Antibacterial deodorant composition and method for producing same

Abstract

The present specification relates to an antibacterial deodorizing composition comprising a first compound of Chemical Formula 1; and a second compound different from the first compound, wherein the first compound is cross-linked to at least a portion of the second compound, and the antibacterial deodorizing composition has a guaiacol content of 300 ng or less, a 3-methylbutanal content of 250 ng or less, and a diacetyl content of 30 ng or less when evaluated for deodorization by Method A, and a method for preparing the same.

Description

[Technical Field]

[0001] This application claims the benefit of the filing date of Korean Patent Application No. 10-2021-0110455, filed with the Korean Intellectual Property Office on August 20, 2021, the entire contents of which are incorporated herein by reference.

[0002] The present specification relates to an antibacterial deodorizing composition and a method for producing the same. [Background technology]

[0003] In recent years, antibacterial and deodorizing properties have been required for a variety of products, including household goods and sanitary products. These products must have excellent antibacterial and deodorizing properties while maintaining properties suited to their respective functions. For example, sanitary products such as diapers and sanitary napkins are products for which water absorption is of paramount importance, and since these products come into direct contact with the human body, the importance of antibacterial and deodorizing effects is increasing.

[0004] However, when the above-mentioned products are manufactured by adding an antibacterial agent or a deodorizing agent to impart antibacterial and deodorizing effects, there are problems in that the water absorption ability is reduced or the antibacterial or deodorizing power is not maintained.

[0005] Therefore, there is a need to develop a composition that provides antibacterial and deodorizing effects while having sufficient water absorption and retention capabilities. Summary of the Invention [Problem to be solved by the invention]

[0006] The present specification provides an antibacterial deodorizing composition and a method for producing the same. [Means for solving the problem]

[0007] One embodiment of the present specification provides an antibacterial and deodorizing composition comprising a first compound represented by the following Chemical Formula 1; and a second compound different from the first compound, wherein the first compound is cross-linked to at least a portion of the second compound, and the antibacterial and deodorizing composition has a guaiacol content of 300 ng or less, a 3-methylbutanal content of 250 ng or less, and a diacetyl content of 30 ng or less when evaluated for deodorization, and the deodorizing evaluation is measured by the following Method A.

[0008] [ka]

[0009] In the above chemical formula 1, R1 to R3 each independently represent an alkyl group having 1 to 12 carbon atoms which is unsubstituted or substituted with a hydroxy group, At least one of R1 to R3 is an alkyl group having 8 to 12 carbon atoms, R4 is an alkylene group having 1 to 6 carbon atoms, X is a halogen;

[0010] [Method A] 1 g of the antibacterial and deodorant composition was placed in a 500 ml lab bottle, and 25 ml of artificial urine inoculated with microorganisms was poured into the bottle and incubated at 35°C for 24 hours. After that, guaiacol, 3-methylbutanal, and diacetyl were respectively collected in an adsorption tube, and the mass of each collected component was analyzed using GC / MS.

[0011] Another embodiment of the present disclosure provides a method for producing an antibacterial and deodorizing composition, comprising: (a) preparing a mixture of a first compound of Formula 1 and a second compound different from the first compound; and (b) crosslinking the mixture.

[0012] Another embodiment of the present specification provides a deodorizing composition comprising a first compound of Chemical Formula 1 above. [Effects of the Invention]

[0013] The antibacterial and deodorizing composition according to the present specification includes a surface cross-linked structure formed by an alcohol-based antibacterial and deodorizing monomer containing quaternary ammonium, thereby providing a composition that not only provides excellent antibacterial and deodorizing effects but also has high water retention capacity upon centrifugation and water absorption capacity under pressure.

[0014] The antibacterial deodorizing monomer of the present invention is contained in the composition in a crosslinked form rather than in the form of an additive, so that the durability of the antibacterial deodorizing composition is excellent and no elution problem occurs.

[0015] In particular, the antibacterial and deodorizing monomer of the present invention has both hydrophobic and hydrophilic properties due to having a long alkyl group having 8 to 12 carbon atoms and a hydroxy group, making it suitable for surface treatment and capable of achieving antibacterial and deodorizing effects.

[0016] Furthermore, by crosslinking the antibacterial and deodorizing monomer at 150°C to 220°C for more than 20 minutes, the desired antibacterial and deodorizing properties are obtained, and the centrifugal water retention capacity and pressure water absorption capacity are improved. [Brief explanation of the drawings]

[0017] [Figure 1] 1 illustrates an example of the particle structure of the antibacterial and deodorant composition of the present invention. [Figure 2] 1 shows NMR data of the antibacterial and deodorizing monomer produced in Production Example 1. [Figure 3] 1 shows NMR data of the antibacterial and deodorizing monomer produced in Production Example 1. [Figure 4] 1 shows NMR data of the antibacterial and deodorizing monomer produced in Production Example 1. [Figure 5] 1 shows NMR data of the antibacterial and deodorizing monomer produced in Production Example 1. [Figure 6] 1 shows NMR data of the antibacterial and deodorizing monomer produced in Production Example 1. [Figure 7] 1 shows NMR data of the antibacterial and deodorizing monomer produced in Production Example 1. [Figure 8] 1 shows NMR data of the antibacterial and deodorizing monomer produced in Production Example 1. DETAILED DESCRIPTION OF THE INVENTION

[0018] In this specification, when a part is said to "comprise" a certain component, this means that it can further include other components, rather than excluding other components, unless otherwise specified.

[0019] As used herein, an alkyl group may be straight or branched.

[0020] As used herein, an alkylene group refers to a divalent alkyl group, which may be straight or branched.

[0021] As used herein, halogen may be fluorine (F), chlorine (Cl), bromine (Br), or iodine (I).

[0022] The present specification will be explained in more detail below.

[0023] One embodiment of the present specification provides an antibacterial and deodorizing composition comprising a first compound represented by the following Chemical Formula 1; and a second compound different from the first compound, wherein the first compound is cross-linked to at least a portion of the second compound, and the antibacterial and deodorizing composition has a guaiacol content of 300 ng or less, a 3-methylbutanal content of 250 ng or less, and a diacetyl content of 30 ng or less when evaluated for deodorization, and the deodorizing evaluation is measured by the following Method A.

[0024] [ka]

[0025] In the above chemical formula 1, R1 to R3 each independently represent an alkyl group having 1 to 12 carbon atoms which is unsubstituted or substituted with a hydroxy group, At least one of R1 to R3 is an alkyl group having 8 to 12 carbon atoms, R4 is an alkylene group having 1 to 6 carbon atoms, X is a halogen;

[0026] [Method A] 1 g of the antibacterial and deodorant composition was placed in a 500 ml lab bottle, and 25 ml of artificial urine inoculated with microorganisms was poured into the bottle and incubated at 35°C for 24 hours. After that, guaiacol, 3-methylbutanal, and diacetyl were respectively collected in an adsorption tube, and the mass of each collected component was analyzed using GC / MS.

[0027] The antibacterial and deodorizing composition according to one embodiment of the present specification has antibacterial and deodorizing effects, and also provides excellent water retention capacity upon centrifugation and water absorption capacity under pressure.

[0028] Specifically, the antibacterial deodorizing composition of the present invention includes a structure in which the first compound of Chemical Formula 1 is crosslinked to at least a portion of the second compound, and when the antibacterial deodorizing composition is evaluated for deodorizing effect, the content of guaiacol is 300 ng or less, the content of 3-methylbutanal is 250 ng or less, and the content of diacetyl is 30 ng or less.

[0029] In one embodiment of the present specification, the deodorizing evaluation is measured by the following method A.

[0030] [Method A] 1 g of the antibacterial and deodorant composition was placed in a 500 ml lab bottle, and 25 ml of artificial urine inoculated with microorganisms was poured into the bottle and incubated at 35°C for 24 hours. After that, guaiacol, 3-methylbutanal, and diacetyl were respectively collected in an adsorption tube, and the mass of each collected component was analyzed using GC / MS.

[0031] In one embodiment of the present specification, the deodorizing evaluation can be carried out on odor components of artificial urine such as DMDS+DMTS, p-cresol, etc. in addition to guaiacol, diacetyl, and 3-methylbutanal. That is, in the above-mentioned method A, DMDS+DMTS or p-cresol is collected instead of guaiacol, diacetyl, or 3-methylbutanal, and the mass is analyzed.

[0032] In one embodiment of the present specification, when evaluating the deodorizing effect of the antibacterial deodorizing composition, the guaiacol content may be 300 ng or less, 260 ng or less, or 251 ng or less, preferably 200 ng or less, 199 ng or less, or 180 ng or less, and more preferably 173 ng or less, 170 ng or less, or 168 ng or less. There is no lower limit, but it may be, for example, 0 ng or more. The lower the content, the higher the deodorizing power against guaiacol.

[0033] In one embodiment of the present specification, when evaluating the deodorizing effect of the antibacterial deodorizing composition, the content of 3-methylbutanal may be 250 ng or less, 210 ng or less, or 205 ng or less, preferably 180 ng or less or 150 ng or less, and more preferably 130 ng or less, 129 ng or less, 124 ng or less, 102 ng or less, or 99 ng or less. There is no lower limit, but it may be, for example, 0 ng or more. A lower content means a higher deodorizing power against 3-methylbutanal.

[0034] In one embodiment of the present specification, when evaluating the deodorizing effect of the antibacterial deodorizing composition, the diacetyl content may be 30 ng or less, 29 ng or less, or 28 ng or less, preferably 25 ng or less or 24 ng or less, and more preferably 21 ng or less or 20 ng or less. There is no lower limit, but it may be, for example, 0 ng or more. The lower the content, the higher the deodorizing power against diacetyl.

[0035] In one embodiment of the present specification, the artificial urine used in the deodorization evaluation can be manufactured with the same composition as that described in the ESSITY document (J Wound Ostomy Continence Nurs. 2019;46(6):519-523.). Among the substances used in the deodorization evaluation, those that can be sterilized can be sterilized using an autoclave, and those that cannot be sterilized at high temperatures can be sterilized using a 0.20 μm membrane filter.

[0036] In one embodiment of the present specification, microorganisms used in the deodorizing evaluation include, but are not limited to, Escherichia coli (E. coli, CCUG 3274), Proteus mirabilis (P. mirabilis CCUG 4637), and Enterobacter Cloacae (E. Cloacae, CCUG 71839).

[0037] In one embodiment of the present specification, the microorganisms used in the deodorization evaluation may be a mixture of bacteria, i.e., one or more types of microorganisms may be mixed and used in the deodorization evaluation.

[0038] In one embodiment of the present specification, the concentration of one or more microorganisms used in the deodorization evaluation is 10 5 CFU / ml ~10 6 It may be CFU / ml.

[0039] In one embodiment of the present specification, the deodorizing evaluation is 10 5 CFU / ml of E. coli, 10 6 CFU / ml of Proteus mirabilis and 10 6 A mixture of CFU / ml of E. cloacae can be used.

[0040] In one embodiment of the present specification, the first compound is a monomer having antibacterial and deodorizing properties, and serves as a surface crosslinking agent.

[0041] The first compound represented by the above formula 1 is a quaternary ammonium compound with antibacterial properties, in which the cations of the ammonium molecules electrostatically adsorb to the anionic sites on the surface of microbial cells, and kill them by physicochemically destroying the cell surface structure through hydrophobic interactions. The hydrophobicity of the first compound varies depending on the number of carbon atoms in the alkyl group linked to the quaternary ammonium, resulting in different antibacterial properties.

[0042] In one embodiment of the present specification, R1 to R3 in the above Chemical Formula 1 are each independently an alkyl group having 1 to 12 carbon atoms which is unsubstituted or substituted with a hydroxy group, and at least one of R1 to R3 is an alkyl group having 8 to 12 carbon atoms.

[0043] In one embodiment of the present specification, the above R3 may be an alkyl group having 8 to 12 carbon atoms.

[0044] In one embodiment of the present specification, the above R3 may be a linear alkyl group having 8 to 12 carbon atoms.

[0045] In one embodiment of the present specification, the above R3 may be a linear alkyl group having 10 to 12 carbon atoms.

[0046] In one embodiment of the present specification, R3 may be a linear alkyl group having 8 carbon atoms.

[0047] In one embodiment of the present specification, R3 may be a linear alkyl group having 10 carbon atoms.

[0048] In one embodiment of the present specification, R3 may be a linear alkyl group having 12 carbon atoms.

[0049] If the number of carbon atoms in R3 is less than 8, for example, 4, the antibacterial and deodorizing properties of the antibacterial and deodorizing composition will be inferior.

[0050] In one embodiment of the present specification, the above R1 and R2 may each independently be an alkyl group having 1 to 12 carbon atoms which is unsubstituted or substituted with a hydroxy group.

[0051] In one embodiment of the present specification, the above R1 and R2 may each independently be an alkyl group having 1 to 8 carbon atoms which is unsubstituted or substituted with a hydroxy group.

[0052] In one embodiment of the present specification, the above R1 and R2 may each independently be an alkyl group having 1 to 5 carbon atoms which is unsubstituted or substituted with a hydroxy group.

[0053] In one embodiment of the present specification, the above R1 and R2 may each independently be a linear alkyl group having 1 to 5 carbon atoms which is unsubstituted or substituted with a hydroxy group.

[0054] In one embodiment of the present specification, the above R1 and R2 may each independently be a linear alkyl group having 1 to 3 carbon atoms which is unsubstituted or substituted with a hydroxy group.

[0055] In one embodiment of the present specification, at least one of R1 and R2 may be an alkyl group having 1 to 5 carbon atoms.

[0056] In one embodiment of the present specification, at least one of R1 and R2 may be a linear alkyl group having 1 to 5 carbon atoms.

[0057] In one embodiment of the present specification, at least one of R1 and R2 may be a linear alkyl group having 1 to 3 carbon atoms.

[0058] In one embodiment of the present specification, at least one of R1 and R2 may be a methyl group.

[0059] In one embodiment of the present specification, either one of the above R1 and R2 may be an alkyl group having 1 to 5 carbon atoms which is unsubstituted or substituted with a hydroxy group.

[0060] In one embodiment of the present specification, either one of the above R1 and R2 may be an alkyl group having 1 to 5 carbon atoms substituted with a hydroxy group.

[0061] In one embodiment of the present specification, either one of the above R1 and R2 may be an alkyl group having 1 to 5 carbon atoms.

[0062] In one embodiment of the present specification, the above R1 may be an alkyl group having 1 to 12 carbon atoms.

[0063] In one embodiment of the present specification, the above R2 may be an alkyl group having 1 to 12 carbon atoms which is substituted or unsubstituted with a hydroxy group.

[0064] In one embodiment of the present specification, R4 in the above Chemical Formula 1 may be a linear alkylene group having 1 to 6 carbon atoms.

[0065] In one embodiment of the present specification, R4 may be a linear alkylene group having 1 to 4 carbon atoms.

[0066] In one embodiment of the present specification, the above R4 may be a linear alkylene group having 2 to 4 carbon atoms.

[0067] In one embodiment of the present specification, R4 may be a linear alkylene group having 2 carbon atoms.

[0068] In one embodiment of the present specification, R4 may be a linear alkylene group having 3 carbon atoms.

[0069] In one embodiment of the present specification, R4 may be a linear alkylene group having 4 carbon atoms.

[0070] In one embodiment of the present specification, X in the above formula 1 may be Br or Cl.

[0071] In one embodiment of the present specification, the first compound may be any one of the following compounds:

[0072] [ka]

[0073] In the above compound, X is a halogen.

[0074] In one embodiment of the present specification, when the bacterial inhibition rate of the first compound is evaluated by the following method C, the bacterial inhibition rate against E. coli may be 88% or more, 89.3% or more, 90% or more, 93% or more, 94.4% or more, 95% or more, 96.1% or more, 98% or more, 98.9% or more, or 99% or more, and the bacterial inhibition rate against Proteus mirabilis may be 83% or more, 90% or more, 91.2% or more, 95% or more, 96.9% or more, 98% or more, 99% or more, or 99.9% or more. The higher the bacterial inhibition rate, the better the antibacterial activity. There is no upper limit, but it may be, for example, 100% or less.

[0075] [Method C] 25 ml of broth-type medium (Nutreint broth, BD DIFCP., 8 g / L) inoculated with 3,000 CFU / ml of bacteria was transferred to a 50 ml conical tube, and 0.01 g of the first compound was added and vortexed. The thoroughly mixed solution was incubated for 16 hours in a shaking water bath maintained at 35°C. After incubation, the solution was diluted 1 / 5 with 1X phosphate buffered saline (PBS) buffer solution and the absorbance (λ = 600 nm) was measured using a UV / Vis spectrophotometer. The measured absorbance was compared with the control, and the bacterial inhibition rate was calculated using the following formula: where the control refers to the medium solution without the first compound.

[0076] Bacterial suppression rate (%)={1-(A sample ) / (A reference )}×100 (A sample : absorbance of the medium solution containing the first compound, A reference : absorbance of the medium solution not containing the first compound)

[0077] In one embodiment of the present specification, bacteria used for evaluating the bacterial inhibition rate include E. coli and Proteus mirabilis.

[0078] In one embodiment herein, the second compound is a compound different from the first compound.

[0079] In one embodiment of the present specification, the second compound may be a super absorbent polymer (SAP).

[0080] The superabsorbent polymer is a functional polymer capable of absorbing several hundred times its own weight in water and several tens of times its own weight in artificial urine, and is an excellent polymeric substance with an excellent ability to retain water even under external pressure. Such superabsorbent polymers are widely used in sanitary products such as diapers and sanitary napkins.

[0081] In one embodiment of the present specification, the second compound can include a hydrogel polymer. In other words, the second compound can be a superabsorbent polymer, and the superabsorbent polymer can include a hydrogel polymer.

[0082] The hydrogel polymer refers to a polymer with a water content of 40% to 80% by weight based on the total weight of the hydrogel polymer. Here, the water content is the amount of water in the total weight of the hydrogel polymer, calculated by subtracting the weight of the polymer in a dry state from the total weight of the hydrogel polymer. Specifically, the water content is calculated by measuring the weight loss due to evaporation of water in the polymer during the drying process, in which the temperature of the polymer is increased using infrared heating. The drying conditions are to increase the temperature from room temperature to approximately 180°C and then maintain the temperature at 180°C. The total drying time is set to 20 minutes, including a 5-minute temperature increase step, and the water content is measured.

[0083] The hydrogel polymer can be prepared by crosslinking an acrylic acid-based monomer, in which at least a portion of the acidic groups have been neutralized, with an internal crosslinking agent. To this end, a monomer composition in a solution state containing the acrylic acid-based monomer, in which at least a portion of the acidic groups have been neutralized, a polymerization initiator, an internal crosslinking agent, and a solvent can be used.

[0084] The acrylic acid monomer is a compound represented by the following chemical formula 2.

[0085] [Case 2] R-COO-R'

[0086] In the above chemical formula 2, R is an alkyl group having 2 to 5 carbon atoms and containing an unsaturated bond, and R' is hydrogen, a monovalent or divalent metal, an ammonium group, or an organic amine salt.

[0087] Preferably, the acrylic acid monomer includes at least one selected from the group consisting of acrylic acid, methacrylic acid, and their monovalent metal salts, divalent metal salts, ammonium salts, and organic amine salts.

[0088] Here, the acrylic acid-based monomer may have an acidic group, and at least a portion of the acidic group may be neutralized. Preferably, the monomer may be partially neutralized with an alkaline substance such as sodium hydroxide, potassium hydroxide, or ammonium hydroxide. In this case, the degree of neutralization of the acrylic acid-based monomer may be 40 mol% or more, or about 45 mol% or more, and 95 mol% or less, 80 mol% or less, or 75 mol% or less. The range of the neutralization degree may be adjusted depending on the final physical properties. However, if the degree of neutralization is too high, the neutralized monomer may precipitate, making it difficult to smoothly proceed with polymerization. Conversely, if the degree of neutralization is too low, the water absorption of the polymer may be significantly reduced and the polymer may exhibit properties similar to elastic rubber, which makes it difficult to handle.

[0089] The concentration of the acrylic acid-based monomer may be about 20% by weight or more, or about 40% by weight or more, and about 60% by weight or less, or about 50% by weight or less, based on the monomer composition containing the raw materials for the superabsorbent polymer, including the acrylic acid-based monomer with at least a portion of the acidic groups neutralized, a polymerization initiator, and an internal crosslinking agent, and a solvent. The concentration may be set appropriately, taking into consideration the polymerization time and reaction conditions. However, if the concentration of the monomer is too low, the yield of the superabsorbent polymer may be low, resulting in economical problems. Conversely, if the concentration is too high, process problems may occur, such as partial precipitation of the monomer or reduced pulverization efficiency during pulverization of the polymerized hydrogel polymer, and the physical properties of the superabsorbent polymer may be reduced.

[0090] The internal crosslinking agent is used to crosslink the inside of a polymer obtained by polymerizing an acrylic acid-based monomer, and specific examples thereof include polyethylene glycol diacrylate, N,N'-methylenebisacrylamide, trimethylolpropane tri(meth)acrylate, ethylene glycol di(meth)acrylate, polyethylene glycol (meth)acrylate, propylene glycol di(meth)acrylate, polypropylene glycol (meth)acrylate, butanediol di(meth)acrylate, butylene glycol di(meth)acrylate, and diethylene glycol. One or more selected from the group consisting of di(meth)acrylate, hexanediol di(meth)acrylate, triethylene glycol di(meth)acrylate, tripropylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acrylate, dipentaerythritol pentaacrylate, glycerin tri(meth)acrylate, pentaerythritol tetraacrylate, triarylamine, ethylene glycol diglycidyl ether, propylene glycol, glycerin, and ethylene carbonate can be used, but the examples are not limited to those mentioned above.

[0091] The internal crosslinking agent is included in an amount of 0.01 to 1 part by weight based on 100 parts by weight of the acrylic acid-based monomer, and can crosslink the polymerized polymer. If the content of the internal crosslinking agent is less than 0.01 part by weight, the improvement effect due to crosslinking will be negligible. If the content of the internal crosslinking agent is more than 1 part by weight, the water absorption capacity of the superabsorbent resin may be reduced. More specifically, the internal crosslinking agent may be included in an amount of 0.01 parts by weight or more, 0.05 parts by weight or more, or 0.1 parts by weight or more, and 1 part by weight or less, 0.5 parts by weight or less, or 0.3 parts by weight or less based on 100 parts by weight of the acrylic acid-based monomer.

[0092] The polymerization initiator is not particularly limited as long as it is one that is generally used in the production of highly water-absorbent resins.

[0093] Specifically, the polymerization initiator may be a thermal polymerization initiator or a photopolymerization initiator using UV irradiation, depending on the polymerization method. However, even in the photopolymerization method, a certain amount of heat is generated by irradiation such as UV irradiation, and a certain amount of heat is generated as the polymerization reaction, which is an exothermic reaction, progresses, so a thermal polymerization initiator may also be included.

[0094] The photopolymerization initiator may be any compound capable of forming radicals by exposure to light such as ultraviolet light, and any structure thereof may be used.

[0095] The photopolymerization initiator may be at least one selected from the group consisting of benzoin ether, dialkyl acetophenone, hydroxyl alkyl ketone, phenyl glyoxylate, benzyl dimethyl ketal, acyl phosphine, and α-aminoketone. Specific examples of acyl phosphines include commercially available Irgacure 819 (bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide) and lucirin TPO (diphenyl(2,4,6-trimethylbenzoyl)-phosphine oxide). A wide variety of photoinitiators are described in detail in Reinhold Schwalm's book, "UV Coatings: Basics, Recent Developments and New Applications" (Elsevier, 2007), p. 115, and are not limited to the above examples.

[0096] The photopolymerization initiator may be included in an amount of 0.001 to 1 part by weight based on 100 parts by weight of the acrylic acid-based monomer. If the amount of the photopolymerization initiator is less than 0.001 part by weight, the polymerization rate may be slow. If the amount of the photopolymerization initiator is more than 1 part by weight, the molecular weight of the superabsorbent resin may be small, resulting in inconsistent physical properties. More specifically, the photopolymerization initiator may be included in an amount of 0.005 parts by weight or more, 0.007 parts by weight or more, or 0.01 parts by weight or more, and 0.5 parts by weight or less, 0.3 parts by weight or less, or 0.1 parts by weight or less based on 100 parts by weight of the acrylic acid-based monomer.

[0097] In addition, when a thermal polymerization initiator is further included as the polymerization initiator, the thermal polymerization initiator may be at least one selected from the group consisting of persulfate initiators, azo initiators, hydrogen peroxide, and ascorbic acid. Specific examples of persulfate initiators include sodium persulfate (NaSO), potassium persulfate (KSO), and ammonium persulfate ((NHSO). Examples of azo initiators include 2,2-azobis(2-amidinopropane) dihydrochloride and 2,2-azobis(N,N-dimethylene)isobutyramidine dihydrochloride. dihydrochloride, 2-(carbamoylazo)isobutylonitrile, 2,2-azobis[2-(2-imidazolin-2-yl)propane]dihydrochloride, and 4,4-azobis-(4-cyanovaleric acid). A more comprehensive list of thermal initiators is provided on page 203 of Odian's book, "Principle of Polymerization" (Wiley, 1981), and is not limited to the examples mentioned above.

[0098] The thermal polymerization initiator may be included in an amount of 0.001 to 1 part by weight based on 100 parts by weight of the acrylic acid-based monomer. If the amount of the thermal polymerization initiator is less than 0.001 part by weight, little additional thermal polymerization occurs, resulting in insignificant benefits from the addition of the thermal polymerization initiator. If the amount of the thermal polymerization initiator is more than 1 part by weight, the molecular weight of the superabsorbent resin may be small, resulting in inconsistent physical properties. More specifically, the thermal polymerization initiator may be included in an amount of 0.005 parts by weight or more, or 0.01 parts by weight or more, or 0.1 parts by weight or more, and 0.5 parts by weight or less, or 0.3 parts by weight or less based on 100 parts by weight of the acrylic acid-based monomer.

[0099] In addition to the polymerization initiator, one or more additives such as surfactants, thickeners, plasticizers, storage stabilizers, and antioxidants may be further included as needed during crosslinking polymerization.

[0100] The monomer composition including the acrylic acid-based monomer, the internal crosslinking agent, the polymerization initiator, and optional additives may be prepared in the form of a solution dissolved in a solvent.

[0101] The solvent may be any solvent capable of dissolving the above-mentioned components, and may be, for example, water, ethanol, ethylene glycol, diethylene glycol, triethylene glycol, 1,4-butanediol, propylene glycol, ethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, methyl ethyl ketone, acetone, methyl amyl ketone, cyclohexanone, cyclopentanone, diethylene glycol monomethyl ether, diethylene glycol ethyl ether, toluene, xylene, butyrolactone, carbitol, methyl cellosolve acetate, and N,N-dimethylacetamide. The solvent may be present in an amount that is the balance of the total content of the monomer composition excluding the above-mentioned components.

[0102] On the other hand, the method for forming a hydrogel polymer by photopolymerizing such a monomer composition is not particularly limited as long as it is a commonly used polymerization method.

[0103] Specifically, the photopolymerization can be carried out by irradiating ultraviolet light having an intensity of 5 mW or more, 8 mW or more, or 10 mW or more, and 30 mW or less, or 20 mW or less, at a temperature of 60° C. or more, or 70° C. or more, and 90° C. or less, or 85° C. or less. Under these conditions, a crosslinked polymer can be formed with excellent polymerization efficiency during photopolymerization.

[0104] In addition, when the photopolymerization is carried out, it may be carried out in a reactor equipped with a movable conveyor belt. However, the above-mentioned polymerization method is only an example, and the present invention is not limited to the above-mentioned polymerization method.

[0105] Furthermore, when photopolymerization is carried out in a reactor equipped with a movable conveyor belt as described above, the resulting hydrogel polymer is typically in the form of a sheet-like hydrogel polymer having the width of the belt. The thickness of the polymer sheet varies depending on the concentration and injection rate of the monomer composition injected, but it is preferable to supply the monomer composition so as to obtain a sheet-like polymer having a thickness of about 0.5 cm to about 5 cm. Supplying the monomer composition so that the thickness of the sheet-like polymer is too thin is undesirable because it reduces production efficiency, while a thickness of more than 5 cm can result in the polymerization reaction not occurring uniformly throughout the entire thickness due to the excessive thickness.

[0106] The hydrogel polymer polymerized as described above can finally take on the form of particles through the processes of drying, pulverization and classification.

[0107] The drying method may be any method commonly used in the drying process of hydrogel polymers, without limitation. Specifically, the drying step may be carried out by a method such as supplying hot air, irradiating with infrared rays, irradiating with ultrashort waves, or irradiating with ultraviolet rays.

[0108] The water content of the hydrogel polymer after drying may be 1% by weight to 10% by weight, or 1% by weight to 5% by weight.

[0109] The pulverization process may be carried out so that the particle size of the hydrogel polymer is 150 μm to 850 μm. Specifically, the polymer may be pulverized using a pulverizer such as a pin mill, a hammer mill, a screw mill, a roll mill, a disc mill, or a jog mill, but is not limited thereto.

[0110] After the pulverization step, the hydrogel polymer may be subjected to a step of classifying the polymer by particle size.

[0111] In the antibacterial and deodorant composition according to one embodiment of the present specification, the first compound is cross-linked to at least a portion of the second compound.

[0112] In one embodiment of the present specification, the antibacterial deodorizing composition may exist in the form of particles having a sea-island structure. Specifically, the second compound forms a core structure, and the first compound is crosslinked to at least a portion of the second compound, thereby forming a discontinuous crosslinked structure in the form of islands on the core. An example of the particle structure of the antibacterial deodorizing composition of the present invention is shown in Figure 1.

[0113] Conventionally, antibacterial agents have been introduced as additives to impart antibacterial properties to superabsorbent polymers, but this has led to problems such as a decrease in the safety of the superabsorbent polymer or a decrease in basic physical properties such as water absorption, and the durability of the antibacterial properties.

[0114] However, as in the present invention, when a first compound having antibacterial and deodorizing properties is present in a cross-linked form on the surface of a second compound, it is possible to have antibacterial and deodorizing effects while maintaining water absorption.

[0115] In one embodiment of the present specification, the antibacterial and deodorizing composition may contain the first compound in an amount of 0.4 parts by weight or more and 2.5 parts by weight or less, or 0.5 parts by weight or more and 2 parts by weight or less, based on 100 parts by weight of the total of the second compound.

[0116] When the first compound is contained within the above range, the first compound is appropriately cross-linked to the surface of the second compound, and the composition has sufficient water absorption and water retention capabilities, while also being expected to have excellent antibacterial and deodorizing effects.

[0117] If the first compound is contained in an amount less than 0.4 parts by weight, the antibacterial and deodorizing effects will be insignificant, and if it is contained in an amount more than 2.5 parts by weight, there will be a problem of reduced water absorption and water retention capabilities.

[0118] In one embodiment of the present specification, the antibacterial deodorizing composition may have an antibacterial activity of 90% or more when subjected to an antibacterial evaluation.

[0119] In one embodiment of the present specification, the antibacterial activity of the antibacterial deodorizing composition may be 90% or more, 90.5% or more, 91.1% or more, or 92.1% or more, preferably 95% or more, 97% or more, or 97.5% or more, and more preferably 99% or more, or 99.2% or more. The higher the antibacterial activity, the better the antibacterial activity. There is no upper limit, but it may be, for example, 100% or less.

[0120] In one embodiment of the present specification, when the antibacterial deodorizing composition is subjected to antibacterial evaluation, the antibacterial activity against E. coli may be 90% or more, or 93% or more, preferably 95% or more, and more preferably 97% or more, or 99% or more.

[0121] In one embodiment of the present specification, when the antibacterial deodorizing composition is subjected to antibacterial evaluation, the antibacterial activity against Proteus mirabilis may be 90% or more, 90.5% or more, 91.1% or more, or 92.1% or more, preferably 95% or more, 97% or more, or 97.5% or more, and more preferably 99% or more, or 99.2% or more.

[0122] In one embodiment of the present specification, the antibacterial evaluation can be measured by the following method B.

[0123] [Method B] 40 ml of artificial urine inoculated with 3,000 CFU / ml of bacteria was poured into 2 g of the antibacterial and deodorant composition, and then cultured at 35°C for 12 hours. After the culture was completed, the solution was diluted with 160 ml of saline solution, and serially diluted samples with saline were placed on agar plates for counting.

[0124] Specifically, 100 μm of the diluted sample was dropped onto an agar plate and incubated at 30° C. for about 24 hours, after which the number of bacteria was counted and evaluated by calculating the number of bacteria in a control group not surface-treated with the first compound (antibacterial and deodorizing monomer) using the following formula: Here, the control group refers to a composition not surface-treated with the first compound.

[0125] Antibacterial activity (%)={1-(N sample ) / (N reference )}×100 (N sample : Number of bacteria in the sample containing the first compound, N reference : Number of bacteria in the control group not containing the first compound)

[0126] In one embodiment of the present specification, the bacteria used in the antibacterial evaluation may be at least one of gram-positive bacteria and gram-negative bacteria.

[0127] In one embodiment of the present specification, the bacteria used in the antibacterial evaluation may be at least one of Proteus mirabilis, E. coli, E. Cloacae, and E. faecalis.

[0128] In one embodiment of the present specification, the bacteria used in the antibacterial evaluation may be Proteus mirabilis or E. coli.

[0129] In one embodiment of the present specification, the ammonia content of the antibacterial deodorizing composition when evaluated for ammonia deodorization may be 190 ppm or less.

[0130] In one embodiment of the present specification, the ammonia content of the antibacterial deodorizing composition when evaluated for ammonia deodorization may be 190 ppm or less, 180 ppm or less, 160 ppm or less, or 150 ppm or less, preferably 100 ppm or less, 80 ppm or less, 60 ppm or less, or 50 ppm or less, more preferably 20 ppm or less, or 10 ppm or less, and there is no lower limit, but it may be, for example, 0 ppm or more. The lower the ammonia content, the better the deodorizing power against ammonia.

[0131] In one embodiment of the present specification, the ammonia deodorizing evaluation can be measured by the following method D.

[0132] [Method D] 40 ml of artificial urine inoculated with 3,000 CFU / ml of bacteria is poured into 2 g of the antibacterial and deodorant composition, and then cultured at 35°C for 12 hours. After the culture is completed, the solution is passed through an ammonia detector tube to analyze and measure the ammonia content.

[0133] In one embodiment of the present specification, a 3M ammonia detect tube can be used as the ammonia detect tube.

[0134] In one embodiment of the present specification, the bacteria used in the evaluation of ammonia deodorization may be at least one of gram-positive bacteria and gram-negative bacteria.

[0135] In one embodiment of the present specification, the bacteria used in the evaluation of ammonia deodorization may be at least one of Proteus mirabilis, E. coli, E. Cloacae, and E. faecalis.

[0136] In one embodiment of the present specification, the bacteria used in the evaluation of ammonia deodorization may be Proteus mirabilis or E. coli.

[0137] In one embodiment of the present specification, the antibacterial deodorant composition may have a Centrifuge Retention Capacity (CRC) of 30 g / g or more and 60 g / g or less.

[0138] In one embodiment of the present specification, the centrifugal water retention capacity of the antibacterial deodorizing composition may be 30 g / g or more, 32 g / g or more, 34 g / g or more, 36 g / g or more, or 37 g / g or more. Also, the centrifugal water retention capacity of the antibacterial deodorizing composition may be 60 g / g or less, 55 g / g or less, 50 g / g or less, 48 g / g or less, 45 g / g or less, 43 g / g or less, or 42 g / g or less.

[0139] When an antibacterial and deodorant composition having a centrifugal water retention capacity within the above range is used in a diaper or sanitary napkin, it can absorb water well even when the wearer is standing upright.

[0140] In one embodiment of the present specification, the centrifuge water retention capacity (CRC) can be measured according to EDANA WSP 241.3. Specifically, the antibacterial and deodorizing composition W0 (g) of the present invention is uniformly placed in a nonwoven bag, sealed, and then immersed in physiological saline at room temperature. After 30 minutes, the bag is centrifuged at 250 G for 3 minutes to remove water, and the mass of the bag W2 (g) is measured. In addition, the mass W1 (g) is measured after the same procedure as above, but without the antibacterial and deodorizing composition. Using the obtained masses, the centrifuge water retention capacity (CRC) (g / g) is calculated according to the following formula:

[0141] [Formula 1] CRC(g / g)={[W2(g)-W1(g)] / W0(g)}-1

[0142] In one embodiment of the present specification, the antibacterial deodorant composition may have an absorbency under pressure (AUP) of 10 g / g or more and 40 g / g or less.

[0143] In one embodiment of the present specification, the water absorption capacity under pressure of the antibacterial deodorizing composition may be 10 g / g or more, 14 g / g or more, 18 g / g or more, 20 g / g or more, or 21 g / g or more. The water absorption capacity under pressure of the antibacterial deodorizing composition may be 40 g / g or less, 38 g / g or less, 35 g / g or less, 32 g / g or less, 30 g / g or less, 28 g / g or less, or 27 g / g or less.

[0144] When an antibacterial and deodorant composition having a pressurized water absorption capacity within the above range is used in a diaper or sanitary napkin, water does not leak out again even when the wearer sits or lies down.

[0145] In one embodiment of the present specification, the water absorption capacity under pressure (AUP) can be measured using EDANA WSP 242.3 at a pressure of 0.5 psi to 0.8 psi. Specifically, a 400-mesh stainless steel wire mesh is attached to the bottom of a plastic cylinder with an inner diameter of 60 mm. The antibacterial and deodorizing composition W0 (g) of the present invention is evenly spread on the wire mesh under room temperature and 50% humidity conditions. A piston capable of uniformly applying a load of 0.5 psi to 0.8 psi is placed on the mesh, has an outer diameter slightly smaller than 60 mm, has no gap with the inner wall of the cylinder, and is free to move up and down. The weight W3 (g) of the apparatus is then measured. A glass filter with a diameter of 90 mm and a thickness of 5 mm is placed inside a 150 mm diameter Petri dish, and physiological saline solution containing 0.9 wt% sodium chloride is placed at the same level as the top surface of the glass filter. A sheet of filter paper with a diameter of 90 mm is placed on top of the filter paper. The measuring apparatus is then placed on the filter paper and allowed to absorb the liquid under load for one hour. After 1 hour, the measuring device is lifted and its weight W4 (g) is measured. Using the obtained masses, the water absorption capacity under pressure (AUP) (g / g) is calculated using the following formula.

[0146] [Formula 2] AUP(g / g) = [W4(g) - W3(g)] / W0(g)

[0147] One embodiment of the present disclosure provides a method for making an antibacterial and deodorant composition.

[0148] Specifically, a method for producing an antibacterial and deodorant composition according to one embodiment of the present specification includes the steps of: (a) preparing a mixture of a first compound of Chemical Formula 1 and a second compound different from the first compound; and (b) crosslinking the mixture.

[0149] In one embodiment of the present specification, the step (b) may be carried out at 150°C to 220°C for a time exceeding 20 minutes, or at 170°C to 200°C for a time period of 30 to 80 minutes.

[0150] If the mixture is crosslinked for 20 minutes or less in step (b), the first compound may not be sufficiently crosslinked to the surface of the second compound, resulting in a problem that the desired antibacterial and deodorizing properties cannot be obtained and the water absorption capacity may be poor.

[0151] In one embodiment of the present specification, the mixture in step (b) can be crosslinked for more than 20 minutes, more than 20 minutes to 80 minutes, preferably 50 minutes to 80 minutes. When the first compound and the second compound are crosslinked within this range, optimized water retention and water absorption capabilities can be obtained, and antibacterial and deodorizing functions can also be provided. When crosslinking is performed for more than 80 minutes, there is a problem that the water retention capacity decreases further.

[0152] In one embodiment of the present specification, the mixture can be crosslinked at 150°C to 220°C, or 170°C to 200°C in the step (b).

[0153] In one embodiment of the present specification, the step (a) of preparing a mixture of the first compound and the second compound can include a step (a1) of preparing a first compound of Chemical Formula 1 and a second compound different from the first compound, and a step (a2) of mixing the first compound and the second compound.

[0154] In one embodiment of the present specification, the first compound and the second compound can be directly produced or commercially available products can be used.

[0155] In one embodiment of the present specification, the mixing method is not limited as long as it is a method that can uniformly mix the first compound and the second compound.

[0156] In one embodiment of the present specification, the mixture may further contain a surface cross-linking agent. The surface cross-linking agent forms a cross-linking bond on the surface of the second compound separately from the first compound, and the inclusion of the surface cross-linking agent can improve the water absorption ability.

[0157] In one embodiment of the present specification, the surface cross-linking agent may be one or more selected from polyhydric alcohol compounds, epoxy compounds, polyamine compounds, haloepoxy compounds, condensation products of haloepoxy compounds, oxazoline compounds, mono-, di-, or polyoxazolidinone compounds, cyclic urea compounds, polyvalent metal salts, and alkylene carbonate compounds. Preferably, an alkylene carbonate compound may be used.

[0158] In one embodiment of the present specification, the surface cross-linking agent may include one or more of ethylene carbonate, propylene carbonate, and the like.

[0159] In one embodiment of the present specification, the surface crosslinking agent may be included in an amount of 0.01 parts by weight or more and 4 parts by weight or less, 0.05 parts by weight or more and 3 parts by weight or less, or 0.1 parts by weight or more and 2.5 parts by weight or less, based on 100 parts by weight of the total of the second compound.

[0160] In one embodiment of the present specification, the mixture may further include an ionic crosslinking agent, which serves to increase the surface crosslinking efficiency between the first compound and the second compound.

[0161] In one embodiment herein, the ionic crosslinker is selected from Al2(SO4)3, AlO3, Al2O3·3SiO2, and Al(H2O)6 3+ One or more selected from the following can be used, but the present invention is not limited to these. Preferably, Al2(SO4)3 (aluminum sulfate) can be used.

[0162] In one embodiment of the present specification, the ionic crosslinker may be included in an amount of 0.01 to 3 parts by weight, 0.05 to 2 parts by weight, or 0.1 to 1.5 parts by weight, based on 100 parts by weight of the total of the second compound.

[0163] In one embodiment of the present specification, the mixture may further contain a surfactant, which imparts weak hydrophobicity to water and prevents excessive water absorption during the surface treatment of the superabsorbent polymer.

[0164] In one embodiment of the present specification, the surfactant may be one or more selected from the group consisting of polycarboxylate surfactants and polyethylene glycol surfactants. Preferably, the surfactant may be a polycarboxylate surfactant.

[0165] In one embodiment of the present specification, the surfactant may be included in an amount of 0.005 parts by weight or more and 0.5 parts by weight or less, 0.01 parts by weight or more and 0.3 parts by weight or less, 0.03 parts by weight or more and 0.15 parts by weight or less, or 0.05 parts by weight or more and 0.1 parts by weight or less, based on 100 parts by weight of the total of the second compound.

[0166] In one embodiment of the present specification, the mixture may further contain water or alcohol. By including water or alcohol, the mixture is prepared in the form of a solution, and the first compound can be uniformly dispersed in the second compound.

[0167] In one embodiment of the present specification, the water or alcohol may be included in an amount of 1 to 20 parts by weight, 2 to 15 parts by weight, or 3 to 10 parts by weight, based on 100 parts by weight of the total of the second compound.

[0168] In one embodiment of the present specification, after the step (b), a step (c) of classifying the antibacterial and deodorant composition can be further included.

[0169] In the classification step, a standard mesh sieve according to ASTM standards can be used.

[0170] The antibacterial and deodorizing composition according to one embodiment of the present specification can be used in highly absorbent antibacterial products.

[0171] Such highly absorbent antibacterial products include, but are not limited to, diapers and sanitary napkins.

[0172] One embodiment of the present specification provides a deodorizing composition comprising a first compound of the following chemical formula 1:

[0173] [ka]

[0174] In the above chemical formula 1, R1 to R3 each independently represent an alkyl group having 1 to 12 carbon atoms which is unsubstituted or substituted with a hydroxy group, At least one of R1 to R3 is an alkyl group having 8 to 12 carbon atoms, R4 is an alkylene group having 1 to 6 carbon atoms, X is a halogen.

[0175] The description regarding the first compound of Chemical Formula 1 of the antibacterial deodorizing composition above can be similarly applied to the first compound of Chemical Formula 1 of the deodorizing composition.

[0176] In one embodiment of the present specification, the bacterial inhibition rate of the deodorant composition against at least one strain of gram-positive bacteria and gram-negative bacteria, as evaluated by the following method E, is 80% or more.

[0177] [Method E] 25 ml of broth-type medium (Nutreint broth, BD DIFCP., 8 g / L) inoculated with 3,000 CFU / ml of bacteria was transferred to a 50 ml conical tube, and 0.01 g of the deodorizing composition was added and vortexed. The thoroughly mixed solution was cultured for 16 hours in a shaking water bath maintained at 35°C. After the culture was completed, the solution was diluted 1 / 5 with 1X phosphate buffered saline (PBS) buffer solution and the absorbance (λ = 600 nm) was measured using a UV / Vis spectrophotometer. The measured absorbance was compared with that of a control group, and the bacterial inhibition rate was calculated using the following formula: where the control group refers to a medium solution that did not contain the deodorizing composition.

[0178] Bacterial suppression rate (%)={1-(A sample ) / (A reference )}×100 (A sample : absorbance of the medium solution containing the deodorizing composition, A reference : absorbance of the medium solution not containing the deodorizing composition)

[0179] In one embodiment of the present specification, when the bacterial inhibition rate of the deodorant composition is evaluated by the above-mentioned method E, the bacterial inhibition rate against E. coli may be 88% or more, 89.3% or more, 90% or more, 93% or more, 94.4% or more, 95% or more, 96.1% or more, 98% or more, 98.9% or more, or 99% or more, and the bacterial inhibition rate against Proteus mirabilis may be 83% or more, 90% or more, 91.2% or more, 95% or more, 96.9% or more, 98% or more, 99% or more, or 99.9% or more. The higher the bacterial inhibition rate, the better the antibacterial activity, and there is no upper limit, but it may be, for example, 100% or less. [Example]

[0180] Hereinafter, the present specification will be described in detail with reference to examples. However, the examples of the present specification may be modified in various different forms, and the scope of the present specification should not be construed as being limited to the examples described below. The examples of the present specification are provided to more completely explain the present specification to those skilled in the art.

[0181] <Production Example 1> Production of the first compound (antibacterial deodorizing monomer) Manufacturing example A 130 ml of ethanol, 0.131 mol of methyldiethanolamine, and 0.144 mol of bromodecane were placed in a 250 ml flask and stirred using a magnetic bar at 65°C for 24 hours to allow the reaction to proceed. After 24 hours, the reaction solution was precipitated by adding it to 800 ml of diethyl ether solution, and the reactants were filtered using a vacuum filter. Any diethyl ether remaining in the vacuum oven was completely removed to obtain the final synthesized product, antibacterial and deodorizing monomer A.

[0182] [ka]

[0183] Manufacturing example B Antibacterial and deodorant monomer B was obtained in the same manner as in Preparation Example A, except that bromooctane was used instead of bromodecane.

[0184] [ka]

[0185] Manufacturing example C Antibacterial deodorant monomer C was obtained in the same manner as in Preparation Example A, except that bromododecane was used instead of bromodecane.

[0186] [ka]

[0187] Manufacturing example D Antibacterial deodorizing monomer D was obtained in the same manner as in Preparation Example A, except that dimethylethanolamine was used instead of methyldiethanolamine.

[0188] [ka]

[0189] Manufacturing Example E Antibacterial and deodorizing monomer E was obtained in the same manner as in Preparation Example A, except that dimethylethanolamine was used instead of methyldiethanolamine and bromododecane was used instead of bromodecane.

[0190] [ka]

[0191] Manufacturing example F Antibacterial deodorizing monomer F was obtained in the same manner as in Preparation Example A, except that dimethylethanolamine was used instead of methyldiethanolamine and chlorodecane was used instead of bromodecane.

[0192] [ka]

[0193] Manufacturing example G Antibacterial deodorant monomer G was obtained in the same manner as in Preparation Example A, except that bromobutane was used instead of bromodecane.

[0194] [ka]

[0195] The NMR data of the antibacterial and deodorant monomers A to G produced in Production Example 1 above can be confirmed in FIGS.

[0196] Figure 2 shows the NMR data of antibacterial and deodorizing monomer A.

[0197] Figure 3 shows the NMR data of antibacterial and deodorizing monomer B.

[0198] Figure 4 shows the NMR data of antibacterial and deodorizing monomer C.

[0199] FIG. 5 shows the NMR data of antibacterial and deodorizing monomer D.

[0200] FIG. 6 shows the NMR data of antibacterial and deodorizing monomer E.

[0201] FIG. 7 shows the NMR data of the antibacterial and deodorizing monomer F.

[0202] FIG. 8 shows the NMR data of the antibacterial and deodorizing monomer G.

[0203] <Production Example 2> Production of second compound (superabsorbent polymer 1) The photoinitiator, bis(2,4,6-trimethylbenzoyl)-phenylphosphineoxide (I-819), was dissolved in acrylic acid to prepare a 0.21 wt% solution. The crosslinker, polyethylene glycol diacrylate (PEGDA, Mw = 523), was dissolved in acrylic acid to prepare a 20 wt% PEGDA solution. The thermal initiator, sodium persulfate (SPS), was then dissolved in water to prepare a 4 wt% aqueous solution. Next, 634.6 g of 31.5 wt% caustic soda (NaOH) and 234.7 g of water were added to a Buchi reactor for dilution. Then, 489.7 g of acrylic acid, 5.91 g of 20 wt% PEGDA, and 19.58 g of 0.21 wt% I-819 were added to another Buchi reactor and mixed. 15.42 g of 4 wt% SPS was placed in a 2 L flask beaker. Well-diluted caustic soda was transferred into the Buchi reactor containing the acrylic acid to neutralize the acrylic acid, and when the temperature of the neutralized solution reached 43°C, it was transferred into the 2 L flask beaker containing the SPS. When the temperature of the neutralized solution mixed with SPS reached 40°C, it was placed in a tray in a UV chamber. Then, while maintaining the polymerization atmosphere temperature at 80°C, it was irradiated with ultraviolet light in a UV irradiation device for 1 minute (irradiation dose: 10 mW / cm). 2), and aged for 2 minutes, followed by UV polymerization to produce a hydrogel polymer sheet. The polymerized sheet was taken out and cut into 3cm x 3cm pieces. 180g of water was added and mixed, and then chopped using a meat chopper to produce crumbs. The meat chopper had a hole diameter of 16mm. The crumbs were dried in an oven with an adjustable airflow rate. 185°C hot air was blown from bottom to top for 16 minutes and then from top to bottom for 16 minutes to ensure uniform drying, with the moisture content of the dried product remaining below 2%. After drying, the mixture was pulverized in a pulverizer and then classified for 10 minutes at an amplitude of 1.5 mm (classification mesh combinations: #20-30 / #30-50 / #50-100 / #100). Each classification powder (22% / 64% / 13% / 1%) was collected, and polymers with particle sizes of approximately 850 μm or less were classified and obtained. In this way, a base resin powder was obtained.

[0204] <Production Example 3> Production of second compound (superabsorbent polymer 2) The same procedure as in Preparation Example 2 was carried out, except that before adding the neutralizing solution to the UV chamber, the following antibacterial and deodorizing monomer was measured at 1 to 2 phr based on the weight of acrylic acid and uniformly diluted before being added.

[0205] [ka]

[0206] <Production Example 4> Production of antibacterial and deodorant composition Example 1 A surface cross-linking solution containing 4.4 parts by weight of water, 0.3 parts by weight of ethylene carbonate, 0.075 parts by weight of a polycarboxylate surfactant, 0.3 parts by weight of aluminum sulfate, and 0.5 parts by weight of antibacterial and deodorizing monomer A was sprayed and mixed into 100 parts by weight of the superabsorbent resin 1 prepared in Preparation Example 2 above, and the mixture was placed in a vessel equipped with a stirrer and a double jacket, where a surface cross-linking reaction was carried out at 180°C for 70 minutes. The surface-treated powder was then classified using an ASTM standard mesh sieve to obtain an antibacterial and deodorizing composition containing particles having a size of 150 μm to 850 μm.

[0207] Examples 2 to 6 and Comparative Examples 1 to 7 An antibacterial and deodorizing composition was obtained in the same manner as in Example 1, except that the first compound of the type shown in Table 1 was used instead of the antibacterial and deodorizing monomer A in Example 1, and the surface crosslinking reaction was carried out for the time shown in Table 1 below.

[0208] Comparative Example 8 The superabsorbent resin 2 produced in Production Example 3 was used as an antibacterial and deodorizing composition.

[0209] [Table 1]

[0210] Example 7 A surface cross-linking solution containing 9.46 parts by weight of water, 1.2 parts by weight of ethylene carbonate, 1.2 parts by weight of propylene carbonate, 1.14 parts by weight of aluminum sulfate aqueous solution, and 1 part by weight of antibacterial and deodorizing monomer A was sprayed and mixed into 100 parts by weight of the superabsorbent resin 1 prepared in Preparation Example 2 above, and the mixture was placed in a vessel equipped with a stirrer and a double jacket, where a surface cross-linking reaction was carried out at 190°C for 30 minutes. The surface-treated powder was then classified using an ASTM standard mesh sieve to obtain an antibacterial and deodorizing composition containing particles having a size of 150 μm to 850 μm.

[0211] Examples 8 to 13 and Comparative Example 9 An antibacterial and deodorizing composition was obtained in the same manner as in Example 7, except that the first compound of the type and content shown in Table 2 was used instead of 1 part by weight of the antibacterial and deodorizing monomer A in Example 7.

[0212] Comparative Example 10 The superabsorbent resin 1 produced in Production Example 1 was used as an antibacterial and deodorizing composition.

[0213] [Table 2]

[0214] <Experimental Example 1> Measurement of the antibacterial activity of the first compound (antibacterial deodorizing monomer) 25 ml of broth-type medium (Nutreint broth, BD DIFCP., 8 g / L) inoculated with 3,000 CFU / ml of E. coli (or Proteus mirabilis) was transferred to a 50 ml conical tube, and 0.01 g of Compound 1 (antibacterial and deodorizing monomer) listed in Table 1 above was added and vortexed. The thoroughly mixed solution was incubated for 16 hours in a shaking water bath maintained at 35°C. After incubation, the solution was diluted 1 / 5 with 1X phosphate buffered saline (PBS) buffer solution and the absorbance (λ = 600 nm) was measured using a UV / Vis spectrophotometer. The measured absorbance was compared to a solution incubated without Compound 1 (antibacterial and deodorizing monomer), and the bacterial inhibition rate was calculated using the following formula and reported in Table 3 below.

[0215] Bacterial suppression rate (%)={1-(A sample ) / (A reference )}×100 (A sample : absorbance of the medium solution containing the antibacterial and deodorizing monomer, A reference : Absorbance of medium solution not containing antibacterial and deodorizing monomer)

[0216] [Table 3]

[0217] <Experimental Example 2> Measurement of deodorizing power of antibacterial deodorizing composition 1 g of the antibacterial and deodorizing composition was placed in a 500 ml lab bottle, and E. coli 10 5 CFU / mL, Proteus mirabilis 10 6 CFU / mL and E. cloacae 10 6 25 ml of artificial urine inoculated with CFU / mL was added and incubated. After incubation at 35°C for 24 hours, the odor components of the artificial urine, diacetyl, 3-methylbutanol, DMDS + DMTS, guaiacol, and p-cresol, were collected in adsorption tubes. The mass of each collected component was analyzed using GC / MS, and the results of the odor-eliminating evaluation were listed in Table 4 below.

[0218] In the following Table 4, Reference is data obtained using a highly water-absorbent resin that has not been surface-crosslinked.

[0219] [Table 4]

[0220] From Table 4 above, it can be seen that the deodorizing power was inferior when a compound with a smaller number of carbon atoms in the alkyl group R1 than the compounds of the present invention (Comparative Example 1), a compound different from the present invention (Comparative Example 2), or a compound without a hydroxy group (Comparative Example 3 or 4) was used, or when an antibacterial deodorizing monomer was included in the production of the superabsorbent resin (Comparative Example 8). Furthermore, in Comparative Example 7, the surface crosslinking reaction time was shorter than in the Examples, and sufficient crosslinking did not occur, making it impossible to obtain the desired deodorizing power.

[0221] Furthermore, it can be seen that among the examples, the larger the number of carbon atoms in the alkyl group R1, the better the deodorizing power.

[0222] <Experimental Example 3> Measurement of antibacterial activity of antibacterial deodorant composition 40 ml of artificial urine inoculated with 3,000 CFU / ml of Proteus mirabilis was poured into 2 g of the antibacterial and deodorizing composition and then cultured for 12 hours at 35° C. After the culture was completed, the solution was diluted with 160 ml of saline solution, and the serially diluted samples were spread on agar plates. The results are shown in Table 5 below.

[0223] Specifically, 100 μm of the diluted sample was dropped onto an agar plate and incubated at 30°C for about 24 hours, and then the number of bacteria was counted and evaluated by calculating the number of bacteria in the control group that was not surface-treated with the first compound (antibacterial and deodorizing monomer) using the following formula.

[0224] Antibacterial activity (%)={1-(N sample ) / (N reference )}×100 (N sample : Number of bacteria in the sample containing antibacterial and deodorizing monomer, N reference : Number of bacteria in the control group that does not contain antibacterial and deodorant monomer)

[0225] [Table 5]

[0226] <Experimental Example 4> Measurement of antibacterial activity of antibacterial deodorant composition 50 ml of artificial urine inoculated with 3,000 CFU / ml of E. coli was poured into 2 g of the antibacterial and deodorant composition and then cultured for 12 hours at 35° C. After the culture was completed, the solution was diluted with 150 ml of saline solution, and the serially diluted samples were plated on agar plates. The results are shown in Table 6 below.

[0227] Specifically, 100 μm of the diluted sample was dropped onto an agar plate and incubated at 30°C for about 24 hours, and then the number of bacteria was counted and evaluated by calculating the number of bacteria in the control group that was not surface-treated with the first compound (antibacterial and deodorizing monomer) using the following formula.

[0228] Antibacterial activity (%)={1-(N sample ) / (N reference )}×100 (N sample : Number of bacteria in the sample containing antibacterial and deodorizing monomer, N reference : Number of bacteria in the control group that does not contain antibacterial and deodorant monomer)

[0229] [Table 6]

[0230] From Tables 5 and 6 above, it can be seen that the antibacterial activity was inferior when a compound having a small number of carbon atoms in the alkyl group R1 (Comparative Example 1), a compound different from the present invention (Comparative Example 2), or a compound not containing a hydroxy group (Comparative Example 3 or 4) was used, or a compound containing a long alcohol group having 7 or more carbon atoms (Comparative Example 5), or a compound containing only a long alkyl group having 10 or more carbon atoms (Comparative Example 6) was used. In Comparative Example 7, the surface crosslinking reaction time was shorter than in the Examples, and sufficient crosslinking did not occur, so the desired antibacterial activity could not be obtained.

[0231] Furthermore, among the examples, it can be seen that compounds having two hydroxyl groups have higher antibacterial activity than compounds having one, and that the antibacterial activity improves further as the number of carbon atoms in the alkyl group R1 increases.

[0232] In addition, it has been confirmed that when the content of the first compound of Formula 1 is less than 0.4 parts by weight based on 100 parts by weight of the total of the second compound, the antibacterial activity is not sufficiently exhibited.

[0233] Experimental Example 5: Measurement of ammonia deodorizing power of antibacterial deodorizing composition 40 ml of artificial urine inoculated with 3,000 CFU / ml of Proteus mirabilis was poured into 2 g of the antibacterial and deodorizing composition and then incubated for 12 hours at 35° C. After incubation, the ammonia content (ppm) of the solution was measured using a 3M ammonia detector tube, and the results are shown in Table 7 below.

[0234] [Table 7]

[0235] The results in Table 7 show that the ammonia content of Examples 1 to 6, which contain the antibacterial deodorizing composition of the present invention, was 160 ppm or less, which is even lower than that of Comparative Examples 1 to 8, which measured ammonia levels of 200 ppm to 500 ppm. This confirms that the antibacterial deodorizing composition of the present invention has a superior deodorizing effect against ammonia compared to the compositions used in Comparative Examples 1 to 8. In particular, in the case of Examples 1 to 3, which have two hydroxy groups, the ammonia was measured at a significantly low level of 50 ppm or less.

[0236] <Experimental Example 6> Measurement of water retention capacity by centrifugation Centrifugal water retention capacity (CRC) was measured using EDANA WSP 241.3. First, 1.5 g (W0) of the antibacterial deodorizing composition prepared above was evenly placed in a nonwoven bag, sealed, and then immersed in physiological saline at room temperature. After 30 minutes, the bag was centrifuged at 250 G for 3 minutes to remove water, and the mass of the bag, W2 (g), was measured. In addition, the mass, W1 (g), was measured after proceeding in the same manner as above without using the antibacterial deodorizing composition. Using the obtained masses, the centrifugation water retention capacity (CRC) (g / g) was calculated using the following formula.

[0237] [Formula 1] CRC(g / g)={[W2(g)-W1(g)] / W0(g)}-1

[0238] <Experimental Example 7> Measurement of water absorption capacity under pressure The water absorption capacity under pressure (AUP) was measured using an EDANA WSP 242.3. A 400-mesh stainless steel wire mesh was attached to the bottom of a plastic cylinder with an inner diameter of 60 mm. 1 g (W0) of the prepared antibacterial and deodorizing composition was evenly distributed on the wire mesh under room temperature and 50% humidity conditions. A piston with an outer diameter slightly smaller than 60 mm was used to apply a uniform load of 0.7 psi to the composition. It had no gap between the piston and the inner wall of the cylinder, allowing for unhindered up-and-down movement. The weight of the apparatus, W3 (g), was then measured. A 90-mm diameter and 5-mm thick glass filter was placed inside a 150-mm diameter Petri dish, and a saline solution containing 0.9 wt% sodium chloride was placed flush with the top surface of the glass filter. A 90-mm diameter piece of filter paper was placed on top of the filter. The measuring apparatus was then placed on the filter paper and allowed to absorb the liquid under load for 1 hour. After 1 hour, the measuring device was lifted and its weight W4 (g) was measured. Using the obtained masses, the water absorption capacity under pressure (AUP) (g / g) was calculated using the following formula.

[0239] [Formula 2] AUP(g / g) = [W4(g) - W3(g)] / W0(g)

[0240] The centrifugal water retention capacity and pressure water absorption capacity measured in Experimental Examples 6 and 7 are shown in Table 8 below.

[0241] [Table 8]

[0242] From the above, it can be seen that the antibacterial and deodorizing composition of the present invention not only provides excellent water retention capacity by centrifugation and water absorption capacity under pressure, but also has the effect of improving antibacterial and deodorizing powers.

Claims

1. A first compound of the following formula 1: An antibacterial and deodorizing composition comprising a second compound different from the first compound, the first compound is bound to at least a portion of the second compound; the second compound is a superabsorbent polymer, When the antibacterial deodorizing composition was evaluated for deodorizing effect, the content of guaiacol was 300 ng or less, the content of 3-methylbutanal was 250 ng or less, and the content of diacetyl was 30 ng or less, The deodorizing evaluation is measured by the following method A, An antibacterial and deodorizing composition having a centrifugal water retention capacity of 32 g / g or more and 60 g / g or less: 【Chemical 1】 In the above Chemical Formula 1, R １ ~R ３ are each independently an alkyl group having 1 to 12 carbon atoms which is unsubstituted or substituted with a hydroxy group, R １ ~R ３ at least one of which is an alkyl group having 8 to 12 carbon atoms; At least one of R 1 and R 2 is an alkyl group having 1 to 5 carbon atoms; R ４ is an alkylene group having 1 to 6 carbon atoms, X is a halogen; [Method A] 1 g of the antibacterial and deodorizing composition was placed in a 500 ml lab bottle, and 25 ml of artificial urine inoculated with microorganisms was poured into the bottle and incubated at 35°C for 24 hours. After that, guaiacol, 3-methylbutanal, and diacetyl were respectively collected in an adsorption tube, and the mass of each of the collected components was analyzed using GC / MS.

2. The antibacterial and deodorizing composition according to claim 1 , wherein the first compound is contained in an amount of 0.4 parts by weight to 2.5 parts by weight based on 100 parts by weight of the total amount of the second compound.

3. The antibacterial and deodorizing composition according to claim 1 , wherein the second compound comprises a hydrogel polymer.

4. The antibacterial and deodorizing composition according to claim 1 , wherein the antibacterial and deodorizing composition is present in the form of particles having an island-in-a-sea structure.

5. 2. The antibacterial deodorizing composition according to claim 1, wherein the antibacterial activity of the antibacterial deodorizing composition is 90% or more when the antibacterial activity is evaluated, and the antibacterial activity is measured by the following method B: [Method B] 40 ml of artificial urine inoculated with 3,000 CFU / ml of bacteria was poured into 2 g of the antibacterial and deodorizing composition, and then cultured at 35° C. for 12 hours. After the culture was completed, the solution was diluted with 160 ml of saline, and the samples serially diluted with saline were spread on an agar plate for counting.

6. 2. The antibacterial deodorizing composition according to claim 1, wherein the antibacterial deodorizing composition has a water absorption capacity under pressure of 10 g / g or more and 40 g / g or less.

7. A method for producing the antibacterial and deodorant composition according to any one of claims 1 to 6, comprising: (a) providing a mixture of a first compound of Formula 1 and a second compound different from the first compound; and Step (b) reacting the mixture A method for producing an antibacterial and deodorizing composition, comprising:

8. The method for producing an antibacterial and deodorizing composition according to claim 7, wherein step (b) is carried out at 150°C to 220°C for a time period exceeding 20 minutes.

9. 8. The method for producing an antibacterial and deodorizing composition according to claim 7, wherein step (b) is carried out at 170°C to 200°C for 30 minutes to 80 minutes.

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