JP2009507118A - 重合法 - Google Patents
重合法 Download PDFInfo
- Publication number
- JP2009507118A JP2009507118A JP2008529602A JP2008529602A JP2009507118A JP 2009507118 A JP2009507118 A JP 2009507118A JP 2008529602 A JP2008529602 A JP 2008529602A JP 2008529602 A JP2008529602 A JP 2008529602A JP 2009507118 A JP2009507118 A JP 2009507118A
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- JP
- Japan
- Prior art keywords
- polymerization reactor
- monomer solution
- polymerization
- mixture
- cross
- 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.)
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- 238000006116 polymerization reaction Methods 0.000 title claims abstract description 47
- 238000000034 method Methods 0.000 title claims abstract description 25
- 239000000178 monomer Substances 0.000 claims abstract description 63
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 53
- 229920000642 polymer Polymers 0.000 claims abstract description 30
- 239000000203 mixture Substances 0.000 claims abstract description 20
- 238000004519 manufacturing process Methods 0.000 claims abstract description 8
- 238000010924 continuous production Methods 0.000 claims abstract description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 15
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 14
- 239000000017 hydrogel Substances 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 239000002245 particle Substances 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 3
- 239000000243 solution Substances 0.000 description 45
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 23
- 239000000499 gel Substances 0.000 description 13
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
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- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 4
- 238000010998 test method Methods 0.000 description 4
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- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 2
- BXAAQNFGSQKPDZ-UHFFFAOYSA-N 3-[1,2,2-tris(prop-2-enoxy)ethoxy]prop-1-ene Chemical compound C=CCOC(OCC=C)C(OCC=C)OCC=C BXAAQNFGSQKPDZ-UHFFFAOYSA-N 0.000 description 2
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 2
- ZMGMDXCADSRNCX-UHFFFAOYSA-N 5,6-dihydroxy-1,3-diazepan-2-one Chemical compound OC1CNC(=O)NCC1O ZMGMDXCADSRNCX-UHFFFAOYSA-N 0.000 description 2
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- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
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- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
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- 238000007796 conventional method Methods 0.000 description 2
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
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- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 2
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- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 2
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- LGPAKRMZNPYPMG-UHFFFAOYSA-N (3-hydroxy-2-prop-2-enoyloxypropyl) prop-2-enoate Chemical class C=CC(=O)OC(CO)COC(=O)C=C LGPAKRMZNPYPMG-UHFFFAOYSA-N 0.000 description 1
- NQQRXZOPZBKCNF-NSCUHMNNSA-N (e)-but-2-enamide Chemical compound C\C=C\C(N)=O NQQRXZOPZBKCNF-NSCUHMNNSA-N 0.000 description 1
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- OYELEBBISJGNHJ-UHFFFAOYSA-N 1,3-oxazinan-2-one Chemical compound O=C1NCCCO1 OYELEBBISJGNHJ-UHFFFAOYSA-N 0.000 description 1
- PQUXFUBNSYCQAL-UHFFFAOYSA-N 1-(2,3-difluorophenyl)ethanone Chemical compound CC(=O)C1=CC=CC(F)=C1F PQUXFUBNSYCQAL-UHFFFAOYSA-N 0.000 description 1
- 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 1
- HSOOIVBINKDISP-UHFFFAOYSA-N 1-(2-methylprop-2-enoyloxy)butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(CCC)OC(=O)C(C)=C HSOOIVBINKDISP-UHFFFAOYSA-N 0.000 description 1
- BJELTSYBAHKXRW-UHFFFAOYSA-N 2,4,6-triallyloxy-1,3,5-triazine Chemical compound C=CCOC1=NC(OCC=C)=NC(OCC=C)=N1 BJELTSYBAHKXRW-UHFFFAOYSA-N 0.000 description 1
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- 150000003628 tricarboxylic acids Chemical class 0.000 description 1
- ZTWTYVWXUKTLCP-UHFFFAOYSA-N vinylphosphonic acid Chemical class OP(O)(=O)C=C ZTWTYVWXUKTLCP-UHFFFAOYSA-N 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
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Abstract
Description
A: 架橋剤配量前のモノマー溶液
B: 架橋剤の供給路
C: 架橋剤を有するモノマー溶液
L1: 流入区間
L2: くびれ領域
L3: 拡散部
D1: 管状導管の直径
D2: くびれ領域の直径
最適なベンチュリ管の設計は、当業者に自体公知である。有利には、ベンチュリ管は、区間L2の範囲の圧力が、周囲圧より低い(吸引輸送)及び/又は区間L2の範囲の流動が乱流であるように設計され、その際、レイノルズ数は、少なくとも1000、有利には少なくとも2000、特に有利には少なくとも3000、殊に有利には少なくとも4000、通常は10000000未満であることが望ましい。
a)少なくとも1種のエチレン性不飽和の酸基を有するモノマーと、
b)少なくとも1種の架橋剤と、
c)場合により、モノマーa)と共重合可能な1種以上のエチレン性及び/又はアリル性不飽和のモノマーと、
d)場合により、モノマーa)と、b)と、場合によりc)とが少なくとも部分的にグラフトしうる1種以上の水溶性ポリマーと
を含有するモノマー溶液の重合によって得られる。
− バッチ法もしくは管形反応器中でのゲル重合と、引き続いての肉挽き機、押出機もしくは混練機中での粉砕(EP−A−0445619号、DE−A−19846413号)
− 混練機中での重合、その際、例えば二重反転撹拌軸によって連続的に粉砕される(WO−A−01/38402号)
− ベルト上での重合と、引き続いての肉挽き機、押出機もしくは混練機中での粉砕(DE−A−3825366号、US−6,241,928号)
− 乳化重合、その際、既に比較的狭いゲルサイズ分布のパール重合体が生ずる(EP−A−0457660号)
− 大部分は連続的な作業において事前に水性モノマー溶液が噴霧され、引き続き光重合に供された織物層の現場重合(WO−A−02/94328号、WO−A−02/94329号)。
i)重合反応器と、
ii)重合反応器i)への少なくとも1つの供給路と、
iii)供給路ii)中の少なくとも1つのベンチュリ管と、
iv)ベンチュリ管iii)への少なくとも1つの供給路と
を有する装置である。
測定は、別に記載がない限り、23±2℃の環境温度および50±10%の相対空気湿度で実施される。吸水性ポリマーは、測定前に良く混和する。
吸水性ポリマー粒子の残留架橋剤の含有率は、ZORBAX(登録商標)Eclipse XDB C18(Agilent Technologies,米国)型の逆相カラムを用いたHPLCと、後続のUV/VIS検出と、外部標準での校正によって測定される。移動相として、アセトニトリル/水をグラジエントで使用する。
吸水性ポリマー粒子中の抽出分の含有率は、EDANA(欧州不織布工業会)によって推奨される試験法第470.2−02"抽出分(Extractables)"に従って測定される。
実施例1
水と、50質量%の苛性ソーダ液と、アクリル酸との連続的な混合によって、中和度71.3モル%を有する38.8質量%のアクリル酸/アクリル酸ナトリウム溶液を製造した。該モノマー溶液を、それらの成分の混合に際して熱交換器によって連続的に温度29℃に冷却した。
実施例1と同様に実施した。架橋剤の添加位置は、反応器に入る前3.5mの所であった。重合反応器の前のモノマー溶液中の架橋剤の滞留時間は、5.3秒であった。
実施例1と同様に実施した。架橋剤の添加位置は、反応器に入る前2.5mの所であった。重合反応器の前のモノマー溶液中の架橋剤の滞留時間は、3.8秒であった。
実施例1と同様に実施した。架橋剤の添加位置は、反応器に入る前2.5mの所であった。重合反応器の前のモノマー溶液中の架橋剤の滞留時間は、3.8秒であった。
実施例4と同様に実施した。架橋剤を、内径5mmを有する4つの管状導管を介してベンチュリ管中に配量した。それらの管状導管は、くびれ領域の開始点の後方5cmもしくは13cmの所で合流していた。それらの管状導管は、対になって向かい合っていた。両方の管状導管の対の管軸は、互いに90゜だけ回転していた。
実施例4と同様に実施した。架橋剤を、内径5mmを有する8つの管状導管を介してベンチュリ管中に配量した。それらの管状導管は、くびれ領域の開始点の後方5cmもしくは13cmの所で合流しており、その際、それぞれ4つの管状導管は、互いに垂直であった。
Claims (14)
- モノマー溶液を少なくとも1種の架橋剤と混合し、そして得られた混合物を重合させる、吸水性ポリマーの連続的な製造方法において、少なくとも1種の架橋剤の添加部と重合反応器中への進入との間での該混合物の滞留時間が180秒未満であることを特徴とする方法。
- 請求項1に記載の方法において、少なくとも1種の架橋剤の添加部と重合反応器中への進入との間での該混合物の滞留時間が少なくとも1秒であることを特徴とする方法。
- 請求項1又は2に記載の方法において、少なくとも1種の架橋剤の供給路と重合反応器との間の接続部の内表面が、少なくとも部分的に、水に対して少なくとも60゜の接触角を有することを特徴とする方法。
- 請求項1から3までのいずれか1項に記載の方法において、少なくとも1種の架橋剤が該混合物中で完全に可溶性でないことを特徴とする方法。
- 請求項1から4までのいずれか1項に記載の方法において、該混合物を不活性化することを特徴とする方法。
- 請求項1から5までのいずれか1項に記載の方法において、少なくとも1種の架橋剤を、1つのベンチュリ管を介してモノマー溶液中に配量することを特徴とする方法。
- 請求項1から6までのいずれか1項に記載の方法において、該混合物が、少なくとも1種の架橋剤の添加と重合との間で、少なくとも部分的に、レイノルズ数1000〜10000に相当する速度で流動することを特徴とする方法。
- 請求項1から7までのいずれか1項に記載の方法において、モノマー溶液のモノマーの少なくとも50モル%が、アクリル酸及び/又はそれらの塩であることを特徴とする方法。
- 請求項1から8までのいずれか1項に記載の方法において、重合反応器中のモノマー溶液を重合させてヒドロゲルを得て、それを乾燥させ、粉砕し、そして分級することを特徴とする方法。
- 請求項9に記載の方法において、分級されたポリマー粒子を表面後架橋させることを特徴とする方法。
- 以下の
i)重合反応器と、
ii)重合反応器i)への少なくとも1つの供給路と、
iii)供給路ii)中の少なくとも1つのベンチュリ管と、
iv)ベンチュリ管iii)への少なくとも1つの供給路と
を有し、その際、前記供給路iv)がベンチュリ管iii)中に合流する、連続的な重合のための装置。 - 請求項11に記載の装置であって、重合反応器i)と供給路iii)との間の供給路ii)の内表面が、少なくとも部分的に、水に対して少なくとも60゜の接触角を有することを特徴とする装置。
- 請求項11又は12に記載の装置であって、重合反応器i)とベンチュリ管iii)との間の供給路ii)の長さが、0.5〜20mであることを特徴とする装置。
- 請求項11から13までのいずれか1項に記載の装置であって、流動方向における供給路ii)と供給路iv)との間の角度が、90゜未満であることを特徴とする装置。
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TWI344469B (en) † | 2005-04-07 | 2011-07-01 | Nippon Catalytic Chem Ind | Polyacrylic acid (salt) water-absorbent resin, production process thereof, and acrylic acid used in polymerization for production of water-absorbent resin |
-
2005
- 2005-09-07 DE DE102005042608A patent/DE102005042608A1/de not_active Withdrawn
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2006
- 2006-08-31 US US12/065,358 patent/US7915355B2/en active Active
- 2006-08-31 JP JP2008529602A patent/JP5618482B2/ja active Active
- 2006-08-31 WO PCT/EP2006/065846 patent/WO2007028749A1/de active Application Filing
- 2006-08-31 EP EP06793089.1A patent/EP1926754B2/de active Active
- 2006-08-31 CN CN2006800324377A patent/CN101258167B/zh active Active
- 2006-09-07 TW TW095133000A patent/TW200720294A/zh unknown
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JPS61126103A (ja) * | 1984-11-21 | 1986-06-13 | Nippon Shokubai Kagaku Kogyo Co Ltd | 重合体の製造法 |
JPH01146902A (ja) * | 1987-10-22 | 1989-06-08 | Dow Chem Co:The | 吸収用ポリマー組成物の製造法 |
JP2004155963A (ja) * | 2002-11-07 | 2004-06-03 | Nippon Shokubai Co Ltd | 吸水性樹脂の製造方法および製造装置 |
JP2004359943A (ja) * | 2003-05-09 | 2004-12-24 | Nippon Shokubai Co Ltd | 吸水性樹脂およびその製造方法 |
JP2005162834A (ja) * | 2003-12-01 | 2005-06-23 | Nippon Shokubai Co Ltd | 吸水性樹脂の製法 |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2021178982A (ja) * | 2014-01-10 | 2021-11-18 | 小松マテーレ株式会社 | 繊維強化樹脂材料及びそれを用いた繊維強化樹脂成形体 |
KR20160128350A (ko) | 2014-03-03 | 2016-11-07 | 가부시키가이샤 닛폰 쇼쿠바이 | 폴리아크릴산(염)계 흡수성 수지의 제조 방법 |
US9896529B2 (en) | 2014-03-03 | 2018-02-20 | Nippon Shokubai Co., Ltd. | Method for producing polyacrylic acid (salt)-based water-absorbable resin |
JP2021518874A (ja) * | 2019-01-07 | 2021-08-05 | エルジー・ケム・リミテッド | 高吸水性樹脂およびその製造方法 |
JP7210082B2 (ja) | 2019-01-07 | 2023-01-23 | エルジー・ケム・リミテッド | 高吸水性樹脂およびその製造方法 |
US11718694B2 (en) | 2019-01-07 | 2023-08-08 | Lg Chem, Ltd. | Super absorbent polymer and preparation method thereof |
Also Published As
Publication number | Publication date |
---|---|
EP1926754B1 (de) | 2013-06-05 |
DE102005042608A1 (de) | 2007-03-08 |
TW200720294A (en) | 2007-06-01 |
EP1926754B2 (de) | 2021-12-22 |
US7915355B2 (en) | 2011-03-29 |
CN101258167A (zh) | 2008-09-03 |
CN101258167B (zh) | 2012-05-02 |
WO2007028749A1 (de) | 2007-03-15 |
US20080275195A1 (en) | 2008-11-06 |
EP1926754A1 (de) | 2008-06-04 |
JP5618482B2 (ja) | 2014-11-05 |
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