) 4 C(CH 3 ) 3 or -CH 2 (CH 2 ) 10 CH 3 .

[0009] Further, it is selected from one of the following compounds: .

[0010] The present invention also provides a method for preparing the above compound, the method comprising the following steps: Compound 1 reacts with RY to obtain a mixture under the action of anion exchanger A, and the mixture reacts with anion exchanger B to obtain the compound; Y is a halogen; Preferably, Y is selected from chlorine, bromine and iodine, anion exchanger A is potassium hexafluorophosphate, and anion exchanger B is tetrabutylammonium chloride, tetrabutylammonium bromide or tetrabutylammonium iodide.

[0011] Furthermore, the mass volume ratio of the compound 1 to RY is 20-60 mg:1 mL; the solvent of the reaction is an organic solvent; the temperature of the reaction is 10-90° C., and the reaction time is 5-20 hours.

[0012] Furthermore, the mass volume ratio of the compound 1 to RY is 30-50 mg:1 mL; the solvent of the reaction is methanol or N,N-dimethylformamide; the temperature of the reaction is 15-80° C., and the reaction time is 7-17 hours.

[0013] The invention also provides an antibacterial or antiviral textile, which is the textile impregnated with the solution of the compound.

[0014] Furthermore, the dyeing method is: putting the textile into the solution of the above compound, dyeing, and drying.

[0015] Furthermore, the solvent in the solution is an organic solvent, preferably methanol; the temperature of the dipping is 10-40° C., preferably 15-35° C.; and the time is 2-7 min, preferably 5 min.

[0016] The present invention also provides the use of the above compound in preparing antibacterial or antiviral agents.

[0017] Furthermore, the antibacterial agent or antiviral agent is an agent applied to textiles.

[0018] Furthermore, the antibacterial agent or antiviral agent is a photosensitive antibacterial agent or antiviral agent.

[0019] Further, the antibacterial agent is an agent against Gram-positive bacteria or Gram-negative bacteria, the Gram-positive bacteria is preferably Staphylococcus aureus, and the Gram-negative bacteria is preferably Escherichia coli; The antiviral agent is an agent against herpes virus.

[0020] Definitions of terms used in the present invention: Unless otherwise specified, the initial definitions provided for groups or terms herein apply to the groups or terms throughout the specification; for terms that are not specifically defined in the present invention, the meanings that can be given to them by those skilled in the art should be given according to the disclosure and context. Among them: The minimum and maximum carbon atom content in a hydrocarbon group is indicated by a prefix, for example, the prefix C a~b Alkyl refers to any alkyl group containing from "a" to "b" carbon atoms. 1~12 Alkyl refers to straight or branched chain alkyl groups containing 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12 carbon atoms; and so on.

[0021] "Alkyl" refers to a saturated hydrocarbon chain having a specified number of member atoms. The alkyl group may be straight or branched, and the alkyl group may be optionally substituted with one or more substituents as defined herein. Alkyl groups include methyl, ethyl, propyl (n-propyl and isopropyl).

[0022] "Halogen" is fluorine, chlorine, bromine or iodine.

[0023] The present invention has achieved the following beneficial effects: 1. The compounds of the present invention have the advantages of flexible modification, good biocompatibility, strong bioadhesion and adsorption, and easy binding to cell membranes. The compounds contain abundant positive charges in their structure, which helps them to bind to negatively charged cell membranes or DNA, and can effectively adsorb nucleic acids or proteins of bacteria or viruses, thereby achieving efficient and broad-spectrum antibacterial effects.

[0024] 2. The compounds of the present invention can effectively fight bacteria without light treatment, and have better antibacterial effect after light treatment, showing photosensitization-enhanced antibacterial effect. Excellent antibacterial effect can be achieved under simple light conditions.

[0025] 3. The compounds of the present invention show excellent antibacterial effects on both Gram-positive bacteria (such as Staphylococcus aureus) and Gram-negative bacteria (such as Escherichia coli) and have a broad-spectrum antibacterial effect.

[0026] 4. The textiles treated with the compounds of the present invention have a certain hydrophobicity, which can inhibit bacterial adhesion and have excellent antibacterial effect. They are suitable for antibacterial treatment of various textiles and have broad application prospects. The length of the peripheral alkyl chain of the compounds TP-1, TP-5 and TP-12 of the present invention increases successively, and the hydrophobicity also increases successively. However, compared with the textile samples dyed with TP-1 and the textile samples dyed with TP-12, the antibacterial performance of the textile samples dyed with TP-5 is the best. It shows that the compound TP-5 with specific hydrophobicity of the present invention is the most suitable antibacterial agent for textiles.

[0027] 5. The operation conditions for dyeing textiles with the compounds of the present invention are simple, the cost is low, and it is suitable for industrial production.

[0028] Obviously, according to the above contents of the present invention, in accordance with common technical knowledge and customary means in the art, without departing from the above basic technical ideas of the present invention, other various forms of modification, replacement or change may be made.

[0029] The above contents of the present invention are further described in detail below through specific implementation methods in the form of examples. However, this should not be understood as the scope of the above subject matter of the present invention being limited to the following examples. All technologies realized based on the above contents of the present invention belong to the scope of the present invention. BRIEF DESCRIPTION OF THE DRAWINGS

[0030] Figure 1 The effects of different concentrations of TP-1 in the dark or under light for 2 h on (a) Escherichia coli ( a, E.coil ) and (b) Staphylococcus aureus ( b, S. aureus ) Bacterial activity.

[0031] Figure 2 The flat plate antibacterial graph of non-woven fabrics dyed with different concentrations of TP-1 molecules against Staphylococcus aureus.

[0032] Figure 3 The flat plate antibacterial graph of non-woven fabrics dyed with different concentrations of TP-1 molecules against Escherichia coli.

[0033] Figure 4 The flat plate antibacterial graph of daily-use fabrics dyed with different concentrations of TP-1 molecules against Staphylococcus aureus.

[0034] Figure 5 The plate antibacterial graph of daily-use fabrics dyed with different concentrations of TP-1 molecules against Escherichia coli.

[0035] Figure 6 The flat plate antibacterial graph of non-woven fabrics dyed with TP-5 molecules at different concentrations against Staphylococcus aureus.

[0036] Figure 7 The flat plate antibacterial graph of non-woven fabrics dyed with TP-5 molecules at different concentrations against Escherichia coli.

[0037] Figure 8 The flat plate antibacterial chart of daily-use fabrics dyed with different concentrations of TP-5 molecules against Staphylococcus aureus.

[0038] Fig. 9 The flat plate antibacterial chart of daily-use fabrics dyed with TP-5 molecules of different concentrations against Escherichia coli.

[0039] Fig.10 The flat plate antibacterial graph of non-woven fabrics dyed with different concentrations of TP-12 molecules against Staphylococcus aureus.

[0040] Fig.11 The flat plate antibacterial graph of non-woven fabrics dyed with TP-12 molecules at different concentrations against Escherichia coli.

[0041] Fig.12 The flat plate antibacterial chart of daily-use fabrics dyed with TP-12 molecules of different concentrations against Staphylococcus aureus.

[0042] Fig.13 The plate antibacterial chart of daily-use fabrics dyed with TP-12 molecules of different concentrations against Escherichia coli. DETAILED DESCRIPTION

[0043] The raw materials and equipment used in the present invention are all known products, which are obtained by purchasing commercially available products.

[0044] The "normal temperature or room temperature" referred to in the present invention is 25±10°C.

[0045] The "overnight" referred to in the present invention is 12±5 hours.

[0046] The relevant reagents used in the present invention are represented as follows: PBS: phosphate buffer (0.03 mol / L), LB: Luria-Bertani medium.

[0047] Example 1. Preparation of Compound TP-1 Compound 1 (47.6 mg) and CH 3I (1 mL) was stirred and mixed at room temperature and stirred overnight. Methanol (1 mL) was added and stirred overnight. The solvent was removed, the residue was dissolved in water, and a saturated aqueous solution of potassium hexafluorophosphate was added to the solution to precipitate. The precipitate was dissolved in acetonitrile, and a tetrabutylammonium chloride solution was added to the acetonitrile solution to produce a sediment, which was filtered and washed with acetonitrile five times. The solid was dried in a vacuum oven to obtain a yellow solid compound TP-1 (35 mg, 96%). 1 H NMR (400 MHz, MeOD) δ 4.40 (s, 9H), 7.41-7.43 (d, J = 8.7 Hz, 6H), 8.08-8.11 (d, J =11.8 Hz, 6H), 8.39-8.41 (d, J = 7.1 Hz, 6H), 8.92-8.94 (d, J = 7.0 Hz, 6H).

[0048] Example 2. Preparation of Compound TP-5 Compound 1 (30 mg), bromopentane (1 mL) and N,N-dimethylformamide (DMF) (2 mL) were mixed and stirred at 80°C overnight. The reaction solution was poured into water, and potassium hexafluorophosphate was added to the solution to precipitate. The precipitate was dissolved in acetonitrile, and an excess of tetrabutylammonium chloride solution was added to the acetonitrile solution to produce a precipitate. The precipitate was filtered and washed with acetonitrile five times, and vacuum dried to obtain a yellow solid compound TP-5 (38 mg, 98%). 1 H NMR (400 MHz, MeOD) δ 0.95-0.98 (t, J = 6.9 Hz, 9H), 1.40-1.46 (m, 12H), 2.01-2.09 (m, 6H), 4.58-4.62 (t, J = 7.5 Hz, 6H), 7.41-7.43 (d, J = 8.8 Hz, 6H), 8.08-8.10 (d, J = 8.8 Hz, 6H),8.39-8.41 (d, J = 7.0 Hz, 6H), 8.92-8.94 (d, J = 6.9 Hz, 6H).

[0049] Example 3. Preparation of Compound TP-12 A mixture of compound 1 (30 mg), dodecane bromide (1 mL) and DMF (2 mL) was stirred at 80°C overnight. The solvent was removed, potassium hexafluorophosphate was added to the residue to precipitate, the precipitate was dissolved in ethyl acetate, an excess of tetrabutylammonium chloride aqueous solution was added to the ethyl acetate solution to produce a precipitate, filtered, the precipitate was dissolved in a small amount of methanol, ethyl acetate was added, and the precipitate was precipitated, and repeated five times. The solid was dried in a vacuum oven to obtain a yellow solid compound TP-12 (47 mg, 99%). 1 H NMR (400 MHz, MeOD) δ0.87-0.91(t, J = 6.8 Hz, 9H), 1.44-1.24 (m,54H), 2.05 (m, 6H), 4.58-4.61(t, J = 7.5 Hz, 6H), 7.41-7.43 (d, J = 8.7 Hz, 6H),8.08-8.10 (d, J = 8.8 Hz, 6H), 8.39-8.41 (d, J = 6.9 Hz, 6H), 8.92-8.94 (d, J = 6.8 Hz, 6H).

[0050] Example 4. Preparation of antibacterial textiles The textiles were immersed in methanol solutions of compound TP-1 with different concentrations (50uM, 100uM, 500uM, and 1mM, respectively), immersed for 5 minutes at room temperature, and then naturally dried to obtain various antibacterial textiles.

[0051] Example 5. Preparation of antibacterial textiles The textiles were immersed in methanol solutions of compound TP-5 with different concentrations (50uM, 100uM, 500uM, and 1mM, respectively), immersed for 5 minutes at room temperature, and then naturally dried to obtain various antibacterial textiles.

[0052] Example 6. Preparation of antibacterial textiles The textiles were immersed in methanol solutions of compound TP-12 with different concentrations (50uM, 100uM, 500uM, and 1mM, respectively), immersed for 5 minutes at room temperature, and then naturally dried to obtain various antibacterial textiles.

[0053] The beneficial effects of the present invention are demonstrated by experimental examples below.

[0054] Experimental Example 1: Evaluation of the antibacterial ability of compounds as photosensitizers 1. Experimental methods (1) Preparation of bacterial solution Use an inoculation loop to pick up Escherichia coli (a, E.coil ), Staphylococcus aureus (b, S. aureus ) of the bacterial culture solution (concentration of 10 5 CFU / mL; purchased from Chengdu Xinnuo Biotechnology Co., Ltd.), and then the bacteria were inoculated on solid agar plates by the plate streak method and cultured for 24 h. The single colonies on the solid agar plates were transferred to 4 mL LB liquid culture medium and cultured at 37 °C for 18 h to obtain Escherichia coli bacterial liquid and Staphylococcus aureus bacterial liquid.

[0055] (2) Group processing Blank group: 2 uL of Escherichia coli or Staphylococcus aureus bacterial solution was added to 100 uL PBS solution, incubated for 5 min, and then diluted 200 times continuously. 100 uL was taken on the agar plate, evenly dispersed with a spreader, and cultured for 24 hours before counting.

[0056] Control group: Pipette 100uL of the compound (TP-1, TP-5, TP-12) solutions with concentrations of 2, 5, 10, 20, and 40uM into 500uL EP tubes, respectively, and then pipette 2uL of the above bacterial solution into the compound solutions of different concentrations, incubate in the dark for 5min, take 100uL on the agar plate, spread it evenly with a spreader, culture it for 24 hours, and count.

[0057] Experimental group: 100uL of the compound (TP-1, TP-5, TP-12) solutions with concentrations of 2, 5, 10, 20, and 40uM were transferred to 500uL EP tubes, and 2uL of the above bacterial solution was transferred to the compound solutions with different concentrations. 2 After irradiation with white light for 5 minutes, the sample was diluted 200 times with PBS, 100uL was taken and evenly spread on an agar plate with a spreader, and then cultured for 24 hours and counted.

[0058] The effects of different concentrations of compounds on Escherichia coli (a, E.coil ) and Staphylococcus aureus (b, S. aureus )'s antibacterial effect.

[0059] 2. Experimental results Effects of different concentrations of compounds on Escherichia coli (a, E.coil ) and Staphylococcus aureus colony diagram Figure 1 shown.

[0060] From the experimental results, it can be seen that in the dark environment, the antibacterial ability of the control group becomes stronger with the higher concentration; in the white light environment, the antibacterial ability of the experimental group increases with the increasing concentration, and under the same conditions, the light group has stronger antibacterial ability, showing a photosensitization-enhanced antibacterial effect.

[0061] Experimental Example 2: Evaluation of the antibacterial ability of textile samples dyed with compounds as dyes 1. Experimental methods Cut several samples with a diameter of about 25 mm from textile samples (non-woven fabrics and daily fabrics).

[0062] Each group is processed as follows: (1) Control group: non-woven fabrics and daily-use fabrics without any treatment.

[0063] (2) Experimental group: non-woven fabrics and daily-use fabrics were soaked in methanol solutions of compounds (TP-1, TP-5, TP-12) at different concentrations (50uM, 100uM, 500uM, 1mM, respectively) at room temperature for 5 minutes and then naturally dried.

[0064] Take the sterilized lower culture medium (LB culture medium) and place it in an incubator at 37°C. Prepare the upper culture medium: Take 5 mL of agar culture medium (LB culture medium) and pour it on the lower culture medium, and use sterile tweezers to place the non-woven fabric or daily-use fabric samples of the control group and the experimental group in the center of the plate, and press them evenly on the agar culture medium until the non-woven fabric or daily-use fabric and the agar culture medium are in good contact.

[0065] Take 100ul of each solution with a concentration of 10 5-6 The bacterial solution (Escherichia coli, Staphylococcus aureus) with CFU / mL was evenly spread on the culture medium and cultured without light treatment or after light treatment. The light-treated sample was placed on a sterile operating table with the lid opened and irradiated with 2.55mW / cm 2 After 2 hours of white light irradiation, the samples were placed in the incubator. The samples without light treatment were placed in the dark for 2 hours and then placed in the incubator. The inhibition zone was measured after 20 hours of incubation in the incubator.

[0066] 2. Experimental results According to the national standard GB / T 20944-2007, an inhibition zone larger than 1 mm is considered to have a good antibacterial effect. Figure 2-13As shown, the textile samples dyed with different concentrations of compounds have an inhibition zone of ≧1mm and even up to 7.5mm against Escherichia coli and Staphylococcus aureus without white light irradiation; the textile samples dyed with different concentrations of compounds have better antibacterial effects on Escherichia coli and Staphylococcus aureus under white light irradiation, showing photosensitization enhanced antibacterial effect. Among them, TP-1 and TP-12 have no obvious antibacterial effect on Escherichia coli and Staphylococcus aureus (inhibition zone: 0mm) after dyeing at a lower concentration (50uM), while TP-5 has obvious effects on Escherichia coli (inhibition zone: 3-7mm) and Staphylococcus aureus (inhibition zone: 3.5-14mm) after dyeing at a concentration of 50uM.

[0067] The outer alkyl chain lengths of the compounds TP-1, TP-5, and TP-12 of the present invention increase in sequence, and the hydrophobicity also increases in sequence. However, according to the above experimental results, it is found that the antibacterial properties of the textile samples dyed with TP-5 are the best compared with the textile samples dyed with TP-1 and the textile samples dyed with TP-12. This shows that the compound TP-5 of the present invention with specific hydrophobicity is the most suitable photosensitive antibacterial agent for use in textiles.

[0068] In summary, the present invention provides a class of compounds that can be used for textile antibacterial and its preparation method and use. The present invention has developed a compound with high photosensitivity, and the structure of the compound is shown in Formula I. The compound has the advantages of good modifiability, good biocompatibility, strong bioadhesion and adsorption, easy to combine with cell membrane, etc., can effectively adsorb nucleic acids or proteins of bacteria or viruses, can effectively resist bacteria without light treatment, has better antibacterial effect after light treatment, and shows excellent antibacterial effect on Gram-positive bacteria and Gram-negative bacteria. The textiles treated by the compound of the present invention have certain hydrophobicity, can inhibit bacterial adhesion, play an excellent antibacterial effect, are simple to operate, low cost, suitable for a variety of textile antibacterial treatment, and have broad application prospects.

Claims

1. A compound, characterized in that Its structure is shown in Formula I: Formula I Where R is C 1-15 Alkyl, X is halogen.

2. The compound according to claim 1, characterized in that R is C 1-12 Alkyl, X is selected from chlorine, bromine, and iodine.

3. The compound according to claim 2, characterized in that R is -CH3, -CH2CH3, -CH2CH2CH3, -CH(CH3)CH3, -CH2(CH2)2CH3, -CH(CH3)CH2CH3, -CH2(CH2)3CH3, -CH2CH(CH3)CH2CH3, -CH2CH2CH(CH3)2, -CH2(CH2)4CH3, -CH2(CH2)2CH(CH3)2, -CH2CH2C(CH3)3, -CH2(CH2)5CH3, -CH2(CH2)3CH(CH3)2, -CH2(CH2)2C(CH3)3, -CH2(CH2)6CH3, -CH2(CH2)4CH(CH3)2, -CH2(CH2)3C(CH3)3, -CH2(CH2)7CH3, -CH2(CH2)5CH(CH3)2, -CH2(CH2)4C(CH3)3 or -CH2(CH2) 10 CH3.

4. The compound according to claim 3, characterized in that It is selected from one of the following compounds: 。 5. A method for preparing the compound according to any one of claims 1 to 4, characterized in that: The method comprises the following steps: Compound 1 reacts with RY to obtain a mixture under the action of anion exchanger A, and the mixture reacts with anion exchanger B to obtain the compound; Y is a halogen; Preferably, Y is selected from chlorine, bromine and iodine, anion exchanger A is potassium hexafluorophosphate, and anion exchanger B is tetrabutylammonium chloride, tetrabutylammonium bromide or tetrabutylammonium iodide.

6. An antibacterial or antiviral textile, characterized in that: The textile is dyed with a solution of the compound according to any one of claims 1 to 4.

7. Use of the compound according to any one of claims 1 to 4 in the preparation of an antibacterial agent or an antiviral agent.

8. The use according to claim 7, characterized in that The antibacterial agent or antiviral agent is an agent applied to textiles.

9. The use according to claim 7, characterized in that: The antibacterial agent or antiviral agent is a photosensitive antibacterial agent or antiviral agent.

10. The use according to any one of claims 7 to 9, characterized in that: The antibacterial agent is an agent against Gram-positive bacteria or Gram-negative bacteria, the Gram-positive bacteria is preferably Staphylococcus aureus, and the Gram-negative bacteria is preferably Escherichia coli; The antiviral agent is an agent against herpes virus.

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