Antibacterial anti-ultraviolet compound and preparation method thereof

Abstract

The invention discloses an antibacterial anti-ultraviolet compound and a preparation method thereof. The structure of the antibacterial anti-ultraviolet compound contains an antibacterial group and an anti-ultraviolet group; the antibacterial group and the anti-ultraviolet group are obtained by reacting an antibacterial compound and an anti-ultraviolet compound with cyanuric chloride. The antibacterial and anti-ultraviolet compound can be widely applied to surface modification of polymer fibers, plastics and rubber, endows the polymer fibers, the plastics and the rubber with lasting and efficient antibacterial and anti-ultraviolet modification, and the preparation method is simple and easy to implement, is suitable for industrial production and has wide application prospects.

Description

[0001] This application is a divisional application of the invention patent application filed on May 29, 2024, with patent application number 2024106743406 and invention title "An antibacterial and anti-ultraviolet compound and its preparation method". Technical Field

[0002] This invention relates to a compound and its preparation method, and more particularly to an antibacterial and anti-ultraviolet compound and its preparation method. Background Technology

[0003] Due to the depletion of the Earth's ozone layer, the amount of ultraviolet radiation from the sun is gradually increasing. Prolonged exposure to harmful ultraviolet rays can cause significant damage to the human body, including sunburn, allergies, erythema, premature aging, and even an increased risk of skin cancer. Textiles, acting as a second line of defense, can help protect against ultraviolet radiation to some extent, but their high UV transmittance limits their effectiveness. Among textiles, natural textiles (cotton textiles) are more popular with consumers due to their breathability, moisture permeability, and comfort. However, the porous structure of textiles provides a habitat for microorganisms. Especially when skin flakes, sweat, oils, and metabolic waste come into contact with textiles, they provide nutrients for these microorganisms, promoting their proliferation and causing discoloration, odors, and affecting the textile's original properties. Long-term contact with human skin can also harm human health. Therefore, with increasing consumer demand, consumers desire textiles with antibacterial and UV-protective functions.

[0004] Among commonly used UV absorbers, benzophenone-based UV absorbers can absorb ultraviolet light in the wavelength range of 220–400 nm, and their synthesis and application are relatively widespread. Commonly used antibacterial agents include natural antibacterial agents, inorganic antibacterial agents, and organic antibacterial agents. Natural antibacterial agents are mainly extracts from plants and animals in nature, such as chitosan. Natural antibacterial agents are widely available, have good antibacterial effects, and are biocompatible, but their extraction costs are high. Inorganic antibacterial agents are mainly metals, metal ions, and their oxides, such as silver ions, copper ions, and titanium dioxide. The antibacterial mechanism of inorganic antibacterial agents is leaching-type antibacterial. Long-term use of textiles containing free metal ions inevitably poses a risk to human health. Moreover, metals, whether in free or bound states, are highly toxic even at low concentrations. Chinese Patent No. 202210992192.3 discloses a self-crosslinking type antibacterial and UV-protective finishing agent for textiles and its preparation method. The effective antibacterial components in this antibacterial and UV-protective finishing agent are polylysine and nano-silver. Silver ions can react with -SH on proteins. Nano-silver is toxic to human cells and exhibits dose-, nanoparticle size, and time dependence. Organic antibacterial agents mainly include quaternary ammonium salts, quaternary phosphate salts, halogenated amines, betaine, guanidine, etc. Among them, quaternary ammonium salts have high efficiency and broad-spectrum bactericidal properties.

[0005] Currently, the main methods for modifying textiles to provide antibacterial and UV protection include primary treatment and post-treatment methods. Primary treatment involves adding antibacterial or UV-protective agents to the fiber spinning material before spinning it into textiles. This method can significantly extend the antibacterial and UV-protective effects of textiles and improve durability; however, the process is difficult and requires high technical expertise and sophisticated physicochemical properties of the antibacterial and UV-protective agents. Post-treatment methods mainly include surface coating, impregnation, and microencapsulation. This method directly treats the fabric with antibacterial or UV-protective agents, is simple to operate, and has low cost, but its durability is poor.

[0006] Antibacterial and UV-protective textiles should, without altering the original properties and comfort of the textiles, be treated with antibacterial and UV-protective agents to enable the textiles to effectively resist the damage of bacteria and ultraviolet rays for a long time, without causing harm to human skin. Summary of the Invention

[0007] In view of the shortcomings of the prior art, the purpose of this invention is to provide an antibacterial and UV-protective compound and its preparation method, aiming to solve the problems of existing antibacterial and UV-protective compounds having weak antibacterial and UV-protective properties, high solubility, complex preparation process, and drug resistance to microorganisms.

[0008] To achieve the above objectives, the present invention adopts the following technical solution:

[0009] An antibacterial and UV-resistant compound is provided, comprising an antibacterial group and a UV-resistant group; the antibacterial group and the UV-resistant group are bonded together by a cyanuric chloride active group, and its general structural formula (I) is as follows:

[0010]

[0011] In general formula (I), R1 is an antibacterial group selected from one of haloamines, zwitterions, antibacterial peptides, quaternary ammonium salts, and quaternary phosphorus salts;

[0012] R2 is an anti-ultraviolet group, selected from one of the residues remaining after the reaction of benzophenone and its derivatives, benzotriazole and its derivatives, salicylate and its derivatives with halogen atoms.

[0013] Preferably, the haloamine is one of the residues remaining after the reaction of one of the following general formulas (II1, II2, II3) with a halogen atom:

[0014]

[0015] Wherein, X is selected from halogen atoms, preferably Cl, Br or I; D is H, or terminal hydroxyl or terminal amino, preferably one of -H, -CH2CH2OH, -CH2CH2NH2, -CH2CH2CH2NH2, -CH2CH2CH2OH.

[0016] Preferably, the zwitterion is one of the residues remaining after the reaction of the following general formula (III) structure with a halogen atom:

[0017]

[0018] In structural formula (III), A is a reactive group, preferably OH, NH2, or SH;

[0019] R3 is -(CH2) m NH(CH2) n CH3, or -(CH2) p Where m, n, p = 0~10, preferably 1, 2, 3, 4, 5, 6, 7, 8, 9, 10. m, n and p can be the same or different;

[0020] R4 and R5 are selected from H or -(CH2), respectively. q CH3, where q = 0 to 18, preferably 0, 1, 2, 3, 4, 5, 7, 9, 11, 12; R4 and R5 may be the same or different;

[0021] R6 is -(CH2) r NH(CH2) t , or -(CH2)u Where r, t, u = 1 to 10, preferably 1, 2, 3, 4, 5, 6, 8; r, t, u can be the same or different;

[0022] Y is -SO3 - -COO - and -PO\s\do 3- 3(4).

[0023] Preferably, the quaternary ammonium salt or quaternary phosphonium salt is one of the residues remaining after the reaction of one of the following general formulas (IV1, IV2, IV3) with a halogen atom:

[0024]

[0025] Wherein: B is a reactive group, preferably OH, NH2, or SH;

[0026] Z is either N or P;

[0027] Y is a halogen, preferably Br, Cl or I;

[0028] R7, R 11 R 13 C with heteroatom substitution or no substitution l-18 Hydrocarbon group, preferably C l-18 alkyl;

[0029] R8, R9, R 10 R 12 R 14 C with heteroatom substitution or no substitution l-18 Hydrocarbon group, preferably C l-18 Alkyl, benzene ring, or substituted benzene ring; wherein C 1-18 Alkyl groups are preferably CH3,C2H5;

[0030] R8, R9, R 10 R 12 R 14 They can be the same or different.

[0031] Preferably, the structure of the benzophenone and its derivatives of the general formula (V1, V2) is one of the residues remaining after the reaction with the halogen atom:

[0032]

[0033] Among them, R 15 -R 24 and R 15 '-R 24 Selected from H, SO3H, and monovalently substituted / unsubstituted C 1-18 A type of hydrocarbon group or monovalent polar group;

[0034] R 15 R 16 R 17 R 18 R 19 R 20 R2, R 22 R 23 and R 24 They can be the same or different; R 15 ', R 16 ', R 17 ', R187', R 21 ', R 22 ', R 23 'and R 24 They can be the same or different;

[0035] R 15 -R 24 and R 15 '-R 24 The 'contains at least one terminal NH2 or terminal OH, preferably -(CH2) m NH2、-(CH2) m OH; m = 0 to 10, wherein m is preferably 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10;

[0036] M is selected from O, S, Se, C(O), SO2, NH, C 1-3 One of the hydrocarbon groups.

[0037] Preferably, the residues remaining after the reaction of the benzotriazole and its derivatives with the general formula (VI) are:

[0038]

[0039] R in the general formula (VI) structure 25 It can be H, Cl, or Br;

[0040] R 26 It is CH3 or C(CH3)3;

[0041] R 27 It is H or C(CH3)3 or C(CH3)2C6H5 or CH3.

[0042] Preferably, the salicylate ester and its derivatives of general formula (VII) are one of the residues remaining after the reaction with a halogen atom:

[0043]

[0044] In the general formula (VII) structure, R 28It is H or CH(CH3)2 or C6H5.

[0045] This invention also provides a method for preparing the above-described compound, comprising reacting a compound having the following general formula (VIII) with an antibacterial compound having the general structural formula R1-H and an anti-ultraviolet compound having the general structural formula R2-H to obtain the compound (I):

[0046] X, X1, and X2 are halogens, with Br, Cl, or I being preferred.

[0047] Preferably, the reaction is carried out under the action of a Lewis base, wherein the Lewis base is selected from one or more of alkali metals, alkaline earth metals, inorganic bases, or organic tertiary amines;

[0048] Preferably, the inorganic base is selected from one or more of sodium hydroxide, potassium hydroxide, magnesium hydroxide, calcium hydroxide, potassium carbonate, potassium bicarbonate, sodium carbonate, and sodium bicarbonate.

[0049] Preferably, the reaction temperature is -20 to 50°C; more preferably, it is -20°C, -15°C, -10°C, 0°C, 5°C, 10°C, 15°C, 20°C, 25°C, 30°C, 35°C, 40°C, 45°C, 50°C, 55°C, or 60°C.

[0050] Preferably, the Lewis base is selected from one or more of sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, trisodium phosphate, disodium hydrogen phosphate, sodium silicate, trimethylamine, triethylamine, and tripropylamine.

[0051] The advantages of this invention are as follows: The antibacterial and UV-protective compound of this invention firmly bonds the antibacterial and UV-protective groups together with the cyanuric chloride chemical linking group. Furthermore, the cyanuric chloride is chemically bonded to the surfaces of cotton textiles, plastics, and rubber through the third chlorine atom, resulting in a durable antibacterial and UV-protective surface. Simultaneously, this antibacterial and UV-protective modification does not affect the original physicochemical properties of polymer fibers, plastics, and rubber, does not have harmful effects on human skin, has good biocompatibility, and the synthesis process is simple and easy to implement, possessing industrial production value. Its antibacterial and UV-protective mechanism is as follows: When foreign bacteria invade, the positively charged antibacterial substance can adhere to the negatively charged bacterial cell wall through electrostatic adsorption. The long-chain alkyl groups of the antibacterial substance pierce the bacterial cell wall, simultaneously altering the cell wall permeability, causing cytolysis, and resulting in the outflow of intracellular substances. This disrupts the normal physiological metabolic activities of the bacteria, leading to bacterial death. When exposed to ultraviolet radiation, the UV-protective group can absorb ultraviolet light and convert it into energy, releasing or consuming the energy in the form of heat or harmless low-energy radiation to achieve the effect of resisting ultraviolet radiation. Attached Figure Description

[0052] Figure 1 The present invention modifies the antibacterial properties of cotton textiles with antibacterial and anti-ultraviolet compounds.

[0053] Figure 2 The present invention modifies the UV resistance of cotton textiles with antibacterial and UV-resistant compounds.

[0054] Figure 3 This is a schematic diagram illustrating the synthesis of the antibacterial and anti-UV compound 1 synthesized in Example 1 of the present invention.

[0055] Figure 4 This is a schematic diagram illustrating the synthesis of antibacterial and UV-protective compound 2 in Example 2 of the present invention.

[0056] Figure 5 This is a schematic diagram illustrating the synthesis of antibacterial and UV-protective compound 3 in Example 3 of the present invention.

[0057] Figure 6 This is a schematic diagram illustrating the synthesis of the pyridine quaternary ammonium salt intermediate of the present invention.

[0058] Figure 7 This is a schematic diagram illustrating the synthesis of the antibacterial and UV-protective compound 4 synthesized in Example 4 of the present invention.

[0059] Figure 8 This is a schematic diagram illustrating the synthesis of antibacterial and UV-protective compound 5 in Example 5 of the present invention.

[0060] Figure 9 This is a schematic diagram illustrating the synthesis of antibacterial and UV-protective compound 6 in Example 6 of the present invention.

[0061] Figure 10 This is a schematic diagram illustrating the synthesis of antibacterial and UV-protective compound 7 in Example 7 of the present invention. Detailed Implementation

[0062] To make the objectives, technical solutions, and advantages of this invention clearer, the invention will be further described in detail below with reference to the accompanying drawings and embodiments. It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention. Unless otherwise specified, the experimental methods described below are all routine operations, and the reagents used are commercially available unless otherwise specified.

[0063] Example 1

[0064] Weigh 8.91 g of N,N-dimethylethanolamine and 21.15 g of bromooctane into a 500 ml three-necked flask. Heat to 80 °C with mechanical stirring and continue reacting for 6 h. Cool to room temperature, wash with petroleum ether at least five times, and then distill under reduced pressure to obtain a white powder solid, which is the quaternary ammonium salt intermediate [HO-(CH2)2-N(CH3)2C8H]. 17]Br, with a yield of 97.05%.

[0065] Weigh 3.75g of cyanuric chloride into a three-necked flask, add a small amount of ultrapure water, and under mechanical stirring, add 5.52g of [HO-(CH2)2-N(CH3)2C8H]. 17 Br and 4.16g of potassium carbonate were reacted at a temperature not exceeding 20℃ for 8 hours to obtain a clear and transparent antibacterial compound (intermediate I).

[0066] Weigh 4.30 g of 4,4'-dihydroxybenzophenone and 2.96 g of potassium carbonate into a beaker, add 30 ml of tetrahydrofuran and 30 ml of ultrapure water to dissolve them, and then add them to the intermediate reaction system of the synthesized antibacterial compound. After continuous mechanical stirring and reaction at 60 °C or below for 10 h, wash repeatedly with petroleum ether 5 times, remove the solvent by vacuum distillation, then freeze the crude product at -70 °C for 24 h, and then freeze-dry for 72 h to obtain antibacterial and anti-UV compound 1 (pale yellow powder), with a product yield of 86.12%. The NMR data are (600MHz, DMSO) δ9.68 (s, 1H), δ7.58 (d, 2H), δ6.97 (d, 2H), δ6.80 (d, 2H), δ4.11 (t, 2H), δ2.78 (dd, 2H), δ2.34 (m, 2H), δ2.27 (s, 6H), δ1.36–1.26 (s, 14H), δ0.88 (t, 3H). Figure 3 This is a schematic diagram of the synthesis of antibacterial and anti-UV compound 1 synthesized in Example 1.

[0067] Example 2

[0068] Weigh 8.91 g of N,N-dimethylethanolamine and 22.21 g of 1-bromodecane into a 500 ml three-necked flask. Heat to 90 °C with mechanical stirring and continue reacting for 4 h. Cool to room temperature, wash with petroleum ether at least five times, and distill under reduced pressure to obtain a white powder solid, which is the quaternary ammonium salt intermediate [HO-(CH2)2-N(CH3)2C]. 10 H 21 ]Br, with a yield of 95.15%.

[0069] Weigh 3.75g of cyanuric chloride into a three-necked flask, add a small amount of ultrapure water, and under mechanical stirring, add 3.95g of 4-aminobenzophenone and 4.01g of sodium carbonate. Control the system temperature to not exceed 20℃ and continue the reaction for 8 hours to obtain a clear and transparent antibacterial compound (intermediate II).

[0070] Weigh 6.22g of the quaternary ammonium salt intermediate [HO-(CH2)2-N(CH3)2C] 10 H 21Br and 3.16 g of sodium carbonate were added to the reaction system of the above-synthesized anti-UV compound intermediate. After continuous mechanical stirring and reaction at below 60 °C for 10 h, the mixture was washed five times with petroleum ether, the solvent was removed by vacuum distillation, and the mixture was frozen at -70 °C for 24 h. After freeze-drying for 72 h, a pale yellow powder antibacterial and anti-UV compound 2 was obtained, with a product yield of 81.56%. The NMR data were (600 MHz, DMSO) δ7.81 (d, 1H), δ7.61 (m, 2H), δ7.58 (t, 2H), δ7.51 (t, 2H), δ6.97 (d, 2H), δ4.11 (t, 2H), δ2.78 (dd, 2H), δ2.34 (m, 2H), δ2.27 (s, 6H), δ1.36–1.26 (s, 16H), δ0.88 (t, 3H). Figure 4 This is a schematic diagram illustrating the synthesis of antibacterial and UV-protective compound 2 in Example 2.

[0071] Example 3

[0072] Weigh 8.91 g of N,N-dimethylethanolamine and 24.91 g of bromododecane into a 500 ml three-necked flask. Heat to 60 °C with mechanical stirring and continue reacting for 12 h. Cool to room temperature, wash with petroleum ether at least five times, and distill under reduced pressure to obtain a white powder solid, which is the quaternary ammonium salt intermediate [HO-(CH2)2-N(CH3)2C]. 12 H 25 ]Br, with a yield of 92.31%.

[0073] Weigh 3.75g of cyanuric chloride into a three-necked flask, add a small amount of ultrapure water, and under mechanical stirring, add 6.75g of [HO-(CH2)2-N(CH3)2C]. 12 H 25 Br and 3.86g of sodium bicarbonate were reacted at a temperature not exceeding 20°C for 8 hours to obtain a clear and transparent antibacterial compound (intermediate III).

[0074] Weigh 4.51 g of 2-(2-hydroxy-5-benzyl)benzotriazole and 3.36 g of sodium bicarbonate, and add them to the intermediate reaction system of the synthesized antibacterial compound. After continuous mechanical stirring and reaction at 60°C or below for 10 h, wash the product five times with petroleum ether, remove the solvent by vacuum distillation, freeze the crude product at -70°C for 24 h, and then freeze-dry it for 72 h to obtain the antibacterial and UV-protective compound product (pale yellow powder). The product yield is 82.75%. The NMR data are (600MHz, DMSO) δ8.03(t,2H), δ7.71(s,1H), δ7,54(t,2H), δ7.00(d,1H), δ6.76(d,1H), δ4.11(t ,2H), δ2.78(dd,2H), δ2.34(s,2H), δ2.33(dd,3H), δ2.27(s,6H), δ1.36-1.26(s,20H), δ0.88(t,3H). Figure 5 This is a schematic diagram illustrating the synthesis of antibacterial and UV-protective compound 3 in Example 3.

[0075] Example 4

[0076] Weigh 10.91 g of 4-(aminomethyl)pyridine and 27.7 g of bromotetradecane into a 500 ml three-necked flask. Under mechanical stirring, heat to 90 °C and continue the reaction for 4 h. After cooling to room temperature, wash with petroleum ether more than 5 times and distill under reduced pressure to obtain the pyridine quaternary ammonium salt intermediate (white powder) with a yield of 90%. Figure 6 This is a schematic diagram illustrating the synthesis of pyridine quaternary ammonium salt intermediates.

[0077] Weigh 3.75 g of cyanuric chloride into a three-necked flask, add a small amount of ultrapure water, and under mechanical stirring, add 7.73 g of aminopyridine quaternary ammonium salt and 3.86 g of sodium bicarbonate. Control the system temperature to not exceed 20 °C and continue the reaction for 8 hours to obtain a clear and transparent antibacterial compound (intermediate IV).

[0078] Weigh 6.17 g of 2-hydroxy-4-methoxy-5-sulfonic acid benzophenone and 4.16 g of sodium bicarbonate, and add them to the intermediate IV reaction system of the synthesized antibacterial compound. After continuous mechanical stirring and reaction at 60°C or below for 10 h, wash repeatedly with petroleum ether 5 times, remove the solvent by vacuum distillation, and then freeze the crude product at -70°C for 24 h and freeze-dry for 72 h to obtain the antibacterial and UV-protective compound product (pale yellow powder). The product yield is 82%. The NMR data are (600MHz, DMSO) δ9.68(s,1H), δ8.90(d,2H), δ8.5(s,1H), δ8.09(s,1H), δ7.80(dd,2H), δ7.70(s,1H), δ7.58(dd,2H) , δ6.80(s,2H), δ6.79(s,1H), δ5.01(t,2H), δ4.35(s,2H), δ2.50(s,3H), δ2.01(m,2H), δ1.29-1.26(s,22H), δ0.88(t,3H). Figure 7 This is a schematic diagram of the synthesis of antibacterial and UV-protective compound 4 in Example 4, with a product yield of 90.32%.

[0079] Example 5

[0080] Weigh 3.75g of cyanuric chloride into a three-necked flask, add a small amount of ultrapure water, and under mechanical stirring, add 3.15g of 1-aminohydantoin hydrochloride and 3.86g of sodium bicarbonate. Control the system temperature to not exceed 20℃ and continue the reaction for 8 hours to obtain a clear and transparent antibacterial compound (intermediate V).

[0081] 6.17 g of benzophenone-2-hydroxy-4-methoxy-5-sulfonic acid and 3.36 g of sodium bicarbonate were weighed and added to the reaction system of intermediate V of the synthesized antibacterial compound. After continuous mechanical stirring and reaction at below 60 °C for 10 h, the product was washed five times with petroleum ether, and the solvent was removed by vacuum distillation. The crude product was then frozen at -70 °C for 24 h and freeze-dried for 72 h to obtain the antibacterial and UV-protective compound product (pale yellow powder). The product yield was 81.57%. The NMR data were (600 MHz, DMSO) δ9.68 (s, 1H), δ8.5 (s, 1H), δ8.3 (s, 1H), δ8.09 (s, 1H), δ7.70 (s, 1H), δ7.58 (d, 2H), δ6.80 (d, 2H), δ4.05 (s, 2H), δ2.50 (s, 3H). Figure 8 This is a schematic diagram illustrating the synthesis of antibacterial and UV-protective compound 5 in Example 5.

[0082] Example 6

[0083] Weigh 8.91 g of N,N-dimethylethanolamine and 27.71 g of bromotetradecane into a 500 ml three-necked flask. Heat to 60 °C with mechanical stirring and continue reacting for 12 h. Cool to room temperature, wash with petroleum ether at least five times, and distill under reduced pressure to obtain a white powder solid, which is the quaternary ammonium salt intermediate [HO-(CH2)2-N(CH3)2C]. 14 H 29 ]Br, with a yield of 90.23%.

[0084] Weigh 3.75g of cyanuric chloride into a three-necked flask, add a small amount of ultrapure water, and under mechanical stirring, add 7.32g of [HO-(CH2)2-N(CH3)2C]. 14 H 29 Br and 3.86g of sodium bicarbonate were reacted at a temperature not exceeding 20°C for 8 hours to obtain a clear and transparent antibacterial compound (intermediate III).

[0085] Weigh 2.76 g of salicylic acid and 3.36 g of sodium bicarbonate and add them to the intermediate reaction system of the synthesized antibacterial compound. After continuous mechanical stirring and reaction at 60 °C or below for 10 h, wash the product five times with petroleum ether, remove the solvent by vacuum distillation, freeze the crude product at -70 °C for 24 h, and then freeze-dry it for 72 h to obtain the antibacterial and UV-protective compound product (pale yellow powder). The product yield is 86.72%. The NMR data are (600MHz, DMSO) δ12.04(s,1H), δ8.07(dd,1H), δ7.79(t,1H), δ7.51(t,1H), δ7.34(dd,1H) , δ4.11(t,2H), δ2.78(dd,2H), δ2.34(m,2H), δ2.27(s,6H), δ1.36-1.26(s,24H), δ0.88(t,3H). Figure 9 This is a schematic diagram of the synthesis of antibacterial and UV-protective compound 6 in Example 6.

[0086] Example 7

[0087] Weigh 3.75 g of cyanuric chloride into a three-necked flask, add a small amount of ultrapure water, and under mechanical stirring, add 8.60 g of (5-hydroxypentyl)triphenylphosphine bromide and 3.86 g of sodium bicarbonate. Control the system temperature to not exceed 20 °C and continue the reaction for 18 h to obtain a clear and transparent antibacterial compound (intermediate III).

[0088] 2.76 g of salicylic acid and 3.36 g of sodium bicarbonate were weighed and added to the intermediate reaction system of the synthesized antibacterial compound. After continuous mechanical stirring and reaction at below 60 °C for 10 h, the product was washed five times with petroleum ether, and the solvent was removed by vacuum distillation. The crude product was then frozen at -70 °C for 24 h and freeze-dried for 72 h to obtain the antibacterial and UV-protective compound product (pale yellow powder). The product yield was 85.16%. The NMR data were (600 MHz, DMSO) δ12.04 (s, 1H), δ8.07 (dd, 1H), δ7.79 (t, 1H), δ7.51 (t, 1H), δ7.36–7.33 (s, 16H), δ4.0 (dd, 1H). Figure 10 This is a schematic diagram of the synthesis of antibacterial and UV-protective compound 7 in Example 7.

[0089] The minimum inhibitory concentration of the antibacterial and UV-protective compounds and their UV protection properties on the treated cotton textiles in the embodiments of the present invention are shown in Table 1.

[0090] Table 1

[0091]

[0092] Note: The UV protection is the test result of knitted textiles treated with 1.0wt% antibacterial and UV-resistant compound. The control knitted textiles have UVA>15%, UVB>15%, and UPF<20. Figure 1 This demonstrates the antibacterial properties of cotton textiles modified with typical antibacterial and UV-resistant compounds. Figure 2 This is a typical antibacterial and UV-resistant compound used to modify the UV resistance of cotton textiles.

[0093] The advantages of this invention are as follows: The antibacterial and UV-protective compound of this invention firmly bonds the antibacterial and UV-protective groups together with the cyanuric chloride chemical linking group. The cyanuric chloride then attaches the antibacterial and UV-protective components to the surface of cotton textiles, plastics, and rubber through the third chlorine atom of the cyanuric chloride chemical bond, resulting in a durable antibacterial and UV-protective surface. At the same time, this antibacterial and UV-protective modification does not affect the original physicochemical properties of polymer fibers, plastics, and rubber, does not have a harmful effect on human skin, has good biocompatibility, and the synthesis process is simple and easy to implement, making it valuable for industrial production.

[0094] The above are merely preferred embodiments of the present invention and are not intended to limit the scope of protection of the present invention. Any modifications, equivalent substitutions or improvements within the spirit of the present invention are covered within the scope of the claims of the present invention.

Claims

1. An antibacterial and UV-resistant compound, characterized in that: The antibacterial and anti-UV compound contains antibacterial groups and anti-UV groups; the antibacterial groups and anti-UV groups are linked by cyanuric chloride active groups, and its general structural formula (I) is as follows: In general formula (I), R1 is an antibacterial group selected from one of haloamines, zwitterions, quaternary ammonium salts, and quaternary phosphorus salts; R2 is an anti-ultraviolet group, selected from one of the residues remaining after the reaction of benzophenone and its derivatives, benzotriazole and its derivatives, salicylate and its derivatives with halogen atoms.

2. The antibacterial and anti-UV compound according to claim 1, characterized in that: The haloamine is one of the residues remaining after reacting one of the following general formulas (II1, II2, II3) with a halogen atom: Where X is selected from halogen atoms, specifically Cl, Br, or I; D is H, or a terminal hydroxyl group or a terminal amino group.

3. The antibacterial and anti-UV compound according to claim 1, characterized in that: The zwitterion is one of the residues remaining after the reaction of the following general formula (III) structure with a halogen atom: In structural formula (III), A is a reactive group selected from OH, NH2, or SH; R3 is -(CH2) m NH(CH2) n CH3, or -(CH2) p Where m, n, p = 0 to 10; m, n and p can be the same or different; R4 and R5 are selected from H or -(CH2), respectively. q CH3, where q = 0 to 18; R4 and R5 can be the same or different; R6 is -(CH2) r NH(CH2) t , or -(CH2) u , where r, t, u = 1 to 10; r, t, u can be the same or different; Y is -SO3 - -COO - or -PO\s\do 3- 3(4).

4. The antibacterial and anti-UV compound according to claim 1, characterized in that: The quaternary ammonium salt or quaternary phosphorus salt is one of the residues remaining after the reaction of one of the following general formulas (IV1, IV2, IV3) with a halogen atom: Wherein: B is a reactive group, selected from OH, NH2, or SH; Z is either N or P; Y is a halogen, selected from Br, Cl or I; R7, R 11 R 13 C with heteroatom substitution or no substitution l-18 hydrocarbon group; R8, R9, R 10 R 12 R 14 C with heteroatom substitution or no substitution l-18 The hydrocarbon group is selected from C l-18 Alkyl, benzene ring, or substituted benzene ring; R8, R9, R 10 R 12 R 14 They can be the same or different.

5. The antibacterial and anti-UV compound according to claim 1, characterized in that: One of the residues remaining after the general formula (V1, V2) structure of the benzophenone and its derivatives reacts with a halogen atom: Among them, R 15 -R 24 and R 15 '-R 24 Selected from H, SO3H, and monovalent / unsubstituted C respectively 1-18 A type of hydrocarbon group or monovalent polar group; R 15 R 16 R 17 R 18 R 19 R 20 R2, R 22 R 23 and R 24 They can be the same or different; R 15 ', R 16 ', R 17 ', R187', R 21 ', R 22 ', R 23 'and R 24 They can be the same or different; R 15 -R 24 and R 15 '-R 24 The ' group contains at least one terminal NH2 or terminal OH, selected from -(CH2) m NH2、-(CH2) m OH; m = 0~10; M is selected from O, S, Se, C(O), SO2, NH, or C. 1-3 One of the hydrocarbon groups.

6. The antibacterial and anti-UV compound according to claim 1, characterized in that: One of the residues remaining after the general formula (VI) structure of the benzotriazole and its derivatives reacts with a halogen atom: R in the general formula (VI) structure 25 It can be H, Cl, or Br; R 26 It is CH3 or C(CH3)3; R 27 It is H or C(CH3)3 or C(CH3)2C6H5 or CH3.

7. The antibacterial and anti-UV compound according to claim 1, characterized in that: One of the residues remaining after the general formula (VII) structure of the salicylate ester and its derivatives reacts with a halogen atom: In the general formula (VII) structure, R 28 It is H or CH(CH3)2 or C6H5.

8. A method for preparing the antibacterial and anti-UV compound as described in claim 1, characterized in that, A compound having the following general formula (VIII) is reacted with an antibacterial compound having the general structural formula R1-H and an anti-UV compound having the general structural formula R2-H to obtain compound (I), wherein: X, X1, and X2 are halogens, selected from Br, Cl, or I; The reaction is carried out at a reaction temperature of -20 to 60°C under the action of a Lewis base, wherein the Lewis base is selected from one or more of alkali metals, alkaline earth metals, inorganic bases, or organic tertiary amines.

9. The preparation method according to claim 8, characterized in that, The inorganic bases are selected from one or more of sodium hydroxide, potassium hydroxide, magnesium hydroxide, calcium hydroxide, potassium carbonate, potassium bicarbonate, sodium carbonate, sodium bicarbonate, sodium silicate, trisodium phosphate, and disodium hydrogen phosphate; the Lewis bases are selected from one or more mixtures of sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, trisodium phosphate, disodium hydrogen phosphate, sodium silicate, and trimethylamine.

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