WO2021117786A1 - 被覆樹脂粒子及び被覆樹脂粒子を製造する方法 - Google Patents

被覆樹脂粒子及び被覆樹脂粒子を製造する方法 Download PDF

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Publication number
WO2021117786A1
WO2021117786A1 PCT/JP2020/045932 JP2020045932W WO2021117786A1 WO 2021117786 A1 WO2021117786 A1 WO 2021117786A1 JP 2020045932 W JP2020045932 W JP 2020045932W WO 2021117786 A1 WO2021117786 A1 WO 2021117786A1
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Prior art keywords
water
resin particles
absorbent resin
group
coating
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Ceased
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PCT/JP2020/045932
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English (en)
French (fr)
Japanese (ja)
Inventor
大輝 澤木
知穂 大仁田
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Sumitomo Seika Chemicals Co Ltd
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Sumitomo Seika Chemicals Co Ltd
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Priority to CN202080086087.2A priority Critical patent/CN114829459A/zh
Priority to EP20899834.4A priority patent/EP4074756A4/en
Priority to US17/757,135 priority patent/US12590190B2/en
Priority to JP2021564015A priority patent/JP7713391B2/ja
Priority to KR1020227021181A priority patent/KR20220117878A/ko
Publication of WO2021117786A1 publication Critical patent/WO2021117786A1/ja
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61F—FILTERS IMPLANTABLE INTO BLOOD VESSELS; PROSTHESES; DEVICES PROVIDING PATENCY TO, OR PREVENTING COLLAPSING OF, TUBULAR STRUCTURES OF THE BODY, e.g. STENTS; ORTHOPAEDIC, NURSING OR CONTRACEPTIVE DEVICES; FOMENTATION; TREATMENT OR PROTECTION OF EYES OR EARS; BANDAGES, DRESSINGS OR ABSORBENT PADS; FIRST-AID KITS
    • A61F13/00—Bandages or dressings; Absorbent pads
    • A61F13/15—Absorbent pads, e.g. sanitary towels, swabs or tampons for external or internal application to the body; Supporting or fastening means therefor; Tampon applicators
    • A61F13/53—Absorbent pads, e.g. sanitary towels, swabs or tampons for external or internal application to the body; Supporting or fastening means therefor; Tampon applicators characterised by the absorbing medium
    • A61F2013/530481—Absorbent pads, e.g. sanitary towels, swabs or tampons for external or internal application to the body; Supporting or fastening means therefor; Tampon applicators characterised by the absorbing medium having superabsorbent materials, i.e. highly absorbent polymer gel materials
    • 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
    • C08J2333/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers
    • C08J2333/02—Homopolymers or copolymers of acids; Metal or ammonium salts thereof

Definitions

  • the present invention relates to coated resin particles and a method for producing coated resin particles.
  • Water-absorbent resin particles are widely used in various fields such as disposable diapers, sanitary products, sanitary materials such as simple toilets, agricultural and horticultural materials such as water retention agents and soil conditioners, and industrial materials such as water stop agents and dew condensation inhibitors. ing.
  • the water-absorbent resin particles are required to control the water absorption rate in addition to the performance such as high water absorption capacity and gel strength.
  • the water absorption rate can be controlled, for example, by varying the specific surface area of the water-absorbent resin particles and the amount of the cross-linking agent used.
  • the specific surface area of the water-absorbent resin particles and the amount of the cross-linking agent used are changed to slow down the water absorption rate (for example, the time during which the water-absorbent resin particles are in a swollen state, and / Or, the time to start water absorption is delayed).
  • the water absorption rate for example, the time during which the water-absorbent resin particles are in a swollen state, and / Or, the time to start water absorption is delayed.
  • the present invention has been made in view of such a problem, and provides a coated resin particle whose water absorption rate is controlled to be slow without changing the polymerization condition of the water-absorbent resin particle, and a method for producing the same.
  • the purpose is to produce the same.
  • One aspect of the present invention has water-absorbent resin particles and a coating layer that covers at least a part of the surface of the water-absorbent resin particles, and the coating layer has a solubility in 100 g of water of 1.0 g at 25 ° C.
  • coated resin particles containing a water-soluble component in the range of 150 g or less are provided.
  • Another aspect of the present invention is to mix the water-absorbent resin particles and a coating material containing a water-soluble component having a solubility in 100 g of water in the range of 1.0 g or more and 150 g or less at 25 ° C. to obtain the above-mentioned water-absorbent resin.
  • a method for producing the above-mentioned coated resin particles which comprises a step of forming a coating layer on at least a part of the surface of the particles.
  • the present invention it is possible to provide coated resin particles in which the water absorption rate is controlled to be slow without changing the polymerization conditions of the water-absorbent resin particles, and a method for producing the same.
  • the coated resin particles of the present invention have water-absorbent resin particles and a coating layer that covers at least a part of the surface of the water-absorbent resin particles.
  • the coating layer contains a water-soluble component having a solubility in 100 g of water in the range of 1.0 g or more and 150 g or less at 25 ° C.
  • the coating layer is preferably chemically and / or physically bonded to the surface of the water-absorbent resin particles so that the water-absorbent resin particles do not easily fall off from the water-absorbent resin particles in the state before water absorption.
  • the physical bond is realized, for example, by the anchor effect caused by the coating layer entering the fine recesses existing on the surface of the water-absorbent resin particles.
  • FIG. 1 is a schematic cross-sectional view showing an embodiment of the coated resin particles.
  • the coated resin particles 1 according to the present embodiment have the water-absorbent resin particles 10 and the coating layer 20 that covers at least a part of the surface of the water-absorbent resin particles 10.
  • the entire surface of the water-absorbent resin particles 10 is covered with the coating layer 20.
  • the water-absorbent resin particles 10 are blocked from contact with the liquid at the portion coated by the coating layer 20. Therefore, if the entire surface of the water-absorbent resin particles 10 is covered with the coating layer 20, the water-absorbent resin particles 10 cannot absorb the liquid. On the other hand, although not particularly shown, when a part of the surface of the water-absorbent resin particles 10 is covered with the coating layer 20, the water-absorbent resin particles 10 are not covered with the exposed portion (not covered with the coating layer 20). Although the liquid can be absorbed in the portion), the coating layer 20 functions as a binding tool that inhibits the expansion of the water-absorbent resin particles 10.
  • the coating layer 20 is provided on at least a part of the surface of the water-absorbent resin particles 10, the water-absorbent resin particles 10 cannot exhibit the original water-absorbing ability.
  • the coating layer 20 contains a water-soluble component having a solubility in 100 g of water in the range of 1.0 g or more and 150 g or less at 25 ° C., when the coating resin particles 1 come into contact with the liquid, the coating layer 20 Gradually dissolves and disappears. As the coating layer 20 disappears, the water-absorbent resin particles 10 gradually exhibit their original water-absorbing ability, and finally become the swollen water-absorbent resin particles 10a shown in FIG. 1 (b). ..
  • the coated resin particles of the present invention since the water-absorbent resin particles are coated with a specific coating layer, the water-absorbing ability of the water-absorbent resin particles is suppressed. That is, the time required for the coated resin particles to reach the swollen state is slower than when only the water-absorbent resin particles constituting the coated resin particles are used.
  • changes in the amount of water absorption that can be exhibited by the coated resin particles will be described with reference to FIG.
  • FIG. 2 shows changes in the amount of water absorption over time after contact with the liquid (hereinafter, simply referred to as “water absorption behavior”) for each of the coated resin particles and the water-absorbent resin particles constituting the coated resin particles. It is a graph. Note that FIG. 2 is not a graph obtained by actually measuring specific coated resin particles and water-absorbent resin particles, but is a conceptual diagram showing the concept of the present invention.
  • the water absorption behavior of the coated resin particles is "compared to the water-absorbent resin particles, the time for starting water absorption is the same (the moment when the coated resin particles come into contact with the liquid).
  • the time required to reach the swelling state may be slow, and as shown in FIG. 2 (b), "compared to the water-absorbent resin particles".
  • the time to start water absorption and the time to reach the swelling state may be slow ", and as shown in FIG. 2 (c),” the time to start water absorption as compared with the water-absorbent resin particles ". Is the same (the moment the coated resin particles come into contact with the liquid), but since the amount of water absorbed at the initial stage is extremely small, the time until the swelling state is reached may be slow. "
  • the coated resin particles have a slower water absorption rate than the case where only the water-absorbent resin particles are used. Therefore, by using the coated resin particles of the present invention, the occurrence of the gel blocking phenomenon can be effectively suppressed as compared with the case where only the water-absorbent resin particles are used.
  • the coating resin particles as shown in FIG. 2 (b) or (c), the amount of water absorption preferably increases remarkably after a lapse of a certain period of time, and as shown in FIG. 2 (b), until a certain period of time elapses. Those that do not absorb liquid are more preferable.
  • the coated resin particles exhibiting water absorption behavior as shown in FIG. 2B do not absorb liquid until a certain period of time elapses, so that the occurrence of the gel blocking phenomenon can be suppressed more effectively.
  • the coated resin particles exhibit water absorption behavior as shown in FIG. 2B
  • water absorption is started after the coated resin particles come into contact with a 0.9% by mass sodium chloride aqueous solution (hereinafter, simply referred to as "physiological saline").
  • the time may be, for example, 3 to 120 minutes, 5 to 90 minutes, or 10 to 60 minutes.
  • the time from the contact of the coated resin particles with the physiological saline until the coated resin particles exhibit 10% water absorption is, for example, 3 to 120. Minutes, 5 to 90 minutes, or 10 to 60 minutes.
  • "exhibiting 10% water absorption capacity” means absorbing physiological saline solution corresponding to 10% by mass of the total water absorption amount in the swollen state.
  • the water absorption behavior that is easy to achieve will be explained for each aspect of the coating layer.
  • the coating layer covers the entire surface of the water-absorbent resin particles, even if the coating resin particles come into contact with the liquid, water absorption is not started until the coating layer is dissolved and the surface of the water-absorbent resin particles is exposed. As a result, the coated resin particles tend to exhibit the water absorption behavior as shown in FIG. 2B. In this case, the time until the coating resin particles start absorbing water can be appropriately controlled by the material and / or thickness of the coating layer.
  • the coating layer covers a part of the surface of the water-absorbent resin particles
  • water absorption is started at the moment when the coating resin particles come into contact with the liquid, but the expansion of the water-absorbent resin particles is suppressed by the coating layer. ing. Therefore, the coated resin particles cannot exhibit their original water absorption capacity until the coating layer is sufficiently dissolved, and as a result, the coating resin particles tend to exhibit the water absorption behavior as shown in (a) or (c) of FIG.
  • the coated resin particles show water absorption behavior as shown in FIG. 2 (a) (water absorption amount (water absorption rate) per unit time is relatively constant until reaching a swelling state), or water absorption as shown in FIG. 2 (c). Whether or not the behavior (the amount of water absorption rapidly increases after a certain period of time) is exhibited can be appropriately controlled by the material, thickness, and / or coverage of the coating layer.
  • the water-absorbent resin particles are not particularly limited as long as they are composed of a water-absorbent resin.
  • the water-absorbent resin particles may contain, for example, a crosslinked polymer formed by polymerizing a monomer containing an ethylenically unsaturated monomer.
  • the crosslinked polymer can have a monomeric unit derived from an ethylenically unsaturated monomer.
  • the water-absorbent resin particles can be produced, for example, by a method including a step of polymerizing a monomer containing an ethylenically unsaturated monomer. Examples of the polymerization method include a reverse phase suspension polymerization method, an aqueous solution polymerization method, a bulk polymerization method, and a precipitation polymerization method.
  • the ethylenically unsaturated monomer may be a water-soluble ethylenically unsaturated monomer (an ethylenically unsaturated monomer having a solubility in 100 g of water of 1.0 g or more at 25 ° C.).
  • water-soluble ethylenically unsaturated monomer include (meth) acrylic acid and a salt thereof, 2- (meth) acrylamide-2-methylpropanesulfonic acid and a salt thereof, (meth) acrylamide, N, N-dimethyl.
  • (Meta) acrylamide, 2-hydroxyethyl (meth) acrylate, N-methylol (meth) acrylamide, polyethylene glycol mono (meth) acrylate, N, N-diethylaminoethyl (meth) acrylate, N, N-diethylaminopropyl (meth) Acrylate and diethylaminopropyl (meth) acrylamide can be mentioned.
  • the ethylenically unsaturated monomer has an amino group
  • the amino group may be quaternized.
  • the ethylenically unsaturated monomer may be used alone or in combination of two or more.
  • the acid group may be neutralized with an alkaline neutralizer and then used in the polymerization reaction.
  • the degree of neutralization of the ethylenically unsaturated monomer by the alkaline neutralizing agent is, for example, 10 to 100 mol%, 50 to 90 mol%, or 60 to 80 mol% of the acidic group in the ethylenically unsaturated monomer. May be%.
  • the ethylenically unsaturated monomer is at least one selected from the group consisting of (meth) acrylic acid and salts thereof, acrylamide, methacrylamide, and N, N-dimethylacrylamide. It may contain a compound of the species.
  • the ethylenically unsaturated monomer may contain (meth) acrylic acid and a salt thereof, and at least one compound selected from the group consisting of acrylamide.
  • a monomer other than the above-mentioned ethylenically unsaturated monomer may be used.
  • Such a monomer can be used, for example, by mixing with an aqueous solution containing the above-mentioned ethylenically unsaturated monomer.
  • the amount of the ethylenically unsaturated monomer used may be 70 to 100 mol% with respect to the total amount of the monomers.
  • the ratio of (meth) acrylic acid and a salt thereof may be 70 to 100 mol% with respect to the total amount of the monomer.
  • Cross-linking occurs by self-cross-linking during polymerization, but cross-linking may be promoted by using an internal cross-linking agent.
  • an internal cross-linking agent When an internal cross-linking agent is used, it is easy to control the water absorption characteristics (water retention amount, etc.) of the water-absorbent resin particles.
  • the internal cross-linking agent is usually added to the reaction solution during the polymerization reaction.
  • the water-absorbent resin particles may be crosslinked (surface crosslinked) in the vicinity of the surface. Further, the water-absorbent resin particles may be composed of only polymer particles (crosslinked polymers), but various types selected from, for example, gel stabilizers, metal chelating agents, fluidity improvers (lubricants) and the like. It may further contain additional ingredients. Additional components may be placed inside the polymer particles, on the surface of the polymer particles, or both. The additional component is preferably a fluidity improver (lubricant).
  • the fluidity improver may contain inorganic particles. Examples of the inorganic particles include silica particles such as amorphous silica.
  • the shape of the water-absorbent resin particles is not particularly limited, and may be, for example, substantially spherical, crushed, or granular, or may be a shape in which primary particles having these shapes are aggregated.
  • the medium particle size of the water-absorbent resin particles may be 100 to 800 ⁇ m, 150 to 700 ⁇ m, 200 to 600 ⁇ m, or 250 to 500 ⁇ m.
  • the medium particle size is measured by the method described in Examples.
  • the water absorption amount of the physiological saline of the water-absorbent resin particles may be, for example, 10 to 100 g / g, 20 to 90 g / g, or 30 to 80 g / g at 25 ° C.
  • the amount of water absorption is measured by the method described in the examples.
  • the coating layer contains a water-soluble component (hereinafter, simply referred to as "water-soluble component”) having a solubility in 100 g of water in the range of 1.0 g or more and 150 g or less at 25 ° C.
  • water-soluble component a water-soluble component having a solubility in 100 g of water in the range of 1.0 g or more and 150 g or less at 25 ° C.
  • the solubility of the water-soluble component exceeds 150 g, the entire coating layer is dissolved within a few seconds after the coating resin particles come into contact with the liquid, although it depends on the thickness of the coating layer, and the water absorption rate is substantially controlled. It may not be possible.
  • the lower limit of the solubility of the water-soluble component in 100 g of water at 25 ° C. may be 1.1 g or more, 1.2 g or more, 1.5 g or more, or 2.0 g or more.
  • the upper limit of the solubility of the water-soluble component in 100 g of water at 25 ° C. is preferably 90 g or less, more preferably 80 g or less, further preferably 70 g or less, and more preferably 60 g or less. Even more preferably, it is particularly preferably 50 g or less.
  • the upper limit of solubility may be 40 g or less, 30 g or less, 20 g or less, 10 g or less, or 5 g or less. Solubility is measured by the method described in the Examples.
  • the viscosity of the saturated aqueous solution of the water-soluble component at 25 ° C. is preferably in the range of 1 Pa ⁇ s or more and 2000 Pa ⁇ s or less.
  • the lower limit of the viscosity is more preferably 1.5 Pa ⁇ s or more, further preferably 2 Pa ⁇ s or more, further preferably 2.5 Pa ⁇ s or more, and 3 Pa ⁇ s or more. It is particularly preferable to have.
  • the upper limit of the viscosity is more preferably 1500 Pa ⁇ s or less, further preferably 1000 Pa ⁇ s or less, further preferably 750 Pa ⁇ s or less, and 500 Pa ⁇ s or less. Is particularly preferable.
  • the viscosity of the water-soluble component increases, it becomes easier to bond to the surface of the water-absorbent resin particles, but the handleability of the water-soluble component decreases and it tends to be difficult to form a coating layer having a uniform thickness.
  • the handleability improves and it becomes easy to form a coating layer having a uniform thickness, but it tends to be difficult to bond to the surface of the water-absorbent resin particles.
  • the viscosity of the water-soluble component is within the above range, the water-soluble component can be easily attached to the surface of the water-absorbent resin particles while maintaining an appropriate handleability.
  • the viscosity of the water-soluble component is measured by the following procedure.
  • aqueous solution by mixing thoroughly at ° C. for 1 hour. After cooling the aqueous solution to 25 ° C., the insoluble material is removed by filtering using a JIS Z8801 standard sieve having a mesh size of 1410 ⁇ m, and the filtrate is used as a saturated aqueous solution.
  • a saturated aqueous solution is placed in a 500 mL beaker having an inner diameter of 85 mm ⁇ to a height of 85 mm, the temperature is adjusted to 25 ⁇ 0.5 ° C., and then the viscosity is measured using a B-type viscometer. The value after 60 seconds is converted into the viscosity [Pa ⁇ s] of the saturated aqueous solution using the rotor used and the multiplier corresponding to the rotation speed.
  • B-type viscometer Bismetron VS-H1 type manufactured by Shibaura Semtech Co., Ltd. (former Shibaura System Co., Ltd.) is used.
  • the rotor used is that of the same company.
  • hydrophilic group-containing compound a compound having a hydrophilic group
  • the hydrophilic group that the hydrophilic group-containing compound can have is, for example, at least one group selected from the group consisting of an anionic group, a cationic group, an amphoteric group, and a nonionic group.
  • Examples of the anionic group include a carboxyl group, a sulfonic acid group, and a phosphoric acid group.
  • Examples of the cationic group include an amino group, an imino group, and a quaternary ammonium group.
  • Examples of the amphoteric group include a carbobetaine group, a sulfobetaine group, and a phosphobetaine group.
  • nonionic group examples include a hydroxyl group; an amide group; a cyclic lactam group such as a pyrrolidone group and a caprolactam group; an alkoxy group; and a (poly) oxyalkylene group such as a (poly) oxyethylene group and a (poly) oxypropylene group. Be done.
  • the number of repetitions of the (poly) oxyalkylene group may be, for example, 1 to 150,000 or 150 to 100,000.
  • the (poly) oxyalkylene group is simply referred to as an oxyalkylene group when the number of repetitions is 1, and is referred to as a polyoxyalkylene group when the number of repetitions is 2 or more.
  • the number of carbon atoms of the (poly) oxyalkylene group may be, for example, 1 to 4, or 2 to 3. By appropriately adjusting the number of carbon atoms, the solubility of the water-soluble component can be appropriately adjusted.
  • Polyvinyl alcohol can be exemplified as the compound having a hydroxyl group.
  • Examples of the compound having an amide group include polyacrylamide.
  • Examples of the compound having a (poly) oxyalkylene group include polyalkylene oxide, polyalkylene glycol, and polyoxyalkylene alkyl ether.
  • the hydrophilic group-containing compound is at least one selected from the group consisting of polyvinyl alcohol, polyacrylamide, polyalkylene oxide, polyalkylene glycol, polyoxyalkylene alkyl ether, and a copolymer of monomers constituting these polymers. It is preferably polyvinyl alcohol, polyethylene oxide, polyethylene glycol, or polyoxyethylene alkyl ether.
  • the coating layer is substantially composed of only water-soluble components, but other than the water-soluble components, provided that the solubility of the entire coating layer in 100 g of water is 1.0 g or more and 150 g or less at 25 ° C. (Hereinafter, simply referred to as “other components”) may be contained.
  • the other component is a compound having a solubility in 100 g of water of less than 1.0 g or more than 150 g at 25 ° C.
  • the ratio of the water-soluble component in the entire coating layer may be, for example, 20% by mass or more, 30% by mass or more, or 50% by mass or more, preferably 80% by mass or more, and more preferably 90% by mass or more.
  • the water absorption behavior of the coating resin particles can be appropriately controlled.
  • other components include inorganic substances such as silica and talc, and organic water-insoluble components (organic compounds having a solubility in 100 g of water of less than 1.0 g at 25 ° C.).
  • organic water-insoluble component examples include polyesters such as polyethylene terephthalate, polybutylene terephthalate, polyethylene naphthalate, and polybutylene naphthalate; polyamides such as nylon 6 and nylon 66; polyethylene, polypropylene, ethylene / butene copolymer, and ethylene.
  • Polyesters such as propylene copolymers, copolymers of alkene and water-soluble ethylenically unsaturated monomers; polyesters such as ether-based polyurethanes, ester-based polyurethanes, and carbonate-based polyurethanes; poly- ⁇ -methylstyrene, syndiotactic polystyrene Polyesters such as: Bisphenol A, Polyesters such as polyhexamethylene carbonate; Polyacrylates such as trimethylolpropantri (meth) acrylate, pentaerythritol tri (meth) acrylate, dipentaerythritol hexa (meth) acrylate; Examples thereof include polyacetals such as acetaldehyde, polypropionaldehyde and polybutylaldehyde; halogen-based polymers such as polyvinyl chloride, polyvinylfluoride and vinylidene fluoride; and polysiloxane.
  • organic water-insoluble component polyolefin is preferable, and a copolymer of an alkene and a water-soluble ethylenically unsaturated monomer is more preferable.
  • a copolymer of an alkene and a water-soluble ethylenically unsaturated monomer is used as an organic water-insoluble component, it is preferable to use at least one alkene selected from ethylene, propylene, and butene as the alkene, and ethylene. Is more preferable to use.
  • the above-mentioned compound can be used as the water-soluble ethylenically unsaturated monomer, but (meth) acrylic acid and / or a salt thereof is preferably used.
  • the coating layer may have a one-layer structure or a multi-layer structure having two or more layers.
  • the coating layer has a first layer containing a first water-soluble component and a second layer containing a second water-soluble component that covers at least a part of the surface of the first layer. May be good.
  • the thickness of the coating layer (when the coating layer has a multi-layer structure, it means the total thickness of the total thickness of each layer) is 0.001 to 100 ⁇ m, 0.01. It may be up to 50 ⁇ m or 0.1 to 30 ⁇ m.
  • the thickness of the coating layer can be calculated by observing the cross section of the coating resin particles using an optical microscope. Specifically, it is calculated by processing the cross section of the coated resin particles with an ultramicrotome and then observing the cross section using an optical microscope "SZX16" (manufactured by Olympus) and a confocal microscope OPTELEICS HYBRID (manufactured by Lasertech). To.
  • the coating layer may cover at least a part of the surface of the water-absorbent resin particles, and the water-absorbing behavior of the coated resin particles can be controlled according to the coating ratio.
  • the coverage of the surface of the water-absorbent resin particles by the coating layer may be 30% or more, 40% or more, or 50% or more, and may be 100% or less, 90% or less, or 80% or less.
  • the coverage is calculated by RAMAN touch (manufactured by Nanophoton Corporation).
  • the coated resin particles of the present invention are coated with at least a part of the surface of the water-absorbent resin particles by a coating layer containing a water-soluble component. Therefore, the water-absorbent resin particles cannot exhibit their original water-absorbing ability until most or all of the water-soluble components are dissolved in the liquid. Therefore, the time required for the coated resin particles to reach the swelling state is delayed as compared with the case where the water-absorbent resin particles as the constituent material are used alone, and as a result, the occurrence of the gel blocking phenomenon can be suppressed.
  • the coated resin particles of the present invention can be easily produced by providing a coating layer on the surface of the water-absorbent resin particles. Therefore, it is not necessary to use a complicated method of changing the polymerization conditions of the water-absorbent resin particles as in the conventional case.
  • the water absorption rate (cm) of the physiological saline of the coated resin particles can be measured by the method described in the examples.
  • the water absorption rate of the coated resin particles at 25 ° C. after 1 minute is preferably 1.7 cm or less, and may be 1.6 cm or less, 1.5 cm or less, or 1.4 cm or less.
  • the water absorption rate of the coated resin particles at 25 ° C. after 5 minutes is preferably 4.5 cm or less, and may be 4.4 cm or less, 4.3 cm or less, or 4.2 cm or less.
  • the coated resin particles of the present invention can be used alone, but can be obtained as mixed particles by mixing with water-absorbent resin particles other than the coated resin particles (hereinafter, simply referred to as "other water-absorbent resin particles"). It can also be used. By using the mixed particles, the time until the swelling state is reached can be delayed as compared with the case where the other water-absorbent resin particles are used alone, and as a result, the occurrence of the gel blocking phenomenon can be suppressed. it can. When mixed particles are used, arbitrary water absorption behavior is realized by appropriately changing the type of the coated resin particles, the types of other water-absorbent resin particles, the mixing ratio of the coated resin particles and the other water-absorbent resin particles, and the like. obtain.
  • the water-absorbent resin particles and a coating material containing a water-soluble component having a solubility in 100 g of water in the range of 1.0 to 150 g at 25 ° C. are mixed to absorb the water.
  • a step of forming a coating layer on at least a part of the surface of the sex resin particles is provided.
  • the coating material is a compound containing a water-soluble component capable of forming the above-mentioned coating layer.
  • the coating material may be solid and used for mixing with water-absorbent resin particles, or may be liquid and used for mixing with water-absorbent resin.
  • a specific method for producing the coated resin particles will be described for each state of the coating material.
  • the coating material can be pressure-bonded to the surface of the water-absorbent resin particles using a particle composite device to form a coating layer. Specifically, a predetermined amount of water-absorbent resin particles and a solid (for example, powdery) coating material are charged into the particle composite device. After that, stress (compressive stress and shear stress) is applied to the water-absorbent resin particles and the coating material by the rotation of the stirring blade provided in the apparatus, and the coating material is pressure-bonded to the surface of the water-absorbent resin particles by the stress to coat the water-absorbent resin particles and the coating material. Prepare resin particles.
  • the thickness and coverage of the coating layer can be arbitrarily adjusted by appropriately adjusting the amounts of the water-absorbent resin particles and the coating material to be charged into the particle composite device.
  • the water-absorbent resin particles and the coating material may be separately charged into the particle compounding device, but since more uniform coating can be expected, the particle compounding device is in a state where the water-absorbent resin particles and the coating material are mixed in advance. It is preferable to put it in.
  • the coated resin particles are (a) or (c) of FIG. It is considered that it is easy to show the water absorption behavior like.
  • the particle compounding device for example, the particle compounding device Nobilta MINI (manufactured by Sugino Machine Limited) can be used.
  • the liquid coating material (hereinafter, simply referred to as "coating liquid”) can be obtained, for example, by melting the coating material, or by dissolving or dispersing the coating material in an arbitrary solvent or dispersion medium. .. Since it is easy to form a coating layer having a uniform thickness, the coating liquid is preferably obtained by dissolving or dispersing the coating material in an arbitrary solvent or dispersion medium.
  • the solvent examples include water, a hydrophilic solvent, a mixed solvent of water and a hydrophilic solvent, and the like.
  • the hydrophilic solvent is a solvent that dissolves substantially uniformly in water.
  • examples of the hydrophilic solvent include alcohols such as methanol and isopropyl alcohol; glycols such as ethylene glycol; cellosolves such as methyl cellosolve and ethyl cellosolve; ketones such as acetone and methyl ethyl ketone; esters such as ethyl acetate; ethers such as tetrahydrofuran. Be done.
  • the hydrophilic solvent may be used alone or in combination of two or more.
  • hydrocarbon dispersion medium a hydrocarbon dispersion medium is preferably used.
  • hydrocarbon dispersion medium include chain aliphatic hydrocarbons such as n-hexane, n-heptane, 2-methylhexane, 3-methylhexane, 2,3-dimethylpentane, 3-ethylpentane, and n-octane.
  • Alicyclic hydrocarbons such as cyclohexane, methylcyclohexane, cyclopentane, methylcyclopentane, trans-1,2-dimethylcyclopentane, cis-1,3-dimethylcyclopentane, trans-1,3-dimethylcyclopentane;
  • aromatic hydrocarbons such as benzene, toluene and xylene.
  • the hydrocarbon dispersion medium may be used alone or in combination of two or more.
  • the concentration of the coating material in the coating liquid is not particularly limited, and can be appropriately adjusted in consideration of the amount of water-absorbent resin particles to be coated in order to obtain a coating layer having a desired thickness. It may be% by mass, 3 to 30% by mass, or 5 to 20% by mass.
  • the coating layer is, for example, (1) a method of adding the coating liquid to the hydrocarbon dispersion medium in which the water-absorbent resin particles are dispersed, and (2) the coating liquid and the water-absorbent resin particles in the hydrocarbon dispersion medium. It can be formed by a method of adding the coating liquid substantially at the same time, or (3) a method of bringing the coating liquid into contact with the water-absorbent resin particles in a dry state.
  • each method will be specifically described.
  • the separable flask After adding the coating liquid into the separable flask and stirring sufficiently, the separable flask is immersed in an oil bath set at a high temperature (for example, 100 to 125 ° C.), and the hydrocarbon dispersion medium and water are azeotroped. By distillation, the hydrocarbon dispersion medium is refluxed, and water that can be contained in the reaction system is extracted from the system. Then, by evaporating the hydrocarbon dispersion medium, coated resin particles in which the coating material is coated on the surface of the water-absorbent resin particles can be obtained.
  • a high temperature for example, 100 to 125 ° C.
  • the above method (3) is various, and as typical examples thereof, (3-1) a method using an eggplant flask, (3-2) a method using a sprayer, and (3-3) various granulators. The method using the above will be described.
  • the coating liquid is charged into the eggplant flask, and then the water-absorbent resin particles are charged.
  • the eggplant flask is attached to an evaporator and heated while rotating, and the solvent or dispersion medium contained in the coating liquid is distilled off under reduced pressure conditions.
  • coated resin particles in which the coating material is coated on the surface of the water-absorbent resin particles can be obtained.
  • (3-2) Water-absorbent resin particles are added to a separable flask provided with a stirring blade and stirred.
  • the coating liquid is sprayed on the water-absorbent resin particles wound up by stirring with a stirring blade.
  • the coating liquid can be sprayed using, for example, a two-fluid nozzle. Since uniform coating can be expected, it is desirable that the coating liquid is atomized and sprayed by an air flow of an inert gas such as nitrogen. Then, the contents of the separable flask are taken out, heated by a hot air dryer, and then cooled to room temperature to obtain coated resin particles.
  • Examples of the granulator used for producing the coated resin particles include a rolling granulator, a stirring granulator, and a fluidized bed granulator.
  • a rolling granulator When using a rolling granulator, a shallow circular container equipped with a rolling granulator is rotated, water-absorbent resin particles are supplied to the circular container, and an appropriate amount of coating liquid is added. Then, a coating layer is formed on the surface of the water-absorbent resin particles during rolling while being agglomerated by the solvent or dispersion medium contained in the coating liquid.
  • the step of adding the water-absorbent resin particles and the coating liquid can be performed a plurality of times if necessary.
  • the water-absorbent resin particles When using a stirring granulator, the water-absorbent resin particles are put into a mixer installed in the stirring granulator, and the mixture is mixed by stirring and the coating liquid is added. Then, a coating layer is formed on the surface of the water-absorbent resin particles during stirring while being agglomerated by the solvent or dispersion medium contained in the coating liquid.
  • the step of adding the water-absorbent resin particles and the coating liquid may be performed a plurality of times if necessary. Excessive aggregation of the water-absorbent resin particles can be suppressed by controlling the shearing force of the mixer.
  • the water-absorbent resin particles are put into a container equipped in the fluidized bed granulator that can send hot air from the lower part, and the water-absorbent resin particles are fluidized in advance. After that, when the coating liquid is sprayed from the nozzle provided in the container, a coating layer is formed on the surface of the water-absorbent resin particles during stirring while a part of the water-absorbent resin particles during stirring is aggregated by the solvent or the dispersion medium contained in the coating liquid. ..
  • the coating liquid can be sprayed multiple times if necessary.
  • Excessive aggregation of the water-absorbent resin particles can be suppressed by adjusting the spraying amount and spraying frequency of the coating liquid.
  • a fluidized bed granulator FBD / SG manufactured by YENCHEN MACHINERY
  • YENCHEN MACHINERY a fluidized bed granulator FBD / SG
  • the coating material When the coating layer is formed using the coating liquid, the coating material easily comes into contact with the water-absorbent resin particles evenly, so that it is considered that the coating layer is easily formed on the entire surface.
  • the method using the fluidized bed granulators (1), (2), and (3) described above can easily obtain a coating layer having a more uniform thickness than the other methods.
  • hydroxyethyl cellulose manufactured by Sumitomo Seika Co., Ltd., HEC AW-15F
  • HEC AW-15F hydroxyethyl cellulose
  • 0.0736 g 0.0736 g (0.272 mmol) of potassium persulfate as a water-soluble radical polymerization initiator
  • ethylene as an internal cross-linking agent.
  • An aqueous solution of the first stage was prepared by adding 0.010 g (0.057 mmol) of glycol diglycidyl ether and then dissolving the mixture.
  • the first-stage polymer slurry liquid in the flask was cooled to 25 ° C., and the entire amount of the second-stage aqueous solution was added.
  • the flask is again immersed in a water bath at 70 ° C. to raise the temperature of the reaction solution, and the second-stage polymerization reaction is carried out for 60 minutes to obtain a hydrogel polymer. Obtained.
  • the flask was immersed in an oil bath set at 125 ° C., and 257.7 g of water was extracted from the system by azeotropic distillation of n-heptane and water.
  • Example 1 As a coating material, polyethylene oxide (Sumitomo Seika Chemical Co., Ltd., PEO-1) was prepared. 7.5 g of polyethylene oxide was mixed with 150 g of distilled water to prepare a coating liquid.
  • the flask was immersed in an oil bath set at 125 ° C., and 140 g of water was extracted from the system while refluxing n-heptane by azeotropic distillation of n-heptane and water. Then, the precursor of the coated resin particles was obtained by removing n-heptane at 125 ° C. This precursor was passed through a sieve having an opening of 850 ⁇ m to obtain 5 g of coated resin particles.
  • Example 2 As a coating material, polyoxyethylene stearyl ether (Nikko Emulsion Co., Ltd., EMALX625) was prepared.
  • n-heptane 250 g of n-heptane, 100 g of water-absorbent resin particles, and 10 g of polyoxyethylene stearyl ether were placed in the same flask as in Example 1, and the mixture was stirred at 1000 rpm and 85 ° C. for 10 minutes. Then, the flask was immersed in an oil bath set at 125 ° C., and n-heptane was removed at 125 ° C. to obtain a precursor of coated resin particles. This precursor was passed through a sieve having an opening of 850 ⁇ m to obtain 88 g of coated resin particles.
  • Example 3 Polyvinyl alcohol (Kuraray Co., Ltd., Kuraray Poval 3-98) was prepared as a coating material. 150 g of polyvinyl alcohol was mixed with 1995 g of distilled water and 855 g of ethanol to prepare a coating liquid.
  • Example 4 Polyethylene glycol (Tokyo Chemical Industry Co., Ltd., PEG6000) was prepared as a coating material. A solution prepared by mixing 600 g of polyethylene glycol with 2700 g of distilled water was put into a spray tank equipped with a stirrer, and 2700 g of ethanol was further added to prepare a coating liquid.
  • 3000 g of water-absorbent resin particles were put into a container of a fluidized bed granulator (Paurek Co., Ltd., MP-01mini) and blown from the bottom of the container.
  • 6000 g of the coating liquid was sprayed on the water-absorbent resin particles wound up with warm air at 50 ° C. while being dried. After spraying the coating liquid, it was dried at 50 ° C. for 30 minutes to obtain a precursor of the coating resin particles. This precursor was passed through a sieve having an opening of 850 ⁇ m to obtain 2998 g of coated resin particles.
  • Ethylene-sodium acrylate copolymer (Sumitomo Seika Chemical Co., Ltd., Zyxen N) and polyethylene glycol (Tokyo Chemical Industry Co., Ltd., PEG6000) were prepared as coating materials.
  • a coating solution (ethylene-sodium acrylate copolymer and polyethylene glycol 2: 1 (mass)) was mixed with 525 g of distilled water, 200 g of a 25 mass% aqueous dispersion emulsion of ethylene-sodium acrylate copolymer, and 25 g of polyethylene glycol. Included in ratio) was prepared.
  • 500 g of water-absorbent resin particles were put into a container of a fluidized bed granulator (Paurek Co., Ltd., FD-MP-01) and blown with warm air at 50 ° C. from the bottom of the container.
  • 750 g of the coating liquid was sprayed on the water-absorbent resin particles wound up by the blast while being dried. After spraying the coating liquid, it was dried at 50 ° C. for 30 minutes to obtain a precursor of the coating resin particles. This precursor was passed through a sieve having an opening of 850 ⁇ m to obtain 506 g of coated resin particles.
  • a Teflon-coated bat (bottom size 250 x 185 mm) was filled with 100 g of a 25% aqueous dispersion emulsion of an ethylene-sodium acrylate copolymer, covered with aluminum foil, and covered.
  • the aluminum foil was perforated and dried in a hot air dryer (ADVANTEC, FV-320) at 60 ° C. for 1 hour and then at 80 ° C. for 1 hour to obtain a polymer film of an ethylene-sodium acrylate copolymer.
  • the polymer membrane was cut into small pieces with scissors, placed in a Teflon-coated vat, covered with aluminum foil, and covered.
  • the aluminum foil was perforated and heated in a hot air dryer (FV-320) at 105 ° C. for 2 hours to completely dry the mixture to obtain 22.5 g of a solid ethylene-sodium acrylate copolymer.
  • Polyethylene glycol and ethylene-sodium acrylate copolymer were each classified, and 1.67 g of polyethylene glycol and 3.33 g of ethylene-sodium acrylate copolymer remained on the sieve having an opening of 850 ⁇ m and remaining on the sieve having an opening of 75 ⁇ m.
  • a coating material containing an ethylene-sodium acrylate copolymer and polyethylene glycol in a ratio of 2: 1 (mass ratio)).
  • the measurement liquid was obtained by the same procedure as the preparation of the measurement liquids of Examples 1 to 4.
  • the relationship between the mesh size of the sieve and the integrated value of the mass percentage of the particles remaining on the sieve was plotted on a logarithmic probability paper by integrating on the sieve in order from the one having the largest particle size with respect to this particle size distribution. By connecting the plots on the probability paper with a straight line, the particle size corresponding to the cumulative mass percentage of 50% by mass was obtained as the medium particle size.
  • Coated resin particles 10, 10a ... Water-absorbent resin particles, 20 ... Coating layer.

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WO2023119798A1 (ja) * 2021-12-21 2023-06-29 住友精化株式会社 被覆樹脂粒子、吸水性樹脂組成物及び吸収体
US20240253015A1 (en) * 2021-05-18 2024-08-01 Sumitomo Seika Chemicals Co., Ltd. Water-absorbing resin particle, absorber, and absorbent article

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JP7538429B2 (ja) * 2021-06-23 2024-08-22 日本製鉄株式会社 焼結鉱の比表面積の測定方法
KR20240117096A (ko) * 2021-11-30 2024-07-31 스미토모 세이카 가부시키가이샤 피복 수지 입자의 제조 방법 및 피복 수지 입자
JPWO2023100479A1 (https=) * 2021-11-30 2023-06-08
JPWO2023233925A1 (https=) * 2022-05-30 2023-12-07
EP4620444A4 (en) * 2022-12-20 2026-04-01 Sumitomo Seika Chemicals ABSORBER AND ABSORBENT ITEM
WO2025204794A1 (ja) * 2024-03-28 2025-10-02 住友精化株式会社 吸水性樹脂粒子
CN119192455A (zh) * 2024-07-30 2024-12-27 上海华谊新材料有限公司 一种高吸水性树脂及其制备方法和用途
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