JP6806903B2 - 高吸水性樹脂の製造方法 - Google Patents
高吸水性樹脂の製造方法 Download PDFInfo
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- JP6806903B2 JP6806903B2 JP2019529927A JP2019529927A JP6806903B2 JP 6806903 B2 JP6806903 B2 JP 6806903B2 JP 2019529927 A JP2019529927 A JP 2019529927A JP 2019529927 A JP2019529927 A JP 2019529927A JP 6806903 B2 JP6806903 B2 JP 6806903B2
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- absorbent resin
- water
- polymer
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- highly water
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- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- PODOEQVNFJSWIK-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethoxyphenyl)methanone Chemical compound COC1=CC(OC)=CC(OC)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 PODOEQVNFJSWIK-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 235000019326 ethyl hydroxyethyl cellulose Nutrition 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000010417 guar gum Nutrition 0.000 description 1
- 239000000665 guar gum Substances 0.000 description 1
- 229960002154 guar gum Drugs 0.000 description 1
- 235000019314 gum ghatti Nutrition 0.000 description 1
- MHIBEGOZTWERHF-UHFFFAOYSA-N heptane-1,1-diol Chemical compound CCCCCCC(O)O MHIBEGOZTWERHF-UHFFFAOYSA-N 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 229920003063 hydroxymethyl cellulose Polymers 0.000 description 1
- 229940031574 hydroxymethyl cellulose Drugs 0.000 description 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical class Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 description 1
- 235000014413 iron hydroxide Nutrition 0.000 description 1
- NCNCGGDMXMBVIA-UHFFFAOYSA-L iron(ii) hydroxide Chemical class [OH-].[OH-].[Fe+2] NCNCGGDMXMBVIA-UHFFFAOYSA-L 0.000 description 1
- 235000010494 karaya gum Nutrition 0.000 description 1
- 239000000231 karaya gum Substances 0.000 description 1
- 229940039371 karaya gum Drugs 0.000 description 1
- TYQCGQRIZGCHNB-JLAZNSOCSA-N l-ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(O)=C(O)C1=O TYQCGQRIZGCHNB-JLAZNSOCSA-N 0.000 description 1
- 235000010420 locust bean gum Nutrition 0.000 description 1
- 239000000711 locust bean gum Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 235000011147 magnesium chloride Nutrition 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical group C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 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
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000011148 porous material Substances 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
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
Classifications
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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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- C—CHEMISTRY; METALLURGY
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- C08F222/00—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 a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
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- 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
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- B01J20/28—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties
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- B01J20/3085—Chemical treatments not covered by groups B01J20/3007 - B01J20/3078
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- C08F2/00—Processes of polymerisation
- C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
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- C08F20/00—Homopolymers and 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 a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
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- C08F20/06—Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
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- C08F220/00—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 a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
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- C08F6/00—Post-polymerisation treatments
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- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
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Description
本出願は、2017年10月27日付の韓国特許出願第10−2017−01451504号および2018年10月12日付の韓国特許出願第10−2018−0121994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。
前記含水ゲル重合体を乾燥および粉砕する段階;
前記粉砕された重合体を少なくとも10〜150μmの粒径を有する重合体粒子、150〜200μmの粒径を有する重合体粒子、および200〜850μmの粒径を有する重合体粒子に分級して150〜850μmの粒径を有するベース樹脂粉末を形成する段階;および
前記ベース樹脂粉末を表面架橋する段階を含み、
前記架橋重合段階では、前記分級段階で得られた10〜200μmの粒径を有する重合体粒子および陰イオン性界面活性剤の存在下、発泡重合を進行させる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。
(段階1)
アクリル酸に0.5%に希釈したIRGACURE819開始剤9g(単量体組成物に対して80ppmw)とアクリル酸に5%に希釈したポリエチレングリコールジアクリレート(PEGDA、Mw=400)40gを混合した溶液(A溶液)を製造した。
次に、上部に光照射装置が装着されており、内部が80℃に予熱された正方形重合器内に設けられたVat形態のトレイ(tray、横15cm×15cm)に、前記段階1で準備した混合溶液を注いだ。この後、前記混合溶液に光を照射した。光照射時点から約20秒後に表面からゲルが形成されることを確認し、光照射時点から約30秒後に発泡と同時に重合反応が起こることを確認した。次に、追加的に2分間重合反応を進行させ、重合されたシートを取り出して、3cm×3cmの大きさに裁断した。そして、ミートチョッパー(meat chopper)を用いてチョップ工程(chopping)により前記裁断されたシートを粉(crump)に製造した。製造された粉(crump)の平均粒子サイズは1.5mmであった。
次に、上下に風量調節が可能なオーブンで前記段階2で製造した粉(crump)を乾燥させた。乾燥した粉の含水量が約2%以下となるように、180℃のホットエア(hot air)を15分間下方から上方に流れるようにし、再び15分間上方から下方に流れるようにして、前記粉(crump)を均一に乾燥させた。乾燥した粉を紛砕機で粉砕した後、分級して150〜850μmサイズのベース樹脂を得た。これを得て残った10〜150μmの粒径を有するベース樹脂粉末の重合体粒子は、前述した段階1に再循環させて使用した。
この後、前記段階3で製造したベース樹脂100gに、水4g、エチレンカーボネート1g、アエロジル200(Aerosil200、Evonik社)0.1gを混合した架橋剤溶液と混合した後、190℃で30分間表面架橋反応をさせた。そして、得られた生成物を粉砕し、シーブ(sieve)を用いて粒径が150〜850μmの表面架橋された高吸水性樹脂を得た。得られた高吸水性樹脂にアエロジル200 0.1gを乾式で追加して、乾式状態で混合して高吸水性樹脂を製造した。
(段階1)
アクリル酸に0.5%に希釈したIRGACURE819開始剤9g(単量体組成物に対して80ppmw)とアクリル酸に5%に希釈したポリエチレングリコールジアクリレート(PEGDA、Mw=400)40gを混合した溶液(A溶液)を製造した。
(段階1)
アクリル酸に0.5%に希釈したIRGACURE819開始剤9g(単量体組成物に対して80ppmw)とアクリル酸に5%に希釈したポリエチレングリコールジアクリレート(PEGDA、Mw=400)40gを混合した溶液(A溶液)を製造した。
(段階1)
アクリル酸に0.5%に希釈したIRGACURE819開始剤9g(単量体組成物に対して80ppmw)とアクリル酸に5%に希釈したポリエチレングリコールジアクリレート(PEGDA、Mw=400)40gを混合した溶液(A溶液)を製造した。
段階1で、ソジウムドデシルスルフェート(sodium dodecylsulfate)溶液(D−1溶液)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を製造した。
段階1で、ソジウムドデシルスルフェート(sodium dodecylsulfate)溶液(D−1溶液)を用いないことを除けば、実施例2と同様の方法で高吸水性樹脂を製造した。
前記実施例および比較例で製造した高吸水性樹脂の物性を以下の方法で評価し、その結果を表1に示した。
高吸水性樹脂約100gを漏斗形態のバルク密度測定機器に入れて、100mlの容器に流した後、容器内に入った高吸水性樹脂の重量を測定した。バルク密度は(高吸水性樹脂の重量)/(容器の体積、100ml)で計算した。(単位:g/ml)。
実施例および比較例の高吸水性樹脂の吸水速度は、国際特許公開番号第1987−003208号に記載された方法に準じて秒単位で測定された。
具体的には、吸水速度(あるいはvortex time)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31.8mm)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。
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、実施例および比較例によりそれぞれ得られた樹脂から、#30−50の篩で分級した樹脂を得た。このような樹脂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、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0.9psiの加圧吸水能を、EDANA法WSP242.3により測定した。
まず、加圧吸水能の測定時には、前記CRC測定時の樹脂分級粉を使用した。
具体的には、内径25mmのプラスチックの円筒底にステンレス製400meshの金網を装着させた。常温および湿度50%の条件下、金網上に吸水性樹脂W0(g)(0.16g)を均一に散布し、その上に0.9psiの荷重を均一にさらに付与できるピストンは、外径25mmよりやや小さく、円筒の内壁と隙がなく、上下の動きが妨げられないようにした。この時、前記装置の重量W3(g)を測定した。
直径150mmのペトロ皿の内側に直径90mmおよび厚さ5mmのガラスフィルタを置き、0.9重量%塩化ナトリウムで構成された生理食塩水をガラスフィルタの上面と同一レベルとなるようにした。その上に直径90mmの濾紙1枚を載せた。濾紙上に前記測定装置を載せて、液を荷重下で1時間吸収させた。1時間後に測定装置を持ち上げて、その量W4(g)を測定した。
得られた各質量を用いて、次の式により加圧吸水能(g/g)を算出した。
[数式2]
AUL(g/g)=[W4(g)−W3(g)]/W0(g)
Claims (9)
- 内部架橋剤の存在下、少なくとも一部が中和された酸性基を有する水溶性エチレン系不飽和単量体を架橋重合して第1架橋重合体を含む含水ゲル重合体を形成する段階;
前記含水ゲル重合体を乾燥および粉砕する段階;
前記粉砕された重合体を少なくとも10〜150μmの粒径を有する重合体粒子、150〜200μmの粒径を有する重合体粒子、および200〜850μmの粒径を有する重合体粒子に分級して150〜850μmの粒径を有するベース樹脂粉末を形成する段階;および
前記ベース樹脂粉末を表面架橋する段階を含み、
前記架橋重合段階では、前記分級段階で得られた10〜150μmの粒径を有する重合体粒子および陰イオン性界面活性剤の存在下、発泡重合を進行させており、
前記架橋重合段階で、前記10〜150μmの粒径を有する重合体粒子は、前記単量体100重量部を基準として、0.1〜3重量部使用される、高吸水性樹脂の製造方法。 - 前記単量体は、(メタ)アクリル酸が一部中和された(メタ)アクリル酸およびそのアルカリ金属塩を含み、55〜95モル%の中和度を有する、請求項1に記載の高吸水性樹脂の製造方法。
- 前記陰イオン性界面活性剤は、ソジウムドデシルスルフェート、アンモニウムラウリルスルフェート、ソジウムラウレススルフェート、ジオクチルソジウムスルホスクシネート、パーフルオロオクタンスルホネート、パーフルオロブタンスルホネート、アルキル−アリールエーテルホスフェート、アルキルエーテルホスフェート、ソジウムミレススルフェート、およびカルボキシレート塩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。
- 前記架橋重合段階で、前記陰イオン性界面活性剤は、前記単量体100重量部を基準として、0.002〜0.05重量部使用される、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。
- 前記架橋重合段階で、前記単量体、内部架橋剤、前記10〜150μmの粒径を有する重合体粒子、および陰イオン性界面活性剤が含まれている単量体水溶液が使用され、前記水溶液は、30〜60℃の温度を有する、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。
- 前記単量体水溶液は、多価金属塩、光開始剤、熱開始剤、およびポリアルキレングリコール系高分子からなる群より選択された1種以上の添加剤をさらに含む、請求項5に記載の高吸水性樹脂の製造方法。
- 前記添加剤は、前記単量体100重量部に対して、2000ppmw以下の含有量で使用される、請求項6に記載の高吸水性樹脂の製造方法。
- 前記高吸水性樹脂は、バルク密度が0.55〜0.65g/mlであり、Vortex測定方法により測定した吸水速度が30秒〜41秒である、請求項1〜7のいずれかに記載の高吸水性樹脂の製造方法。
- 前記高吸水性樹脂は、EDANA法WSP241.3により測定した遠心分離保水能(CRC)が28〜35g/gであり、EDANA法WSP242.3により測定した0.9psiの加圧吸水能(AUL)が16〜23g/gである、請求項1〜8のいずれかに記載の高吸水性樹脂の製造方法。
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