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WO2003106551A1 - Resine absorbant l'eau et procede d'elaboration correspondant - Google Patents

Resine absorbant l'eau et procede d'elaboration correspondant Download PDF

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Publication number
WO2003106551A1
WO2003106551A1 PCT/JP2003/006979 JP0306979W WO03106551A1 WO 2003106551 A1 WO2003106551 A1 WO 2003106551A1 JP 0306979 W JP0306979 W JP 0306979W WO 03106551 A1 WO03106551 A1 WO 03106551A1
Authority
WO
WIPO (PCT)
Prior art keywords
water
absorbent resin
weight
polysaccharide
parts
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP2003/006979
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English (en)
Japanese (ja)
Inventor
吉野　一寛
縄田　康博
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sumitomo Seika Chemicals Co Ltd
Original Assignee
Sumitomo Seika Chemicals Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Sumitomo Seika Chemicals Co Ltd filed Critical Sumitomo Seika Chemicals Co Ltd
Publication of WO2003106551A1 publication Critical patent/WO2003106551A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L5/00—Compositions of polysaccharides or of their derivatives not provided for in groups C08L1/00 or C08L3/00
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
    • C08K5/092—Polycarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L29/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical; Compositions of hydrolysed polymers of esters of unsaturated alcohols with saturated carboxylic acids; Compositions of derivatives of such polymers
    • C08L29/02—Homopolymers or copolymers of unsaturated alcohols
    • C08L29/04—Polyvinyl alcohol; Partially hydrolysed homopolymers or copolymers of esters of unsaturated alcohols with saturated carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L1/00—Compositions of cellulose, modified cellulose or cellulose derivatives

Definitions

  • the present invention relates to a water-absorbing resin and a method for producing the same. More specifically, the present invention relates to a water-absorbent resin which is excellent in water-absorbing ability and biodegradability and has a low dissolved content, and a method for producing the same. Background art
  • water-absorbent resins have been used not only as sanitary materials such as paper mummies and sanitary products, but also in the medical field such as bodily fluid absorbents; civil engineering and construction fields such as sealing materials (water-stopping materials) and anti-condensation materials; It is used in a wide variety of fields such as food fields such as holding materials; industrial fields such as dehydrating agents that remove water from solvents; and agriculture and horticulture fields such as greening.
  • various water-absorbing resins according to these uses have been proposed.
  • polyacrylic acid (salt) -based water-absorbing resins are widely used because of their excellent water-absorbing ability and low cost.
  • the polyacrylic acid (salt) -based water-absorbing resin has some photodegradability in the water-absorbing state, but hardly any biodegradability. Therefore, when treating a polyacrylic acid (salt) -based water-absorbent resin as waste, for example, if it is landfilled, it is less likely to be decomposed by bacteria and microorganisms in the soil, causing problems such as environmental pollution. is there.
  • examples of the water-absorbing resin having excellent water-absorbing ability and biodegradability include, for example, a water-absorbing resin obtained by crosslinking a polysaccharide itself (JP-A-56-137, JP-A-58-137). 79006, JP-A-60-58443, JP-A-8-89796), a water-absorbent resin obtained by using a cellulose derivative as a polysaccharide derivative and cross-linking the cellulose derivative (Japanese Patent Laid-Open No.
  • the biodegradability of the water-absorbent resin obtained by crosslinking the polysaccharide or polysaccharide derivative is inferior to that of the raw material polysaccharide or polysaccharide derivative. Furthermore, in order to increase the water absorbing ability of the water-absorbing resin, it is theoretically necessary to reduce the crosslink density. There is a problem that the minutes become high. Therefore, a water-absorbent resin excellent in water-absorbing ability and biodegradability and having a low solubility in water, and a method for producing the same are desired.
  • An object of the present invention is to provide a water-absorbing resin which is excellent in water-absorbing ability and biodegradability and has a small amount of dissolved components, and a method for producing the same.
  • a water-absorbing resin obtained by crosslinking a polysaccharide and polyvinyl alcohol with a crosslinking agent has excellent water-absorbing ability and biodegradability, and has a small amount of dissolved components, and has completed the present invention.
  • the present invention relates to a water-absorbing resin obtained by crosslinking a polysaccharide and polyvinyl alcohol with a crosslinking agent.
  • the water-absorbent resin preferably has a water-absorbing capacity of 10 g Z g or more in physiological saline, a dissolved content in physiological saline of 30% or less, and a biodegradation rate of 15% or more.
  • the proportion of the polyvinyl alcohol is preferably 0.1 to 200 parts by weight based on 100 parts by weight of the polysaccharide.
  • the amount of the crosslinking agent used is preferably 0.05 to 50 parts by weight based on 100 parts by weight of the total amount of the polysaccharide and the polybutyl alcohol.
  • the crosslinking agent is preferably a dialdehyde or a polycarboxylic acid.
  • the polysaccharide is carboxymethyl cellulose.
  • the present invention also relates to a method for producing a water-absorbent resin, which comprises mixing a polysaccharide, a polybiol alcohol, and a crosslinking agent and heating the mixture.
  • polysaccharide used in the present invention examples include, but are not limited to, polysaccharides, polysaccharide derivatives, and alkali metal salts such as sodium salts and potassium salts.
  • Polysaccharides include, for example, cellulose, methinoresenorelose, ethylcellulose, methylethylcellulose, hemicenolerose, starch, methinolestarch, ethinole starch, methylethylstarch, agar, carrageenan, alginic acid, pectic acid, Guar gum, tamarind gum, locust bean gum, konnyaku mannan, dextran, xanthan gum, pullulan, gellan gum, chitin, chitosan, chondroitin sulfate, heparin, hyaluronic acid and the like.
  • polysaccharide derivative examples include canolepoxymethylcellulose obtained by carboxyalkylating or hydroxylating the polysaccharide, hydroxyshethylcenolorose, starch glycolic acid, agar derivatives, carrageenan-inducing conductor, and the like. It is possible.
  • the polysaccharide also includes a polysaccharide derivative and a metal salt thereof.
  • polysaccharides, polysaccharide derivatives and metal salts thereof may be used alone or in combination of two or more.
  • carboxymethylcellulose and alkali metal salts thereof such as sodium salt and potassium salt are preferably used from the viewpoint of obtaining a water-absorbing resin having high water-absorbing ability.
  • the degree of substitution of the polysaccharide metal salt and the polysaccharide derivative by the metal salt is preferably from 0.2 to 1.2, and more preferably from 0.4 to 0.9. If the degree of substitution is less than 0.2, the resulting water-absorbent resin may have a reduced water-absorbing ability. If the degree of substitution exceeds 1.2, the biodegradability of the resulting water-absorbent resin may be reduced.
  • the weight average molecular weight of the polyvinyl alcohol used in the present study is not particularly limited, but is preferably 100,000 or less, more preferably 900,000 or less, and still more preferably 800,000 to 1 0 0 0 0. When the weight average molecular weight exceeds 100,000, the biodegradability of the obtained water-absorbent resin may be reduced.
  • the saponification degree of the polybutyl alcohol is not particularly limited, and is preferably 60 to 99.9%, more preferably 80 to 99%. If the degree of saponification is less than 60%, or if it exceeds 99.9%, the water absorbing ability of the resulting water-absorbing resin may decrease.
  • a preferable ratio of the polybutyl alcohol is 0.1 to 200 parts by weight, more preferably 1 to 150 parts by weight, and still more preferably 10 to 120 parts by weight with respect to 100 parts by weight of the polysaccharide. It is. If the proportion of polyvinyl alcohol is less than 0.1 part by weight, the resulting water-absorbent resin may have an increased amount of dissolved components. If the proportion of the polybutyl alcohol exceeds 200 parts by weight, the water absorbing ability of the resulting water-absorbing resin may be reduced.
  • the cross-linking agent used in the present invention is not particularly limited, and examples include a dialdehyde, a polycarboxylic acid, and an epoxy compound. Among them, dialdehydes and polycarboxylic acids are preferred.
  • dialdehydes examples include glioxal, glutaraldehyde, telephthalaldehyde and the like. Among them, darioxizal and glutaraldehyde are preferably used from the viewpoint of easy availability and low cost.
  • polycarboxylic acids examples include oxalic acid, maleic acid, succinic acid, aspartic acid, polyacrylic acid, and the like.
  • succinic acid is preferably used from the viewpoint of high safety.
  • Epoxy compounds include ethylene glycol diglycidyl ether, polyethylene glycol monoresidic glycidyl ether, glycerol polyglycidinole ether, diglycerol monoglycidyl ether, polyglycerol polyglycidyl ether, and propylene glycol. Monoglycidinoleate ether, polypropylene glycol diglycidyl ether, glycidol, ⁇ -glycidoxypropyltrimethoxysilane and the like.
  • the preferred amount of the crosslinking agent used is 0.05 to 50 parts by weight, more preferably 0.1 to 20 parts by weight, more preferably 0.1 to 20 parts by weight, based on 100 parts by weight of the total amount of the polysaccharide and the polybutyl alcohol. Preferably it is 1 to 10 parts by weight. If the amount of the crosslinking agent used is less than 0.05 part by weight, the amount of the dissolved water-absorbent resin obtained may increase. Use of cross-linking agent When the amount exceeds 50 parts by weight, not only the effect corresponding to the amount used is not obtained, but also the water absorbing ability of the obtained water-absorbing resin may be reduced.
  • the water-absorbent resin of the present invention can be produced by mixing a polysaccharide, polybutyl alcohol, and a crosslinking agent, heating and crosslinking.
  • the polysaccharide and the polybutyl alcohol are cross-linked by a cross-linking agent, they are preferably mixed uniformly and sufficiently so that a uniform cross-linking reaction is performed.
  • a method of mixing powders a method of mixing in a slurry state, a method of mixing in a solution state, and the like.
  • a method of mixing in a solution state is preferably used from the viewpoint of more uniform and sufficient mixing.
  • Examples of the solvent used in the mixing method include water and hydrophilic organic solvents such as lower alcohols such as methyl alcohol, ethyl alcohol, and propyl alcohol.
  • the concentration of the solution is preferably 0.1 to 20% by weight, more preferably 0.5 to 10% by weight.
  • the concentration is less than 0.1% by weight, the amount of the solution becomes large, and a long time of heating is required to remove the solvent, which may reduce the production efficiency.
  • the concentration is 20 weight. If the ratio exceeds / 0 , the viscosity of the aqueous solution increases, and it may be difficult to uniformly and sufficiently mix the polysaccharide and polyvier alcohol.
  • the concentration of the solution is preferably 1% by weight to a saturated concentration, more preferably 5% by weight to a saturated concentration. If the concentration is less than 1% by weight, the amount of the solution increases, and a long heating time is required to remove the solvent, which may lower the production efficiency.
  • the heating temperature for crosslinking by heating is preferably from 60 to 180 ° C, and more preferably from 70 to 150 ° C. If the heating temperature is lower than 60 ° C, the crosslinking reaction may not easily proceed. If the heating temperature exceeds 180 ° C., the polysaccharide may be colored or the crosslinking reaction may proceed too much, resulting in a decrease in water absorption capacity.
  • the heating method is not particularly limited, and examples thereof include a method of irradiating far infrared rays, microwaves, and the like, and a method of using a hot air dryer, a reduced pressure dryer, and the like.
  • the heating time is not particularly limited, and includes polysaccharides, polyvinyl alcohol, It may be appropriately set according to the type and combination of the crosslinking agent and the solvent, the heating temperature, and the desired physical properties of the water-absorbing resin. .
  • a catalyst may be added to carry out the crosslinking reaction so that the crosslinking reaction proceeds smoothly.
  • acids such as sulfuric acid, hydrochloric acid, phosphoric acid, and nitric acid are suitably used.
  • the amount of the catalyst used is preferably 1 to 200 parts by weight based on 100 parts by weight of the crosslinking agent. If the amount of the catalyst is less than 1 part by weight, the reaction may not easily proceed. If the amount of the catalyst exceeds 200 parts by weight, there is no effect corresponding to the amount of the catalyst, and it is not economical.
  • a water-absorbent resin of the present invention for example, an aqueous solution of a polysaccharide, a polyvinyl alcohol, and a crosslinking agent are used, and an aqueous solution of a polysaccharide and a polyvinyl alcohol are mixed in advance, and then an aqueous solution of a crosslinking agent is added. And mix again.
  • the obtained aqueous solution is heated to remove the water from the aqueous solution while the crosslinking reaction proceeds, and then dried to obtain a dried product.
  • a water-absorbent resin can be produced by pulverizing the obtained dried product.
  • the water-absorbing resin thus obtained has a water-absorbing capacity for physiological saline of 10 gZg or more, preferably 15 to 80 gZg. If the water absorption capacity is less than 10 g Z g, the amount of the water-absorbing resin used is undesirably increased.
  • the water-absorbing ability in the present invention refers to a water-absorbent resin obtained by putting 1 g of a water-absorbent resin into 0.9 ml of 0.9% by weight saline solution, sufficiently swelling, and then filtering the water-absorbent resin through a 200-mesh wire net. When the weight A (g) of the water-absorbent resin is measured, the value is calculated by the following equation.
  • the content of the water-absorbent resin of the present invention in physiological saline is 30% or less, and preferably 25% or less. If the dissolved content exceeds 30%, the water absorption capacity is undesirably reduced.
  • the dissolved matter was 1 g of a water-absorbent resin in 25 Oml of 0.9% by weight saline solution, stirred for 3 hours with a stirrer, and then collected by filtration through a 200-mesh wire net.
  • the filtrate (5 Om1) was accurately measured in a previously dried beaker of known weight A (g), and the weight B (g) after drying at 140 ° C for 16 hours was measured. Value.
  • the biodegradability of the water-absorbent resin of the present invention is 15% or more. It is preferably at least 20%. If the biodegradation rate is less than 15%, the biodegradability is poor and may cause environmental pollution and other problems.
  • the biodegradation rate in the present invention is based on JIS K 6951, 8.5 g of anhydrous dihydrogen phosphate, 21.75 g of anhydrous hydrogen phosphate, 21.75 g of disodium hydrogen phosphate, Dissolve 33.4 g of the hydrate and 0.5 g of ammonium chloride in distilled water: Add 400 mg of the water-absorbent resin to 400 ml of the standard test culture broth made LOO Oml, and then add The total amount A (mg) of carbon dioxide generated when culturing at 25 ° C for 28 days while stirring the culture solution to which raw sludge was added to 30 ppm with a stirrer was determined.
  • the total amount B (mg) of carbon dioxide generated from the culture solution to which no water was added was calculated in the same manner, and the calculated value C (mg) of carbon dioxide generated when the water-absorbent resin was completely decomposed was calculated. Sometimes it is a value calculated by the following equation.
  • Biodegradation rate (%) (A-B) / C 100
  • the water-absorbent resin of the present invention may contain, as necessary, inorganic fine particles such as silica fine particles, a filler made of pulp fiber, and the like, activated carbon and iron phthalocyanine derivatives, and vegetable properties in order to improve processability and quality performance.
  • Deodorant mainly composed of zeolite etc. to which essential oil is adsorbed, aromatic agent, antibacterial agent mainly composed of metals such as silver, copper, zinc, etc., bactericide, antibacterial agent, preservative, deoxidizer (Antioxidants), additives such as surfactants, foaming agents, and fragrances may be added.
  • the amount of the additive to be added is not generally determined by the type of the additive, but is usually about 0.01 to 5 parts by weight based on 100 parts by weight of the water absorbent resin.
  • the water-absorbent resin of the present invention can be used not only in the field of hygiene such as sanitary materials such as paper mummies and sanitary products, but also in the medical field such as a bodily fluid absorbent at the time of surgery and a wound protecting material; Civil engineering and construction fields such as concrete curing materials, gel blisters, and anti-condensation materials; drip absorbing materials such as meat and fish; food products such as freshness preserving materials and freshness preserving materials such as vegetables; dehydration to remove water from solvents Industrial fields such as lumber; soil water retention materials for greening, etc .; water retention materials for plant cultivation, seed coating materials, etc.
  • Example 1 23.8 g of a water-absorbent resin was obtained in the same manner as in Example 1, except that the standing time in the hot air dryer was changed from 7 hours to 10 hours.
  • Example 1 23.4 g of a water-absorbent resin was obtained in the same manner as in Example 1, except that the set temperature of the hot air dryer was changed from 100 ° C to 140 ° C. (Example 4)
  • Example 1 24.4 g of a water-absorbent resin was obtained in the same manner as in Example 1, except that glyoxal was changed to dartalaldehyde.
  • Example 5 In Example 1, 24.4 g of a water-absorbent resin was obtained in the same manner as in Example 1, except that succinic acid was used instead of dalioxal.
  • Example 1 the amount of 5 wt% aqueous solution of 5 weight 0/0 aqueous solution and poly Biel alcohol carboxymethylcellulose, except for changing each 250 g of Example 1 a water-absorbent resin 24. 2 g in the same manner Obtained.
  • Dissolution (%) [(B-A) / 50x250- 250xO. 009] xl O O
  • Biodegradation rate (%) (AB) / Cxi 00 Water absorption capacity
  • the present invention it is possible to provide a water-absorbing resin which is excellent in water-absorbing ability and biodegradability and has a small amount of dissolved components, and a method for producing the same.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Molecular Biology (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Materials Engineering (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Biological Depolymerization Polymers (AREA)
  • Processes Of Treating Macromolecular Substances (AREA)
  • Solid-Sorbent Or Filter-Aiding Compositions (AREA)

Abstract

L'invention concerne une résine absorbant l'eau qui a une capacité d'absorption d'eau et une biodégradabilité excellentes, et qui présente un faible contenu soluble. L'invention concerne également un procédé d'élaboration correspondant. Cette résine résulte de la réticulation d'un polysaccharide et d'un alcool de polyvinyle, au moyen d'un agent de réticulation.
PCT/JP2003/006979 2002-06-03 2003-06-03 Resine absorbant l'eau et procede d'elaboration correspondant Ceased WO2003106551A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2002-161917 2002-06-03
JP2002161917A JP4132993B2 (ja) 2002-06-03 2002-06-03 吸水性樹脂およびその製造方法

Publications (1)

Publication Number Publication Date
WO2003106551A1 true WO2003106551A1 (fr) 2003-12-24

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JP (1) JP4132993B2 (fr)
TW (1) TW200307721A (fr)
WO (1) WO2003106551A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110845635A (zh) * 2019-11-29 2020-02-28 江苏哈齐诺生物环保科技有限公司 一种两性多糖吸水材料的制备方法

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4655505B2 (ja) * 2004-04-28 2011-03-23 東レ株式会社 架橋生分解性粒子およびその製造方法
WO2009022358A1 (fr) * 2007-08-10 2009-02-19 Luigi Ambrosio Hydrogels de polymère superabsorbant et leur procédé de préparation
JP5188824B2 (ja) * 2008-02-07 2013-04-24 サンダイヤポリマー株式会社 吸収性樹脂粒子及びこの製造方法
JP5430091B2 (ja) * 2008-07-09 2014-02-26 旭化成せんい株式会社 高吸水性樹脂およびその製造方法
WO2011024021A1 (fr) * 2009-08-31 2011-03-03 Ovc Intellectual Capital, Llc Composition d'ensimage contenant un polymère biodégradable
ES2693236T3 (es) 2011-06-07 2018-12-10 Gelesis Llc Método para la producción de hidrogeles
CN115381850A (zh) 2014-06-20 2022-11-25 吉莱斯公司 用于治疗超重或肥胖症的方法
KR102849940B1 (ko) 2015-01-29 2025-08-22 젤레시스 엘엘씨 높은 탄성 계수 및 흡수율로 결합되는 하이드로겔을 제조하는 방법
CA3022090A1 (fr) 2016-04-25 2017-11-02 Gelesis, Llc. Methode de traitement de la constipation
BR112022002662A2 (pt) * 2019-08-12 2022-05-03 Solutum Tech Ltd Compostos e usos dos mesmos

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US5736595A (en) * 1993-05-03 1998-04-07 Chemische Fabrik Stockhausen Gmbh Polymer composition, absorbent material composition, their production and their use
JPH10279693A (ja) * 1997-04-03 1998-10-20 Fuji Xerox Co Ltd 吸水性ゲル粒子の製造方法
WO1999025393A2 (fr) * 1997-11-19 1999-05-27 Amcol International Corporation Particules multicomposant a gel superabsorbant
JP2001011294A (ja) * 1999-07-02 2001-01-16 Miyoshi Oil & Fat Co Ltd 生分解性樹脂水系分散体及び生分解性複合材料
JP2001114803A (ja) * 1999-10-18 2001-04-24 Unitika Ltd 吸水剤及びその製造方法
US6358580B1 (en) * 1998-01-09 2002-03-19 Thomas Mang Sealing material which swells when treated with water

Patent Citations (6)

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Publication number Priority date Publication date Assignee Title
US5736595A (en) * 1993-05-03 1998-04-07 Chemische Fabrik Stockhausen Gmbh Polymer composition, absorbent material composition, their production and their use
JPH10279693A (ja) * 1997-04-03 1998-10-20 Fuji Xerox Co Ltd 吸水性ゲル粒子の製造方法
WO1999025393A2 (fr) * 1997-11-19 1999-05-27 Amcol International Corporation Particules multicomposant a gel superabsorbant
US6358580B1 (en) * 1998-01-09 2002-03-19 Thomas Mang Sealing material which swells when treated with water
JP2001011294A (ja) * 1999-07-02 2001-01-16 Miyoshi Oil & Fat Co Ltd 生分解性樹脂水系分散体及び生分解性複合材料
JP2001114803A (ja) * 1999-10-18 2001-04-24 Unitika Ltd 吸水剤及びその製造方法

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110845635A (zh) * 2019-11-29 2020-02-28 江苏哈齐诺生物环保科技有限公司 一种两性多糖吸水材料的制备方法

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TW200307721A (en) 2003-12-16
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