JP6837141B2 - 高吸水性樹脂およびその製造方法 - Google Patents
高吸水性樹脂およびその製造方法 Download PDFInfo
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- JP6837141B2 JP6837141B2 JP2019520362A JP2019520362A JP6837141B2 JP 6837141 B2 JP6837141 B2 JP 6837141B2 JP 2019520362 A JP2019520362 A JP 2019520362A JP 2019520362 A JP2019520362 A JP 2019520362A JP 6837141 B2 JP6837141 B2 JP 6837141B2
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- Prior art keywords
- absorbent resin
- water
- acrylate
- cross
- linking agent
- Prior art date
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- 239000003431 cross linking reagent Substances 0.000 claims description 80
- 229920000642 polymer Polymers 0.000 claims description 56
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 52
- 239000000178 monomer Substances 0.000 claims description 50
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 26
- 150000001875 compounds Chemical class 0.000 claims description 26
- 238000001035 drying Methods 0.000 claims description 24
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 23
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 23
- 150000003839 salts Chemical class 0.000 claims description 21
- 239000002245 particle Substances 0.000 claims description 20
- 239000000017 hydrogel Substances 0.000 claims description 19
- 229910052751 metal Inorganic materials 0.000 claims description 19
- 239000002184 metal Substances 0.000 claims description 19
- 230000002378 acidificating effect Effects 0.000 claims description 15
- UWFRVQVNYNPBEF-UHFFFAOYSA-N 1-(2,4-dimethylphenyl)propan-1-one Chemical group CCC(=O)C1=CC=C(C)C=C1C UWFRVQVNYNPBEF-UHFFFAOYSA-N 0.000 claims description 14
- 229920005862 polyol Polymers 0.000 claims description 14
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- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 9
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 229920006037 cross link polymer Polymers 0.000 claims description 7
- 239000004593 Epoxy Substances 0.000 claims description 5
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 claims description 5
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- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims description 4
- AOBIOSPNXBMOAT-UHFFFAOYSA-N 2-[2-(oxiran-2-ylmethoxy)ethoxymethyl]oxirane Chemical compound C1OC1COCCOCC1CO1 AOBIOSPNXBMOAT-UHFFFAOYSA-N 0.000 claims description 4
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- 230000000379 polymerizing effect Effects 0.000 claims description 3
- 150000005846 sugar alcohols Polymers 0.000 claims description 3
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 claims description 3
- HDPLHDGYGLENEI-UHFFFAOYSA-N 2-[1-(oxiran-2-ylmethoxy)propan-2-yloxymethyl]oxirane Chemical compound C1OC1COC(C)COCC1CO1 HDPLHDGYGLENEI-UHFFFAOYSA-N 0.000 claims description 2
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 claims description 2
- 125000003504 2-oxazolinyl group Chemical class O1C(=NCC1)* 0.000 claims description 2
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 claims description 2
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 claims description 2
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims 2
- XEUCQOBUZPQUMQ-UHFFFAOYSA-N Glycolone Chemical compound COC1=C(CC=C(C)C)C(=O)NC2=C1C=CC=C2OC XEUCQOBUZPQUMQ-UHFFFAOYSA-N 0.000 claims 1
- 241000282376 Panthera tigris Species 0.000 claims 1
- 229940093476 ethylene glycol Drugs 0.000 claims 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 1
- 238000010521 absorption reaction Methods 0.000 description 34
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- 238000000034 method Methods 0.000 description 27
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- 239000000843 powder Substances 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- 230000000052 comparative effect Effects 0.000 description 13
- 230000000704 physical effect Effects 0.000 description 13
- 239000003999 initiator Substances 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 10
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- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
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- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 7
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- 239000000463 material Substances 0.000 description 6
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- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- LRDFRRGEGBBSRN-UHFFFAOYSA-N isobutyronitrile Chemical compound CC(C)C#N LRDFRRGEGBBSRN-UHFFFAOYSA-N 0.000 description 1
- QWDJLDTYWNBUKE-UHFFFAOYSA-L magnesium bicarbonate Chemical compound [Mg+2].OC([O-])=O.OC([O-])=O QWDJLDTYWNBUKE-UHFFFAOYSA-L 0.000 description 1
- 229910000022 magnesium bicarbonate Inorganic materials 0.000 description 1
- 239000002370 magnesium bicarbonate Substances 0.000 description 1
- 235000014824 magnesium bicarbonate Nutrition 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- RHNCWXBNLBPQLA-UHFFFAOYSA-L magnesium;sodium;carbonate Chemical compound [Na+].[Mg+2].[O-]C([O-])=O RHNCWXBNLBPQLA-UHFFFAOYSA-L 0.000 description 1
- 238000006011 modification reaction Methods 0.000 description 1
- LSHROXHEILXKHM-UHFFFAOYSA-N n'-[2-[2-[2-(2-aminoethylamino)ethylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound NCCNCCNCCNCCNCCN LSHROXHEILXKHM-UHFFFAOYSA-N 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000223 polyglycerol Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 239000011802 pulverized particle Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229940083542 sodium Drugs 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
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- C08L33/04—Homopolymers or copolymers of esters
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Description
本出願は、2017年12月8日付の韓国特許出願第10−2017−0168684号および2018年9月3日付の韓国特許出願第10−2018−0104572号に基づく優先権の利益を主張し、当該韓国特許出願の文献に開示されたすべての内容は本明細書の一部として含まれる。
表面架橋剤および多価金属塩の存在下、前記ベース樹脂を昇温して前記ベース樹脂に対する表面改質を行う段階を含み、
前記内部架橋剤は、ポリオールのポリ(メタ)アクリレート系の第1内部架橋剤:ポリオールのポリグリシジルエーテル系の第2内部架橋剤を1:20〜1:300の重量比で含む高吸水性樹脂の製造方法を提供する。
前記ベース樹脂の粒子表面に形成されており、前記架橋重合体が表面架橋剤を介在させて追加架橋された表面架橋層;および
前記表面架橋層上に形成された多価金属塩を含み、
前記内部架橋剤は、ポリオールのポリ(メタ)アクリレート系の第1内部架橋剤:ポリオールのポリグリシジルエーテル系の第2内部架橋剤を1:20〜1:300の重量比で含む高吸水性樹脂を提供する。
酸性基の少なくとも一部が中和されたアクリル酸系単量体および内部架橋剤が架橋重合されたベース樹脂(base resin)を形成する段階;および
表面架橋剤および多価金属塩の存在下、前記ベース樹脂を昇温して前記ベース樹脂に対する表面改質を行う段階を含み、
前記内部架橋剤は、ポリオールのポリ(メタ)アクリレート系の第1内部架橋剤:ポリオールのポリグリシジルエーテル系の第2内部架橋剤を1:20〜1:300の重量比で含む高吸水性樹脂の製造方法が提供される。
[化学式1]
R1−COOM1
前記化学式1において、
R1は、不飽和結合を含む炭素数2〜5のアルキルグループであり、
M1は、水素原子、1価または2価金属、アンモニウム基、または有機アミン塩である。
具体的には、重合方法は、重合エネルギー源に応じて、大きく熱重合および光重合に分けられ、通常、熱重合を進行させる場合、ニーダー(kneader)のような撹拌軸を有する反応器で行われ、光重合を進行させる場合、移動可能なコンベヤベルトを備えた反応器で行われるが、前述した重合方法は一例であり、発明が前述した重合方法に限定されない。
前記ベース樹脂の粒子表面に形成されており、前記架橋重合体が表面架橋剤を介在させて追加架橋された表面架橋層;および
前記表面架橋層上に形成された多価金属塩を含み、
前記内部架橋剤は、ポリオールのポリ(メタ)アクリレート系の第1内部架橋剤:ポリオールのポリグリシジルエーテル系の第2内部架橋剤を1:20〜1:300の重量比で含むものになってもよい。
[高吸水性樹脂の製造]
(比較例1)
撹拌機、温度計を装着した3Lガラス容器に、アクリル酸470.5g、内部架橋剤のPEGDA400(ポリエチレングリコールジアクリレート400)の9000ppm、光開始剤ジフェニル(2,4,6−トリメチルベンゾイル)−ホスフィンオキシド80ppmを添加して溶解させた後、24.5%水酸化ナトリウム溶液805.6gを添加して水溶性不飽和単量体水溶液を製造した(中和度:70モル%;固形分含有量:45重量%)。前記水溶性不飽和単量体水溶液の温度が中和熱によって45℃になると、界面活性剤のソジウムドデシルスルフェート(sodium dodecyl sulfate)250ppmを添加した。この後、前記単量体水溶液の温度が43℃になると、SBC0.15%およびSPS0.12%の入った容器に入れた後、1分間紫外線を照射(照射量:10mV/cm2)してUV重合を実施し、含水ゲル状重合体を得た。得られた含水ゲル状重合体を2mm×2mmの大きさに粉砕した後、含水量を測定した結果、40.1%であった。
水溶性不飽和単量体水溶液に、内部架橋剤として、PEGDA400(ポリエチレングリコールジアクリレート400)の60ppmおよびエチレングリコールジグリシジルエーテル(EJ1030)2500ppm(第1内部架橋剤:第2内部架橋剤=1:41.7)を共に含ませたことを除けば、比較例1と同様の方法で高吸水性樹脂粉末を得た。
水溶性不飽和単量体水溶液に、内部架橋剤として、PEGDA400(ポリエチレングリコールジアクリレート400)の30ppmおよびエチレングリコールジグリシジルエーテル(EJ1030)2700ppm(第1内部架橋剤:第2内部架橋剤=1:90)を共に含ませたことを除けば、比較例1と同様の方法で高吸水性樹脂粉末を得た。
水溶性不飽和単量体水溶液に、内部架橋剤として、PEGDA400(ポリエチレングリコールジアクリレート400)の100ppmおよびエチレングリコールジグリシジルエーテル(EJ1030)2700ppm(第1内部架橋剤:第2内部架橋剤=1:27)を共に含ませたことを除けば、比較例1と同様の方法で高吸水性樹脂粉末を得た。
水溶性不飽和単量体水溶液に、内部架橋剤として、PEGDA400(ポリエチレングリコールジアクリレート400)の10ppmおよびエチレングリコールジグリシジルエーテル(EJ1030)2400ppm(第1内部架橋剤:第2内部架橋剤=1:240)を共に含ませたことを除けば、比較例1と同様の方法で高吸水性樹脂粉末を得た。
水溶性不飽和単量体水溶液に、内部架橋剤として、PEGDA400(ポリエチレングリコールジアクリレート400)の4000ppmおよびエチレングリコールジグリシジルエーテル(EJ1030)1500ppm(第1内部架橋剤:第2内部架橋剤=2.7:1)を共に含ませたことを除けば、比較例1と同様の方法で高吸水性樹脂粉末を得た。
表面架橋溶液の製造時に、硫酸アルミニウムを用いないことを除けば、実施例1と同様の方法で高吸水性樹脂粉末を得た。
前記実施例および比較例で製造した高吸水性樹脂に対して、次の方法で物性を評価した。
各樹脂の無荷重下の吸水倍率による保水能をEDANA WSP241.3により測定した。
具体的には、高吸水性樹脂W0(g)(約0.2g)を不織布製の封筒に均一に入れて密封(seal)した後、常温で生理食塩水(0.9重量%)に浸水させた。30分経過後、遠心分離機を用いて、250Gの条件下で前記封筒から3分間水気を切って、封筒の質量W2(g)を測定した。また、樹脂を用いずに同じ操作をした後に、その時の質量W1(g)を測定した。得られた各質量を用いて、次の式によりCRC(g/g)を算出した。
[数式1]
CRC(g/g)={[W2(g)−W1(g)]/W0(g)}−1
各樹脂の0.3psiの加圧吸水能を、EDANA法WSP242.3により測定した。
[数式2]
AUP(g/g)=[W4(g)−W3(g)]/W0(g)
吸水速度(vortex)は、国際公開出願第1987−003208号に記載された方法に準じて秒単位で測定した。
具体的には、23℃〜24℃の50mLの生理食塩水に2gの高吸水性樹脂を入れて、マグネチックバー(直径8mm、長さ30mm)を600rpmで撹拌して、渦流(vortex)が無くなるまでの時間を秒単位で測定して算出された。
水可溶成分はEDANA法WSP270.2の方法により測定した。
以下の方法で短期再湿潤特性を測定した。このような再湿潤特性の測定時、水道水としては、電気伝導度が170〜180μS/cmのものを使用した。このような電気伝導度は、Orion Star A222(会社:Thermo Scientific)の電気伝導度測定装置を用いて測定した。
[1]コップ(上部分の直径7cm、下の直径5cm、高さ8cm、体積192ml)に高吸水性樹脂1gを入れて、水道水(tap water)100gを注いだ後、膨潤させた。
[2]水道水を注いだ時点から10分後に濾紙(製造会社:whatman、catalog No.1004−110、pore size20−25μm、直径11cm)5枚の上に膨潤された高吸水性樹脂の入ったコップをひっくり返した。
[3]水道水を注いだ時点から60分後にコップと高吸水性樹脂を除去し、フィルタペーパーについた水道水の量(単位:g)を測定した。
Claims (9)
- 酸性基の少なくとも一部が中和されたアクリル酸系単量体および内部架橋剤が架橋重合されたベース樹脂(baseresin)を形成する段階;および
表面架橋剤および多価金属塩の存在下、前記ベース樹脂を昇温して前記ベース樹脂に対する表面改質を行う段階を含み、
前記内部架橋剤は、炭素数2〜10のポリオールのジ(メタ)アクリレート系の第1内部架橋剤:炭素数2〜10のポリオールのジグリシジルエーテル系の第2内部架橋剤を1:20〜1:300の重量比で含む高吸水性樹脂の製造方法。 - 前記第1内部架橋剤は、エチレングリコールジ(メタ)アクリレート、ポリエチレングリコールジ(メタ)アクリレート、プロピレングリコールジ(メタ)アクリレート、ポリプロピレングリコールジ(メタ)アクリレート、ブタンジオールジ(メタ)アクリレート、ブチレングリコールジ(メタ)アクリレート、ジエチレングリコールジ(メタ)アクリレート、ヘキサンジオールジ(メタ)アクリレート、トリエチレングリコールジ(メタ)アクリレート、トリプロピレングリコールジ(メタ)アクリレート、およびテトラエチレングリコールジ(メタ)アクリレートからなる群より選択された1種以上を含む、請求項1に記載の高吸水性樹脂の製造方法。
- 前記第2内部架橋剤は、エチレングリコールジグリシジルエーテル(ethyleneglycol diglycidyl ether)、ポリエチレングリコールジグリシジルエーテル、プロピレングリコールジグリシジルエーテル、およびポリプロピレングリコールジグリシジルエーテルからなる群より選択された1種以上を含む、請求項1または2に記載の高吸水性樹脂の製造方法。
- 前記表面架橋剤は、多価アルコール系化合物、多価エポキシ系化合物、ポリアミン化合物、ハロエポキシ化合物、ハロエポキシ化合物の縮合産物、オキサゾリン化合物類、およびアルキレンカーボネート系化合物からなる群より選択された1種以上を含む、請求項1〜3のいずれかに記載の高吸水性樹脂の製造方法。
- 前記表面改質段階は、100〜200℃の温度で20分〜60分間進行させる、請求項1〜4のいずれかに記載の高吸水性樹脂の製造方法。
- 前記多価金属塩は、アルミニウム塩を含む、請求項1〜5のいずれかに記載の高吸水性樹脂の製造方法。
- 前記ベース樹脂の形成段階は、
酸性基の少なくとも一部が中和されたアクリル酸系単量体、前記第1および第2内部架橋剤、そして重合開始剤を含むモノマー組成物を重合して含水ゲル状重合体を形成する段階;
前記含水ゲル状重合体を乾燥する段階;
前記乾燥した重合体を粉砕する段階;および
前記粉砕された重合体を分級する段階を含む、請求項1〜6のいずれかに記載の高吸水性樹脂の製造方法。 - 酸性基の少なくとも一部が中和されたアクリル酸系単量体が内部架橋剤を介在させて架橋重合された架橋重合体を含むベース樹脂;
前記ベース樹脂の粒子表面に形成されており、前記架橋重合体が表面架橋剤を介在させて追加架橋された表面架橋層;および
前記表面架橋層上に形成された多価金属塩を含み、
前記内部架橋剤は、炭素数2〜10のポリオールのジ(メタ)アクリレート系の第1内部架橋剤:炭素数2〜10のポリオールのジグリシジルエーテル系の第2内部架橋剤を1:20〜1:300の重量比で含み、
前記高吸水性樹脂の1gを水道水100gに浸漬させて10分間膨潤させた後、50分間濾紙上で放置してから、前記高吸水性樹脂から滲み出た水の重量で定義される再湿潤特性が1.0g以下である高吸水性樹脂。 - 前記多価金属塩は、アルミニウム塩を含む、請求項8に記載の高吸水性樹脂。
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