WO2018199725A2 - Procédé de préparation d'un polymère super-absorbant contenant de l'acide citraconique à l'aide d'une solution aqueuse de nitrate d'argent et polymère superabsorbant antibactérien ainsi préparé - Google Patents

Procédé de préparation d'un polymère super-absorbant contenant de l'acide citraconique à l'aide d'une solution aqueuse de nitrate d'argent et polymère superabsorbant antibactérien ainsi préparé Download PDF

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Publication number
WO2018199725A2
WO2018199725A2 PCT/KR2018/005034 KR2018005034W WO2018199725A2 WO 2018199725 A2 WO2018199725 A2 WO 2018199725A2 KR 2018005034 W KR2018005034 W KR 2018005034W WO 2018199725 A2 WO2018199725 A2 WO 2018199725A2
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WO
WIPO (PCT)
Prior art keywords
super absorbent
absorbent polymer
citraconic acid
vinylpyrrolidinone
silver nitrate
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PCT/KR2018/005034
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English (en)
Korean (ko)
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WO2018199725A3 (fr
Inventor
김정수
김동현
강병관
박노형
김진훈
김민성
김해찬
장지은
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한국생산기술연구원
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Publication of WO2018199725A2 publication Critical patent/WO2018199725A2/fr
Publication of WO2018199725A3 publication Critical patent/WO2018199725A3/fr

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    • 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
    • A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
    • A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
    • A61L15/42—Use of materials characterised by their function or physical properties
    • A61L15/46—Deodorants or malodour counteractants, e.g. to inhibit the formation of ammonia or bacteria
    • 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
    • A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
    • A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
    • A61L15/42—Use of materials characterised by their function or physical properties
    • A61L15/60—Liquid-swellable gel-forming materials, e.g. super-absorbents
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/46—Polymerisation initiated by wave energy or particle radiation
    • C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
    • C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
    • C08F222/02—Acids; Metal salts or ammonium salts thereof, e.g. maleic acid or itaconic acid
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F226/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
    • C08F226/06—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a heterocyclic ring containing nitrogen
    • C08F226/10—N-Vinyl-pyrrolidone
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/28—Nitrogen-containing compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/07—Aldehydes; Ketones
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/10—Esters; Ether-esters
    • C08K5/101—Esters; Ether-esters of monocarboxylic acids
    • C08K5/103—Esters; Ether-esters of monocarboxylic acids with polyalcohols

Definitions

  • the present invention provides a method for producing a superabsorbent polymer having antimicrobial activity, wherein an aqueous solution of silver nitrate is added to a solution containing citraconic acid (CCA) and vinylpyrrolidinone (VP) as a monomer and irradiated with ultraviolet rays.
  • CCA citraconic acid
  • VP vinylpyrrolidinone
  • the present invention relates to a super absorbent polymer having an increased antimicrobial content and a sanitary article prepared therefrom.
  • superabsorbent polymers are materials capable of absorbing and retaining water of about 500 to 1,000 times its own weight, and crosslinked polymers are generally used. These superabsorbent polymers are used as agricultural, horticultural soil repair agents, seedling sheets, packaging materials for food distribution, and the like, and demand for diapers for infants, adults, and animals is increasing rapidly.
  • the superabsorbent polymer is used as a material that directly or indirectly contacts the human body, such as food packaging materials and diapers
  • research for imparting antimicrobial properties to materials has been in the spotlight.
  • the resin was prepared using an antimicrobial monomer, and when the resin thus prepared is used in a diaper or a sanitary napkin, there is an advantage of reducing odor caused by bacteria.
  • the super absorbent polymers currently used in products close to the human body are suitable for absorbing performance such as pressure absorbing ability and water holding ability, but have a disadvantage of inferior antimicrobial properties.
  • the superabsorbent polymer has different absorbency under certain conditions such as absorption rate, water holding capacity and pressure depending on the type of monomer, crosslinking agent and clay mineral used in the preparation thereof, and post-treatment process. Accordingly, in the case of the crosslinked polymer prepared to have appropriate antimicrobial properties, it may not have the absorption capacity required in the industrial field, or only a small amount of a material such as a crosslinking agent may have antimicrobial properties. For example, it is difficult to find a material having appropriate antimicrobial properties while maintaining excellent absorbency.
  • the present inventors have diligently researched to find a simple and economical method for preparing a superabsorbent polymer having excellent antimicrobial activity while maintaining high absorption ability.
  • the inventors used citraconic acid and vinylpyrrolidinone as monomers for crosslinking.
  • To prepare a hydrogel but by adding a silver nitrate solution to the solution mixed with a cross-linking agent and a photoinitiator to the monomer, it was confirmed that the water-absorbing performance can be improved as well as to prepare a resin having antibacterial, and completed the present invention.
  • One object of the present invention is a first step of adding and mixing vinylpyrrolidinone (VP) and a crosslinking agent to a solution containing partially or completely neutralized citraconic acid (CCA); A second step of adding and mixing an aqueous solution of silver nitrate to the solution obtained from the first step; A third step of adding and mixing a photoinitiator and ammonium persulfate to the solution obtained from the second step; And a fourth step of pouring the solution obtained from the third step into a mold and irradiating ultraviolet rays.
  • VP vinylpyrrolidinone
  • CCA partially or completely neutralized citraconic acid
  • Another object of the present invention is to provide a superabsorbent polymer having antimicrobial properties containing silver nanoions and citraconic acid.
  • Still another object of the present invention is to provide a sanitary article made of a super absorbent polymer having the antibacterial property.
  • a solution containing citraconic acid and vinylpyrrolidinone as a monomer is added with an aqueous solution of silver nitrate as a silver precursor and irradiated with ultraviolet rays to form a hydrogel by crosslinking reaction, and at the same time, silver nanoions are formed therein.
  • a superabsorbent polymer containing silver nanoions in a higher content.
  • the production method of the present invention can be carried out through a simple and economical process of simply adding an aqueous solution of silver nitrate, and the resin produced therefrom exhibits excellent antibacterial properties and maintains its unique properties, high absorption, and therefore, It can be usefully used for contacting diapers or women's sanitary products.
  • 1 is a diagram showing the results of ICP-MS measurement over time of a super absorbent polymer prepared by adding a silver nitrate aqueous solution and silver nanoparticles.
  • the present invention is to add a mixture of vinylpyrrolidinone (VP) and a crosslinking agent to a solution containing partially or completely neutralized citraconic acid (CCA) First step; A second step of adding and mixing an aqueous solution of silver nitrate to the solution obtained from the first step; A third step of adding and mixing a photoinitiator and ammonium persulfate to the solution obtained from the second step; And a fourth step of pouring the solution obtained from the third step into a mold and irradiating ultraviolet rays.
  • VP vinylpyrrolidinone
  • CCA citraconic acid
  • the present invention provides a resin having a high absorption capacity by irradiating UV-crosslinked solution containing citraconic acid and vinylpyrrolidinone, but when silver nitrate aqueous solution is added to the solution is crosslinked by UV irradiation and at the same time silver nano Since ions are formed, it is possible to provide an antimicrobial and superabsorbent resin that maintains a high absorbing capacity of the resin itself while exhibiting significantly increased antimicrobial properties including silver nanoions in a uniform and much higher content than adding preformed silver nanoparticles. Based on finding
  • the first step is to add a vinylpyrrolidinone and a crosslinking agent to a solution containing citraconic acid at the same time, or to mix, or to add a vinylpyrrolidinone first and then to add a crosslinking agent It may be mixed, but is not limited thereto.
  • vinylpyrrolidinone in the first step, may be added in a molar ratio of 2: 8 to 8: 2 relative to citraconic acid.
  • citraconic acid and vinylpyrrolidinone may be mixed in a molar ratio of 4: 6 to 8: 2, 3: 7 to 7: 3, or 4: 6 to 6: 4, but are not limited thereto.
  • the molar ratio of citraconic acid to vinylpyrrolidinone to be used is less than 2: 8, it may be difficult to exhibit the desired degree of antimicrobial activity.
  • the molar ratio of citraconic acid to vinyl pyrrolidinone to be used is greater than 8: 2
  • the adsorption of silver nano ions becomes disadvantageous due to the relatively low content of vinylpyrrolidinone, and thus the silver contained in the resin It may be difficult to achieve the desired degree of antimicrobial activity as the content of nano ions decreases, thereby lowering the antimicrobial improvement rate.
  • the crosslinking agent may be a material having a functional group in the sock end so as to crosslink through the vinyl group of the citraconic acid and vinylpyrrolidinone which is a monomer having a vinyl group when UV irradiation.
  • the crosslinking agent polyethylene glycol diacrylate (PEGDA) having a reactive acrylate group in the sock end of polyethylene glycol may be used, but is not limited thereto, and is known by ultraviolet irradiation known in the art.
  • PEGDA polyethylene glycol diacrylate
  • the material used as a crosslinking agent in the preparation of the superabsorbent polymer to be formed can be used without limitation.
  • the crosslinking agent in the first step may be added in an amount of 0.3 to 1.7wt% based on the solution containing citraconic acid and vinylpyrrolidinone.
  • the crosslinking agent may be added in an amount of 0.5 to 1.5 wt% based on the solution obtained from the first step, but is not limited thereto.
  • the content of the crosslinking agent is less than 0.3wt%, the water-retaining capacity is increased but the pressure-absorbing capacity is decreased, and thus it may be difficult to achieve a desired level.
  • the content of the crosslinking agent is more than 1.7wt%, the water-absorbing capacity is increased, but the water-retaining capacity is increased.
  • This decrease can be difficult to achieve the desired level. That is, when the cross-linking agent is added in an amount outside the above range, it may be difficult to provide a resin having a desired water absorption performance, that is, a water holding capacity and a pressure absorbing capacity combined in a desired range.
  • the silver nitrate in the third step may be added in a ratio of 0.1 to 1.5 mol% relative to the total moles of citraconic acid and vinylpyrrolidinone. Specifically, it may be added in a ratio of 0.2 to 1.2 mol% or 0.3 to 1 mol% with respect to the total moles of citraconic acid and vinylpyrrolidinone, but is not limited thereto.
  • the amount of nitric acid is less than 0.1 mol% based on the total moles of citraconic acid and vinylpyrrolidinone, it may be difficult to achieve a desired level of antimicrobial activity.
  • the amount of the nitric acid used is more than 1.5 mol% based on the total moles of citraconic acid and vinylpyrrolidinone, the synthesis of the resin itself is difficult due to the excessive generation of silver nanoions, which may lower the absorption performance.
  • the photoinitiator is 2-hydroxy-2-methylpropiophenone, and 2-hydroxy-4 '-(2-hydroxyethoxy) -2-methylpropiope.
  • Alpha hydroxy ketone compounds such as non- (2-hydroxy-4 '-(2-hydroxyethoxy) -2-methylpropiophenone) can be used.
  • Irgacure 1173 or Irgacure 2959 which are commercially available and commercially available based on the alpha hydroxy ketone, may be used, but is not limited thereto.
  • the production method of the present invention may further comprise a sixth step of drying the product obtained from the fifth step at 40 to 100 °C for 6 to 48 hours.
  • the sixth step may be performed at 50 to 70 °C, but is not limited thereto. If the drying temperature is less than 40 °C may require a long time for drying, or incomplete drying can be made, if it exceeds 100 °C may deteriorate the performance by modifying the structure of the super absorbent polymer.
  • the sixth step may be performed for 12 to 36 hours, but is not limited thereto. Through the additional drying step it is possible to further improve the absorption performance of the superabsorbent polymer of the present invention.
  • the polymer Due to the nature of the polymer, it may be accompanied by structural modification over high temperature and / or time, and in the super absorbent polymer, such structural modification may cause a decrease in absorption performance.
  • the citraconic acid used in the superabsorbent polymer of the present invention has a somewhat lower heat resistance than the acrylic acid used in the conventional superabsorbent resin, so it is important to select a temperature that is not too high so that structural modification does not occur in the drying step.
  • the drying time may also be another factor of denaturation, and the drying time and temperature may be selected in a mutually complementary combination so as not to cause structural modification of the prepared superabsorbent polymer.
  • the present invention provides a superabsorbent polymer having antimicrobial properties containing silver nanoions and citraconic acid.
  • the super absorbent polymer having the antimicrobial property may be prepared by the method of the present invention, but is not limited thereto.
  • silver nanoion may refer to charged particles having a size of nanoscale.
  • the super absorbent polymer of the present invention may exhibit antimicrobial activity against E. coli, Staphylococcus aureus, Pseudomonas aeruginosa, and Salmonella.
  • the super absorbent polymer of the present invention may exhibit antimicrobial activity against E. coli, but is not limited thereto.
  • the present invention provides a sanitary article made of a super absorbent polymer having the antimicrobial properties.
  • the super absorbent polymer may be used in the form of particles of several hundred micrometers in size, for example, 200 to 600 micrometers in size, but is not limited thereto.
  • the hygiene article made of the superabsorbent polymer having the antimicrobial properties of the present invention may be a baby diaper, an adult diaper or a women's physiological article in direct contact with the human body.
  • it may be used as a food packaging material or an agricultural soil repair agent that may indirectly affect the human body, but is not limited thereto.
  • Example 1 antimicrobial activity using silver nitrate Citraconic acid Preparation of Containing Super Absorbent Resin
  • Citraconic acid CCA
  • 1-vinyl-2-pyrrolidinone VP
  • polyethylene glycol diacrylate PEGDA
  • silver nitrate AgNO 3
  • Superabsorbent polymer was prepared in the same manner as in Example 1, except that CCA and VP were used in a molar ratio of 5: 5 to 3: 7.
  • Superabsorbent polymer was prepared in the same manner as in Example 1, except that CCA and VP were used in a molar ratio of 5: 5 to 7: 3.
  • a super absorbent polymer was prepared in the same manner as in Example 1, except that the amount of silver nitrate was reduced from 10 mmol to 5 mmol.
  • Super absorbent polymer was prepared in the same manner as in Example 1, except that the amount of silver nitrate was increased from 10 mmol to 15 mmol.
  • Superabsorbent polymer was prepared in the same manner as in Example 1, except that the amount of the crosslinking agent was reduced from 1% by weight to 0.5% by weight.
  • Superabsorbent polymer was prepared in the same manner as in Example 1, except that the amount of the crosslinking agent was increased from 1 wt% to 1.5 wt%.
  • Comparative example 1 antimicrobial activity using silver nanoparticles Citraconic acid Preparation of Containing Super Absorbent Resin
  • Superabsorbent polymer was prepared in the same manner as in Example 1, except that silver nanoparticles were added instead of the silver nitrate solution.
  • Superabsorbent polymer was prepared in the same manner as in Example 1, except that the aqueous solution of nitric acid was not included.
  • Comparative example 3 Citraconic acid Preparation of superabsorbent polymers, including but not limited to silver silver nitrate
  • Superabsorbent polymer was prepared in the same manner as in Example 1, except that only VP was used instead of CCA.
  • W 1 is the weight of the swollen superabsorbent resin and W 0 is the weight of the dried superabsorbent polymer.
  • W 1 is the weight of the dried superabsorbent polymer and W 2 is the weight of the swollen superabsorbent polymer.
  • Example 1 As shown in Table 2, the highest absorption performance for the super absorbent polymer of Example 1 was measured.
  • the results for Example 1 were compared with the results for the resin of Comparative Example 2, which is a silver-free comparison group, water retention and pressure absorption capacity were increased, which is the internal structure of the resin due to the silver nanoions contained in the resin. It has been shown that the expansion of increases the water holding capacity and the increase in the strength of the gel due to the inclusion of the silver nanoions contributes to the improvement of the pressure absorption capacity.
  • Example 1 prepared by adding a silver nitrate aqueous solution to the monomer mixture solution was compared with the results of the resin of Comparative Example 1 prepared by containing the silver nanoparticles prepared in advance in both the water holding capacity and the pressure absorption capacity. It was shown to have excellent absorption performance compared to the resin of Example 1. It is considered that this is because the absorption capacity due to osmotic pressure is improved by increasing the concentration of ions in the superabsorbent polymer when the aqueous solution of silver nitrate is used.
  • Example 1 Compared with Example 1, the results for Examples 2 and 3 in which the ratio of citraconic acid to vinylpyrrolidinone was increased or decreased, it was found that both have better absorption performance than Comparative Examples 1 to 3, There was a tendency to decrease somewhat compared to Example 1. This is presumably because when the comonomer is used in a ratio outside of a certain range, a homopolymer of a monomer present in excess in addition to the copolymer having a desired structure is additionally formed and incorporated.
  • Example 1 Compared with Example 1, the results for Examples 4 and 5 in which the amount of silver nitrate increased or decreased, it was shown that all have better absorption performance than Comparative Examples 1 to 3, compared to Example 1 There was a tendency to decrease somewhat. This means that as the content of silver nitrate increases, the ion content and gel strength in the superabsorbent resin increase, so that the water-retaining capacity and the pressure-absorbing capacity can be improved at the same time. It indicates that it may be a factor that inhibits the synthesis of the polymer resin by crosslinking.
  • ICP-MS of the superabsorbent polymers prepared according to Example 1 and Comparative Example 1 of the present invention was prepared for 9 days at an interval of 1 day immediately after preparation. It measured until, and the result is shown in FIG.
  • Example 1 when comparing the resins of Example 1 and Comparative Example 1 prepared in the same manner except for using silver aqueous solution and silver nanoparticles, respectively, the resin of Example 1 was immediately prepared as well as 9 Even after days passed, the silver nano ions were contained and maintained at a significantly higher content than the resin of Comparative Example 1. This results in the formation of silver nanoions at the same time as the crosslinking to form the superabsorbent resin, thereby increasing the bonding strength between the superabsorbent resin itself and the silver nanoions, as well as dispersing them evenly. In particular, even after 9 days after the manufacture of some loss is still contained in a high content appeared to maintain antibacterial.

Abstract

La présente invention concerne un procédé de préparation d'un polymère superabsorbant antibactérien par ajout d'une solution aqueuse de nitrate d'argent à une solution contenant de l'acide citraconique (CCA) et de la vinylpyrrolidone (VP) en tant que monomères, suivi d'une irradiation UV, à un polymère superabsorbant antibactérien préparé par le procédé, le polymère superabsorbant antibactérien ayant une teneur accrue en ions nano-argent, et un produit d'hygiène fabriqué à partir du polymère superabsorbant antibactérien.
PCT/KR2018/005034 2017-04-28 2018-04-30 Procédé de préparation d'un polymère super-absorbant contenant de l'acide citraconique à l'aide d'une solution aqueuse de nitrate d'argent et polymère superabsorbant antibactérien ainsi préparé WO2018199725A2 (fr)

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KR1020170054878A KR101860884B1 (ko) 2017-04-28 2017-04-28 질산은 수용액을 이용한 시트라콘산 함유 고흡수성 수지의 제조방법 및 이에 따라 제조된 항균성을 갖는 고흡수성 수지
KR10-2017-0054878 2017-04-28

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US6566575B1 (en) * 2000-02-15 2003-05-20 3M Innovative Properties Company Patterned absorbent article for wound dressing
BR0116761A (pt) * 2000-12-29 2004-02-25 Dow Global Technologies Inc Processo para a preparação de partìculas de resina absorventes de água de polìmeros contendo carboxila reticulados com baixo teor de monÈmero, partìculas obtidas e seu uso
AU2002322368A1 (en) * 2001-06-29 2003-03-03 Dow Global Technologies Inc. Superabsorbent carboxyl-containing polymers with odor control
BR0212878A (pt) * 2001-10-01 2004-10-13 Basf Ag Mistura polimérica, artigo de higiene, e, uso de misturas poliméricas
WO2008024426A2 (fr) * 2006-08-24 2008-02-28 Neuwirth Robert S Articles absorbants contenant des nanoparticules d'argent
KR20100041143A (ko) * 2008-10-13 2010-04-22 박종훈 하이드록시에시드 은나노염을 이용한 항균 탈취 비드 및 그제조방법
AU2012303778B2 (en) * 2011-08-26 2015-01-15 Saudi Basic Industries Corporation (Sabic) Water expandable polymer beads

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