WO2018180864A1 - 吸水性樹脂 - Google Patents
吸水性樹脂 Download PDFInfo
- Publication number
- WO2018180864A1 WO2018180864A1 PCT/JP2018/011351 JP2018011351W WO2018180864A1 WO 2018180864 A1 WO2018180864 A1 WO 2018180864A1 JP 2018011351 W JP2018011351 W JP 2018011351W WO 2018180864 A1 WO2018180864 A1 WO 2018180864A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- water
- mass
- amount
- disintegration
- absorbing resin
- Prior art date
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- 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
- A61L15/22—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons containing macromolecular materials
- A61L15/24—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives thereof
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- A61L15/42—Use of materials characterised by their function or physical properties
- A61L15/60—Liquid-swellable gel-forming materials, e.g. super-absorbents
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- B01J20/28—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties
- B01J20/28002—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties characterised by their physical properties
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- B01J20/28014—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties characterised by their form
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- B01J20/28—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties
- B01J20/28014—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties characterised by their form
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- B01J20/30—Processes for preparing, regenerating, or reactivating
- B01J20/3007—Moulding, shaping or extruding
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
- C08F265/02—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of acids, salts or anhydrides
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
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- 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
- A61F2013/530131—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 being made in fibre but being not pulp
- A61F2013/530226—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 being made in fibre but being not pulp with polymeric fibres
- A61F2013/530299—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 being made in fibre but being not pulp with polymeric fibres being hydrophilic fibres
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- A—HUMAN NECESSITIES
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- A61F13/00—Bandages or dressings; Absorbent pads
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- 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
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and 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 a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/04—Acids, Metal salts or ammonium salts thereof
- C08F20/06—Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2810/00—Chemical modification of a polymer
- C08F2810/20—Chemical modification of a polymer leading to a crosslinking, either explicitly or inherently
Definitions
- the present invention relates to a water absorbent resin. More specifically, the present invention relates to a water-absorbing resin that can improve the gel shape stability of an absorber and has excellent water absorption performance.
- water-absorbent resins have been widely used in various fields such as sanitary materials such as disposable diapers and sanitary products, agricultural and horticultural materials such as water retention agents and soil conditioners, and industrial materials such as water-stopping agents and anti-condensation agents. .
- sanitary materials such as disposable diapers and sanitary products
- agricultural and horticultural materials such as water retention agents and soil conditioners
- industrial materials such as water-stopping agents and anti-condensation agents.
- it is often used for sanitary materials such as disposable diapers and sanitary products.
- Examples of such a water-absorbing resin include a hydrolyzate of starch-acrylonitrile graft copolymer, a neutralized product of starch-acrylonitrile graft copolymer, a saponified product of vinyl acetate-acrylic ester copolymer, and acrylic acid.
- a crosslinked product of a partially neutralized polymer is known.
- absorbent articles such as disposable diapers, sanitary napkins, and incontinence pads are in contact with the body, which is mainly disposed in the center and absorbs and retains body fluids excreted from the body, such as urine and menstrual blood. It consists of a liquid-permeable top sheet (top sheet) disposed on the side and a liquid-permeable back sheet (back sheet) disposed on the opposite side in contact with the body.
- the absorber is normally comprised from hydrophilic fibers, such as a pulp, and water absorbing resin.
- the absorber temporarily holds the liquid that has entered through the surface sheet with hydrophilic fibers, and then holds the liquid with a water absorbent resin.
- a water absorbent resin In order to improve the liquid absorption amount of the absorbent body, it is effective to increase the amount of the water-absorbing resin and relatively reduce the amount of hydrophilic fibers.
- the absorbent body absorbs the liquid, the volume of the absorbent body increases due to the swelling of the water absorbent resin, resulting in a decrease in the entanglement between the fibers or the water absorbent resin and the fiber. Increasing the amount of the water-absorbing resin and relatively reducing the amount of hydrophilic fibers becomes more prominent.
- Such a decrease in the entanglement between fibers or between the water-absorbent resin and the fibers may cause deformation such as cracking or biasing when compression or shearing force is applied to the absorbent body. Since reversion occurs, it becomes a major drawback when the water absorbing material is used as a sanitary material.
- the gel shape of the absorbent body is obtained by expressing the adhesive force between the hot melt fibers and between the pulp and the heat melt fibers by mixing the hot melt fibers into the pulp.
- a method for improving the stability is known (see Patent Document 1).
- the method of Patent Document 1 improves the gel shape stability of the absorber, but has a drawback that the liquid penetration rate and the amount of absorption are reduced because the hot-melt fiber is hydrophobic.
- the present application aims to provide a water-absorbing resin that can improve the gel shape stability of an absorber and has excellent water-absorbing performance.
- the present inventors diligently studied to solve the above problems.
- the amount of disintegration at the time of 20 times swelling and the amount dissolved in physiological saline contribute to the gel shape stability of the absorber and the water absorption performance of the water absorbent resin. I found it to have an impact.
- the present invention is an invention that has been completed through further intensive studies based on such findings.
- the present invention provides an invention having the following configuration.
- Item 1 A polymer of a water-soluble ethylenically unsaturated monomer, A water absorbent resin having the following characteristics (1) and (2).
- (1) The amount of disintegration during 20-fold swelling is 30% by mass or less.
- (2) The amount dissolved in physiological saline is 25% by mass or less.
- the obtained gel is divided into five substantially equal parts, and each gel is put into a cylindrical mold having a length of 3.6 cm and a radius of 2.8 cm.
- the mass of the five molded cylindrical gels is measured, and three gels excluding the heaviest and lightest are used as samples.
- Wa (g) of each sample the sample whose mass was measured was put in the uppermost sieve in which the 5.6 mm sieve of the JIS standard sieve and the tray were combined in this order, and a low-tap shaker (rotation speed: 290 rpm)
- the mass Wb (g) passed under the sieve is measured by shaking for 10 minutes using an impact number of 165 rpm.
- the amount of disintegration of the sample is calculated from the following formula.
- Sample collapse amount (%) Wb (g) / Wa (g) ⁇ 100
- the average value of the disintegration amount about three samples made into the measuring object be a disintegration amount at the time of 20 times swelling of a water absorbing resin.
- Item 2. Item 8. The water absorbent resin according to Item 1, wherein the median particle diameter is 200 ⁇ m to 600 ⁇ m.
- Item 3. Item 3. The water-absorbent resin according to Item 1 or 2 used for an absorbent body together with hydrophilic fibers.
- the water absorbent resin according to Item 1 or 2 which is used in an absorbent article including a liquid permeable sheet and a liquid impermeable sheet.
- the present invention it is possible to improve the gel shape stability of the absorbent body and provide a water-absorbing resin having excellent water-absorbing performance.
- Water-absorbent resin The water-absorbent resin of the present invention is a polymer of a water-soluble ethylenically unsaturated monomer and has the following characteristics (1) and (2). (1) The amount of disintegration during 20-fold swelling is 30% by mass or less. (2) The amount dissolved in physiological saline is 25% by mass or less.
- the water-absorbent resin of the present invention having such a configuration has the characteristics that it can improve the gel shape stability of the absorber and further has excellent water absorption performance.
- the water-absorbent resin of the present invention having such characteristics can suppress the deformation of the absorbent body even when compression or shear force is applied due to the movement of the wearer when it is used as a sanitary material. Can be prevented.
- the water-absorbent resin can suppress diaper rash due to a dissolved component eluted from the water-absorbent resin. Therefore, the water-absorbent resin of the present invention can be suitably used for absorbers and absorbent articles for various uses.
- the water-absorbent resin of the present invention can be suitably used for sanitary materials such as disposable diapers.
- the water absorbent resin of the present invention will be described in detail.
- the amount of disintegration at 20-fold swelling may be 30% by mass or less, but further improved water absorption performance while further improving the gel shape stability of the absorber. From the viewpoint of exhibiting, it is preferably 28% by mass or less, more preferably 26% by mass or less, and still more preferably 15% or less.
- the amount of disintegration during 20-fold swelling is 0% by mass or more.
- the amount of disintegration of the water-absorbent resin when it is swollen 20 times is a value measured by the above method, and more specifically is measured by the method described in Examples.
- the amount dissolved in physiological saline may be 25% by mass or less, and further improved water-absorbing performance while further improving the gel shape stability of the absorber. From the viewpoint of exhibiting, preferably, it is 23% by mass or less, more preferably 21% by mass or less, and still more preferably 20% or less.
- the amount dissolved in physiological saline is 0% by mass or more, and usually 5% by mass or more.
- the “dissolution amount in physiological saline” means the amount (ratio) of low molecular weight polymers and oligomers flowing out from the water absorbent resin together with physiological saline when the water absorbent resin absorbs physiological saline and swells. means. If this amount of dissolution is large, the polymer or oligomer that has flowed out of the water-absorbent resin will come into contact with the wearer's skin and cause diaper rash.
- the amount dissolved in physiological saline is measured by the method described in Examples.
- the median particle diameter of the water-absorbent resin of the present invention is not particularly limited, and examples thereof include 200 ⁇ m to 600 ⁇ m, preferably 250 ⁇ m to 550 ⁇ m, more preferably 300 ⁇ m to 500 ⁇ m.
- the median particle diameter of the water-absorbent resin can be measured using a JIS standard sieve, and is specifically a value measured by the method described in the examples.
- Examples of the shape of the water absorbent resin of the present invention include a substantially spherical shape, a shape in which substantially spherical particles are aggregated, an irregularly crushed shape, a shape in which irregularly crushed particles are aggregated, and a plate shape.
- a water-absorbing resin having a substantially spherical particle shape such as a spherical shape or an elliptical spherical shape or a shape in which substantially spherical particles are aggregated is obtained. It is done.
- a water absorbing resin is manufactured by the aqueous solution polymerization method, the water absorbing resin which has the shape which the particle
- the water absorbent resin of the present invention may contain an additive according to the purpose.
- additives include inorganic powders, surfactants, oxidizing agents, reducing agents, metal chelating agents, radical chain inhibitors, antioxidants, antibacterial agents, and deodorants.
- the flowability of the water absorbent resin can be improved by adding 0.05 to 5 parts by mass of amorphous silica as an inorganic powder to 100 parts by mass of the water absorbent resin.
- the water-absorbent resin of the present invention can be produced by polymerizing a water-soluble ethylenically unsaturated monomer.
- a typical polymerization method such as an aqueous solution polymerization method, an emulsion polymerization method, a reverse phase suspension polymerization method, or the like is used.
- aqueous solution polymerization method polymerization is performed by heating a water-soluble ethylenically unsaturated monomer aqueous solution while stirring as necessary.
- reverse phase suspension polymerization method polymerization is performed by heating a water-soluble ethylenically unsaturated monomer in a hydrocarbon dispersion medium with stirring.
- the reverse phase suspension polymerization method is preferred from the viewpoint of precise polymerization reaction control and wide particle size control.
- the method for producing a water-absorbent resin include a method for producing a water-absorbent resin by reverse-phase suspension polymerization of a water-soluble ethylenically unsaturated monomer in a hydrocarbon dispersion medium, and an internal crosslinking agent and radical polymerization.
- the production method include a step of performing polymerization in the presence of an initiator, and a step of post-crosslinking the hydrogel having an internal cross-linked structure obtained by polymerization in the presence of a post-crosslinking agent.
- water-soluble ethylenically unsaturated monomer examples include (meth) acrylic acid (in the present specification, “acryl” and “methacryl” are collectively referred to as “(meth) acryl”; the same shall apply hereinafter) and 2- (meth) acrylamide-2-methylpropanesulfonic acid and salts thereof; (meth) acrylamide, N, N-dimethyl (meth) acrylamide, 2-hydroxyethyl (meth) acrylate, N-methylol (meth) Nonionic monomers such as acrylamide and polyethylene glycol mono (meth) acrylate; amino groups such as N, N-diethylaminoethyl (meth) acrylate, N, N-diethylaminopropyl (meth) acrylate and diethylaminopropyl (meth) acrylamide Examples thereof include unsaturated monomers and
- water-soluble ethylenically unsaturated monomers (meth) acrylic acid or a salt thereof, (meth) acrylamide, and N, N-dimethylacrylamide are preferable from the viewpoint of industrial availability. , (Meth) acrylic acid and salts thereof are more preferred.
- these water-soluble ethylenically unsaturated monomers may be used independently and may be used in combination of 2 or more types.
- acrylic acid and its salt are widely used as raw materials for water-absorbing resins, and when these acrylic acid and its salt are used by copolymerizing the other water-soluble ethylenically unsaturated monomers described above There is also.
- acrylic acid and a salt thereof are preferably used as a main water-soluble ethylenically unsaturated monomer in an amount of 70 to 100 mol% with respect to the total water-soluble ethylenically unsaturated monomer.
- the water-soluble ethylenically unsaturated monomer is preferably dispersed in a hydrocarbon dispersion medium in the form of an aqueous solution and subjected to reverse phase suspension polymerization.
- a hydrocarbon dispersion medium in the form of an aqueous solution and subjected to reverse phase suspension polymerization.
- the concentration of the water-soluble ethylenically unsaturated monomer in this aqueous solution is preferably in the range of 20% by mass to the saturated concentration.
- concentration of a water-soluble ethylenically unsaturated monomer it is more preferable that it is 55 mass% or less, It is further more preferable that it is 50 mass% or less, It is further more preferable that it is 45 mass% or less.
- concentration of the water-soluble ethylenically unsaturated monomer is more preferably 25% by mass or more, further preferably 28% by mass or more, and further preferably 30% by mass or more.
- the acid group is previously alkaline if necessary. You may use what was neutralized with the neutralizing agent.
- alkaline neutralizer include alkali metal salts such as sodium hydroxide, sodium carbonate, sodium hydrogen carbonate, potassium hydroxide, and potassium carbonate; ammonia and the like. These alkaline neutralizers may be used in the form of an aqueous solution in order to simplify the neutralization operation.
- the alkaline neutralizer mentioned above may be used independently, and may be used in combination of 2 or more types.
- the degree of neutralization of the water-soluble ethylenically unsaturated monomer with the alkaline neutralizing agent is 10 to 100 mol% as the degree of neutralization for all acid groups of the water-soluble ethylenically unsaturated monomer. It is preferably 30 to 90 mol%, more preferably 40 to 85 mol%, still more preferably 50 to 80 mol%.
- Internal cross-linking agent examples include those capable of crosslinking the polymer of the water-soluble ethylenically unsaturated monomer to be used.
- (poly) ethylene glycol ““(poly)” is prefixed with “poly”. It means the case with and without. The same shall apply hereinafter), (poly) propylene glycol, 1,4-butanediol, trimethylolpropane, diols such as (poly) glycerin, polyols such as triol, and (meth) acrylic acid, maleic acid, fumaric acid, etc.
- Unsaturated polyesters obtained by reacting with acids bisacrylamides such as N, N-methylenebisacrylamide; di (meth) acrylates or tris obtained by reacting polyepoxides with (meth) acrylic acid (Meth) acrylic acid esters; di (meth) acrylic acid carbamyl esters obtained by reacting polyisocyanates such as tolylene diisocyanate and hexamethylene diisocyanate with hydroxyethyl (meth) acrylate; allylated starch, allyl Cellulose, diallyl phthalate, N, Compounds having two or more polymerizable unsaturated groups such as', N ′′ -triallyl isocyanate, divinylbenzene; (poly) ethylene glycol diglycidyl ether, (poly) propylene glycol diglycidyl ether, (poly) glycerin diglycidyl Polyglycidyl compounds such as diglycidyl compounds such as ether and t
- polyglycidyl compounds are preferably used, diglycidyl ether compounds are more preferably used, (poly) ethylene glycol diglycidyl ether, (poly) propylene glycol diglycidyl ether, (poly) glycerin. It is preferable to use diglycidyl ether.
- diglycidyl ether may be used alone or in combination of two or more.
- the amount of the internal crosslinking agent used is preferably 0.000001 to 0.02 mol, preferably 0.00001 to 0.01 mol, per 1 mol of the water-soluble ethylenically unsaturated monomer. More preferably, it is 0.00001 to 0.005 mol.
- hydrocarbon dispersion medium examples include those having 6 to 8 carbon atoms such as n-hexane, n-heptane, 2-methylhexane, 3-methylhexane, 2,3-dimethylpentane, 3-ethylpentane, and n-octane.
- Aliphatic hydrocarbons cyclohexane, methylcyclohexane, cyclopentane, methylcyclopentane, trans-1,2-dimethylcyclopentane, cis-1,3-dimethylcyclopentane, trans-1,3-dimethylcyclopentane, etc.
- Aromatic hydrocarbons such as benzene, toluene and xylene.
- hydrocarbon dispersion media n-hexane, n-heptane, and cyclohexane are particularly preferably used because they are easily available industrially, have stable quality, and are inexpensive.
- These hydrocarbon dispersion media may be used alone or in combination of two or more.
- the mixture of the hydrocarbon dispersion medium include commercially available products such as Exol heptane (manufactured by ExxonMobil Corp .: containing 75 to 85% by mass of hydrocarbon of heptane and its isomer). Even if such a mixture is used, suitable results can be obtained.
- the amount of the hydrocarbon dispersion medium used is such that the water-soluble ethylenically unsaturated monomer is uniformly dispersed, and the water-soluble ethylenic polymer used in the first stage polymerization is easy to control the polymerization temperature.
- the amount is preferably 100 to 1500 parts by weight, more preferably 200 to 1400 parts by weight with respect to 100 parts by weight of the unsaturated monomer.
- the reverse-phase suspension polymerization is performed in one stage (single stage) or in multiple stages of two or more stages.
- the first stage polymerization described above is the first stage in single stage polymerization or multistage polymerization. (Hereinafter the same).
- a dispersion stabilizer In the reverse phase suspension polymerization, a dispersion stabilizer can be used in order to improve the dispersion stability of the water-soluble ethylenically unsaturated monomer in the hydrocarbon dispersion medium. As the dispersion stabilizer, a surfactant can be used.
- surfactant examples include sucrose fatty acid ester, polyglycerin fatty acid ester, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, polyoxyethylene glycerin fatty acid ester, sorbitol fatty acid ester, polyoxyethylene sorbitol fatty acid ester, polyoxyethylene Alkyl ether, polyoxyethylene alkylphenyl ether, polyoxyethylene castor oil, polyoxyethylene hydrogenated castor oil, alkylallyl formaldehyde condensed polyoxyethylene ether, polyoxyethylene polyoxypropylene block copolymer, polyoxyethylene polyoxypropyl alkyl ether, Polyethylene glycol fatty acid ester, alkyl glucoside, N-alkyl gluconami , Polyoxyethylene fatty acid amides, polyoxyethylene alkyl amines, phosphoric esters of polyoxyethylene alkyl ethers, can be used phosphoric acid ester of polyoxyethylene alkyl ary
- sorbitan fatty acid ester sorbitan fatty acid ester, polyglycerin fatty acid ester, and sucrose fatty acid ester are preferably used from the viewpoint of dispersion stability of the monomer.
- These surfactants may be used alone or in combination of two or more.
- the amount of the surfactant used is preferably 0.1 to 30 parts by mass with respect to 100 parts by mass of the water-soluble ethylenically unsaturated monomer subjected to the first stage polymerization. More preferably, it is 0.3 to 20 parts by mass.
- a polymer dispersant may be used in combination with the above-described surfactant.
- polymeric dispersant examples include maleic anhydride-modified polyethylene, maleic anhydride-modified polypropylene, maleic anhydride-modified ethylene / propylene copolymer, maleic anhydride-modified EPDM (ethylene / propylene / diene / terpolymer), and anhydrous.
- maleic acid-modified polybutadiene maleic anhydride / ethylene copolymer, maleic anhydride / propylene copolymer, maleic anhydride / ethylene / propylene copolymer, maleic anhydride / butadiene copolymer, polyethylene, polypropylene, ethylene / propylene
- the copolymer include oxidized polyethylene, oxidized polypropylene, oxidized ethylene / propylene copolymer, ethylene / acrylic acid copolymer, ethyl cellulose, and ethyl hydroxyethyl cellulose.
- polymeric dispersants in particular, from the viewpoint of dispersion stability of the monomer, maleic anhydride-modified polyethylene, maleic anhydride-modified polypropylene, maleic anhydride-modified ethylene / propylene copolymer, maleic anhydride / Ethylene copolymer, maleic anhydride / propylene copolymer, maleic anhydride / ethylene / propylene copolymer, polyethylene, polypropylene, ethylene / propylene copolymer, oxidized polyethylene, oxidized polypropylene, oxidized ethylene / propylene copolymer It is preferable to use a polymer. These polymer dispersants may be used alone or in combination of two or more.
- the amount of the polymeric dispersant used is preferably 0.1 to 30 parts by mass with respect to 100 parts by mass of the water-soluble ethylenically unsaturated monomer subjected to the first stage polymerization. More preferably, it is 0.3 to 20 parts by mass.
- radical polymerization initiator for example, a peroxide or an azo compound can be used.
- the peroxide include persulfates such as potassium persulfate, ammonium persulfate, and sodium persulfate; methyl ethyl ketone peroxide, methyl isobutyl ketone peroxide, di-t-butyl peroxide, t-butyl cumyl peroxide, t And peroxides such as -butyl peroxyacetate, t-butyl peroxyisobutyrate, t-butyl peroxypivalate, and hydrogen peroxide.
- potassium persulfate, ammonium persulfate, sodium persulfate, and hydrogen peroxide are preferably used, and potassium persulfate, ammonium persulfate, and sodium persulfate persulfates are more preferable.
- azo compounds include 1- ⁇ (1-cyano-1-methylethyl) azo ⁇ formamide, 2,2′-azobis [2- (N-phenylamidino) propane] dihydrochloride, 2,2′- Azobis ⁇ 2- [N- (4-chlorophenyl) amidino] propane ⁇ dihydrochloride, 2,2′-azobis ⁇ 2- [N- (4-hydroxyphenyl) amidino] propane ⁇ dihydrochloride, 2,2 ′ -Azobis [2- (N-benzylamidino) propane] dihydrochloride, 2,2'-azobis [2- (N-allylamidino) propane] dihydrochloride, 2,2'-azobis (2-amidinopropane) Dihydrochloride, 2,2′-azobis ⁇ 2- [N- (2-hydroxyethyl) amidino] propane ⁇ dihydrochloride, 2,2′-azobis [2- (5-methyl-2-imidazoline-2- Yl) propane] dihydrochloride
- 2,2′-azobis (2-amidinopropane) dihydrochloride 2,2′-azobis ⁇ 2- [1- (2-hydroxyethyl) -2-imidazolin-2-yl] propane ⁇ 2 Hydrochloride, 2,2′-azobis [N- (2-carboxyethyl) -2-methylpropionamidine] tetrahydrate azo compound, and the like.
- radical polymerization initiators potassium persulfate, ammonium persulfate, sodium persulfate and 2,2′-azobis (2-amidinopropane) dihydrochloride are preferable from the viewpoint of availability and ease of handling. It is done.
- These radical polymerization initiators may be used alone or in combination of two or more. In particular, when two or more kinds are used in combination, azo compounds and persulfates are preferable.
- the radical polymerization initiator can also be used as a redox polymerization initiator in combination with a reducing agent such as sodium sulfite, sodium hydrogen sulfite, ferrous sulfate, and L-ascorbic acid.
- a reducing agent such as sodium sulfite, sodium hydrogen sulfite, ferrous sulfate, and L-ascorbic acid.
- the amount of the radical polymerization initiator used is not particularly limited, and examples thereof include 0.00005 to 0.01 mol with respect to 1 mol of the water-soluble ethylenically unsaturated monomer. By satisfying such a use amount, a rapid polymerization reaction can be avoided and the polymerization reaction can be completed in an appropriate time.
- reverse phase suspension polymerization may be carried out by adding other components to an aqueous solution containing a water-soluble ethylenically unsaturated monomer as desired.
- various additives such as a thickener and a chain transfer agent can be added.
- reverse phase suspension polymerization In carrying out reverse phase suspension polymerization, for example, an aqueous monomer solution containing a water-soluble ethylenically unsaturated monomer is added to a hydrocarbon dispersion medium in the presence of a dispersion stabilizer and dispersed. At this time, before the polymerization reaction is started, the dispersion stabilizer (surfactant or polymer dispersant) may be added before or after the monomer aqueous solution is added.
- the dispersion stabilizer surfactant or polymer dispersant
- the surfactant is further added. It is preferable to carry out the polymerization after dispersing.
- Reverse phase suspension polymerization can be carried out in one stage or in multiple stages of two or more stages. Also, it is preferably performed in 2 to 3 stages from the viewpoint of increasing productivity.
- reverse-phase suspension polymerization When reverse-phase suspension polymerization is performed in two or more stages, water-soluble ethylenic unsaturation is performed on the reaction mixture obtained by the first-stage polymerization reaction after the first-stage reverse-phase suspension polymerization. Monomers may be added and mixed, and reverse phase suspension polymerization in the second and subsequent stages may be performed in the same manner as in the first stage.
- the reverse phase suspension polymerization in each stage after the second stage in addition to the water-soluble ethylenically unsaturated monomer, the internal crosslinking agent and the radical polymerization initiator described above are used in each stage after the second stage.
- the amount of the water-soluble ethylenically unsaturated monomer added during the reverse phase suspension polymerization is added within the range of the molar ratio of each component to the water-soluble ethylenically unsaturated monomer described above. It is preferable to perform phase suspension polymerization.
- the reaction temperature of the polymerization reaction is 20 to 110 ° C. from the viewpoint of allowing the polymerization to proceed rapidly and shortening the polymerization time, thereby improving economy and allowing the reaction to be carried out smoothly by easily removing the heat of polymerization. It is preferable that the temperature is 40 to 90 ° C.
- the reaction time is preferably 0.5 to 4 hours.
- the water-absorbing resin according to the present invention is obtained by post-crosslinking with a post-crosslinking agent to a hydrogel having an internal cross-linked structure obtained by polymerizing a water-soluble ethylenically unsaturated monomer (post-crosslinking reaction). ).
- This post-crosslinking reaction is preferably performed in the presence of a post-crosslinking agent after the polymerization of the water-soluble ethylenically unsaturated monomer.
- the cross-linking density in the vicinity of the surface of the water-absorbent resin is increased, and various performances such as water absorption capacity under load. Can be obtained.
- post-crosslinking agent examples include compounds having two or more reactive functional groups.
- polyols such as ethylene glycol, propylene glycol, 1,4-butanediol, trimethylolpropane, glycerin, polyoxyethylene glycol, polyoxypropylene glycol, polyglycerin; (poly) ethylene glycol diglycidyl ether, (poly) Polyglycidyl compounds such as glycerin diglycidyl ether, (poly) glycerin triglycidyl ether, trimethylolpropane triglycidyl ether, (poly) propylene glycol diglycidyl ether, polyglycerol polyglycidyl ether; epichlorohydrin, epibromohydrin, ⁇ -methyl Haloepoxy compounds such as epichlorohydrin; isocyanates such as 2,4-tolylene diisocyanate and hexamethylene diisocyanate Com
- post-crosslinking agents (poly) ethylene glycol diglycidyl ether, (poly) glycerin diglycidyl ether, (poly) glycerin triglycidyl ether, trimethylolpropane triglycidyl ether, (poly) propylene glycol diglycidyl ether, poly Polyglycidyl compounds such as glycerol polyglycidyl ether are preferred.
- These post-crosslinking agents may be used alone or in combination of two or more.
- the post-crosslinking agent is preferably used in an amount of 0.00001 to 0.01 mol, preferably 0.00005 to 0.005, based on 1 mol of the water-soluble ethylenically unsaturated monomer used in the polymerization.
- the molar ratio is more preferably 0.0001 to 0.002 mol.
- the amount of the water-soluble ethylenically unsaturated monomer used as a reference for the amount of post-crosslinking agent used is the water-soluble ethylenic monomer used in each stage. This is the total amount of saturated monomer.
- the post-crosslinking agent may be added as it is or may be added as an aqueous solution, but if necessary, it may be added as a solution using a hydrophilic organic solvent as a solvent.
- a hydrophilic organic solvent include lower alcohols such as methyl alcohol, ethyl alcohol, n-propyl alcohol and isopropyl alcohol; ketones such as acetone and methyl ethyl ketone; ethers such as diethyl ether, dioxane and tetrahydrofuran; N, N Amides such as dimethylformamide; sulfoxides such as dimethyl sulfoxide.
- These hydrophilic organic solvents may be used alone or in combination of two or more or as a mixed solvent with water.
- the post-crosslinking agent may be added after the polymerization reaction of the water-soluble ethylene purified unsaturated monomer is almost completed.
- the post-crosslinking agent is preferably added in the presence of water in the range of 1 to 400 parts by weight with respect to 100 parts by weight of the water-soluble ethylenically unsaturated monomer, and in the presence of water in the range of 5 to 200 parts by weight. More preferably, it is added in the presence of water in the range of 10 to 100 parts by mass, and still more preferably in the presence of water in the range of 20 to 60 parts by mass.
- the amount of moisture means the total amount of moisture contained in the reaction system and moisture used as necessary when the post-crosslinking agent is added.
- the reaction temperature in the post-crosslinking reaction is preferably 50 to 250 ° C., more preferably 60 to 180 ° C., further preferably 60 to 140 ° C., and more preferably 70 to 120 ° C. Further preferred.
- the reaction time for the post-crosslinking reaction is preferably 1 to 300 minutes, more preferably 5 to 200 minutes.
- ⁇ Drying process> In the method for producing a water-absorbent resin of the present invention, after performing the above-described reverse phase suspension polymerization, water, hydrocarbon dispersion medium, and the like are removed from the system by distillation by applying energy such as heat to the system from the outside. A drying step may be included.
- dehydration is performed from a hydrous gel after reversed-phase suspension polymerization, water and the hydrocarbon dispersion medium are temporarily removed from the system by azeotropic distillation by heating the system in which the hydrogel is dispersed in the hydrocarbon dispersion medium. Distill off. At this time, if only the distilled hydrocarbon dispersion medium is returned to the system, continuous azeotropic distillation is possible.
- the drying treatment may be performed under normal pressure or under reduced pressure. Moreover, you may carry out under airflow, such as nitrogen, from a viewpoint of improving drying efficiency.
- the drying temperature is preferably 70 to 250 ° C., more preferably 80 to 180 ° C., further preferably 80 to 140 ° C., and more preferably 90 to More preferably, it is 130 degreeC.
- the drying temperature is preferably 40 to 160 ° C., more preferably 50 to 110 ° C.
- the post-crosslinking step with the post-crosslinking agent is performed after the polymerization of the monomer by reverse phase suspension polymerization, it is preferable to perform the above-described drying step after the completion of the cross-linking step.
- a chelating agent such as a chelating agent, a reducing agent, an oxidizing agent, an antibacterial agent, and a deodorizing agent after superposition
- polymerization during drying, or after drying with respect to a water absorbing resin as needed.
- the water-absorbent resin according to the present invention constitutes an absorbent body used for sanitary materials such as sanitary products and paper diapers, and is suitably used for absorbent articles including the absorbent body. It is done.
- the absorbent body using the water-absorbent resin is composed of, for example, a water-absorbent resin and hydrophilic fibers.
- the structure of the absorber is a mixed dispersion obtained by mixing the water-absorbent resin and the hydrophilic fiber so as to have a uniform composition, and a sandwich in which the water-absorbent resin is sandwiched between layered hydrophilic fibers. Examples include a structure, a structure in which a water-absorbing resin and a hydrophilic fiber are wrapped with a tissue.
- the absorbent body may contain other components, for example, an adhesive binder such as a heat-fusible synthetic fiber, a hot melt adhesive, and an adhesive emulsion for enhancing the shape retention of the absorbent body. .
- the content of the water-absorbing resin in the absorber is preferably 5 to 100% by mass, more preferably 20 to 95% by mass, and further preferably 30 to 90% by mass. Further, from the viewpoint of reducing the thickness of the absorber, the content of the water absorbent resin in the absorber is preferably 50% by mass or more.
- hydrophilic fibers include cellulose fibers such as cotton-like pulp, mechanical pulp, chemical pulp, and semi-chemical pulp obtained from wood, synthetic cellulose fibers such as rayon and acetate, and polyamides, polyesters, and polyolefins that have been hydrophilized. Examples thereof include fibers made of resin.
- the water-absorbent resin of the present invention can improve the gel shape stability of the absorber, and further has excellent water-absorbing performance, so that it is preferably used for an absorber having a small proportion of hydrophilic fibers. Can do.
- liquid permeable sheet top sheet
- liquid impermeable sheet back sheet
- An absorbent article can be constructed.
- the liquid permeable sheet is disposed on the side in contact with the body, and the liquid impermeable sheet is disposed on the opposite side in contact with the body.
- liquid permeable sheet examples include air-through type, spunbond type, chemical bond type, needle punch type nonwoven fabrics and porous synthetic resin sheets made of fibers such as polyethylene, polypropylene, and polyester.
- liquid impermeable sheet examples include synthetic resin films made of resins such as polyethylene, polypropylene, and polyvinyl chloride.
- the water-absorbent resin of the present invention can improve the gel shape stability of the absorber, and further has excellent water absorption performance.
- Absorbent articles for example, absorbent articles having an absorbent body thickness of preferably 5 mm or less, more preferably 3 mm or less).
- a cylindrical mold having a radius of 2.8 cm was provided in a series of 5))) and was uniformly placed. Place a weight of 5 kg from the top of the mold and leave it for 10 minutes. Then, take out the mass of 5 water-absorbent resins that have been pressed and solidified from the mold with a spatula and measure their masses. Three masses except the heaviest and lightest were used as measurement samples.
- ⁇ Medium particle size> As a lubricant, 50 g of the water-absorbent resin was mixed with 0.1 g of amorphous silica (Degussa Japan Co., Ltd., Sipernat 200). This is passed through a sieve of JIS standard sieve with an opening of 250 ⁇ m. When the amount remaining on the sieve is less than 50% by mass, the combination of ⁇ A> sieves is used. When the amount is 50% by mass or more, The median particle diameter was measured using the combination of ⁇ B> sieves.
- the above water-absorbing resin was put into the combined uppermost sieve and classified by shaking for 10 minutes using a low-tap shaker. After classification, the mass of the water-absorbent resin remaining on each sieve was calculated as a mass percentage with respect to the total amount to obtain a particle size distribution. Based on this particle size distribution, by integrating the mass percentage of the water-absorbing resin particles remaining on the sieve in order from the larger opening, the integrated value of the sieve aperture and the mass percentage of the water-absorbing resin remaining on the sieve Are plotted on a log-probability paper. By connecting the plots on the probability paper with a straight line, the particle diameter corresponding to an integrated mass percentage of 50 mass% was defined as the median particle diameter.
- the physiological saline water-absorbing ability under the load of the water-absorbent resin was measured using a measuring apparatus Y schematically shown in FIG.
- the measuring apparatus Y shown in FIG. 1 includes a burette unit 7, a conduit 8, a measuring table 9, and a measuring unit 10 placed on the measuring table 9.
- the burette part 7 has a rubber stopper 74 connected to the upper part of the burette 70, an air introduction pipe 71 and a cock 72 connected to the lower part, and the air introduction pipe 71 has a cock 73 at the tip.
- a conduit 8 is attached between the buret unit 7 and the measuring table 9, and the inner diameter of the conduit 8 is 6 mm.
- the measuring unit 10 includes a cylinder 100 (made of acrylic resin), a nylon mesh 101 bonded to the bottom of the cylinder 40, and a weight 102.
- the inner diameter of the cylinder 100 is 20 mm.
- the opening of the nylon mesh 101 is 75 ⁇ m (200 mesh).
- the water-absorbing resin 11 is uniformly distributed on the nylon mesh 101.
- the weight 102 has a diameter of 19 mm and a mass of 119.6 g. The weight is placed on the water absorbent resin 11 so that a load of 4.14 kPa can be applied to the water absorbent resin 11.
- the measurement is performed in a room at 25 ° C.
- the cock 72 and the cock 73 of the burette part 7 are closed, 0.9 mass% saline adjusted to 25 ° C. is poured from the upper part of the burette 70, the stopper is plugged on the upper part of the burette, and then the cock of the burette part 7 is placed. 72, open the cock 73.
- the height of the measuring table 9 is adjusted so that the surface of the 0.9% by mass saline solution coming out from the conduit port at the center of the measuring table 9 and the upper surface of the measuring table 9 have the same height. It was.
- the physiological saline water absorption capacity under load is an index indicating the water absorption performance of the water absorbent resin, preferably 15 (ml / g) or more, and more preferably 20 (ml / g).
- the magnetic stirrer bar was adjusted to rotate at 600 rpm, and further, the bottom of the vortex generated by the rotation of the magnetic stirrer bar was adjusted to be close to the top of the magnetic stirrer bar, and then the water-absorbent resin was added thereto. 2.0 g was added and stirred for 1 hour. After stirring was stopped and allowed to stand for 15 minutes, the height Wf (mm) from the bottom of the beaker to the top of the gel was measured. In addition, when the height of the gel differs depending on the measurement position, the average value of the highest value and the lowest value was used.
- the presence or absence of a decrease in gel height over time (15-hour gel height relative to 1-hour gel height) is an indicator of the gel shape stability of the absorber, and should not be decreased.
- Example 1 As a reflux condenser, a dropping funnel, a nitrogen gas introduction tube, and a stirrer, a round bottom cylindrical separable flask with an inner diameter of 100 mm equipped with a stirring blade having two inclined paddle blades with a blade diameter of 50 mm in two stages was prepared.
- HLB3 sucrose stearate manufactured by Mitsubishi Chemical Foods Co., Ltd., Ryoto Sugar Ester S-370
- maleic anhydride-modified ethylene / propylene copolymer Mitsubishi Chemical Foods Co., Ltd., High Wax 1105A 0.80 g was added, the temperature was raised to 80 ° C. to dissolve the surfactant, and then cooled to 50 ° C.
- HEC AW-15F hydroxyethyl cellulose
- EX-821 n 4 manufactured by Nagase ChemteX Corp.
- the monomer aqueous solution is added to the separable flask, and the system is replaced with nitrogen, maintained at 40 ° C. for 30 minutes, then immersed in a 70 ° C. water bath and heated to carry out polymerization for 30 minutes. As a result, a slurry after polymerization was obtained.
- EX-830, n 9, manufactured by Nagase ChemteX Corp.
- EX-861, n 22, manufactured by Nagase ChemteX Corp.
- EX-821 n 4, manufactured by Nagase ChemteX Corp.
- Example 1 (Comparative Example 1)
- the internal cross-linking agent was changed to 0.028 g (0.0000158 mol) of ethylene glycol diglycidyl ether, and the amount of water extracted during azeotropic distillation was changed to 112.9 g.
- the same operation was performed to obtain 112.1 g of a substantially spherical water-absorbing resin. Table 1 shows the measurement results of each performance.
- HEC AW-15F hydroxyethyl cellulose
- 2,2′-azobis (2-amidinopropane) 2 as a radical polymerization initiator 0.092 g (0.000339 mol) of hydrochloride, 0.018 g (0.0000681 mol) of potassium persulfate, and 0.0046 g (0.0000264 mol) of ethylene glycol diglycidyl ether as an internal cross-linking agent were added and dissolved.
- a meter aqueous solution was prepared.
- the first aqueous monomer solution was added to the separable flask, and the system was replaced with nitrogen, maintained at 40 ° C. for 30 minutes, and then immersed in a 70 ° C. water bath to raise the temperature. By performing the polymerization, a first post-polymerization slurry was obtained.
- the post-polymerization slurry was cooled to 23 ° C., the second-stage monomer aqueous solution was added to the system, and maintained for 30 minutes while being replaced with nitrogen. Again, the flask was immersed in a 70 ° C. water bath, the temperature was raised, and polymerization was carried out to obtain a second post-polymerization slurry.
- the temperature of the aqueous solution was adjusted to 18 ° C. under a nitrogen atmosphere, and then 1.19 ⁇ g of 5% aqueous sodium persulfate solution and 1.19 ⁇ g of 5% 2,2′-azobis (2-amidinopropane) hydrochloride aqueous solution, 1.15 g of a 5% L-ascorbic acid aqueous solution and 1.28 g of a 0.35% hydrogen peroxide aqueous solution were added dropwise with stirring in this order.
- the water-absorbent resins of Examples 1 to 4 having a dissolution amount in physiological saline of 25% by mass or less and a disintegration amount at 20 times swelling of 30% by mass or less. It can be seen that the gel shape stability of the absorber can be improved, and further, the saline water absorption capacity under load is high, and it has excellent water absorption performance. On the other hand, in Comparative Examples 1 and 3, it can be seen that the amount of disintegration at the time of 20-fold swelling is large and the gel shape stability of the absorbent body is poor. Moreover, in the comparative example 2, it turns out that the dissolved amount with respect to physiological saline is large, and it is inferior also to the physiological saline absorptivity (water absorption performance) under load.
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Abstract
Description
項1. 水溶性エチレン性不飽和単量体の重合体であって、
下記(1)及び(2)の特性を備える、吸水性樹脂。
(1)20倍膨潤時の崩壊量が30質量%以下である。
(2)生理食塩水に対する溶解量が25質量%以下である。
(20倍膨潤時の崩壊量の測定方法)
生理食塩水100g中に吸水性樹脂5gを加え、吸水性樹脂に生理食塩水を吸収させてゲルを得る。得られたゲルを、略均等に5分割し、それぞれ、長さ3.6cm、半径2.8cmの円筒形の型に入れて成形する。成形された5つの円筒形のゲルの質量を測定し、最も重いものと最も軽いものを除いた3つのゲルを試料とする。各試料の質量Wa(g)測定した後、JIS標準篩の目開き5.6mm篩と受け皿の順に組み合わせた最上の篩に、質量を測定した試料を入れ、ロータップ式振とう器(回転数290rpm、衝撃数165rpm)を用いて10分間振とうさせて、篩下に通過した質量Wb(g)を測定する。試料の崩壊量を以下の式から算出する。
試料の崩壊量(%)=Wb(g)/Wa(g)×100
測定対象とした3つの試料についての崩壊量の平均値を、吸水性樹脂の20倍膨潤時の崩壊量とする。
項2. 中位粒子径が200μm~600μmである、項1に記載の吸水性樹脂。
項3. 親水性繊維と共に吸収体に用いる項1または2に記載の吸水性樹脂。
項4. 液体透過性シートおよび液体不透過性シートを含む吸収性物品に用いる項1または2に記載の吸水性樹脂。
本発明の吸水性樹脂は、水溶性エチレン性不飽和単量体の重合体であって、下記(1)及び(2)の特性を備えることを特徴とする。
(1)20倍膨潤時の崩壊量が30質量%以下である。
(2)生理食塩水に対する溶解量が25質量%以下である。
生理食塩水100g中に吸水性樹脂5gを加え、吸水性樹脂に生理食塩水を吸収させてゲルを得る。得られたゲルを、略均等に5分割し、それぞれ、長さ3.6cm、半径2.8cmの円筒形の型に入れて成形する。成形された5つの円筒形のゲルの質量を測定し、最も重いものと最も軽いものを除いた3つのゲルを試料とする。各試料の質量Wa(g)測定した後、JIS標準篩の目開き5.6mm篩と受け皿の順に組み合わせた最上の篩に、質量を測定した試料を入れ、ロータップ式振とう器(回転数290rpm、衝撃数165rpm)を用いて10分間振とうさせて、篩下に通過した質量Wb(g)を測定する。試料の崩壊量を以下の式から算出する。
試料の崩壊量(%)=Wb(g)/Wa(g)×100
測定対象とした3つの試料についての崩壊量の平均値を、吸水性樹脂の20倍膨潤時の崩壊量とする。
本発明の吸水性樹脂は、水溶性エチレン性不飽和単量体を重合させることによって製造することができる。
[水溶性エチレン性不飽和単量体]
水溶性エチレン性不飽和単量体としては、例えば、(メタ)アクリル酸(本明細書においては、「アクリ」及び「メタクリ」を合わせて「(メタ)アクリ」と表記する。以下同様)及びその塩;2-(メタ)アクリルアミド-2-メチルプロパンスルホン酸及びその塩;(メタ)アクリルアミド、N,N-ジメチル(メタ)アクリルアミド、2-ヒドロキシエチル(メタ)アクリレート、N-メチロール(メタ)アクリルアミド、ポリエチレングリコールモノ(メタ)アクリレート等の非イオン性単量体;N,N-ジエチルアミノエチル(メタ)アクリレート、N,N-ジエチルアミノプロピル(メタ)アクリレート、ジエチルアミノプロピル(メタ)アクリルアミド等のアミノ基含有不飽和単量体及びその4級化物等が挙げられる。これらの水溶性エチレン性不飽和単量体の中でも、工業的に入手が容易であること等の観点から、(メタ)アクリル酸又はその塩、(メタ)アクリルアミド、N,N-ジメチルアクリルアミドが好ましく、(メタ)アクリル酸及びその塩がより好ましい。なお、これらの水溶性エチレン性不飽和単量体は、単独で用いてもよく、2種類以上を組み合わせて用いてもよい。
内部架橋剤としては、使用する水溶性エチレン性不飽和単量体の重合体を架橋できるものが挙げられ、例えば、(ポリ)エチレングリコール〔「(ポリ)」とは「ポリ」の接頭語がある場合とない場合を意味する。以下同様〕、(ポリ)プロピレングリコール、1,4-ブタンジオール、トリメチロールプロパン、(ポリ)グリセリン等のジオール、トリオール等のポリオール類と(メタ)アクリル酸、マレイン酸、フマル酸等の不飽和酸とを反応させて得られる不飽和ポリエステル類;N,N-メチレンビスアクリルアミド等のビスアクリルアミド類;ポリエポキシドと(メタ)アクリル酸とを反応させて得られるジ(メタ)アクリル酸エステル類又はトリ(メタ)アクリル酸エステル類;トリレンジイソシアネート、ヘキサメチレンジイソシアネート等のポリイソシアネートと(メタ)アクリル酸ヒドロキシエチルとを反応させて得られるジ(メタ)アクリル酸カルバミルエステル類;アリル化澱粉、アリル化セルロース、ジアリルフタレート、N,N’,N’’-トリアリルイソシアネート、ジビニルベンゼン等の重合性不飽和基を2個以上有する化合物;(ポリ)エチレングリコールジグリシジルエーテル、(ポリ)プロピレングリコールジグリシジルエーテル、(ポリ)グリセリンジグリシジルエーテル等のジグリシジル化合物、トリグリシジル化合物等のポリグリシジル化合物;エピクロルヒドリン、エピブロムヒドリン、α-メチルエピクロルヒドリン等のエピハロヒドリン化合物;2,4-トリレンジイソシアネート、ヘキサメチレンジイソシアネート等のイソシアネート化合物等の反応性官能基を2個以上有する化合物;3-メチル-3-オキセタンメタノール、3-エチル-3-オキセタンメタノール、3-ブチル-3-オキセタンメタノール、3-メチル-3-オキセタンエタノール、3-エチル-3-オキセタンエタノール、3-ブチル-3-オキセタンエタノール等のオキセタン化合物等が挙げられる。これらの内部架橋剤の中でも、ポリグリシジル化合物を用いることが好ましく、ジグリシジルエーテル化合物を用いることがより好ましく、(ポリ)エチレングリコールジグリシジルエーテル、(ポリ)プロピレングリコールジグリシジルエーテル、(ポリ)グリセリンジグリシジルエーテルを用いることが好ましい。これらの内部架橋剤は単独で用いてもよく、2種類以上を組み合わせて用いてもよい。
炭化水素分散媒としては、例えば、n-ヘキサン、n-ヘプタン、2-メチルヘキサン、3-メチルヘキサン、2,3-ジメチルペンタン、3-エチルペンタン、n-オクタン等の炭素数6~8の脂肪族炭化水素;シクロヘキサン、メチルシクロヘキサン、シクロペンタン、メチルシクロペンタン、trans-1,2-ジメチルシクロペンタン、cis-1,3-ジメチルシクロペンタン、trans-1,3-ジメチルシクロペンタン等の脂環族炭化水素;ベンゼン、トルエン、キシレン等の芳香族炭化水素等が挙げられる。これらの炭化水素分散媒の中でも、特に、工業的に入手が容易であり、品質が安定しており且つ安価である点で、n-ヘキサン、n-ヘプタン、シクロヘキサンが好適に用いられる。これらの炭化水素分散媒は、単独で用いてもよく、2種類以上を組み合わせて用いてもよい。なお、炭化水素分散媒の混合物の例としては、エクソールヘプタン(エクソンモービル社製:ヘプタン及びその異性体の炭化水素75~85質量%含有)等の市販品が挙げられる。このような混合物を用いても好適な結果を得ることができる。
(界面活性剤)
逆相懸濁重合では、水溶性エチレン性不飽和単量体の炭化水素分散媒中での分散安定性を向上させるために、分散安定剤を用いることもできる。その分散安定剤としては、界面活性剤を用いることができる。
また、逆相懸濁重合で用いられる分散安定剤としては、上述した界面活性剤と共に、高分子系分散剤を併せて用いてもよい。
ラジカル重合開始剤としては、例えば、過酸化物や、アゾ化合物を用いることができる。過酸化物としては、例えば、過硫酸カリウム、過硫酸アンモニウム、過硫酸ナトリウム等の過硫酸塩類;メチルエチルケトンパーオキシド、メチルイソブチルケトンパーオキシド、ジ-t-ブチルパーオキシド、t-ブチルクミルパーオキシド、t-ブチルパーオキシアセテート、t-ブチルパーオキシイソブチレート、t-ブチルパーオキシピバレート、過酸化水素等の過酸化物類が挙げられる。これらの過酸化物の中でも、過硫酸カリウム、過硫酸アンモニウム、過硫酸ナトリウム、過酸化水素を用いることが好ましく、さらに、過硫酸カリウム、過硫酸アンモニウム、過硫酸ナトリウムの過硫酸塩類が好ましい。アゾ化合物の例としては、1-{(1-シアノ-1-メチルエチル)アゾ}ホルムアミド、2,2’-アゾビス[2-(N-フェニルアミジノ)プロパン]二塩酸塩、2,2’-アゾビス{2-[N-(4-クロロフェニル)アミジノ]プロパン}二塩酸塩、2,2’-アゾビス{2-[N-(4-ヒドロキシフェニル)アミジノ]プロパン}二塩酸塩、2,2’-アゾビス[2-(N-ベンジルアミジノ)プロパン]二塩酸塩、2,2’-アゾビス[2-(N-アリルアミジノ)プロパン]二塩酸塩、2,2’-アゾビス(2-アミジノプロパン)二塩酸塩、2,2’-アゾビス{2-[N-(2-ヒドロキシエチル)アミジノ]プロパン}二塩酸塩、2,2’-アゾビス[2-(5-メチル-2-イミダゾリン-2-イル)プロパン]二塩酸塩、2,2’-アゾビス[2-(2-イミダゾリン-2-イル)プロパン]二塩酸塩、2,2’-アゾビス[2-(4,5,6,7-テトラヒドロ-1H-1,3-ジアゼピン-2-イル)プロパン]二塩酸塩、2,2’-アゾビス[2-(5-ヒドロキシ-3,4,5,6-テトラヒドロピリミジン-2-イル)プロパン]二塩酸塩、2,2’-アゾビス{2-[1-(2-ヒドロキシエチル)-2-イミダゾリン-2-イル]プロパン}二塩酸塩、2,2’-アゾビス[2-(2-イミダゾリン-2-イル)プロパン]、2,2’-アゾビス{2-メチル-N-[1,1-ビス(ヒドロキシメチル)-2-ヒドロキシエチル]プロピオンアミド}、2,2’-アゾビス{2-メチル-N-[1,1-ビス(ヒドロキシメチル)エチル]プロピオンアミド}、2,2’-アゾビス[2-メチル-N-(2-ヒドロキシエチル)プロピオンアミド]、2,2’-アゾビス(2-メチルプロピオンアミド)二塩酸塩、4,4’-アゾビス-4-シアノバレイン酸、2,2’-アゾビス[2-(ヒドロキシメチル)プロピオニトリル]、2,2’-アゾビス[2-(2-イミダゾリン-2-イル)プロパン]二硫酸塩二水和物、2,2’-アゾビス[N-(2-カルボキシエチル)-2-メチルプロピオンアミジン]四水和物、2,2’-アゾビス[2-メチル-N-(2-ヒドロキシエチル)プロピオンアミド]等のアゾ化合物が挙げられる。これらの中でも、2,2’-アゾビス(2-アミジノプロパン)二塩酸塩、2,2’-アゾビス{2-[1-(2-ヒドロキシエチル)-2-イミダゾリン-2-イル]プロパン}二塩酸塩、2,2’-アゾビス[N-(2-カルボキシエチル)-2-メチルプロピオンアミジン]四水和物のアゾ化合物等が挙げられる。これらのラジカル重合開始剤の中でも、入手が容易で取り扱い安居という観点から、好ましくは、過硫酸カリウム、過硫酸アンモニウム、過硫酸ナトリウム及び2,2'-アゾビス(2-アミジノプロパン)2塩酸塩が挙げられる。これらラジカル重合開始剤は、1種単独で用いてもよく、また2種以上を組み合わせて用いてもよい。特に2種以上を組み合わせて用いる場合、アゾ化合物と過硫酸塩類が好ましい。
吸水性樹脂の製造方法において、所望によりその他の成分を、水溶性エチレン性不飽和単量体を含む水溶液に添加して逆相懸濁重合を行うようにしてもよい。その他の成分としては、増粘剤、連鎖移動剤等の各種の添加剤を添加することができる。
逆相懸濁重合を行うにあたっては、例えば、分散安定剤の存在下に、水溶性エチレン性不飽和単量体を含む単量体水溶液を、炭化水素分散媒に添加し、分散させる。このとき、重合反応を開始する前であれば、分散安定剤(界面活性剤や高分子系分散剤)の添加時期は、単量体水溶液添加の前後どちらであってもよい。
本発明に係る吸水性樹脂は、水溶性エチレン性不飽和単量体を重合して得られた内部架橋構造を有する含水ゲル状物に対して、後架橋剤で後架橋すること(後架橋反応)で得てもよい。この後架橋反応は、水溶性エチレン性不飽和単量体の重合後以降に後架橋剤の存在下に行うことが好ましい。このように、重合後以降に、内部架橋構造を有する含水ゲル状物に対して後架橋反応を施すことによって、吸水性樹脂の表面近傍の架橋密度を高めて、荷重下吸水能等の諸性能を高めた吸水性樹脂を得ることができる。
本発明の吸水性樹脂の製造方法は、上述した逆相懸濁重合を行った後、系に熱等のエネルギーを外部から加えることで、水、炭化水素分散媒等を蒸留により系から除去する乾燥工程を含んでいてもよい。逆相懸濁重合後の含水ゲルから脱水を行う場合、炭化水素分散媒中に含水ゲルが分散している系を加熱することで、水と炭化水素分散媒を共沸蒸留により系外に一旦留去する。このとき、留去した炭化水素分散媒のみを系内へ返送すると、連続的な共沸蒸留が可能となる。その場合、乾燥中の系内の温度が、炭化水素分散媒との共沸温度以下に維持されるため、樹脂が劣化しにくい。引き続き、水及び炭化水素分散媒を留去することにより、吸水性樹脂の粒子が得られる。この重合後における乾燥工程の処理条件を制御して脱水量を調整することにより、得られる吸水性樹脂の諸性能を制御することが可能である。
本発明に係る吸水性樹脂は、例えば、生理用品、紙オムツ等の衛生材料に用いられる吸収体を構成するものであり、前記吸収体を含む吸収性物品に好適に用いられる。
100mL容のビーカーに0.9質量%塩化ナトリウム水溶液(生理食塩水)100gを量り取り、600rpmで撹拌しながら、吸水性樹脂5gをママコが発生しないように分散させた。吸水性樹脂が吸水し、撹拌が止まった後、5分間静置した。その後、500mL容のビーカーに膨潤した吸水性樹脂を取り出し、スパチュラで固まった吸水性樹脂をほぐし、取り出した吸水性樹脂を全て押し型(錦化成株式会社製 幕の内 押し型(長さ3.6cm、半径2.8cmの円筒形の型が連続して5つ設けられたもの))の中に均一に入れた。押し型のふたの上から5kgの重しを置き、10分間放置した後、押し型から円柱状に押し固められた5個の吸水性樹脂の塊をスパチュラで取り出し、それぞれの質量を測定し、最も重いものと最も軽いものを除いた3つの塊を測定試料として使用した。試料1つの質量Wa(g)測定した後、JIS標準篩の目開き5.6mm篩(篩内径20cmφ)と受け皿の順に組み合わせた最上の篩に質量を測定した試料を入れ、ロータップ式振とう器(株式会社飯田製作所製、回転数290rpm、衝撃数165rpm)を用いて10分間振とうさせて、篩下に通過した質量Wb(g)を測定した。測定は3回行い、その平均値を20倍膨潤時の崩壊量とした。試料の崩壊量は以下の式から算出した。測定対象とした3つの試料についての崩壊量の平均値を、20倍膨潤時の崩壊量とした。
試料の崩壊量(%)=Wb(g)/Wa(g)×100
500mL容のビーカーに、0.9質量%塩化ナトリウム水溶液(生理食塩水)500±0.1gを量り取り、マグネチックスターラーバー(8mmφ×30mmのリングなし)を投入し、マグネチックスターラー〔小池精密機器製作所製(KPI)社製、品番:マイティスターラーM-16GM×6〕の上に配置した。引き続きマグネチックスターラーバーを600rpmで回転するように調整し、さらに、マグネチックスターラーバーの回転により生ずる渦の底部は、マグネチックスターラーバーの上部近くになるように調整した。次に、吸水性樹脂2.0±0.002gを、ビーカー中の渦中央とビーカー側面の間に素早く流し込み分散させ、3時間撹拌した。3時間撹拌後の吸水性樹脂分散水を、標準篩(目開き75μm)でろ過し、得られたろ液をさらに桐山式ロート(ろ紙No.6)を用い吸引ろ過した。得られたろ液を恒量化した100mL容のビーカーに80±0.1g量り取り、140℃の熱風乾燥機〔アドバンテック(ADVANTEC)社製〕で恒量になるまで乾燥させ、ろ液固形分の質量Wc(g)を測定した。一方、吸水性樹脂を用いずに上記操作と同様に行ない、ろ液固形分の質量Wd(g)測定し、以下の式によって、生理食塩水に対する溶解量を算出した。
生理食塩水に対する溶解量(質量%)=〔[(Wc-Wd)×(500/80)]/2〕×100
吸水性樹脂50gに、滑剤として、0.1gの非晶質シリカ(デグサジャパン(株)、Sipernat200)を混合した。これを、JIS標準篩の目開き250μmの篩を用いて通過させ、篩上に残る量がその50質量%未満の場合には<A>の篩の組み合わせを、50質量%以上の場合には<B>の篩の組み合わせを、用いて中位粒子径を測定した。
(B)JIS標準篩を上から、目開き850μmの篩、目開き600μmの篩、目開き500μmの篩、目開き425μmの篩、目開き300μmの篩、目開き250μmの篩、目開き150μmの篩及び受け皿の順に組み合わせた。
吸水性樹脂の荷重下の生理食塩水吸水能は、図1に概略を示した測定装置Yを用いて測定した。図1に示した測定装置Yは、ビュレット部7と導管8、測定台9、測定台9上に置かれた測定部10からなっている。ビュレット部7は、ビュレット70の上部にゴム栓74、下部に空気導入管71とコック72が連結されており、さらに、空気導入管71は先端にコック73を有している。ビュレット部7と測定台9の間には、導管8が取り付けられており、導管8の内径は6mmである。測定台9の中央部には、直径2mmの穴があいており、導管8が連結されている。測定部10は、円筒100(アクリル樹脂製)と、この円筒40の底部に接着されたナイロンメッシュ101と、重り102とを有している。円筒100の内径は、20mmである。ナイロンメッシュ101の目開きは、75μm(200メッシュ)である。そして、測定時にはナイロンメッシュ101上に吸水性樹脂11が均一に撒布されている。重り102は、直径19mm、質量119.6gである。この重りは、吸水性樹脂11上に置かれ、吸水性樹脂11に対して4.14kPaの荷重を加えることができるようになっている。
荷重下の生理食塩水吸水能(ml/g)=We/0.10
以下の1時間ゲル高さWf(mm)と15時間ゲル高さWg(mm)とを比較し、吸水性樹脂の時間経過によるゲル高さの減少の有無を判断した。
(1時間ゲル高さ)
500mLビーカーに0.9質量%塩化ナトリウム水溶液(生理食塩水)500±0.1gを入れ、マグネチックスターラーバー(8mmφ×30mmのリングなし)を投入し、マグネチックスターラー〔小池精密機器製作所製(KPI)社製、品番:マイティスターラーM-16GM×6〕の上に配置した。引き続きマグネチックスターラーバーを600rpmで回転するように調整し、さらに、マグネチックスターラーバーの回転により生ずる渦の底部は、マグネチックスターラーバーの上部近くになるように調整した後、これに吸水性樹脂2.0gを添加して、1時間攪拌した。攪拌を止め、15分間静置した後、ビーカー底面からゲル上部までの高さWf(mm)を測定した。なお、ゲルの高さが測定位置によって異なる場合は、最も高い値と最も低い値の平均値とした。
(15時間ゲル高さ)
500mLビーカーに0.9質量%塩化ナトリウム水溶液(生理食塩水)500±0.1gを入れ、マグネチックスターラーバー(8mmφ×30mmのリングなし)を投入し、マグネチックスターラー〔小池精密機器製作所製(KPI)社製、品番:マイティスターラーM-16GM×6〕の上に配置した。引き続きマグネチックスターラーバーを600rpmで回転するように調整し、さらに、マグネチックスターラーバーの回転により生ずる渦の底部は、マグネチックスターラーバーの上部近くになるように調整した後、これに吸水性樹脂2.0gを添加して、15時間攪拌した。攪拌を止め、15分間静置した後、ビーカー底面からゲル上部までの高さWg(mm)を測定した。なお、ゲルの高さが測定位置によって異なる場合は、最も高い値と最も低い値の平均値とした。
(実施例1)
還流冷却器、滴下ロート、窒素ガス導入管、攪拌機として、翼径50mmの4枚傾斜パドル翼を2段で有する攪拌翼を備えた内径100mmの丸底円筒型セパラブルフラスコを準備した。このフラスコにn-ヘプタン500mlをとり、HLB3のショ糖ステアリン酸エステル(三菱化学フーズ(株)製、リョートーシュガーエステルS-370)0.80g、無水マレイン酸変性エチレン・プロピレン共重合体(三井化学(株)製、ハイワックス1105A)0.80gを添加し、80℃まで昇温して界面活性剤を溶解した後、50℃まで冷却した。
実施例1において、内部架橋剤をポリエチレングリコールジグリシジルエーテル(ナガセケムテックス(株)製 EX-830、n=9)0.0139g(0.0000264モル)に変更し、共沸蒸留の際に抜き出す水の量を116.22gに変更した以外は、実施例1と同様の操作を行い、略球状の吸水性樹脂93.5gを得た。各性能の測定結果を表1に示す。
実施例1において、内部架橋剤をポリエチレングリコールジグリシジルエーテル(ナガセケムテックス(株)製 EX-861、n=22)0.029g(0.0000264モル)に変更し、共沸蒸留の際に抜き出す水の量を116.5gに変更した以外は、実施例1と同様の操作を行い、略球状の吸水性樹脂92.1gを得た。各性能の測定結果を表1に示す。
実施例1において、内部架橋剤をポリエチレングリコールジグリシジルエーテル(ナガセケムテックス(株)製 EX-821 n=4)0.0081g(0.0000264モル)に変更し、共沸蒸留の際に抜き出す水の量を117.5gに変更した以外は、実施例1と同様の操作を行い、略球状の吸水性樹脂96.0gを得た。各性能の測定結果を表1に示す。
実施例1において、内部架橋剤をエチレングリコールジグリシジルエーテル0.028g(0.0000158モル)に変更し、共沸蒸留の際に抜き出す水の量を112.9gに変更した以外は、実施例1と同様の操作を行い、略球状の吸水性樹脂112.1gを得た。各性能の測定結果を表1に示す。
還流冷却器、滴下ロート、窒素ガス導入管、攪拌機として、翼径50mmの4枚傾斜パドル翼を2段で有する攪拌翼を備えた内径100mmの丸底円筒型セパラブルフラスコを準備した。このフラスコにn-ヘプタン500mlをとり、HLB3のショ糖ステアリン酸エステル(三菱化学フーズ(株)製、リョートーシュガーエステルS-370)0.80gを添加し、80℃まで昇温して界面活性剤を溶解した後、50℃まで冷却した。
特許第5143073の実施例を参考に実施した。37%アクリル酸ナトリウム水溶液670.0g、アクリル酸102.0gを混合し、65mol%中和のアクリル酸部分中和液を作製した。このアクリル酸部分中和液772.0gにポリエチレングリコールジアクリレート(平均ポリエチレンオキサイドユニット数9)0.86g及び水220.0gを混合しモノマー水溶液を調製した。このモノマー水溶液をバット(ステンレス製:直径188 mm、高さ60 mm)中に745.5g量り取り、窒素を吹き込み溶液中の溶存酸素を0.1ppm以下とした。
得られた透明の含水ゲルを1L容の双腕型ニーダーで砕き、次いで180℃で30分間乾燥した。
乾燥物を粉砕機(ロータビータミル)で粉砕し、500μmの篩を通過し105μmの篩上に残るものを分級し、吸水性樹脂を得た。
7 ビュレット部
70 ビュレット
71 空気導入管
72 コック
73 コック
74 ゴム栓
8 導管
9 測定台
10 測定部
100 円筒
101 ナイロンメッシュ
102 重り
11 吸水性樹脂
Claims (4)
- 水溶性エチレン性不飽和単量体の重合体であって、
下記(1)及び(2)の特性を備える、吸水性樹脂。
(1)20倍膨潤時の崩壊量が30質量%以下である。
(2)生理食塩水に対する溶解量が25質量%以下である。
(20倍膨潤時の崩壊量の測定方法)
生理食塩水100g中に吸水性樹脂5gを加え、吸水性樹脂に生理食塩水を吸収させてゲルを得る。得られたゲルを、略均等に5分割し、それぞれ、長さ3.6cm、半径2.8cmの円筒形の型に入れて成形する。成形された5つの円筒形のゲルの質量を測定し、最も重いものと最も軽いものを除いた3つのゲルを試料とする。各試料の質量Wa(g)測定した後、JIS標準篩の目開き5.6mm篩と受け皿の順に組み合わせた最上の篩に、質量を測定した試料を入れ、ロータップ式振とう器(回転数290rpm、衝撃数165rpm)を用いて10分間振とうさせて、篩下に通過した質量Wb(g)を測定する。試料の崩壊量を以下の式から算出する。
試料の崩壊量(%)=Wb(g)/Wa(g)×100
測定対象とした3つの試料についての崩壊量の平均値を、吸水性樹脂の20倍膨潤時の崩壊量とする。 - 中位粒子径が200μm~600μmである、請求項1に記載の吸水性樹脂。
- 親水性繊維と共に吸収体に用いる請求項1または2に記載の吸水性樹脂。
- 液体透過性シートおよび液体不透過性シートを含む吸収性物品に用いる請求項1または2に記載の吸水性樹脂。
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EP18777573.9A EP3604366A4 (en) | 2017-03-29 | 2018-03-22 | Water-absorbing resin |
CN201880013519.XA CN110325562A (zh) | 2017-03-29 | 2018-03-22 | 吸水性树脂 |
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JPWO2020184386A1 (ja) * | 2019-03-08 | 2020-09-17 | ||
WO2020184398A1 (ja) * | 2019-03-08 | 2020-09-17 | 住友精化株式会社 | 吸水性樹脂粒子及びその製造方法、吸収体、並びに、吸収性物品 |
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CN113302229A (zh) * | 2019-09-18 | 2021-08-24 | 株式会社Lg化学 | 超吸收性聚合物及其制备方法 |
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US11504695B2 (en) | 2022-11-22 |
US20200353442A1 (en) | 2020-11-12 |
KR102501011B1 (ko) | 2023-02-17 |
KR20190127706A (ko) | 2019-11-13 |
JP7194101B2 (ja) | 2022-12-21 |
JPWO2018180864A1 (ja) | 2020-02-06 |
EP3604366A1 (en) | 2020-02-05 |
CN110325562A (zh) | 2019-10-11 |
EP3604366A4 (en) | 2021-01-13 |
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