JP5989650B2 - 吸水性樹脂の製造方法、及びそれにより得られる吸水性樹脂 - Google Patents
吸水性樹脂の製造方法、及びそれにより得られる吸水性樹脂 Download PDFInfo
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- JP5989650B2 JP5989650B2 JP2013531261A JP2013531261A JP5989650B2 JP 5989650 B2 JP5989650 B2 JP 5989650B2 JP 2013531261 A JP2013531261 A JP 2013531261A JP 2013531261 A JP2013531261 A JP 2013531261A JP 5989650 B2 JP5989650 B2 JP 5989650B2
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- water
- absorbent resin
- ether
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- suspension polymerization
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- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
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- QYZFTMMPKCOTAN-UHFFFAOYSA-N n-[2-(2-hydroxyethylamino)ethyl]-2-[[1-[2-(2-hydroxyethylamino)ethylamino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCNCCO QYZFTMMPKCOTAN-UHFFFAOYSA-N 0.000 description 1
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- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
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- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical class O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
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- 239000005056 polyisocyanate Substances 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 238000007717 redox polymerization reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 229940079827 sodium hydrogen sulfite Drugs 0.000 description 1
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- 239000002904 solvent Substances 0.000 description 1
- 235000019337 sorbitan trioleate Nutrition 0.000 description 1
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- 150000004685 tetrahydrates Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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Images
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F120/00—Homopolymers 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
- C08F120/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F120/04—Acids; Metal salts or ammonium salts thereof
- C08F120/06—Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/12—Polymerisation in non-solvents
- C08F2/16—Aqueous medium
- C08F2/20—Aqueous medium with the aid of macromolecular dispersing agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
- A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
- A61L15/42—Use of materials characterised by their function or physical properties
- A61L15/60—Liquid-swellable gel-forming materials, e.g. super-absorbents
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
- B01J20/26—Synthetic macromolecular compounds
- B01J20/261—Synthetic macromolecular compounds obtained by reactions only involving carbon to carbon unsaturated bonds
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/30—Processes for preparing, regenerating, or reactivating
- B01J20/3085—Chemical treatments not covered by groups B01J20/3007 - B01J20/3078
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
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- C08F2/12—Polymerisation in non-solvents
- C08F2/16—Aqueous medium
- C08F2/22—Emulsion polymerisation
- C08F2/24—Emulsion polymerisation with the aid of emulsifying agents
- C08F2/30—Emulsion polymerisation with the aid of emulsifying agents non-ionic
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- C08F2/00—Processes of polymerisation
- C08F2/32—Polymerisation in water-in-oil emulsions
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- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/24—Crosslinking, e.g. vulcanising, of macromolecules
- C08J3/245—Differential crosslinking of one polymer with one crosslinking type, e.g. surface crosslinking
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- 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
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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Description
〔1〕 ラジカル重合開始剤及び分散安定剤の存在下、石油系炭化水素分散媒中で、水溶性エチレン性不飽和単量体を逆相懸濁重合させる工程を含む吸水性樹脂の製造方法であって、前記分散安定剤としてエーテル・エステル型ノニオン界面活性剤を使用することを特徴とする吸水性樹脂の製造方法、並びに
〔2〕 前記〔1〕記載の製造方法により得られる、生理食塩水保水能が25g/g以上、生理食塩水吸水速度が50秒以下、吸湿流動指数が70%以上である吸水性樹脂
に関する。
なかでも、工業的に入手が容易である点から、(メタ)アクリル酸及びその塩、(メタ)アクリルアミド、N,N−ジメチルアクリルアミド等が好ましく、(メタ)アクリル酸及びその塩がより好ましい。
還流冷却器、滴下ロート、窒素ガス導入管、撹拌機として翼径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321g をとり、HLB値4のステアリン酸ポリオキシエチレンステアリルエーテル(日本エマルジョン(株)、エマレックスSWS-4)0.92g、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)、ハイワックス1105A)0.92gを添加し、80℃まで昇温して界面活性剤を溶解したのち、55℃まで冷却した。
界面活性剤をHLB値5のステアリン酸ポリオキシエチレンステアリルエーテル(日本エマルジョン(株)、エマレックスSWS-6)0.92gに変更した以外は、実施例1と同条件で、球状の吸水性樹脂98.3gを得た。
界面活性剤をHLB値6のステアリン酸ポリオキシエチレンステアリルエーテル(日本エマルジョン(株)、エマレックスSWS-9)0.92gに変更した以外は、実施例1と同条件で、球状の吸水性樹脂103.7gを得た。
界面活性剤をHLB値7のステアリン酸ポリオキシエチレンステアリルエーテル(日本エマルジョン(株)、エマレックスSWS-10)0.92gに、さらに系外に抜き出した水の量を128gに変更した以外は、実施例1と同条件で、球状の吸水性樹脂108.1gを得た。
界面活性剤をHLB値8のステアリン酸ポリオキシエチレンステアリルエーテル(日本エマルジョン(株)、エマレックスSWS-12)0.92gに変更した以外は、実施例4と同条件で、球状の吸水性樹脂107.0gを得た。
還流冷却器、滴下ロート、窒素ガス導入管、撹拌機として翼径50mmの4枚傾斜パドル翼2段で有する攪拌翼を備えた内径100mmの円筒型丸底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321gをとり、HLB値5のステアリン酸ポリオキシエチレンステアリルエーテル(日本エマルジョン(株)、エマレックスSWS-6)0.92g、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)、ハイワックス1105A)0.92gを添加し、80℃まで昇温して界面活性剤を溶解したのち、55℃まで冷却した。
還流冷却器、滴下ロート、窒素ガス導入管、撹拌機として翼径50mmの4枚傾斜パドル翼2段で有する攪拌翼を備えた内径100mmの円筒型丸底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321g をとり、HLB値7のステアリン酸ポリオキシエチレンステアリルエーテル(日本エマルジョン(株)、エマレックスSWS-10)0.92gを添加し、80℃まで昇温して界面活性剤を溶解したのち、55℃まで冷却した。
界面活性剤をHLB値7のステアリン酸ポリオキシエチレンセチルエーテル(日本エマルジョン(株)、エマレックスCWS-10)0.92gに変更した以外は、実施例6と同条件で、球状粒子が凝集した形態の吸水性樹脂202.4gを得た。
界面活性剤をHLB値3のショ糖ステアリン酸エステル(三菱化学フーズ(株)、リョートーシュガーエステルS-370)0.92g、さらに系外に抜き出した水の量を116gに変更した以外は、実施例1と同条件で行い、球状の吸水性樹脂98.0gを得た。
還流冷却器、滴下ロート、窒素ガス導入管、撹拌機として翼径50mmの4枚傾斜パドル翼2段で有する攪拌翼を備えた内径100mmの円筒型丸底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321g をとり、HLB値3のショ糖ステアリン酸エステル(三菱化学フーズ(株)、リョートーシュガーエステルS-370)0.92g、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)、ハイワックス1105A)0.92gを添加し、80℃まで昇温して界面活性剤を溶解したのち、55℃まで冷却した。
還流冷却器、滴下ロート、窒素ガス導入管、撹拌機として、翼径50mmの4枚傾斜パドル翼2段で有する攪拌翼を備えた内径100mmの円筒型丸底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321g をとり、HLB値3のショ糖ステアリン酸エステル(三菱化学フーズ(株)、リョートーシュガーエステルS-370)0.92g、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)、ハイワックス1105A)0.92gを添加し、80℃まで昇温して界面活性剤を溶解したのち、55℃まで冷却した。
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)500gを量り取り、600r/minで攪拌させながら、吸水性樹脂2.0gを、ママコが発生しないように分散させた。攪拌させた状態で30分間放置し、吸水性樹脂を十分に膨潤させた。その後、綿袋(メンブロード60番、横100mm×縦200mm)中に注ぎ込み、綿袋の上部を輪ゴムで縛り、遠心力が167Gとなるよう設定した脱水機(国産遠心機株式会社製、品番:H-122)を用いて綿袋を1分間脱水し、脱水後の膨潤ゲルを含んだ綿袋の質量Wa(g)を測定した。吸水性樹脂を添加せずに同様の操作を行い、綿袋の湿潤時の空質量Wb(g)を測定し、以下の式から保水能を算出した。
吸水性樹脂の2.07kPa荷重下での生理食塩水吸水能は、図1に概略の構成を示した装置Xを用いて測定した。
ビュレット部1は、ビュレット10の上部にゴム栓14、下部に空気導入管11とコック12が連結されており、さらに、空気導入管11は先端にコック13を有している。ビュレット部1と測定台3の間には、導管2が取り付けられており、導管2の内径は6mmである。測定台3の中央部には、直径2mmの穴があいており、導管2が連結されている。測定部4は、アクリル樹脂製の円筒40と、この円筒40の底部に接着されたナイロンメッシュ41と、重り42とを有している。円筒40の内径は、20mmである。ナイロンメッシュ41は目開き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41上に吸水性樹脂5が均一に撒布されている。重り42は、直径19mm、質量59.8gである。この重りは、吸水性樹脂5上に置かれ、吸水性樹脂5に対して2.07kPaの荷重を加えることができるようになっている。
2.07kPa荷重下の生理食塩水吸水能(ml/g)=Wc(ml)÷吸水性樹脂の質量(g)
100mL容のビーカーに、25±0.2℃の温度の生理食塩水50±0.01gを入れ、マグネチックスターラーバー(8mmφ×30mm、リング無し)を用いて、回転数が600r/minになるように調整した。次に吸水性樹脂2.0±0.002gを前記ビーカーに素早く添加し、添加し終わると同時にストップウォッチをスタートした。吸水性樹脂が生理食塩水を吸水し、渦がなくなるまでの時間(秒)をストップウォッチで測定し、生理食塩水吸水速度とした。
目開き850μmのJIS標準篩を通過させた吸水性樹脂5.0gを、平滑なアルミ製板(サイズ120×120mm、厚み0.3mm、質量約11g)の上に均一に散布した。このサンプルを30±1℃、相対湿度80±5%の条件に調整した恒温恒湿器(ナガノ科学機械製作所(株)、型番:LH-20)内に90分間放置し、吸湿させた。吸湿後の吸水性樹脂の質量(Wd)を測定した後、受け皿を付した目開き1400μmの篩い上に、アルミ製板を、吸水性樹脂を載せた面を下向きにして載置した。
篩いにふたをして、ロータップ式振とう機を用いて5回タッピングし、篩いを通過した吸水性樹脂の質量(We)を測定した。下式により吸湿流動指数を算出した。
吸湿流動指数(%)=(We/Wd)×100
吸水性樹脂50gに、滑剤として、0.25g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%以上の場合には<α>の篩の組み合わせを、50質量%未満の場合には<β>の篩の組み合わせを、用いて中位粒子径を測定した。
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400μm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。
JIS標準篩を上から、目開き500μmの篩、目開き250μmの篩、目開き180μmの篩、目開き150μmの篩、目開き106μmの篩、目開き75μmの篩、目開き45μmの篩及び受け皿の順に組み合わせた。
吸水性樹脂2.0gを、あらかじめ恒量(Wf(g))としたアルミホイールケース(8号)にとり精秤した(Wg(g))。上記サンプルを、内温を105℃に設定した熱風乾燥機(ADVANTEC社製)で2時間乾燥させた後、デシケーター中で放冷して、乾燥後の質量Wh(g)を測定した。以下の式から、吸水性樹脂の水分率を算出した。
水分率(質量%)=[(Wg−Wf)−(Wh−Wf)]/(Wg−Wf)×100
一方、比較例においては、高い保水能を有するも吸湿下での流動性が悪いもの(比較例1)、吸水速度が遅いもの(比較例2)、及び吸湿下での流動性は優れるが保水能が低いもの(比較例3)であり、保水能と吸水速度、吸湿下での流動性を同時に満足できる吸水性樹脂は得られなかった。
1 ビュレット部
10 ビュレット
11 空気導入管
12 コック
13 コック
14 ゴム栓
2 導管
3 測定台
4 測定部
40 円筒
41 ナイロンメッシュ
42 重り
5 吸水性樹脂
Claims (5)
- ラジカル重合開始剤及び分散安定剤の存在下、石油系炭化水素分散媒中で、水溶性エチレン性不飽和単量体を逆相懸濁重合させる工程を含む吸水性樹脂の製造方法であって、前記分散安定剤としてエーテル・エステル型ノニオン界面活性剤を使用することを特徴とし、前記エーテル・エステル型ノニオン界面活性剤が、ステアリン酸ポリオキシエチレンセチルエーテル、ステアリン酸ポリオキシエチレンステアリルエーテル、ステアリン酸ポリオキシエチレンラウリルエーテル及びイソステアリン酸ポリオキシエチレンラウリルエーテルからなる群より選ばれた少なくとも1種である、吸水性樹脂の製造方法。
- 分散安定剤として、さらに、無水マレイン酸変性ポリエチレン、無水マレイン酸変性ポリプロピレン、無水マレイン酸変性エチレン・プロピレン共重合体、酸化型ポリエチレン及びエチレン・アクリル酸共重合体からなる群より選ばれた少なくとも1種をエーテル・エステル型ノニオン界面活性剤と併用する請求項1記載の吸水性樹脂の製造方法。
- 逆相懸濁重合反応を2段以上の多段で行う請求項1又は2記載の吸水性樹脂の製造方法。
- 水溶性エチレン性不飽和単量体の逆相懸濁重合工程終了後、後架橋剤を添加して後架橋を行う工程を含む、請求項1〜3いずれか記載の吸水性樹脂の製造方法。
- 逆相懸濁重合反応を2段以上の多段で行い、かつ水溶性エチレン性不飽和単量体の逆相懸濁重合工程終了後、後架橋剤を添加して後架橋を行う工程を含む、請求項1又は2記載の吸水性樹脂の製造方法。
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