JPWO2015104971A1 - ビニル系重合体粒子および該粒子を含有する組成物 - Google Patents
ビニル系重合体粒子および該粒子を含有する組成物 Download PDFInfo
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- JPWO2015104971A1 JPWO2015104971A1 JP2015556757A JP2015556757A JPWO2015104971A1 JP WO2015104971 A1 JPWO2015104971 A1 JP WO2015104971A1 JP 2015556757 A JP2015556757 A JP 2015556757A JP 2015556757 A JP2015556757 A JP 2015556757A JP WO2015104971 A1 JPWO2015104971 A1 JP WO2015104971A1
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- particles
- vinyl polymer
- polymer particles
- crosslinking agent
- test tube
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 39
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 34
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- 238000012360 testing method Methods 0.000 claims description 16
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- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
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- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical class C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
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- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229960003351 prussian blue Drugs 0.000 description 1
- 239000013225 prussian blue Substances 0.000 description 1
- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical compound C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 description 1
- VGTPCRGMBIAPIM-UHFFFAOYSA-M sodium thiocyanate Chemical compound [Na+].[S-]C#N VGTPCRGMBIAPIM-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000012798 spherical particle Substances 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical compound S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 238000000954 titration curve Methods 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
- 235000013799 ultramarine blue Nutrition 0.000 description 1
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- 239000011787 zinc oxide Substances 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
- NDKWCCLKSWNDBG-UHFFFAOYSA-N zinc;dioxido(dioxo)chromium Chemical compound [Zn+2].[O-][Cr]([O-])(=O)=O NDKWCCLKSWNDBG-UHFFFAOYSA-N 0.000 description 1
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Abstract
Description
(1) カルボキシル基を有し、かつエステル系架橋剤およびエステル構造を有さないエーテル系架橋剤を共重合成分として含む球状のビニル系重合体粒子。
(2) カルボキシル基を1〜10mmol/g有することを特徴とする(1)に記載のビニル系重合体粒子。
(3) エステル系架橋剤の共重合割合が5〜30重量%であり、かつエステル構造を有さないエーテル系架橋剤の共重合割合が0.01〜10重量%であることを特徴とする(1)または(2)に記載のビニル系重合体粒子。
(5) 下記式で示される水膨潤度の値が1〜3であることを特徴とする(1)〜(4)のいずれかに記載のビニル系重合体粒子。
式:[水膨潤度]=X/Y
ここで、
X:1gの粒子を直径16.5mmの試験管に入れ、次いで10mlの目盛りまで水を添加し、試験管を垂直にして静置した後の試験管底部から沈降粒子の最上部までの高さ
Y:1gの粒子を直径16.5mmの試験管に入れ、次いで10mlの目盛りまでメチルエチルケトンを添加し、試験管を垂直にして静置した後の試験管底部から沈降粒子の最上部までの高さ
(7) (1)〜(5)のいずれかに記載のビニル系重合体粒子を含有する塗料組成物。
(8) (1)〜(5)のいずれかに記載のビニル系重合体粒子を含有するインキ組成物。
(9) (1)〜(5)のいずれかに記載のビニル系重合体粒子を含有する繊維構造物。
本発明における円形度とは下記式にて算出される粒子の円形度を指して言う。
粒子投影像の円形度=(粒子投影面積と同じ面積の円の周長)/(粒子投影像の周長)
粒子投影像の円形度の平均値=粒子の円形度
すなわち、円形度は真円の場合に1となり、不定形の度合いが増すにつれ、より小さい値となる。かかる円形度は、例えば、シスメックス株式会社製フロー式粒子像分析装置「FPIA−3000S」を用いて測定することができる。
試料粒子を5%含有する水分散体を作成し、該水分散体を吸引濾過した時の状態を以下の基準によって評価した。
○:吸引開始後1時間以内に濾過が完了する
×:吸引開始後1時間を経過しても濾過が完了しない
試料を水中に分散し、1Nの塩酸を添加してpH2.0に調整する。次いで、試料を濾別、乾燥し重量(W1[g])を測定する。重量測定後の試料を水中に再分散し、0.1Nの水酸化ナトリウム水溶液により滴定を行う。得られる滴定曲線から、カルボキシル基に消費された水酸化ナトリウム水溶液消費量(V[ml])を求め、次式によってカルボキシル基量を算出する。
カルボキシル基量[mmol/g]=0.1×V/W1
直径16.5mmの試験管に乾燥させた試料粒子1gを入れる。次いで、10mlの目盛りまで水を添加し、該粒子を膨潤させる。試験管を垂直にして60時間静置した後、試験管底部から沈降した粒子の最上部までの高さ(X[cm])を測定する。他方、水のかわりにメチルエチルケトンを使用すること以外は同様にして、試料粒子をメチルエチルケトンに膨潤させたときの試験管底部から沈降した粒子の最上部までの高さ(Y[cm])を測定する。得られる測定値から、次式によって水膨潤度を算出する。
水膨潤度=X/Y
島津製作所製レーザー回折式粒度分布測定装置「SALD-200V」を使用して水を分散媒として測定し、体積基準で表した粒子径分布から、平均粒子径(μm)を求める。
試料約5.0gを105℃、16時間乾燥して重量(W2[g])を測定する。次に該試料を温度20℃、相対湿度65%に調節した恒温恒湿器に24時間入れる。このようにして吸湿した試料の重量(W3[g])を測定する。以上の測定結果から、次式によって算出する。
飽和吸湿率[%]=(W3−W2)/W2×100
1辺が10cmの正方形の試料を105℃、16時間乾燥して重量(W4[g])を測定する。次に該試料を温度20℃、相対湿度40%に調節した恒温恒湿器に16時間入れる。このようにして吸湿した試料の重量(W5[g])を測定する。次に、測定後の試料を温度40℃、相対湿度90%に調節した恒温恒湿器に2時間入れた後、試料の重量(W6[g])を測定する。以上の測定結果から、各条件下におけるシートの吸湿率を次式によって算出する。
温度20℃、相対湿度40%下での吸湿率[g/m2]=(W5−W4)/0.01
温度40℃、相対湿度90%下での吸湿率[g/m2]=(W6−W4)/0.01
アクリル酸メチル82部、トリメチロールプロパントリメタアクリレート17部、ペンタエリスリトールトリアリルエーテル1部、2,2’-アゾビス(2,4-ジメチルバレロニトリル)1部からなる単量体混合物を、水400部に分散させる。次いで、50℃で2時間重合を行い、水洗、脱水して原料粒子を得る。該原料粒子150部と水810部を混合し、水酸化ナトリウム40部を添加して、95℃で10時間加水分解を行い、水洗、脱水、乾燥、解砕を行うことで、ナトリウム塩型カルボキシル基を有する実施例1のビニル系重合体粒子を得た。該粒子の特性を評価した結果を表1に示す。また、該粒子のSEM写真を図1に示す。
実施例1における単量体混合物の代わりに、アクリル酸メチル80部、トリメチロールプロパントリメタアクリレート20部、2,2’-アゾビス(2,4-ジメチルバレロニトリル)1部からなる単量体混合物を用いること以外は実施例1と同様にして、ナトリウム塩型カルボキシル基を有する比較例1の粒子を得た。該粒子の特性を評価した結果を表1に示す。
実施例1における単量体混合物の代わりに、アクリル酸メチル80部、ペンタエリスリトールトリアリルエーテル20部、2,2’-アゾビス(2,4-ジメチルバレロニトリル)1部からなる単量体混合物を用いること以外は実施例1と同様にして、ナトリウム塩型カルボキシル基を有する比較例2の粒子を得た。該粒子の特性を評価した結果を表1に示す。
実施例1における単量体混合物の代わりに、アクリル酸メチル80部、トリメチロールプロパントリメタアクリレート19部、ペンタエリスリトールトリアリルエーテル1部、2,2’-アゾビス(2,4-ジメチルバレロニトリル)1部、およびカーボンブラック2部からなる単量体混合物を用いること以外は実施例1と同様にして、ナトリウム塩型カルボキシル基を有する実施例2のビニル系重合体粒子を得た。該粒子の特性を評価した結果を表1に示す。
実施例1における単量体混合物の代わりに、アクリル酸メチル85部、トリメチロールプロパントリメタアクリレート10部、ペンタエリスリトールトリアリルエーテル5部、2,2’-アゾビス(2,4-ジメチルバレロニトリル)1部からなる単量体混合物を用いること以外は実施例1と同様にして、ナトリウム塩型カルボキシル基を有する実施例3のビニル系重合体粒子を得た。該粒子の特性を評価した結果を表1に示す。
実施例1における単量体混合物の代わりに、アクリル酸メチル69.5部、トリメチロールプロパントリメタアクリレート30部、ペンタエリスリトールトリアリルエーテル0.5部、2,2’-アゾビス(2,4-ジメチルバレロニトリル)1部からなる単量体混合物を用いること以外は実施例1と同様にして、ナトリウム塩型カルボキシル基を有する実施例4のビニル系重合体粒子を得た。該粒子の特性を評価した結果を表1に示す。
実施例2のビニル系重合体粒子67部、ウレタン樹脂「クリスボンNY−373」(DIC株式会社製)500部(固形分20%)、ジメチルホルムアミド175部を混合し、剥離紙上に塗工する。次いで、塗工後の剥離紙を水に浸漬して、脱溶媒を行い、乾燥させて、本発明のビニル系重合体粒子を含有するウレタン樹脂シートを得た。該シートの目付は145g/m2であった。
Claims (9)
- カルボキシル基を有し、かつエステル系架橋剤およびエステル構造を有さないエーテル系架橋剤を共重合成分として含む球状のビニル系重合体粒子。
- カルボキシル基を1〜10mmol/g有することを特徴とする請求項1に記載のビニル系重合体粒子。
- エステル系架橋剤の共重合割合が5〜30重量%であり、かつエステル構造を有さないエーテル系架橋剤の共重合割合が0.01〜10重量%であることを特徴とする請求項1または2に記載のビニル系重合体粒子。
- 粒子内部に微小粒子状の添加剤を含有することを特徴とする請求項1〜3のいずれかに記載のビニル系重合体粒子。
- 下記式で示される水膨潤度の値が1〜3であることを特徴とする請求項1〜4のいずれかに記載のビニル系重合体粒子。
式:[水膨潤度]=X/Y
ここで、
X:1gの粒子を直径16.5mmの試験管に入れ、次いで10mlの目盛りまで水を添加し、試験管を垂直にして静置した後の試験管底部から沈降粒子の最上部までの高さ
Y:1gの粒子を直径16.5mmの試験管に入れ、次いで10mlの目盛りまでメチルエチルケトンを添加し、試験管を垂直にして静置した後の試験管底部から沈降粒子の最上部までの高さ - 請求項1〜5のいずれかに記載のビニル系重合体粒子を含有する樹脂成型体。
- 請求項1〜5のいずれかに記載のビニル系重合体粒子を含有する塗料組成物。
- 請求項1〜5のいずれかに記載のビニル系重合体粒子を含有するインキ組成物。
- 請求項1〜5のいずれかに記載のビニル系重合体粒子を含有する繊維構造物。
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KR102191690B1 (ko) | 2020-12-16 |
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CN105899551A (zh) | 2016-08-24 |
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