WO2023022363A1 - 항균 소취 조성물 및 이의 제조방법 - Google Patents
항균 소취 조성물 및 이의 제조방법 Download PDFInfo
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- WO2023022363A1 WO2023022363A1 PCT/KR2022/009359 KR2022009359W WO2023022363A1 WO 2023022363 A1 WO2023022363 A1 WO 2023022363A1 KR 2022009359 W KR2022009359 W KR 2022009359W WO 2023022363 A1 WO2023022363 A1 WO 2023022363A1
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- Prior art keywords
- antibacterial
- deodorant composition
- compound
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- weight
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- 238000000034 method Methods 0.000 claims abstract description 49
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 claims abstract description 28
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- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- FAQJJMHZNSSFSM-UHFFFAOYSA-N phenylglyoxylic acid Chemical compound OC(=O)C(=O)C1=CC=CC=C1 FAQJJMHZNSSFSM-UHFFFAOYSA-N 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000768 polyamine Chemical class 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Images
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/41—Amines
- A61K8/416—Quaternary ammonium compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L9/00—Disinfection, sterilisation or deodorisation of air
- A61L9/01—Deodorant compositions
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/02—Amines; Quaternary ammonium compounds
- A01N33/12—Quaternary ammonium compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/34—Alcohols
- A61K8/347—Phenols
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L9/00—Disinfection, sterilisation or deodorisation of air
- A61L9/01—Deodorant compositions
- A61L9/012—Deodorant compositions characterised by being in a special form, e.g. gels, emulsions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q15/00—Anti-perspirants or body deodorants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/005—Antimicrobial preparations
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/24—Crosslinking, e.g. vulcanising, of macromolecules
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/57—Compounds covalently linked to a(n inert) carrier molecule, e.g. conjugates, pro-fragrances
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2300/00—Characterised by the use of unspecified polymers
- C08J2300/14—Water soluble or water swellable polymers, e.g. aqueous gels
Definitions
- the present specification relates to an antibacterial deodorant composition and a manufacturing method thereof.
- sanitary products such as diapers and sanitary napkins are products for which absorbency is most important.
- the present specification is to provide an antibacterial deodorant composition and a manufacturing method thereof.
- An exemplary embodiment of the present specification is a first compound represented by Formula 1; And an antibacterial deodorant composition comprising 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 when the antibacterial deodorant composition is evaluated for deodorization, the content of Guaiacol is 300 ng or less, The content of 3-methylbutanal is 250 ng or less, the content of diacetyl is 30 ng or less, and the deodorization evaluation is provided by the method A below.
- R 1 to R 3 are each independently an alkyl group having 1 to 12 carbon atoms unsubstituted or substituted with a hydroxyl group;
- At least one of R 1 to R 3 is an alkyl group having 8 to 12 carbon atoms
- R 4 is an alkylene group having 1 to 6 carbon atoms
- X is a halogen
- Another exemplary embodiment of the present specification is preparing a mixture of a first compound of Formula 1 and a second compound different from the first compound (a); And it provides a method for producing an antibacterial deodorant composition comprising the step (b) of crosslinking the mixture.
- Another exemplary embodiment of the present specification provides a deodorant composition including the first compound of Formula 1 above.
- the antimicrobial deodorant composition according to the present specification includes a form in which the surface is cross-linked by an alcohol-based antibacterial deodorant monomer containing quaternary ammonium, thereby providing excellent antibacterial and deodorant effects, as well as high centrifugal water retention capacity and absorbency under pressure It provides a composition having.
- the antibacterial and deodorant monomer of the present invention is included in the composition in a crosslinked form rather than in the form of an additive, the antibacterial and deodorant composition has excellent durability and does not cause a dissolution problem.
- the antibacterial and deodorizing monomer of the present invention has both hydrophobic and hydrophilic properties by having a long alkyl group having 8 to 12 carbon atoms and a hydroxyl group, it is suitable for surface treatment and can obtain antibacterial and deodorizing effects.
- FIG 1 illustrates the particle structure of the antibacterial deodorant composition of the present invention.
- the alkyl group may be straight-chain or branched-chain.
- an alkylene group means a divalent alkyl group, and may be a straight chain or branched chain.
- halogen may be fluorine (F), chlorine (Cl), bromine (Br), or iodine (I).
- An exemplary embodiment of the present specification is a first compound represented by Formula 1; And an antibacterial deodorant composition comprising 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 deodorant composition has a Guaiacol content of 300 ng or less, The content of 3-methylbutanal is 250 ng or less, the content of diacetyl is 30 ng or less, and the deodorization evaluation is provided by the method A below.
- R 1 to R 3 are each independently an alkyl group having 1 to 12 carbon atoms unsubstituted or substituted with a hydroxyl group;
- At least one of R 1 to R 3 is an alkyl group having 8 to 12 carbon atoms
- R 4 is an alkylene group having 1 to 6 carbon atoms
- X is a halogen
- the antibacterial and deodorant composition according to an exemplary embodiment of the present specification provides excellent centrifugal separation water retention capacity and pressure absorption capacity while having antibacterial and deodorant effects.
- the antibacterial deodorant composition of the present invention includes a form in which the first compound of Formula 1 is cross-linked to at least a portion of the second compound, so that when the antibacterial deodorant composition is evaluated for deodorization, the content of Guaiacol is 300 ng or less, The content of 3-methylbutanal is less than 250ng and the content of diacetyl is less than 30ng.
- the deodorization evaluation is measured by Method A below.
- the deodorant evaluation may be performed on odor components of artificial urine such as DMDS+DMTS and p -Cresol in addition to Guaiacol, Diacetyl, and 3-methylbutanal. That is, in Method A, instead of Guaiacol, Diacetyl, or 3-methylbutanal, DMDS+DMTS, or p -Cresol is collected and the mass is analyzed.
- the content of Guaiacol when evaluating deodorization of the antibacterial deodorant composition, may be 300ng or less, 260ng or less, or 251ng or less, preferably 200ng or less, 199ng or less, or 180ng or less, more preferably It may be 173 ng or less, 170 ng or less, or 168 ng or less.
- the lower limit is not limited, but may be, for example, 0 ng or more. The lower the content, the higher the deodorizing power of Guaiacol.
- the content of 3-methylbutanal when evaluating deodorization of the antibacterial deodorant composition, 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, more preferably 130 ng or less or less, 129 ng or less, 124 ng or less, 102 ng or less, or 99 ng or less.
- the lower limit is not limited, but may be, for example, 0 ng or more. The smaller the content, the higher the deodorizing power for 3-methylbutanal.
- the content of Diacetyl when evaluating deodorization of the antibacterial deodorant composition, 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, more preferably 21 ng or less, or less than 20 ng.
- the lower limit is not limited, but may be, for example, 0 ng or more. The smaller the content, the higher the deodorizing power for Diacetyl.
- the artificial urine used for the deodorization evaluation may be prepared with the same composition as in the ESSITY literature (J Wound Ostomy Continence Nurs. 2019;46(6):519-523.).
- sterilizable materials can be sterilized using an autoclave, and materials that cannot be sterilized at high temperatures can be sterilized using a 0.20 ⁇ m membrane filter.
- microorganisms used for the deodorization evaluation include Escberichia Coli (E. Coli, CCUG 3274), Proteus mirabilis (P. mirabilis CCUG 4637), Enterobacter Cloacae (E. Cloacae, CCUG 71839), and the like. There is, but is not limited to this.
- the microorganisms used for the deodorization evaluation may be mixed bacteria. That is, one or more microorganisms may be mixed and used for deodorization evaluation.
- the concentration of one or more microorganisms used for the deodorization evaluation may be 10 5 CFU/ml to 10 6 CFU/ml, respectively.
- 10 5 CFU/ml of E. Coli 10 6 CFU/ml of Proteus mirabilis, and 10 6 CFU/ml of E. Cloacae may be mixed and used for the deodorization evaluation.
- the first compound is a monomer having antibacterial activity and deodorizing activity, and serves as a surface crosslinking agent.
- the first compound represented by Formula 1 is a quaternary ammonium-based compound having antibacterial properties. Positive ions of ammonium molecules are electrostatically adsorbed to anion sites on the surface of microbial cells, and cell surface layer structures are physicochemically formed by hydrophobic interactions. to destroy and perish. The hydrophobicity of the first compound depends on the carbon number of the alkyl group connected to the quaternary ammonium, and as a result, the antibacterial properties are changed.
- R 1 to R 3 in Formula 1 are each independently an alkyl group having 1 to 12 carbon atoms unsubstituted or substituted with a hydroxyl group, and at least one of R 1 to R 3 has 8 to 8 carbon atoms It is an alkyl group of 12.
- R 3 may be an alkyl group having 8 to 12 carbon atoms.
- R 3 may be a straight-chain alkyl group having 8 to 12 carbon atoms.
- R 3 may be a straight-chain alkyl group having 10 to 12 carbon atoms.
- R 3 may be a straight-chain alkyl group having 8 carbon atoms.
- R 3 may be a straight-chain alkyl group having 10 carbon atoms.
- R 3 may be a straight-chain alkyl group having 12 carbon atoms.
- the carbon number of R 3 is less than 8, for example, when the number of carbon atoms is 4, the antibacterial and deodorizing power of the antibacterial and deodorizing composition is deteriorated.
- R 1 and R 2 may each independently be an alkyl group having 1 to 12 carbon atoms unsubstituted or substituted with a hydroxyl group.
- R 1 and R 2 may each independently be an alkyl group having 1 to 8 carbon atoms unsubstituted or substituted with a hydroxyl group.
- R 1 and R 2 may each independently be an alkyl group having 1 to 5 carbon atoms unsubstituted or substituted with a hydroxyl group.
- R 1 and R 2 may each independently be a straight-chain alkyl group having 1 to 5 carbon atoms unsubstituted or substituted with a hydroxyl group.
- R 1 and R 2 may each independently be a straight-chain alkyl group having 1 to 3 carbon atoms unsubstituted or substituted with a hydroxyl group.
- At least one of R 1 and R 2 may be an alkyl group having 1 to 5 carbon atoms.
- At least one of R 1 and R 2 may be a straight-chain alkyl group having 1 to 5 carbon atoms.
- At least one of R 1 and R 2 may be a straight-chain alkyl group having 1 to 3 carbon atoms.
- At least one of R 1 and R 2 may be a methyl group.
- any one of R 1 and R 2 may be an alkyl group having 1 to 5 carbon atoms unsubstituted or substituted with a hydroxyl group.
- any one of R 1 and R 2 may be an alkyl group having 1 to 5 carbon atoms substituted with a hydroxyl group.
- any one of R 1 and R 2 may be an alkyl group having 1 to 5 carbon atoms.
- R 1 may be an alkyl group having 1 to 12 carbon atoms.
- R 2 may be an alkyl group having 1 to 12 carbon atoms unsubstituted or substituted with a hydroxyl group.
- R 4 in Formula 1 may be a straight-chain alkylene group having 1 to 6 carbon atoms.
- R 4 may be a straight-chain alkylene group having 1 to 4 carbon atoms.
- R 4 may be a straight-chain alkylene group having 2 to 4 carbon atoms.
- R 4 may be a straight-chain alkylene group having 2 carbon atoms.
- R 4 may be a straight-chain alkylene group having 3 carbon atoms.
- R 4 may be a straight-chain alkylene group having 4 carbon atoms.
- X in Chemical Formula 1 may be Br or Cl.
- the first compound may be any one of the following compounds.
- X is halogen
- the bacterial inhibition rate against E. Coli is 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
- the bacterial inhibition rate for Proteus mirabilis is 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 the upper limit is not limited, but may be, for example, 100% or less.
- Bacterial inhibition rate (%) ⁇ 1-(A sample )/(A reference ) ⁇ ⁇ 100
- the bacteria used to evaluate the bacteria inhibition rate include E. Coli, Proteus mirabilis, and the like.
- the second compound is a compound different from the first compound.
- the second compound may be a super absorbent polymer (SAP).
- SAP super absorbent polymer
- the superabsorbent polymer is a resin having a function of absorbing more than several hundred times its own weight in water and tens of times more artificial urine, and is a functional polymer material having excellent ability to retain water even under external pressure. These superabsorbent polymers are widely used in sanitary products such as diapers and sanitary napkins.
- the second compound may include a hydrogel polymer.
- the second compound is a superabsorbent polymer, and the superabsorbent polymer may include a hydrogel polymer.
- the water-containing gel polymer refers to a polymer having a water content of 40% to 80% by weight based on the total weight of the water-containing gel polymer.
- the moisture content is the content of moisture with respect to the total weight of the hydrogel polymer, and is a value obtained by subtracting the weight of the polymer in a dry state from the total weight of the hydrogel polymer. Specifically, it is defined as a value calculated by measuring the weight loss due to evaporation of moisture in the polymer in the process of raising the temperature of the polymer through infrared heating and drying.
- the drying condition is a method of raising the temperature from room temperature to about 180 ° C and then maintaining it at 180 ° C.
- the total drying time is set to 20 minutes including 5 minutes of the temperature raising step, and the moisture content is measured.
- the water-containing gel polymer may be prepared by cross-linking polymerization of an acrylic acid-based monomer in which at least a part of acidic groups are neutralized and an internal cross-linking agent.
- a monomer composition in a solution state including an acrylic acid-based monomer in which at least a portion of acidic groups are neutralized, a polymerization initiator, an internal crosslinking agent, and a solvent may be used.
- the acrylic acid-based monomer is a compound represented by Formula 2 below.
- R is an alkyl group having 2 to 5 carbon atoms including an unsaturated bond
- R' is hydrogen, a monovalent or divalent metal, an ammonium group, or an organic amine salt.
- the acrylic acid-based monomer includes at least one selected from the group consisting of acrylic acid, methacrylic acid, and monovalent metal salts, divalent metal salts, ammonium salts, and organic amine salts thereof.
- the acrylic acid-based monomer may have an acidic group and at least a portion of the acidic group may be neutralized.
- those obtained by partially neutralizing the monomers with alkali substances such as sodium hydroxide, potassium hydroxide, and ammonium hydroxide may be used.
- 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 degree of neutralization may be adjusted according to final physical properties. However, if the degree of neutralization is too high, neutralized monomers may precipitate out, making it difficult for the polymerization to proceed smoothly. Conversely, if the degree of neutralization is too low, the absorbency of the polymer is greatly reduced, and it may exhibit properties such as elastic rubber that are difficult to handle. there is.
- the concentration of the acrylic acid-based monomer is about 20% by weight or more relative to the monomer composition including the solvent and raw materials of the superabsorbent polymer including the acrylic acid-based monomer in which at least a part of acidic groups are neutralized, a polymerization initiator, and an internal crosslinking agent. , or about 40% by weight or more, about 60% by weight or less, or about 50% by weight or less, and may be an appropriate concentration in consideration of polymerization time and reaction conditions. However, if the concentration of the monomer is too low, the yield of the superabsorbent polymer is low and economic problems may arise.
- the internal crosslinking agent is for crosslinking the inside of a polymer in which acrylic acid-based monomers are polymerized, and specific examples include polyethylene glycol diacrylate, N,N'-methylenebisacrylamide, and 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, diethylene glycol di(meth)acrylate, hexanediol di(meth)acrylate, triethylene glycol di(meth)acrylate, tripropylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acrylate selected from (meth)acrylate, dipentaerythritol pentaacrylate, glycerin tri(meth)acrylate, pentaerythritol tetraacrylate, triarylamine, ethylene glycol diglycidyl ether, propylene glycol, glycerin, and ethylene carbonate
- one or more types can be used, it is not limited
- 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 to crosslink the polymerized polymer. If the content of the internal cross-linking agent is less than 0.01 part by weight, the improvement effect due to cross-linking is insignificant, and if the content of the internal cross-linking agent exceeds 1 part by weight, the absorbency of the superabsorbent polymer may decrease. More specifically, the internal crosslinking agent is 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 monomer. may be included in quantity.
- the polymerization initiator is not particularly limited as long as it is generally used in the production of superabsorbent polymer.
- the polymerization initiator may be a thermal polymerization initiator or a photopolymerization initiator according to UV irradiation according to a polymerization method.
- a thermal polymerization initiator may be additionally included.
- any compound capable of forming radicals by light such as ultraviolet light may be used without limitation in its configuration.
- photopolymerization initiator examples include benzoin ether, dialkyl acetophenone, hydroxyl alkylketone, phenyl glyoxylate, and benzyl dimethyl ketal. Ketal), acyl phosphine, and alpha-aminoketone ( ⁇ -aminoketone) may be used at least one selected from the group consisting of.
- acylphosphine commercially available Irgacure 819 (bis (2,4,6-trimethylbenzoyl) -phenylphosphine oxide), lucirin TPO (diphenyl (2,4,6-trimethylbenzoyl) -phosphine) pin oxide), etc. can be used.
- Irgacure 819 bis (2,4,6-trimethylbenzoyl) -phenylphosphine oxide
- lucirin TPO diphenyl (2,4,6-trimethylbenzoyl) -phosphine
- the photopolymerization initiator may be included in an amount of 0.001 part by weight to 1 part by weight based on 100 parts by weight of the acrylic acid-based monomer.
- the content of the photopolymerization initiator is less than 0.001 parts by weight, the polymerization rate may be slowed down, and when the content of the photopolymerization initiator exceeds 1 part by weight, the molecular weight of the superabsorbent polymer may be small and physical properties may become non-uniform.
- the photopolymerization initiator is 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 monomers. can be included in the amount of
- thermal polymerization initiator when a thermal polymerization initiator is further included as the polymerization initiator, at least one selected from the group consisting of a persulfate-based initiator, an azo-based initiator, hydrogen peroxide, and ascorbic acid may be used as the thermal polymerization initiator.
- examples of the persulfate-based initiator include sodium persulfate (Na 2 S 2 O 8 ), potassium persulfate (K 2 S 2 O 8 ), and ammonium persulfate ((NH 4 ) 2 S 2 O 8 ), and examples of the azo-based initiator include 2, 2-azobis (2-amidinopropane) dihydrochloride, 2 , 2-azobis- (N, N-dimethylene) isobutyramidine dihydrochloride (2,2-azobis- (N, Ndimethylene) isobutyramidine dihydrochloride), 2- (carbamoyl azo) isobutyronitrile (2 -(carbamoylazo)isobutylonitril), 2,2-azobis[2-(2-imidazolin-2-yl)propane] dihydrochloride (2,2-azobis[2-(2-imidazolin-2-yl) propane]dihydrochloride), 4,4-azobis-(4-cyan
- the thermal polymerization initiator may be included in an amount of 0.001 part by weight to 1 part by weight based on 100 parts by weight of the acrylic acid-based monomer. If the content of the thermal polymerization initiator is less than 0.001 part by weight, additional thermal polymerization hardly occurs, and the effect of adding the thermal polymerization initiator may be insignificant. If the content of the thermal polymerization initiator exceeds 1 part by weight, the molecular weight of the super absorbent polymer is small. Physical properties may be non-uniform.
- 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 monomer. there is.
- one or more additives such as a surfactant, a thickener, a plasticizer, a storage stabilizer, and an antioxidant may be further included as needed during crosslinking polymerization.
- the monomer composition including the above-described acrylic acid-based monomer, internal crosslinking agent, polymerization initiator, and optionally additives may be prepared in the form of a solution dissolved in a solvent.
- the solvent that can be used at this time can be used without limitation in composition as long as it can dissolve the above-mentioned components, and 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 At least one selected from ethyl ether, toluene, xylene, butyrolactone, carbitol, methyl cellosolve acetate, and N, N-dimethylacetamide may be used in combination, but is not limited to the above examples.
- the solvent may be included in a residual amount excluding the components described above with respect to the total content of
- the method of forming a hydrogel polymer by photopolymerizing such a monomer composition is also not particularly limited as long as it is a commonly used polymerization method.
- the photopolymerization is performed at a temperature of 60 ° C or higher, 70 ° C or higher, 90 ° C or lower, or 85 ° C or lower, irradiating ultraviolet rays having an intensity of 5 mW or higher, 8 mW or higher, or 10 mW or higher, 30 mW or lower, or 20 mW or lower. It can be done by doing Under the above conditions, it is possible to form a crosslinked polymer with better polymerization efficiency during photopolymerization.
- the photopolymerization when it is performed, it may be performed in a reactor equipped with a movable conveyor belt, but the polymerization method described above is an example, and the present invention is not limited to the polymerization method described above.
- the form of a water-containing gel polymer that is usually obtained may be a sheet-like water-containing gel polymer having the width of a belt.
- the thickness of the polymer sheet varies depending on the concentration and injection speed of the monomer composition to be injected, but it is preferable to supply the monomer composition so that a polymer sheet having a thickness of about 0.5 cm to about 5 cm can be obtained.
- the monomer composition is supplied to such an extent that the thickness of the polymer on the sheet is too thin, production efficiency is low, which is undesirable.
- the thickness of the polymer on the sheet exceeds 5 cm, the polymerization reaction does not occur evenly over the entire thickness due to the excessively thick thickness. may not be
- the water-containing gel polymer polymerized as described above may finally take the form of particles through drying, pulverization, and classification processes.
- the drying method may be used without limitation as long as it is commonly used as a drying process for a water-containing gel polymer.
- the drying step may be performed by a method such as hot air supply, infrared ray irradiation, microwave irradiation, or ultraviolet ray irradiation.
- the moisture content of the hydrogel polymer may be 1% to 10% by weight or 1% to 5% by weight.
- the grinding process may be performed so that the particle size of the hydrogel polymer is 150 ⁇ m to 850 ⁇ m.
- a grinder such as a pin mill, a hammer mill, a screw mill, a roll mill, a disc mill, or a jog mill
- the polymer may be milled, but is not limited thereto.
- a process of classifying the hydrogel polymer according to the particle size may be performed.
- the first compound is cross-linked to at least a portion of the second compound.
- the antibacterial and deodorant composition may be present in the form of particles having a sea-island structure.
- the second compound forms a core structure
- the first compound is cross-linked to at least a portion of the second compound to form an incombustible cross-linked structure in the form of an island on the core.
- the particle structure of the antibacterial and deodorant composition of the present invention is exemplified.
- antibacterial agents have been introduced in the form of additives, but there have been problems with safety of the superabsorbent polymers, deterioration in basic physical properties such as water absorption, and durability of antimicrobial properties.
- the first compound having antibacterial and deodorizing properties when present in a cross-linked form on the surface of the second compound, antibacterial and deodorizing effects can be obtained while maintaining absorbency.
- the antibacterial and deodorant composition may include 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 second compound.
- the first compound When the first compound is included within the above range, the first compound is appropriately cross-linked to the surface of the second compound to have sufficient absorption and water retention capabilities, and excellent antibacterial and deodorizing effects can be expected.
- the first compound When the first compound is included in an amount of less than 0.4 parts by weight, antibacterial and deodorizing effects are insignificant, and when included in an amount exceeding 2.5 parts by weight, there is a problem in that absorption capacity and water retention capacity are lowered.
- the antibacterial activity of the antibacterial deodorant composition may be 90% or more upon antibacterial evaluation.
- the antibacterial activity of the antibacterial deodorant 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. % or more, more preferably 99% or more, or 99.2% or more.
- the higher the antimicrobial activity, the better the antibacterial activity, and the upper limit is not limited, but may be, for example, 100% or less.
- the antimicrobial activity against E. Coli may be 90% or more, or 93% or more, preferably 95% or more, more preferably 97% or more, or 99% or more.
- the antibacterial activity against Proteus mirabilis of the antibacterial deodorant 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 more, or 97.5% or more, more preferably 99% or more, or 99.2% or more.
- the antibacterial evaluation may be measured by Method B below.
- the diluted sample was dropped 100 ⁇ m on an agar plate, incubated at 30 ° C for about 24 hours, and then the number of bacteria was counted. was calculated and evaluated.
- the control group means a composition that is not surface-treated with the first compound.
- Antibacterial activity ⁇ 1-(N sample )/(N reference ) ⁇ ⁇ 100
- N sample number of bacteria in the sample containing the first compound
- N refernce number of bacteria in the control group not containing the first compound
- the bacteria used for the antibacterial evaluation may be at least one of gram-positive bacteria and gram-negative bacteria.
- the bacteria used for the antibacterial evaluation may be at least one of Proteus mirabilis, E. Coli, E. Cloacae and E. faecalis.
- the bacteria used for the antibacterial evaluation may be Proteus mirabilis or E. Coli.
- the ammonia content when ammonia deodorization is evaluated in the antibacterial deodorant composition, the ammonia content may be 190 ppm or less.
- the ammonia content of the antibacterial deodorizing composition may be less than 190ppm, less than 180ppm, less than 160ppm, or less than 150ppm, preferably less than 100ppm, less than 80ppm, less than 60ppm, or less than 50ppm. or less, more preferably 20 ppm or less, or may be 10 ppm or less, and the lower limit is not limited, but may be, for example, 0 ppm or more. The lower the ammonia content, the better the deodorizing power of ammonia.
- the ammonia deodorization evaluation may be measured by Method D below.
- a 3M ammonia detect tube may be used as the ammonia detection tube.
- the bacteria used for the ammonia deodorization evaluation may be at least one of gram-positive bacteria and gram-negative bacteria.
- the bacteria used to evaluate the ammonia deodorization may be at least one of Proteus mirabilis, E. Coli, E. Cloacae, and E. faecalis.
- the bacteria used to evaluate the ammonia deodorization may be Proteus mirabilis or E. Coli.
- the antibacterial deodorant composition may have a centrifuge retention capacity (CRC) of 30 g/g or more and 60 g/g or less.
- CRC centrifuge retention capacity
- the centrifugal water retention capacity of the antibacterial and deodorant 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. there is.
- the centrifugal water retention capacity of the antibacterial deodorant composition is 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. g/g or less.
- the antibacterial and deodorant composition having centrifugal water retention capacity within the above range When used for diapers or sanitary napkins, it can absorb water well even in a standing state.
- the centrifuge retention capacity (CRC) may be measured according to EDANA WSP 241.3.
- the antibacterial and deodorant composition W 0 (g) of the present invention is uniformly placed in a bag made of nonwoven fabric, sealed, and then immersed in physiological saline at room temperature. After 30 minutes, water is drained from the bag for 3 minutes under the condition of 250 G using a centrifugal separator, and the mass W 2 (g) of the bag is measured.
- the mass W 1 (g) after proceeding in the same manner as the above-described method without using the antibacterial and deodorizing composition is measured.
- the centrifugal retention capacity (CRC) (g/g) is calculated according to the following equation.
- the absorbent under pressure (AUP) of the antibacterial and deodorant composition may be 10 g/g or more and 40 g/g or less.
- the pressure absorption capacity of the antibacterial and deodorant 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 pressure absorption capacity of the antibacterial deodorant composition is 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. g or less.
- the antibacterial and deodorant composition having a pressurized absorbency within the above range is used for diapers or sanitary napkins, water does not leak out again even when sitting or lying down.
- the absorbent capacity under pressure may be measured in the range of 0.5 psi to 0.8 psi according to EDANA WSP 242.3.
- a stainless steel 400 mesh wire mesh is mounted on the bottom of a plastic cylinder having an inner diameter of 60 mm.
- a piston capable of uniformly spraying the antibacterial deodorant composition W 0 (g) of the present invention on a wire mesh under conditions of room temperature and 50% humidity and uniformly further applying a load of 0.5 psi to 0.8 psi thereon has an outer diameter greater than 60 mm. It is slightly smaller, there is no gap with the inner wall of the cylinder, and the vertical movement is not hindered.
- the weight W 3 (g) of the device is measured.
- a glass filter having a diameter of 90 mm and a thickness of 5 mm is placed inside a petro dish having a diameter of 150 mm, and physiological saline solution composed of 0.9% by weight sodium chloride is leveled with the upper surface of the glass filter.
- the measuring device is placed on a filter paper, and the liquid is absorbed for 1 hour under a load. After 1 hour, the measuring device is lifted and its weight W 4 (g) is measured. Using each mass obtained, the absorbency under pressure (AUP) (g/g) is calculated according to the following equation.
- AUP absorbency under pressure
- AUP(g/g) [W 4 (g) - W 3 (g)]/W 0 (g)
- An exemplary embodiment of the present specification provides a method for preparing an antibacterial deodorant composition.
- the method for preparing an antibacterial deodorant composition includes preparing a mixture of a first compound of Chemical Formula 1 and a second compound different from the first compound (a); and (b) crosslinking the mixture.
- step (b) may be performed at 150 ° C to 220 ° C for more than 20 minutes, and at 170 ° C to 200 ° C for 30 minutes to 80 minutes. .
- step (b) when the mixture is cross-linked for 20 minutes or less, the first compound is not sufficiently cross-linked on the surface of the second compound, so that desired antibacterial and deodorizing power cannot be obtained, and absorption capacity is poor.
- the mixture in the step (b), may be crosslinked for more than 20 minutes, more than 20 minutes and less than 80 minutes, preferably more than 50 minutes and less than 80 minutes.
- first compound and the second compound are crosslinked for a time within the above range, an optimized water retention and absorption ability can be obtained, and antibacterial and deodorizing functions can be obtained.
- crosslinking exceeds 80 minutes, there is a problem in that the water retention ability gradually decreases.
- the mixture in step (b), may be crosslinked at 150 °C to 220 °C, or 170 °C to 200 °C.
- preparing a mixture of the first compound and the second compound (a) comprises preparing a first compound of Formula 1 and a second compound different from the first compound (a1) and mixing the first compound and the second compound (a2).
- the first compound and the second compound may be directly prepared or commercially available products may be used.
- the mixing method is not limited as long as the first compound and the second compound can be uniformly mixed.
- the mixture may further include a surface crosslinking agent.
- the surface crosslinking agent forms a crosslinking bond on the surface of the second compound separately from the first compound, and by including the surface crosslinking agent, absorption capacity can be improved.
- a polyhydric alcohol-based compound as the surface crosslinking agent; 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 at least one selected from alkylene carbonate-based compounds may be used.
- an alkylene carbonate-based compound may be used.
- the surface crosslinking agent may include one or more kinds of ethylene carbonate, propylene carbonate, and the like.
- the surface crosslinking agent is 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 second compound. can be included
- the mixture may further include an ionic crosslinking agent.
- the ionic crosslinking agent serves to increase surface crosslinking efficiency of the first compound and the second compound.
- the ionic crosslinking agent is Al 2 (SO 4 ) 3 , AlO 3 , Al 2 O 3 3SiO 2 , and Al (H 2 O) 6 3+ at least one selected from It may, but is not limited thereto.
- Al 2 (SO 4 ) 3 aluminum sulfate
- Al 2 (SO 4 ) 3 aluminum sulfate
- the ionic crosslinking agent is 0.01 parts by weight or more and 3 parts by weight or less, 0.05 parts by weight or more and 2 parts by weight or less, or 0.1 parts by weight or more and 1.5 parts by weight or less based on 100 parts by weight of the total second compound. can be included
- the mixture may further include a surfactant.
- a surfactant When the surfactant is included, there is an effect of imparting weak hydrophobicity to water to prevent excessive water absorption during surface treatment of the superabsorbent polymer.
- the surfactant is a polycarboxylate-based surfactant; And at least one selected from polyethylene glycol-based surfactants may be used. Preferably, a polycarboxylate-based surfactant may be used.
- the surfactant is 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 based on 100 parts by weight of the total second compound, or It may be included in 0.05 parts by weight or more and 0.1 parts by weight or less.
- the mixture may further include water or alcohol.
- water or alcohol By including water or alcohol, a mixture is prepared in the form of a solution, and the first compound can be evenly dispersed in the second compound.
- the water or alcohol is 1 part by weight or more and 20 parts by weight or less, 2 parts by weight or more and 15 parts by weight or less, or 3 parts by weight or more and 10 parts by weight or less based on 100 parts by weight of the total second compound. can be included as
- a step (c) of classifying the antibacterial deodorant composition may be further included after the step (b).
- the classification process may use a standard mesh sieve of ASTM standards.
- the antibacterial deodorant composition according to an exemplary embodiment of the present specification may be used for superabsorbent antibacterial articles.
- Examples of the superabsorbent antibacterial article include diapers and sanitary napkins, but are not limited thereto.
- An exemplary embodiment of the present specification provides a deodorant composition including a first compound represented by Formula 1 below.
- R 1 to R 3 are each independently an alkyl group having 1 to 12 carbon atoms unsubstituted or substituted with a hydroxyl group;
- At least one of R 1 to R 3 is an alkyl group having 8 to 12 carbon atoms
- R 4 is an alkylene group having 1 to 6 carbon atoms
- X is halogen
- the description of the first compound of Chemical Formula 1 of the deodorant composition may be applied in the same manner as the description of the first compound of Chemical Formula 1 of the above-described antibacterial deodorant composition.
- the deodorant composition has a bacterial inhibition rate of 80% or more, as evaluated by method E below, with respect to at least one strain of gram-positive bacteria and gram-negative bacteria.
- Bacterial inhibition rate (%) ⁇ 1-(A sample )/(A reference ) ⁇ ⁇ 100
- the bacterial inhibition rate of the deodorant composition when evaluated by the method E, the bacterial inhibition rate against E. Coli is 88% or more, 89.3% or more, 90% or more, 93% or more, 94.4% 95% or more, 96.1% or more, 98% or more, 98.9% or more, or 99% or more, and the bacterial inhibition rate for Proteus mirabilis is 83% or more, 90% or more, 91.2% or more, 95% or more, 96.9% It may be 98% or more, 99% or more, or 99.9% or more.
- the higher the bacterial inhibition rate, the better the antibacterial activity, and the upper limit is not limited, but may be, for example, 100% or less.
- Antibacterial and deodorizing monomer B was obtained in the same manner as in Preparation Example A, except that bromooctane was used instead of bromodecane in the preparation method of Preparation Example A.
- An antibacterial and deodorizing monomer C was obtained in the same manner as in Preparation A, except that bromododecane was used instead of bromodecane in the preparation method of Preparation Example A.
- Antibacterial and deodorizing monomer D was obtained in the same manner as in Preparation A, except that dimethylethanolamine was used instead of methyldiethanolamine in the preparation method of Preparation Example A.
- Antibacterial and deodorizing monomer G was obtained in the same manner as in Preparation Example A, except that bromobutane was used instead of bromodecane in the preparation method of Preparation Example A.
- NMR data of the antibacterial and deodorant monomers A to G prepared in Preparation Example 1 can be seen in FIGS. 2 to 8.
- the temperature of the neutralization solution mixed to SPS reached 40 ° C, it was placed in a tray in the UV chamber. Thereafter, ultraviolet rays were irradiated with a UV irradiation device for 1 minute while maintaining a polymerization atmosphere temperature of 80°C (irradiation amount: 10 mW/cm 2 ), and aging was performed for 2 minutes to perform UV polymerization, thereby preparing a hydrogel polymer sheet.
- the polymerized sheet was taken out and cut into a size of 3 cm ⁇ 3 cm, mixed with 180 g of water, and then chopped using a meat chopper to prepare crumbs. At this time, the hole size of the meat chopper was 16 pie.
- the crumb was dried in an oven capable of transferring air volume up and down. Hot air at 185 ° C. was flowed from the bottom to the top for 16 minutes and from the top to the bottom for 16 minutes to uniformly dry, and after drying, the water content of the dried body was set to 2% or less. After drying, it was pulverized with a grinder, and then classified with Amplitute 1.5 mm for 10 minutes (classification mesh combination: #20-30/#30-50/#50-100/#100), and each classification (22%/64%) /13%/1%) was collected and obtained by classifying a polymer having a particle diameter of about 850 ⁇ m or less, and in this way a base resin powder was obtained.
- Preparation Example 2 the same procedure as in Preparation Example 2 was performed except that the following antibacterial and deodorizing monomer was quantified and diluted evenly in an amount of 1 to 2 phr based on the weight of acrylic acid before adding the neutralization solution to the UV chamber.
- Example 2 It was prepared 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 deodorant monomer A in Example 1, and the surface crosslinking reaction was performed for the time shown in Table 1 below. A deodorant composition was obtained.
- Superabsorbent polymer 2 prepared in Preparation Example 3 was used as an antibacterial and deodorant composition.
- An antibacterial deodorant composition was obtained in the same manner as in Example 7, except that the first compound having the type and content shown in Table 2 was used instead of 1 part by weight of antibacterial and deodorant monomer A in Example 7.
- Superabsorbent polymer 1 prepared in Preparation Example 1 was used as an antibacterial and deodorant composition.
- Bacterial inhibition rate (%) ⁇ 1-(A sample )/(A reference ) ⁇ ⁇ 100
- the diluted sample was dropped 100 ⁇ m on an agar plate, incubated at 30 ° C for about 24 hours, and then the number of bacteria was counted. was calculated and evaluated.
- Antibacterial activity ⁇ 1-(N sample )/(N reference ) ⁇ ⁇ 100
- N sample the number of bacteria in the sample containing the antibacterial deodorizing monomer
- N refernce the number of bacteria in the control group not containing the antibacterial deodorizing monomer
- the diluted sample was dropped 100 ⁇ m on an agar plate, incubated at 30 ° C for about 24 hours, and then the number of bacteria was counted. was calculated and evaluated.
- Antibacterial activity ⁇ 1-(N sample )/(N reference ) ⁇ ⁇ 100
- N sample the number of bacteria in the sample containing the antibacterial deodorizing monomer
- N refernce the number of bacteria in the control group not containing the antibacterial deodorizing monomer
- antibacterial activity is higher when two hydroxyl groups are present than compounds having one hydroxyl group, and antibacterial activity is further improved as the number of carbon atoms in the alkyl group R 1 increases.
- the antibacterial activity is not sufficiently expressed 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 second compound.
- the ammonia content of Examples 1 to 6 including the antibacterial deodorant composition of the present invention is 160 ppm or less, much lower than that of Comparative Examples 1 to 8 in which 200 ppm to 500 ppm ammonia was measured. there is. Therefore, it can be confirmed that the antibacterial deodorant composition of the present invention has an excellent 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 having two hydroxyl groups, ammonia was measured at 50 ppm or less, remarkably low.
- Centrifuge retention capacity was measured according to EDANA WSP 241.3. First, 1.5 g (W 0 ) of the antibacterial and deodorant composition prepared above was uniformly placed in a non-woven bag and sealed, and then immersed in physiological saline at room temperature. After 30 minutes, water was drained from the bag for 3 minutes under the condition of 250 G using a centrifuge, and the mass W 2 (g) of the bag was measured. In addition, the mass W 1 (g) after proceeding in the same manner as the above-described method without using the antibacterial and deodorizing composition was measured. Using each mass obtained, centrifugal retention capacity (CRC) (g/g) was calculated according to the following equation.
- Absorbency under pressure was measured according to EDANA WSP 242.3 at 0.7 psi under pressure.
- a 400 mesh stainless steel wire mesh was attached to the bottom of a plastic cylinder having an inner diameter of 60 mm.
- a piston capable of uniformly spraying 1 g (W 0 ) of the antibacterial deodorant composition prepared above on a wire mesh under conditions of room temperature and 50% humidity and uniformly applying a load of 0.7 psi thereon is slightly smaller than the outer diameter of 60 mm. , there is no gap with the inner wall of the cylinder, and the vertical movement is not hindered.
- the weight W 3 (g) of the device was measured.
- a glass filter having a diameter of 90 mm and a thickness of 5 mm was placed inside a petro dish having a diameter of 150 mm, and physiological saline solution composed of 0.9% by weight sodium chloride was leveled with the upper surface of the glass filter.
- a sheet of filter paper having a diameter of 90 mm was placed thereon.
- the measuring device was placed on a filter paper, and the liquid was absorbed for 1 hour under a load. After 1 hour, the measuring device was lifted up and its weight W 4 (g) was measured. Using each mass obtained, the absorbency under pressure (AUP) (g/g) was calculated according to the following equation.
- AUP(g/g) [W 4 (g) - W 3 (g)]/W 0 (g)
- the antibacterial and deodorant composition of the present invention not only provides excellent centrifugal water retention capacity and absorbency under pressure, but also has an effect of improving antibacterial and deodorizing power.
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Abstract
Description
Claims (16)
- 하기 화학식 1의 제1 화합물; 및상기 제1 화합물과 상이한 제2 화합물을 포함하는 항균 소취 조성물로서,상기 제1 화합물은 상기 제2 화합물의 적어도 일부에 가교 결합되고,상기 항균 소취 조성물의 소취 평가시 Guaiacol의 함량이 300ng 이하, 3-methylbutanal의 함량이 250ng 이하, Diacetyl의 함량이 30ng 이하이며,상기 소취 평가는 하기 방법 A에 의해 측정되는 것인 항균 소취 조성물:[화학식 1]상기 화학식 1에 있어서,R1 내지 R3은 각각 독립적으로, 히드록시기로 치환 또는 비치환된 탄소수 1 내지 12의 알킬기이고,R1 내지 R3 중 적어도 하나는 탄소수 8 내지 12의 알킬기이며,R4는 탄소수 1 내지 6의 알킬렌기이고,X는 할로겐이며,[방법 A]500ml Lab bottle에 상기 항균 소취 조성물 1g을 넣은 후, 미생물을 접종한 인공뇨 25ml을 주입하여 35℃에서 24시간 동안 배양시킨 후, 흡착관에 Guaiacol, 3-methylbutanal, 및 Diacetyl 성분을 각각 포집하고, GC/MS를 이용하여 각각 포집된 성분의 질량을 분석한다.
- 청구항 1에 있어서, 상기 항균 소취 조성물은 상기 제1 화합물을 상기 제2 화합물 전체 100 중량부를 기준으로 0.4 중량부 이상 2.5 중량부 이하로 포함하는 것인 항균 소취 조성물.
- 청구항 1에 있어서, 상기 화학식 1의 R1 및 R2 중 적어도 하나는 탄소수 1 내지 5의 알킬기인 것인 항균 소취 조성물.
- 청구항 1에 있어서, 상기 제2 화합물은 고흡수성 수지인 것인 항균 소취 조성물.
- 청구항 1에 있어서, 상기 제2 화합물은 함수겔 중합체를 포함하는 것인 항균 소취 조성물.
- 청구항 1에 있어서, 상기 항균 소취 조성물은 바다-섬 구조를 갖는 입자 형태로 존재하는 것인 항균 소취 조성물.
- 청구항 1에 있어서, 상기 항균 소취 조성물의 항균력 평가시, 항균력이 90% 이상이며, 상기 항균력 평가는 하기 방법 B에 의해 측정되는 것인 항균 소취 조성물:[방법 B]3,000 CFU/ml의 균을 접종시킨 인공뇨 40ml을 상기 항균 소취 조성물 2g에 부은 후, 35℃에서 12시간 동안 배양시키고, 배양이 완료된 용액을 생리 식염수 160ml로 희석한 후, 생리 식염수로 연속 희석한 샘플들을 아가 플레이트에 깔아 계산한다.
- 청구항 1에 있어서, 상기 항균 소취 조성물의 원심분리보수능은 30 g/g 이상 60 g/g 이하인 것인 항균 소취 조성물.
- 청구항 1에 있어서, 상기 항균 소취 조성물의 가압흡수능은 10 g/g 이상 40 g/g 이하인 것인 항균 소취 조성물.
- 청구항 1 내지 9 중 어느 하나의 항에 따른 항균 소취 조성물의 제조방법으로서,상기 화학식 1의 제1 화합물 및 상기 제1 화합물과 상이한 제2 화합물의 혼합물을 준비하는 단계 (a); 및상기 혼합물을 가교시키는 단계 (b)를 포함하는 항균 소취 조성물의 제조방법.
- 청구항 10에 있어서, 상기 단계 (b)는 150℃ 내지 220℃에서 20분 초과의 시간 동안 수행되는 것인 항균 소취 조성물의 제조방법.
- 청구항 10에 있어서, 상기 단계 (b)는 170℃ 내지 200℃에서 30분 내지 80분의 시간 동안 수행되는 것인 항균 소취 조성물의 제조방법.
- 청구항 13에 있어서, 그람 양성균 및 그람 음성균 중 적어도 하나의 균주에 대하여, 하기 방법 E로 평가한 상기 소취 조성물의 균 억제율이 80% 이상인 것인 소취 조성물:[방법 E]3,000 CFU/ml의 균을 접종시킨 Broth type 배지(Nutreint broth, BD DIFCP., 8g/L) 25ml를 50ml의 코니칼 튜브(conical tube)에 옮겨 담고, 상기 소취 조성물 0.01g을 첨가한 후, 혼합(vortexing)한다. 충분히 혼합된 용액을 35℃가 유지되는 진탕 항온 수조(shaking water bath) 내에서 16시간 동안 배양시킨다. 배양이 완료된 용액을 1X PBS(phosphate buffered saline) buffer solution을 이용하여 1/5로 희석한 후, UV/Vis Spectrophotometer를 이용하여 흡광도(λ=600nm)를 측정한다. 측정된 흡광도를 대조군과 비교하여 균 억제율을 아래와 같은 수식으로 계산한다. 이 때, 대조군이란 상기 소취 조성물을 함유하지 않은 배지 용액을 의미한다.균 억제율(%)={1-(Asample)/(Areference)} × 100(Asample: 소취 조성물을 함유한 배지 용액의 흡광도, Arefernce: 소취 조성물을 함유하지 않은 배지 용액의 흡광도)
- 청구항 14에 있어서, 상기 방법 E는 E.coli 의 균주에 대하여 측정한 것이고, 상기 균 억제율은 88% 이상인 것인 소취 조성물.
- 청구항 14에 있어서, 상기 방법 E는 Proteus mirabilis 의 균주에 대하여 측정한 것이고, 상기 균 억제율은 83% 이상인 것인 소취 조성물.
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