JP4976679B2 - 吸水性樹脂およびその製造方法 - Google Patents
吸水性樹脂およびその製造方法 Download PDFInfo
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- JP4976679B2 JP4976679B2 JP2005309260A JP2005309260A JP4976679B2 JP 4976679 B2 JP4976679 B2 JP 4976679B2 JP 2005309260 A JP2005309260 A JP 2005309260A JP 2005309260 A JP2005309260 A JP 2005309260A JP 4976679 B2 JP4976679 B2 JP 4976679B2
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- Prior art keywords
- water
- monomer
- absorbent resin
- group
- ketone
- Prior art date
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- 239000011347 resin Substances 0.000 title claims description 91
- 239000002250 absorbent Substances 0.000 title claims description 71
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims description 69
- 230000002745 absorbent Effects 0.000 title claims description 37
- 238000004519 manufacturing process Methods 0.000 title claims description 14
- 239000000178 monomer Substances 0.000 claims description 77
- 238000006116 polymerization reaction Methods 0.000 claims description 27
- 125000003172 aldehyde group Chemical group 0.000 claims description 22
- 125000000468 ketone group Chemical group 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 21
- 239000002243 precursor Substances 0.000 claims description 19
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- 238000006243 chemical reaction Methods 0.000 claims description 15
- 238000004132 cross linking Methods 0.000 claims description 14
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- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 12
- IBVAQQYNSHJXBV-UHFFFAOYSA-N adipic acid dihydrazide Chemical compound NNC(=O)CCCCC(=O)NN IBVAQQYNSHJXBV-UHFFFAOYSA-N 0.000 claims description 12
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 claims description 12
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- ZNGSVRYVWHOWLX-KHFUBBAMSA-N (1r,2s)-2-(methylamino)-1-phenylpropan-1-ol;hydrate Chemical compound O.CN[C@@H](C)[C@H](O)C1=CC=CC=C1.CN[C@@H](C)[C@H](O)C1=CC=CC=C1 ZNGSVRYVWHOWLX-KHFUBBAMSA-N 0.000 claims description 6
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- GRGBENNNGZARRZ-UHFFFAOYSA-N dodecanedihydrazide Chemical compound NNC(=O)CCCCCCCCCCC(=O)NN GRGBENNNGZARRZ-UHFFFAOYSA-N 0.000 claims description 6
- PBZROIMXDZTJDF-UHFFFAOYSA-N hepta-1,6-dien-4-one Chemical compound C=CCC(=O)CC=C PBZROIMXDZTJDF-UHFFFAOYSA-N 0.000 claims description 6
- FUSUHKVFWTUUBE-UHFFFAOYSA-N vinyl methyl ketone Natural products CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 claims description 6
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- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 8
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- JLIDVCMBCGBIEY-UHFFFAOYSA-N 1-penten-3-one Chemical compound CCC(=O)C=C JLIDVCMBCGBIEY-UHFFFAOYSA-N 0.000 description 4
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- 239000011734 sodium Substances 0.000 description 4
- 239000005720 sucrose Substances 0.000 description 4
- UWFRVQVNYNPBEF-UHFFFAOYSA-N 1-(2,4-dimethylphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(C)C=C1C UWFRVQVNYNPBEF-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
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- SNVRDQORMVVQBI-OWOJBTEDSA-N (e)-but-2-enedihydrazide Chemical compound NNC(=O)\C=C\C(=O)NN SNVRDQORMVVQBI-OWOJBTEDSA-N 0.000 description 2
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- 229940104261 taurate Drugs 0.000 description 1
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Images
Description
攪拌機、2段パドル翼、蒸留装置付還流冷却器、滴下ロートおよび窒素ガス導入管を備えた2L容の5つ口円筒型丸底フラスコに、n−ヘプタン321gを加え、ショ糖脂肪酸エステル(三菱化学フーズ株式会社製、商品名:S−370)0.92gを加えて、分散させながら80℃まで昇温して溶解させた後、55℃まで冷却した。
実施例1において、ジアセトンアクリルアミドの量を0.92g(5.4mmol)に変更し、2%アジピン酸ジヒドラジド水溶液の量を1.8g(0.21mmol)に変更した以外は、実施例1と同様にして、吸水性樹脂98.6gを得た。
攪拌機、2段パドル翼、蒸留装置付還流冷却器、滴下ロートおよび窒素ガス導入管を備えた2L容の5つ口円筒型丸底フラスコに、n−ヘプタン321gを加え、ショ糖脂肪酸エステル(三菱化学フーズ株式会社製、商品名:S−370)0.92gを加えて、分散させながら80℃まで昇温して溶解させた後、55℃まで冷却した。
攪拌機、2段パドル翼、蒸留装置付還流冷却器、滴下ロートおよび窒素ガス導入管を備えた2L容の5つ口円筒型丸底フラスコに、80.5質量%アクリル酸水溶液92gを入れ、これを外部から冷却しつつ、30質量%水酸化ナトリウム水溶液102.8gを滴下して、アクリル酸の75モル%を中和した。さらに、ジアセトンアクリルアミド0.92g(5.4mmol)、過硫酸カリウム、0.11g、N,N’−メチレンビスアクリルアミド27.6mg、水65.1gを添加して溶解させ、系内を窒素ガスで十分に置換し、浴温を65℃に保持し、重合反応を1時間行った。重合終了後、120℃の油浴で加熱し、水分を蒸留により除去し、塊状の吸水性樹脂前駆体を得た。これを卓上ミキサーで粉砕して、粒状の吸水性樹脂前駆体を得た。
実施例1において、ジアセトンアクリルアミドを使用せず、2%アジピン酸ジヒドラジド水溶液3.7g(0.42mmol)を2%エチレングリコールジグリシジルエーテル3.7gに変更した以外は、実施例1と同様にして、吸水性樹脂98.0gを得た。
実施例3において、ジアセトンアクリルアミドを使用せず、2%アジピン酸ジヒドラジド水溶液8.8g(1.0mmol)を2%エチレングリコールジグリシジルエーテル8.8gに変更した以外は、実施例3と同様にして、吸水性樹脂237.2gを得た。
吸水性樹脂2.0gを、綿袋(メンブロード60番、横100mm×縦200mm)中に量り取り、500mL容のビーカー中に入れた。綿袋に生理食塩水(0.9%塩化ナトリウム水溶液、以下同様)500gを一度に注ぎ込み、吸水性樹脂のママコが発生しないように生理食塩水を分散させた。綿袋の上部を輪ゴムで縛り、1時間放置して、吸水性樹脂を十分に膨潤させた。遠心力が167Gになるよう設定した脱水機〔国産遠心機株式会社、品番:H−122〕を用いて綿袋を1分間脱水して、輪ゴムをはずし、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4.14kPaおよび6.21kPaの荷重下における吸水開始から60分後の生理食塩水吸水能は、図1に概略構成を示した測定装置Xを用いて測定した。
1 ビュレット部
10 ビュレット
11 吸気導入管
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 ウェイト
5 吸水性樹脂
Claims (10)
- 吸水性樹脂を構成する単量体成分としてケトン基を有する単量体および/またはアルデヒド基を有する単量体を含み、該単量体がヒドラジド基を複数有する化合物により架橋されていることを特徴とする吸水性樹脂であって、41g/g以上の生理食塩水保水能を有する吸水性樹脂。
- ケトン基を有する単量体および/またはアルデヒド基を有する単量体がジアセトン(メタ)アクリルアミド、ビニルメチルケトン、ビニルブチルケトン、ジアセトン(メタ)アクリレートおよびアクロレインからなる群から選ばれた少なくとも1種である請求項1に記載の吸水性樹脂。
- ヒドラジド基を複数有する化合物がマロン酸ジヒドラジド、アジピン酸ジヒドラジドおよびドデカン二酸ジヒドラジドからなる群から選ばれた少なくとも1種である請求項1または2に記載の吸水性樹脂。
- ケトン基を有する単量体および/またはアルデヒド基を有する単量体を含む水溶性エチレン性不飽和単量体を重合して得られる吸水性樹脂前駆体に、ヒドラジド基を複数有する化合物を添加し後架橋反応させることを特徴とする吸水性樹脂であって、41g/g以上の生理食塩水保水能を有する吸水性樹脂の製造方法。
- ケトン基を有する単量体および/またはアルデヒド基を有する単量体がジアセトン(メタ)アクリルアミド、ビニルメチルケトン、ビニルブチルケトン、ジアセトン(メタ)アクリレートおよびアクロレインからなる群から選ばれた少なくとも1種である請求項4に記載の吸水性樹脂の製造方法。
- ケトン基を有する単量体および/またはアルデヒド基を有する単量体の量が、水溶性エチレン性不飽和単量体全質量の0.01〜10質量%である請求項4または5に記載の吸水性樹脂の製造方法。
- ヒドラジド基を複数有する化合物がマロン酸ジヒドラジド、アジピン酸ジヒドラジドおよびドデカン二酸ジヒドラジドからなる群から選ばれた少なくとも1種である請求項4〜6のいずれか1項に記載の吸水性樹脂の製造方法。
- ヒドラジド基を複数有する化合物の量が、吸水性樹脂前駆体を得るために使用したケトン基を有する単量体および/またはアルデヒド基を有する単量体1モルに対して、0.0001〜2モルである請求項4〜7のいずれか1項に記載の吸水性樹脂の製造方法。
- 重合反応が逆相懸濁重合反応であって、逆相懸濁重合反応によって得られた吸水性樹脂前駆体に水溶性エチレン性不飽和単量体をさらに添加し、2段以上の多段で重合を行う、請求項4〜8のいずれか1項に記載の吸水性樹脂の製造方法。
- 請求項4〜9のいずれか1項に記載の吸水性樹脂の製造方法によって製造される、吸水性樹脂を構成する単量体成分としてケトン基を有する単量体および/またはアルデヒド基を有する単量体を含み、該単量体がヒドラジド基を複数有する化合物により架橋されていることを特徴とする吸水性樹脂であって、41g/g以上の生理食塩水保水能を有する吸水性樹脂。
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