Antibacterial and ultraviolet resistant compounds and methods of making the same

Abstract

The application discloses an antibacterial and anti-ultraviolet compound and a preparation method thereof. The antibacterial and anti-ultraviolet compound contains an antibacterial group and an anti-ultraviolet group in the structure; 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 high polymer fibers, plastics and rubbers, and can endow the high polymer fibers, the plastics and the rubbers with persistent and efficient antibacterial and anti-ultraviolet modification. Moreover, the preparation method is simple and easy to operate, is suitable for industrialized production, and has a wide application prospect.

Description

TECHNICAL FIELD

[0001] The present application relates to a kind of compound and its preparation method, especially to a kind of antibacterial anti-ultraviolet compound and its preparation method. BACKGROUND

[0002] Due to the destruction of the earth's ozone layer, the amount of ultraviolet radiation of the earth's sunlight gradually increases, and long-term harmful ultraviolet radiation can cause great harm to the human body, including skin sunburn, allergy, erythema, premature aging, and even the risk of skin cancer. Textiles, as the second line of defense for the human body, can help people resist the invasion of ultraviolet rays to some extent, but the effect is not good due to high ultraviolet transmittance. In textiles, natural textiles (cotton textiles) are more popular with consumers than synthetic textiles due to their breathability, moisture permeability, and comfort. However, the porous structure of textiles provides a habitat for microorganisms, especially when the skin dander, sweat, sebum, and metabolic products on the skin come into contact with the textiles, providing nutrients for microorganisms living in the textiles, which is conducive to the reproduction of microorganisms on the textiles, causing discoloration, odor, and affecting the original performance of the textiles. Long-term contact with human skin can also harm human health. Therefore, as people's needs increase, consumers want textiles to have antibacterial and anti-ultraviolet functions.

[0003] Among the commonly used anti-ultraviolet agents, benzophenone anti-ultraviolet absorbers can absorb ultraviolet light with a wavelength of 220-400 nm, and their synthesis and application are relatively widespread. Common types of 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 have a wide range of sources, good antibacterial effects, and biocompatibility, but the extraction cost is high; inorganic antibacterial agents are mainly metals, metal ions, and oxides, such as silver ions, copper ions, and titanium dioxide. The antibacterial mechanism of inorganic antibacterial agents is dissolution-type antibacterial, and the use of textiles containing free metal ions can inevitably harm the human body in the long term. Metals, whether in free or bound state, have extremely high toxicity even at low concentrations. Chinese Patent No. 202210992192.3 discloses a self-crosslinking textile antibacterial anti-ultraviolet finishing agent and its preparation method, in which the effective antibacterial component is polylysine and nano-silver. Silver ions can react with -SH on proteins, and nano-silver has toxicity to human cells and exhibits dose, nanoparticle size, and time dependence; organic antibacterial agents mainly include quaternary ammonium salts, quaternary phosphonium salts, halamines, betaines, guanidines, etc., among which quaternary ammonium salts have high efficiency and broad-spectrum bactericidal properties.

[0004] At present, the modification methods of antibacterial and anti-ultraviolet textiles mainly include original treatment method and post-treatment method. The original treatment method is to add antibacterial agent or anti-ultraviolet agent into fiber spinning material, and then spin into fiber to make textile. This method can greatly prolong the antibacterial and anti-ultraviolet effect of textile and improve the durability, but the operation process is difficult, and the physical and chemical properties of antibacterial agent and anti-ultraviolet agent are required to be high. The post-treatment method mainly includes surface coating method, dipping method and microcapsule method. This method directly treats the fabric with antibacterial agent or anti-ultraviolet agent, and the operation process is simple and the cost is low, but the durability is poor.

[0005] The antibacterial and anti-ultraviolet textile should not change the original performance and comfort of the textile, and after the treatment of the antibacterial agent and the anti-ultraviolet agent on the textile, the textile can resist the invasion of bacteria and ultraviolet for a long time, and will not harm the human skin. SUMMARY

[0006] In view of the shortcomings of the prior art, the purpose of the present application is to provide an antibacterial and anti-ultraviolet compound and a preparation method thereof, which aims to solve the problems of the existing antibacterial and anti-ultraviolet compounds, such as poor antibacterial and anti-ultraviolet performance, large dissolution, complex preparation process, and drug resistance to microorganisms.

[0007] In order to achieve the above purpose, the technical scheme adopted by the present application is as follows:

[0008] An antibacterial and anti-ultraviolet compound is provided, which contains an antibacterial group and an anti-ultraviolet group; the antibacterial group and the anti-ultraviolet group are bonded by a trichloroisocyanuric acid active group, and the structure general formula (I) is as follows:

[0009]

[0010] In general formula (I), R1 is an antibacterial group, which is selected from one of halogen amine, zwitterion, antibacterial peptide, quaternary ammonium salt and quaternary phosphonium salt.

[0011] R2 is an anti-ultraviolet group, which is selected from one of benzophenone and its derivatives, benzotriazole and its derivatives, and the residue after reaction of salicylate and its derivatives with halogen atoms.

[0012] Preferably, the halogen amine is one of the residues after reaction of one of the following general formulae (III, II2, II3) with halogen atoms:

[0013]

[0014] wherein X is selected from a halogen atom, preferably Cl, Br or I; D is H, or a terminal hydroxyl or terminal amino group, preferably one of -H, -CH2CH2OH, -CH2CH2NH2, -CH2CH2CH2NH2, -CH2CH2CH2OH.

[0015] Preferably, the zwitterion is one of the following general formula (III) structures after reaction with a halogen atom:

[0016]

[0017] In the structure (III), A is a reactive group, preferably OH, NH2, SH;

[0018] R3 is -(CH2) m NH(CH2) n CH3, or -(CH2) p wherein 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;

[0019] R4 and R5 are independently selected from H or -(CH2) q CH3, wherein q = 0-18, preferably 0, 1, 2, 3, 4, 5, 7, 9, 11, 12; R4 and R5 can be the same or different;

[0020] R6 is -(CH2) r NH(CH2) t , or -(CH2) u wherein r, t, u = 1-10, preferably 1, 2, 3, 4, 5, 6, 8; r, t, u can be the same or different;

[0021] Y is -SO3 - , -COO - and -PO\s\do3-3(4).

[0022] Preferably, the quaternary ammonium or phosphonium salt is one of the following general formula (IV1, IV2, IV3) structures after reaction with a halogen atom:

[0023]

[0024] wherein: B is a reactive group, preferably OH, NH2, SH;

[0025] Z is N or P;

[0026] Y is a halogen, preferably Br, Cl or I;

[0027] R7, R11 R 13 is a hydrocarbon group, preferably C l-18 alkyl, which is substituted or unsubstituted by a heteroatom, preferably by a heteroatom selected from the group consisting of O, N and S, and / or by a halogen atom, preferably by a halogen atom selected from the group consisting of F, Cl, Br and I, and / or by a hydrocarbon group, preferably by a C l-18 alkyl group, and / or by a heteroatom, preferably by a heteroatom selected from the group consisting of O, N and S, and / or by a halogen atom, preferably by a halogen atom selected from the group consisting of F, Cl, Br and I, and / or by a hydrocarbon group, preferably by a C

[0028] R8, R9, R 10 R 12 R 14 is a hydrocarbon group, preferably C l-18 alkyl, which is substituted or unsubstituted by a heteroatom, preferably by a heteroatom selected from the group consisting of O, N and S, and / or by a halogen atom, preferably by a halogen atom selected from the group consisting of F, Cl, Br and I, and / or by a hydrocarbon group, preferably by a C l-18 alkyl group, and / or by a heteroatom, preferably by a heteroatom selected from the group consisting of O, N and S, and / or by a halogen atom, preferably by a halogen atom selected from the group consisting of F, Cl, Br and I, and / or by a hydrocarbon group, preferably by a C 1-18 alkyl group, and / or by a heteroatom, preferably by a heteroatom selected from the group consisting of O, N and S, and / or by a halogen atom, preferably by a halogen atom selected from the group consisting of F, Cl, Br and I, and / or by a hydrocarbon group, preferably by a C

[0029] R8, R9, R 10 R 12 R 14 may be the same or different.

[0030] Preferably, one of the residues left after the reaction of the general structure (V1, V2) of the benzophenone and its derivatives with a halogen atom is:

[0031]

[0032] wherein R 15 -R 24 and R 15 '-R 24 ' is selected from the group consisting of H, SO3H, a monovalent substituted / unsubstituted C 1-18 hydrocarbon group, a monovalent polar group;

[0033] R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R2, R 22 , R 23 and R 24 may be the same or different; R 15 ', R 16 ', R 17 ', R187', R 21 ', R 22 ', R 23 ' and R 24 ' may be the same or different;

[0034] R 15 -R 24 and R 15 '-R 24 ' contain at least one terminal NH2or terminal OH, preferably -(CH2) mNH2, -(CH2) m OH; m = 0 to 10, wherein m is preferably 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10;

[0035] M is selected from O, S, Se, C(O), SO2, NH, C 1-3 one of the hydrocarbon groups.

[0036] Preferably, one of the residues left after the reaction of the structure of general formula (VI) of the benzotriazoles and their derivatives with a halogen atom is:

[0037]

[0038] R in the structure of general formula (VI) 25 is H, or Cl or Br;

[0039] R 26 is CH3or C(CH3)3;

[0040] R 27 is H or C(CH3)3or C(CH3)2C6H5or CH3.

[0041] Preferably, one of the residues left after the reaction of the structure of general formula (VII) of the salicylates and their derivatives with a halogen atom is:

[0042]

[0043] R in the structure of general formula (VII) 28 is H or CH(CH3)2or C6H5.

[0044] The present application also provides a process for the preparation of the above-mentioned compounds, by reacting a compound having the structure of general formula (VIII) with an antibacterial compound having the structure of general formula R1-H and an anti-UV compound having the structure of general formula R2-H, obtaining the compound (I):

[0045] X, X1and X2are halogens, preferably Br, Cl or I;

[0046] Preferably, the reaction is carried out in the presence of a Lewis base selected from one or more of the group consisting of inorganic bases of alkali metals, alkaline-earth metals or organic tertiary amines;

[0047] Preferably, the inorganic bases are selected from one or more of the group consisting of sodium hydroxide, potassium hydroxide, magnesium hydroxide, calcium hydroxide, potassium carbonate, potassium bicarbonate, sodium carbonate and sodium bicarbonate.

[0048] Preferably, the reaction temperature is -20 to 50℃; preferably -20℃, -15℃, -10℃, 0℃, 5℃, 10℃, 15℃, 20℃, 25℃, 30℃, 35℃, 40℃, 45℃, 50℃, 55℃, 60℃.

[0049] 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, tripropylamine.

[0050] The advantage of the present application is that the antibacterial and anti-ultraviolet compound of the present application chemically links the antibacterial group and the anti-ultraviolet group with the chemical linking group cyanuric chloride, firmly bonds the antibacterial component and the anti-ultraviolet component together through chemical bonding, and then chemically bonds the third chlorine atom of cyanuric chloride to the surface of cotton textiles, plastics and rubbers, to obtain a durable antibacterial and anti-ultraviolet surface. At the same time, the antibacterial and anti-ultraviolet modification does not affect the original physical and chemical properties of the high molecular fiber, plastic and rubber, and does not have harmful effects on human skin, has good biocompatibility, the synthesis process is simple and easy to perform, and has industrial production value. The antibacterial and anti-ultraviolet mechanism is that when foreign bacteria invade, the positively charged antibacterial substance can be adsorbed on the negatively charged bacterial cell wall through electrostatic adsorption, the long-chain alkyl group of the antibacterial substance pierces the bacterial cell wall, changes the permeability of the bacterial cell wall, causes cytolysis, intracellular substances flow out, the normal physiological metabolic activity of the bacteria is destroyed, and the bacteria die. When irradiated by ultraviolet light, the anti-ultraviolet group can absorb ultraviolet light and convert energy, release or consume energy in the form of heat energy or harmless low-energy radiation to achieve the effect of anti-ultraviolet. BRIEF DESCRIPTION OF DRAWINGS

[0051] Figure 1 The antibacterial performance of the cotton textile modified by the antibacterial and anti-ultraviolet compound of the present application.

[0052] Figure 2 The anti-ultraviolet performance of the cotton textile modified by the antibacterial and anti-ultraviolet compound of the present application.

[0053] Figure 3 The synthesis schematic diagram of the antibacterial and anti-ultraviolet compound 1 synthesized in Example 1 of the present application.

[0054] Figure 4 The synthesis schematic diagram of the antibacterial and anti-ultraviolet compound 2 synthesized in Example 2 of the present application.

[0055] Figure 5 The synthesis schematic diagram of the antibacterial and anti-ultraviolet compound 3 synthesized in Example 3 of the present application.

[0056] Figure 6 The synthesis schematic diagram of the pyridine quaternary ammonium salt intermediate of the present application.

[0057] Figure 7 Synthesis scheme of antibacterial and anti-ultraviolet compound 4 synthesized for example 4 of the present application.

[0058] Figure 8 Synthesis scheme of antibacterial and anti-ultraviolet compound 5 synthesized for example 5 of the present application.

[0059] Figure 9 Synthesis scheme of antibacterial and anti-ultraviolet compound 6 synthesized for example 6 of the present application.

[0060] Figure 10 Synthesis scheme of antibacterial and anti-ultraviolet compound 7 synthesized for example 7 of the present application. DETAILED DESCRIPTION

[0061] In order to make the purpose, technical solutions and advantages of the present application more clear, the present application is further described in detail below in combination with the drawings and examples. It should be understood that the specific examples described herein are only used to explain the present application, and are not used to limit the present application. The experimental methods of the following examples are conventional operations unless otherwise specified, and the reagents can be obtained through commercial channels.

[0062] Example 1

[0063] Take 8.91g of N,N-dimethyl ethanolamine and 21.15g of bromooctane in a 500ml three-necked flask, heat to 80℃ under mechanical stirring, continue to react for 6h, then cool to room temperature, wash with petroleum ether for more than 5 times, and distill under reduced pressure to obtain white powder solid, i.e. quaternary ammonium salt intermediate [HO-(CH2)2-N(CH3)2C8H 17 ]Br, with a yield of 97.05%.

[0064] Take 3.75g of cyanuric chloride in a three-necked flask, add a small amount of ultrapure water, add 5.52g of [HO-(CH2)2-N(CH3)2C8H 17 ]Br and 4.16g of potassium carbonate under mechanical stirring, control the system temperature not to exceed 20℃, continue to react for 8h, and then obtain clear and transparent antibacterial compound (intermediate I).

[0065] Take 4.30g 4,4'-dihydroxybenzophenone and 2.96g potassium carbonate in a beaker, add 30ml tetrahydrofuran and 30ml ultrapure water to dissolve, then add to the above-synthesized antibacterial compound intermediate reaction system, continue to react for 10h under continuous mechanical stirring and below 60℃, then wash with petroleum ether for 5 times, remove the solvent under reduced pressure, then freeze the crude product in a refrigerator at-70℃ for 24h, then freeze dry for 72h, then the antibacterial and ultraviolet resistant compound 1 (light yellow powder) is obtained, the product yield is 86.12%. The nuclear magnetic resonance data is (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 The synthesis schematic diagram of the antibacterial and ultraviolet resistant compound 1 synthesized in example 1 is shown in the following figure.

[0066] Example 2

[0067] Take 8.91g N,N-dimethylethanolamine and 22.21g 1-bromodecane in a 500ml three-necked flask, heat to 90℃ under mechanical stirring, continue to react for 4h, then cool to room temperature, wash with petroleum ether for more than 5 times, distill under reduced pressure to obtain white powder solid, then the quaternary ammonium salt intermediate [HO-(CH2)2-N(CH3)2C 10 H 21 ]Br is obtained, the yield is 95.15%.

[0068] Take 3.75g cyanuric chloride in a three-necked flask, add a small amount of ultrapure water, then add 3.95g 4-aminobenzophenone and 4.01g sodium carbonate under mechanical stirring, control the system temperature not to exceed 20℃, continue to react for 8h, then the clear and transparent antibacterial compound (intermediate II) is obtained.

[0069] Take 6.22g 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 anti-UV compound intermediate synthesized above, and the reaction was continued for 10 h under continuous mechanical stirring and below 60 °C. After repeated washing with petroleum ether for 5 times, the solvent was removed by reduced pressure distillation, and the product was obtained as a light yellow powder after freezing in a refrigerator at -70 °C for 24 h and freeze-drying for 72 h. The yield of the product was 81.56%. The nuclear magnetic resonance data were (600 MHz, DMSO) δ 7.81 (d, 1H), δ 7.61 (m, 2H), δ 7.58 (t, 2H), δ 7.51 (t, 2H), δ 6.97 (d, 2H), δ 4.11 (t, 2H), δ 2.78 (dd, 2H), δ 2.34 (m, 2H), δ 2.27 (s, 6H), δ 1.36-1.26 (s, 16H), δ 0.88 (t, 3H). Figure 4 The synthesis of the anti-UV compound 2 synthesized in Example 2 is shown in the following schematic diagram.

[0070] Example 3

[0071] 8.91 g of N,N-dimethylethanolamine and 24.91 g of bromododecane were weighed into a 500 ml three-necked flask, heated to 60 °C under mechanical stirring, and the reaction was continued for 12 h. After cooling to room temperature, the product was washed with petroleum ether for more than 5 times, and white powder solid was obtained after reduced pressure distillation, i.e. quaternary ammonium salt intermediate [HO-(CH2)2-N(CH3)2C 12 H 25 ]Br, with a yield of 92.31%.

[0072] 3.75 g of cyanuric chloride was weighed into a three-necked flask, and a small amount of ultrapure water was added. Under mechanical stirring, 6.75 g of [HO-(CH2)2-N(CH3)2C 12 H 25 ]Br and 3.86 g of sodium bicarbonate were added, and the temperature of the system was controlled not to exceed 20 °C. The reaction was continued for 8 h, and the clear and transparent anti-bacterial compound (intermediate III) was obtained.

[0073] To the above synthesized intermediate reaction system, 4.51 g of 2-(2-hydroxy-5- benzyl) benzotriazole and 3.36 g of sodium bicarbonate were weighed and added, and the reaction was continued for 10 h under continuous mechanical stirring and below 60 °C, and then washed repeatedly with petroleum ether for 5 times, and the solvent was removed by distillation under reduced pressure, and then the crude product was frozen in a refrigerator at -70 °C for 24 h, and then freeze-dried for 72 h to obtain the antibacterial and anti-ultraviolet compound product (light yellow powder), and the yield of the product was 82.75%. The nuclear magnetic resonance data were (600 MHz, DMSO) δ 8.03 (t, 2H), δ 7.71 (s, 1H), δ 7.54 (t, 2H), δ 7.00 (d, 1H), δ 6.76 (d, 1H), δ 4.11 (t, 2H), δ 2.78 (dd, 2H), δ 2.34 (s, 2H), δ 2.33 (dd, 3H), δ 2.27 (s, 6H), δ 1.36-1.26 (s, 20H), δ 0.88 (t, 3H). Figure 5 Synthetic scheme for synthesizing antibacterial and anti-ultraviolet compound 3 of Example 3.

[0074] Example 4

[0075] In a three-necked flask, 10.91 g of 4-(aminomethyl) pyridine and 27.7 g of bromotetradecane were weighed and heated to 90 °C under mechanical stirring, and the reaction was continued for 4 h, and then cooled to room temperature, and washed with petroleum ether for more than 5 times, and then distilled under reduced pressure to obtain the pyridine quaternary ammonium salt intermediate (white powder) with a yield of 90%. Figure 6 Synthetic scheme for the synthesis of the pyridine quaternary ammonium salt intermediate.

[0076] In a three-necked flask, 3.75 g of cyanuric chloride was weighed and a small amount of ultrapure water was added, and then 7.73 g of the amino pyridine quaternary ammonium salt and 3.86 g of sodium bicarbonate were added under mechanical stirring, and the temperature of the system was controlled to be not more than 20 °C, and the reaction was continued for 8 h to obtain clear and transparent antibacterial compound (intermediate IV).

[0077] Take 6.17g 2-hydroxy-4-methoxy-5-sulfonic acid benzophenone and 4.16g sodium bicarbonate, add to the above-synthesized antibacterial compound intermediate IV reaction system, continue to react for 10h under the condition of continuous mechanical stirring and below 60℃, then wash repeatedly with petroleum ether for 5 times, remove the solvent by distillation under reduced pressure, then freeze the crude product in the refrigerator at-70℃ for 24h, and freeze dry for 72h, then the antibacterial and anti-ultraviolet compound product (light yellow powder) is obtained, the product yield is 82%. The nuclear magnetic data is (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 The synthesis schematic diagram of the antibacterial and anti-ultraviolet compound 4 synthesized in Example 4 is shown in the following figure, and the product yield is 90.32%.

[0078] Example 5

[0079] Take 3.75g cyanuric chloride in a three-necked flask, add a small amount of ultrapure water, add 3.15g of 1-amino hydantoin hydrochloride and 3.86g of sodium bicarbonate under mechanical stirring, control the system temperature not to exceed 20℃, and continuously react for 8h, then the clear and transparent antibacterial compound (intermediate V) is obtained.

[0080] Take 6.17g 2-hydroxy-4-methoxy-5-sulfonic acid benzophenone and 3.36g sodium bicarbonate, add to the above-synthesized antibacterial compound intermediate V reaction system, continue to react for 10h under the condition of continuous mechanical stirring and below 60℃, then wash repeatedly with petroleum ether for 5 times, remove the solvent by distillation under reduced pressure, then freeze the crude product in the refrigerator at-70℃ for 24h, and freeze dry for 72h, then the antibacterial and anti-ultraviolet compound product (light yellow powder) is obtained, the product yield is 81.57%. The nuclear magnetic data is (600MHz, 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 The synthesis schematic diagram of the antibacterial and anti-ultraviolet compound 5 synthesized in Example 5 is shown in the following figure.

[0081] Example 6

[0082] Take 8.91 g of N,N-dimethyl ethanolamine, 27.71 g of bromotetradecane in a 500 ml three-necked flask, heated to 60°C under mechanical stirring, and the reaction was continued for 12 h, then cooled to room temperature, washed with petroleum ether for 5 times, and distilled under reduced pressure to obtain white powder solid, i.e. quaternary ammonium salt intermediate [HO-(CH2)2-N(CH3)2C 14 H 29 ]Br, with a yield of 90.23%.

[0083] Take 3.75 g of cyanuric chloride in a three-necked flask, add a small amount of ultrapure water, and then add 7.32 g of [HO-(CH2)2-N(CH3)2C 14 H 29 ]Br and 3.86 g of sodium bicarbonate under mechanical stirring, and control the system temperature not to exceed 20°C, and continue the reaction for 8 h to obtain a clear transparent antibacterial compound (intermediate III).

[0084] Take 2.76 g of salicylic acid and 3.36 g of sodium bicarbonate, and add them to the above-synthesized antibacterial compound intermediate reaction system, continue the reaction for 10 h under mechanical stirring and below 60°C, then wash repeatedly with petroleum ether for 5 times, remove the solvent by distillation under reduced pressure, then freeze the crude product in a refrigerator at -70°C for 24 h, and then freeze dry for 72 h to obtain an antibacterial and ultraviolet-resistant compound product (light yellow powder), with a product yield of 86.72%. The nuclear magnetic resonance data are (600 MHz, DMSO) δ 12.04 (s, 1H), δ 8.07 (dd, 1H), δ 7.79 (t, 1H), δ 7.51 (t, 1H), δ 7.34 (dd, 1H), δ 4.11 (t, 2H), δ 2.78 (dd, 2H), δ 2.34 (m, 2H), δ 2.27 (s, 6H), δ 1.36-1.26 (s, 24H), δ 0.88 (t, 3H). Figure 9 The synthesis schematic diagram of the antibacterial and ultraviolet-resistant compound 6 synthesized in Example 6.

[0085] Example 7

[0086] Take 3.75 g of cyanuric chloride in a three-necked flask, add a small amount of ultrapure water, and then add 8.60 g of (5-hydroxypentyl)triphenylphosphonium bromide and 3.86 g of sodium bicarbonate under mechanical stirring, and control the system temperature not to exceed 20°C, and continue the reaction for 18 h to obtain a clear transparent antibacterial compound (intermediate III).

[0087] Take 2.76 g of salicylic acid and 3.36 g of sodium bicarbonate, add to the above-synthesized antibacterial compound intermediate reaction system, continue to react for 10 h under continuous mechanical stirring and below 60℃, then wash repeatedly with petroleum ether for 5 times, remove the solvent under reduced pressure, then freeze the crude product in a refrigerator at -70℃ for 24 h, and then freeze dry for 72 h to obtain the antibacterial and anti-ultraviolet compound product (light yellow powder), with a yield of 85.16%. The nuclear magnetic resonance data are (600 MHz, DMSO) δ 12.04 (s, 1H), δ 8.07 (dd, 1H), δ 7.79 (t, 1H), δ 7.51 (t, 1H), δ 7.36-7.33 (s, 16H), δ 4.0 (dd, 1H). Figure 10 The following is a synthesis schematic diagram of the antibacterial and anti-ultraviolet compound 7 synthesized in Example 7.

[0088] The minimum inhibitory concentration of the antibacterial and anti-ultraviolet compound in the embodiments of the present application and the anti-ultraviolet performance of the cotton textile treated thereby are shown in Table 1.

[0089] Table 1

[0090]

[0091] Note: The anti-ultraviolet is the test result of the 1.0 wt% antibacterial and anti-ultraviolet compound treated knitted textile, and the control knitted textile has UVA>15%, UVB>15%, and UPF<20. Figure 1 The antibacterial performance of the typical antibacterial and anti-ultraviolet compound modified cotton textile. Figure 2 The anti-ultraviolet performance of the typical antibacterial and anti-ultraviolet compound modified cotton textile.

[0092] The present application has the advantages that the antibacterial and anti-ultraviolet compound of the present application chemically connects the antibacterial group and the anti-ultraviolet group to the trichloroisocyanuric acid chemical linker, firmly bonds the antibacterial component and the anti-ultraviolet component through the chemical bond, and then chemically bonds to the cotton textile, plastic and rubber surface through the third chlorine atom of the trichloroisocyanuric acid, to obtain a durable antibacterial and anti-ultraviolet surface. The antibacterial and anti-ultraviolet modification does not affect the original physical and chemical properties of the high molecular fiber, plastic and rubber, does not have harmful effects on human skin, has good biocompatibility, the synthesis process is simple and easy to perform, and has industrial production value.

[0093] The above is only a preferred embodiment of the present application, and is not used to limit the protection scope of the present application, any modification, equivalent replacement or improvement within the spirit of the present application is covered in the claim scope of the present application.

Claims

1. An antibacterial and anti-UV compound, characterized in that: The antibacterial anti-ultraviolet compound contains an antibacterial group and an anti-ultraviolet group; the antibacterial group and the anti-ultraviolet group are linked by a trichloro cyan active group, and the structural formula is as follows:

2. An antibacterial and anti-UV compound, characterized in that: The antibacterial anti-ultraviolet compound contains an antibacterial group and an anti-ultraviolet group; the antibacterial group and the anti-ultraviolet group are linked by a trichloro cyan active group, and the structural formula is as follows:

3. An antibacterial and anti-UV compound, characterized in that: The antibacterial anti-ultraviolet compound contains an antibacterial group and an anti-ultraviolet group; the antibacterial group and the anti-ultraviolet group are linked by a trichloro cyan active group, and the structural formula is as follows:

4. An antibacterial and anti-UV compound, characterized in that: The antibacterial anti-ultraviolet compound contains an antibacterial group and an anti-ultraviolet group; the antibacterial group and the anti-ultraviolet group are linked by a trichloro cyan active group, and the structural formula is as follows:

5. An antibacterial and anti-UV compound, characterized in that: The antibacterial anti-ultraviolet compound contains an antibacterial group and an anti-ultraviolet group; the antibacterial group and the anti-ultraviolet group are linked by a trichloro cyan active group, and the structural formula is as follows:

6. An antibacterial and anti-UV compound, characterized in that: The antibacterial anti-ultraviolet compound contains an antibacterial group and an anti-ultraviolet group; the antibacterial group and the anti-ultraviolet group are linked by a trichloro cyan active group, and the structural formula is as follows:

7. An antibacterial and anti-UV compound, characterized in that: The antibacterial anti-ultraviolet compound contains an antibacterial group and an anti-ultraviolet group; the antibacterial group and the anti-ultraviolet group are linked by a trichloro cyan active group, and the structural formula is as follows: The antibacterial anti-ultraviolet compound contains an antibacterial group and an anti-ultraviolet group; the antibacterial group and the anti-ultraviolet group are linked by a trichloro cyan active group, and the structural formula is as follows:

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