JP7330593B2 - 高吸水性樹脂組成物およびその製造方法 - Google Patents
高吸水性樹脂組成物およびその製造方法 Download PDFInfo
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- JP7330593B2 JP7330593B2 JP2022503872A JP2022503872A JP7330593B2 JP 7330593 B2 JP7330593 B2 JP 7330593B2 JP 2022503872 A JP2022503872 A JP 2022503872A JP 2022503872 A JP2022503872 A JP 2022503872A JP 7330593 B2 JP7330593 B2 JP 7330593B2
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- 238000006467 substitution reaction Methods 0.000 description 1
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- MDDUHVRJJAFRAU-YZNNVMRBSA-N tert-butyl-[(1r,3s,5z)-3-[tert-butyl(dimethyl)silyl]oxy-5-(2-diphenylphosphorylethylidene)-4-methylidenecyclohexyl]oxy-dimethylsilane Chemical compound C1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)C(=C)\C1=C/CP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 MDDUHVRJJAFRAU-YZNNVMRBSA-N 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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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
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- 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
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- C—CHEMISTRY; METALLURGY
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- C08F2/00—Processes of polymerisation
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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
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Description
本出願は、2019年9月30日付の韓国特許出願第10-2019-0120943号および2020年9月28日付の韓国特許出願第10-2020-0126245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全ての内容は本明細書の一部として含まれる。
少なくとも一部が中和した酸性基を有するアクリル酸系単量体および内部架橋剤の架橋重合体を含むベース樹脂、および前記ベース樹脂の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して追加架橋されている表面架橋層を含む高吸水性樹脂;および
前記表面架橋層を形成しない残留表面架橋剤を含む、高吸水性樹脂組成物であって、
前記表面架橋層を形成しない残留表面架橋剤は、カーボネート系化合物およびジオール系化合物を含み、前記残留カーボネート系化合物は、前記高吸水性樹脂組成物の総重量に対して100ppm以上であり、前記残留ジオール系化合物は、前記高吸水性樹脂組成物の総重量に対して1,000ppm以上であり、
下記1)~3)を満たす、高吸水性樹脂組成物を提供する:
1)ボルテックス法による吸収速度(vortex time)が65秒以下;
2)EDANA法WSP270.3の方法により測定した16時間膨潤後、水可溶成分の含有量が前記高吸水性樹脂組成物の総重量に対して15重量%以下;および
3)かさ密度(bulk density)が0.67g/cm3以上。
酸性基を有し、前記酸性基の少なくとも一部が中和したアクリル酸系単量体、内部架橋剤および重合開始剤を含む単量体組成物を重合して前記アクリル酸系単量体が架橋重合された架橋重合体を含むベース樹脂(base resin)を準備する段階と、
表面架橋剤の存在下で、前記ベース樹脂に対する表面架橋反応を行う段階と、を含み、
前記表面架橋剤は、1種以上のカーボネート系化合物および1種以上のジオール系化合物を含む、高吸水性樹脂組成物の製造方法を提供する。
少なくとも一部が中和した酸性基を有するアクリル酸系単量体および内部架橋剤の架橋重合体を含むベース樹脂、および前記ベース樹脂の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して追加架橋されている表面架橋層を含む高吸水性樹脂;および
前記表面架橋層を形成しない残留表面架橋剤を含む、高吸水性樹脂組成物であって、
前記表面架橋層を形成しない残留表面架橋剤は、カーボネート系化合物およびジオール系化合物を含み、前記残留カーボネート系化合物は、前記高吸水性樹脂組成物の総重量に対して100ppm以上であり、前記残留ジオール系化合物は、前記高吸水性樹脂組成物の総重量に対して1,000ppm以上であり、
下記1)~3)を満たすことを特徴とする:
1)ボルテックス法による吸収速度(vortex time)が65秒以下;
2)EDANA法WSP270.3の方法により測定した16時間膨潤後、水可溶成分の含有量が前記高吸水性樹脂組成物の総重量に対して15重量%以下;および
3)かさ密度(bulk density)が0.67g/cm3以上。
酸性基を有し、前記酸性基の少なくとも一部が中和したアクリル酸系単量体、および単量体組成物を重合して前記アクリル酸系単量体が架橋重合された架橋重合体を含むベース樹脂(base resin)を準備する段階と、
表面架橋剤の存在下で、前記ベース樹脂に対する表面架橋反応を行う段階と、を含み、
前記表面架橋剤は、1種以上のカーボネート系化合物および1種以上のジオール系化合物を含むことを特徴とする。
前記ベース樹脂(base resin)を準備する段階は、
酸性基を有し、前記酸性基の少なくとも一部が中和したアクリル酸系単量体、内部架橋剤、および重合開始剤を含む単量体組成物を重合して含水ゲル状重合体を形成する段階と、
前記含水ゲル状重合体を乾燥する段階と、
前記乾燥された重合体を粉砕する段階と、
前記粉砕された重合体を分級する段階と、を含み得る。
R1-COOM1
R1は不飽和結合を含む炭素数2~5のアルキル基であり、
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。
2)EDANA法WSP270.3の方法により測定した16時間膨潤後、水可溶成分の含有量が前記高吸水性樹脂組成物の総重量に対して15重量%以下;および
3)かさ密度(bulk density)が0.67g/cm3以上。
1g/g≦EDANA法WSP241.3により測定したベース樹脂の保水能(CRC)-EDANA法WSP241.3により測定した高吸水性樹脂の保水能(CRC)≦12g/g
高吸水性樹脂の製造
実施例1
撹拌機、温度計を取り付けた3Lガラス製容器に、アクリル酸600g、内部架橋剤であるPEGDA400(ポリエチレングリコールジアクリレート400)2.04g、光開始剤としてジフェニル(2,4,6-トリメチルベンゾイル)-ホスフィンオキシド0.048g、熱開始剤として過硫酸ナトリウム(sodium persulfate、SPS)1.2g、24.0%水酸化ナトリウム溶液974.7gを混合して水溶性不飽和単量体の水溶液を製造した(中和度:70モル%;固形分含有量:45重量%)。
実施例1で表面架橋反応時間を40分間行ったことを除いては、実施例1と同様の方法で高吸水性樹脂を製造した。
実施例1で重合時、PEGDA400を2.16g使用し、表面架橋反応時間を55分間行ったことを除いては、実施例1と同様の方法で高吸水性樹脂を製造した。
実施例1で重合時、PEGDA400を2.54g使用したことを除いては、ベース樹脂の製造方法と同様で、製造されたベース樹脂100重量部に対して、水5.4重量部、エチレンカーボネート0.6重量部、プロピレンカーボネート0.6重量部、プロピレングリコール0.2重量部、Al-S(18水和物)0.4重量部を含む表面処理溶液を均一に混合した後、1つの表面架橋反応器に供給し、186℃で50分間ベース樹脂の表面架橋反応を行った。
実施例4で表面架橋反応時間を60分間行ったことを除いては、実施例1と同様の方法で高吸水性樹脂を製造した。
実施例1で重合時、PEGDA400を1.74g使用したことを除いては、実施例1と同様の方法で高吸水性樹脂を製造した。
実施例1でPEGDA400を1.92g使用したことを除いては、同様の方法でベース樹脂を製造し、製造されたベース樹脂100重量部に対して、水3.0重量部、メタノール3.5重量部、1,3-プロパンジオール0.25重量部、シュウ酸0.15重量部を含む表面処理溶液を均一に混合した後、1つの表面架橋反応器に供給し、195℃で65分間ベース樹脂の表面架橋反応を行った。
比較例1で表面架橋時間を195℃で65分間行ったことを除いては、比較例1と同様の方法で高吸水性樹脂を製造した。
実施例1でPEGDA400を1.32g使用したことを除いては、同様の方法でベース樹脂を製造し、製造されたベース樹脂100重量部に対して、水2.7重量部、メタノール4.0重量部、エチレンカーボネート0.15重量部、Al-S(18水和物)1.0重量部を含む表面処理溶液を均一に混合した後、1つの表面架橋反応器に供給し、195℃で70分間ベース樹脂の表面架橋反応を行った。
比較例3で表面架橋反応を195℃で80分間行ったことを除いては、比較例3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に対して、次のような方法で物性を評価した。
各樹脂の無荷重下吸収倍率による保水能をEDANA WSP241.3により測定した。
CRC(g/g)={[W2(g)-W1(g)]/W0(g)}-1
各樹脂の0.7psiの加圧吸水能を、EDANA法WSP242.3により測定した。
AUP(g/g)=[W4(g)-W3(g)]/W0(g)
吸収速度(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8.5mm、長さ30mm)を600rpmで攪拌して、渦流(vortex)がな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WSP270.3の方法により測定した。
かさ密度は、WSP250.3の方法により測定した。
Claims (9)
- 少なくとも一部が中和した酸性基を有するアクリル酸系単量体および内部架橋剤の架橋重合体を含むベース樹脂、および前記ベース樹脂の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して追加架橋されている表面架橋層を含む高吸水性樹脂;および
前記表面架橋層を形成しない残留表面架橋剤を含む、高吸水性樹脂組成物であって、
前記表面架橋層を形成しない残留表面架橋剤は、カーボネート系化合物およびジオール系化合物を含み、前記残留カーボネート系化合物は、前記高吸水性樹脂組成物の総重量に対して100ppm以上であり、前記残留ジオール系化合物は、前記高吸水性樹脂組成物の総重量に対して1,000ppm以上であり、
前記表面架橋剤は、エチレンカーボネート、プロピレンカーボネート、グリセロールカーボネート、およびプロピレングリコールであるか、または、
エチレンカーボネート、プロピレンカーボネート、およびプロピレングリコールであり、
下記1)~3)を満たす、高吸水性樹脂組成物:
1)ボルテックス法による吸収速度(vortex time)が65秒以下;
2)EDANA法WSP270.3の方法により測定した16時間膨潤後、水可溶成分の含有量が前記高吸水性樹脂組成物の総重量に対して15重量%以下;および
3)かさ密度(bulk density)が0.67g/cm3以上。 - 次の関係式1を満たす、請求項1に記載の高吸水性樹脂組成物:
[関係式1]
1g/g≦EDANA法WSP241.3により測定したベース樹脂の保水能(CRC)-EDANA法WSP241.3により測定した高吸水性樹脂の保水能(CRC)≦12g/g - 前記ボルテックス法による吸収速度(vortex time)が60秒以下である、請求項1に記載の高吸水性樹脂組成物。
- 前記EDANA法WSP270.3の方法により測定した水可溶成分の含有量(16時間膨潤後)が前記高吸水性樹脂組成物の総重量に対して3~15重量%である、請求項1に記載の高吸水性樹脂組成物。
- 酸性基を有し、前記酸性基の少なくとも一部が中和したアクリル酸系単量体、内部架橋剤および重合開始剤を含む単量体組成物を重合して前記アクリル酸系単量体が架橋重合された架橋重合体を含むベース樹脂(base resin)を準備する段階と、
表面架橋剤の存在下で、前記ベース樹脂に対する表面架橋反応を行う段階と、を含み、
前記表面架橋剤は、1種以上のカーボネート系化合物および1種以上のジオール系化合物を含む、高吸水性樹脂組成物の製造方法であって、
前記高吸水性樹脂組成物は、表面架橋層を形成しない残留表面架橋剤を含み、
前記表面架橋層を形成しない残留表面架橋剤は、カーボネート系化合物およびジオール系化合物を含み、前記残留カーボネート系化合物は、前記高吸水性樹脂組成物の総重量に対して100ppm以上であり、前記残留ジオール系化合物は、前記高吸水性樹脂組成物の総重量に対して1,000ppm以上であり、
前記表面架橋剤は、エチレンカーボネート、プロピレンカーボネート、グリセロールカーボネート、およびプロピレングリコールであるか、または、
エチレンカーボネート、プロピレンカーボネート、プロピレングリコールである、高吸水性樹脂組成物の製造方法。 - 前記カーボネート系化合物は、前記ベース樹脂100重量部に対して0.4~2.5重量部で使用され、
前記ジオール系化合物は、前記ベース樹脂100重量部に対して0.2~3.0重量部で使用される、請求項5に記載の高吸水性樹脂組成物の製造方法。 - 前記表面架橋反応は60~190℃の温度で行う、請求項5に記載の高吸水性樹脂組成物の製造方法。
- 前記ベース樹脂(base resin)を準備する段階は、
酸性基を有し、前記酸性基の少なくとも一部が中和したアクリル酸系単量体、内部架橋剤、および重合開始剤を含む単量体組成物を重合して含水ゲル状重合体を形成する段階と、
前記含水ゲル状重合体を乾燥する段階と、
前記乾燥された重合体を粉砕する段階と、
前記粉砕された重合体を分級する段階と、を含む、請求項5に記載の高吸水性樹脂組成物の製造方法。 - 前記単量体組成物は発泡剤を含まない、請求項8に記載の高吸水性樹脂組成物の製造方法。
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