JPWO2019035382A1 - 中空樹脂粒子、感熱記録材料、および、中空樹脂粒子の製造方法 - Google Patents
中空樹脂粒子、感熱記録材料、および、中空樹脂粒子の製造方法 Download PDFInfo
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- JPWO2019035382A1 JPWO2019035382A1 JP2019536740A JP2019536740A JPWO2019035382A1 JP WO2019035382 A1 JPWO2019035382 A1 JP WO2019035382A1 JP 2019536740 A JP2019536740 A JP 2019536740A JP 2019536740 A JP2019536740 A JP 2019536740A JP WO2019035382 A1 JPWO2019035382 A1 JP WO2019035382A1
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- resin particles
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- hollow resin
- active hydrogen
- ring structure
- Prior art date
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Abstract
Description
各合成例、各実施例および各比較例で用いた各成分を以下に記載する。
IPDI:3−イソシアナトメチル−3,5,5−トリメチルシクロヘキシルイソシアネート
H6XDI:1,3−ビス(イソシアナトメチル)シクロヘキサン
XDI:1,3−キシリレンジイソシアネート
HDI:1,6−ヘキサメチレンジイソシアネート
D−170N:HDIのイソシアヌレート誘導体
CHDM:1,4−シクロヘキサンジメタノール
BA−P2M:2,2−ビス(4−ポリオキシプロピレンオキシフェニル)プロパン
NPG:ネオペンチルグリコール
EG:エチレングリコール
1,4−BG:1,4−ブチレングリコール
TMP:トリメチロールプロパン
DMPA:2,2−ジメチロールプロピオン酸
EA:酢酸エチル
MCH:メチルシクロヘキサン
CH:シクロヘキサン
XY:キシレン
TEA:トリエチルアミン
ポイズ530:ポリアクリル酸ソーダ
KBE−9007:3−イソシアナトプロピルトリエトキシシラン、信越化学工業社製
KBM−803:3−メルカプトプロピルトリメトキシシラン、信越化学工業社製
サイメル325:メチル化メラミン樹脂、allnex社製
ユーバン225:ブチル化メラミン樹脂、三井化学社製
2.ウレタンプレポリマーの調製
合成例1
電磁誘導攪拌機、還流冷却管、窒素導入管を取り付けたガラスフラスコに、CHDM 15.0質量部、DMPA 3.8質量部および溶剤としてEA 20.0質量部を加え、撹拌下で40℃に昇温した。次いで、IPDI 61.2質量部を添加し、窒素雰囲気下、70〜80℃で、イソシアネート基濃度が12.0%以下になるまで反応させることで、ウレタンプレポリマーを得た。固形分濃度は79.1%、NCO基濃度は11.8%であった。
配合処方を、表1の記載に従って変更した以外は、合成例1と同様に処理して、ウレタンプレポリマーを得た。
電磁誘導撹拌機、還流冷却付きのフラスコに、D−170N 48.2質量部、グリコール酸 1.8質量部、および、EA 50.0質量部を入れた。次いで、50℃で1時間、さらに、80℃で12時間加熱撹拌することで、ウレタンプレポリマーを得た。固形分濃度は50.2%、イソシアネート基濃度は11.4%であった。
3.中空樹脂粒子の製造
実施例1
合成例1で得たウレタンプレポリマー 75.0質量部、EA 55.0質量部、MCH 70.0、TEA 2.2質量部を混合し、混合液を調製した。次いで、混合液を特殊機化工業社製TKホモミキサー(鋸歯型)を用いて、1000rpmで撹拌しながら、混合液に蒸留水240.0質量部を3回に分けて10分毎に添加した。これにより、ウレタンプレポリマーにより、EAおよびMCHを内包したウレタンプレポリマー液滴を含む水分散液を得た。
配合処方を、表2〜表4の記載に従って変更した以外は、実施例1と同様に処理して、中空樹脂粒子を含む水分散液を得た。
D−170N 20.0質量部、プロピレングリコールモノメチルエーテルアセテート20.0質量部、XY 60.0質量部を混合し、混合液を調製した。次いで、特殊機化工業社製TKホモミキサー(鋸歯型)を用いて、1000rpmで撹拌しながら、分散剤としてのポリビニルピロリドン(PVP)6.0質量部を蒸留水296質量部に溶解させたものに、混合液を添加して5分間撹拌した。次いで、これを攪拌機、還流冷却付きのフラスコに移し、リン酸水素二ナトリウムの5%水溶液を16質量部、ヒドラジン・一水和物を2.5質量部添加して、室温で撹拌したところ、凝集物が大量に発生した。
4.評価
(体積平均粒子径)
各実施例および各比較例の中空樹脂粒子について、中空樹脂粒子の体積平均粒子径を測定した。具体的には、試料1gと蒸留水10gとを30mLガラス製サンプル瓶に採取し、マグネティックスターラーで5分間撹拌した後、粒度分析計マイクロトラックHRA(日機装株式会社製)を用い、下記条件で粒度分布測定を実施した。
Spherical Particles =Yes
Particle Refractive Index=1.50
Fluid Refractive Index =1.333
その結果を表2〜表4に示す。
(形状および体積中空率)
各実施例および各比較例の中空樹脂粒子について、中空樹脂粒子の形状を観察し、また、その体積中空率を測定した。具体的には、中空樹脂粒子を含む水分散液をアルミホイル上に塗布し、40℃で12時間以上乾燥し、塗膜を得た。次いで、この塗膜を、液体窒素に浸して凍結させた後、速やかに切断し、得られた切断面を電子顕微鏡により観察した。無作為に選んだ10個の中空樹脂粒子の粒子径および中空部分の径を測定し、中空率を計算した。得られた中空率の平均値を中空樹脂粒子の体積中空率とした。
(粒子径分布)
各実施例および各比較例の中空樹脂粒子について、中空樹脂粒子の粒子径分布を測定した。
◎:60%以上
○:30%以上60%未満
×:30%未満
(強度評価)
(走査型電子顕微鏡での測定)
各実施例および各比較例の中空樹脂粒子について、中空樹脂粒子の強度を測定した。具体的には、中空樹脂粒子を含む水分散液をアルミホイル上に厚さ20〜30μmで塗布し、40℃で12時間以上乾燥し、塗膜を得た。得られた塗膜の表面と、塗膜の切断面を、走査型電子顕微鏡により倍率2000倍で観察した。塗膜の切断面は、塗膜を液体窒素に浸して凍結させた後に速やかに切断することにより得た。
◎:表面の粒子がすべて形状を維持、断面が空隙を保つ
○:表面の粒子が一部凹んでいる、断面が空隙を保つ
△:表面の粒子がすべて凹んでいる、断面が空隙を保つ
×表面の粒子がすべて凹んでいる、断面が空隙を維持できていない
(キャレンダー試験)
各実施例および各比較例の中空樹脂粒子について、中空樹脂粒子の強度を測定した。具体的には、蒸留水で不揮発分10%に調整した中空樹脂粒子を含む水分散液を市販のコート紙(坪量74g/m2)の片面に、乾燥後の塗布量が2g/m2となるように塗布し、エアドライヤー方式にて80℃で1分間乾燥させて、中空樹脂粒子を含む層(中空樹脂粒子層)を設け、中空樹脂粒子が塗工された塗工紙を得た。キャレンダー装置(「卓上キャレンダー 単板型」 由利ロール社製)を用いて、室温、線圧200kg/cm、処理速度2m/分で、この塗工紙にキャレンダー処理を施した。キャレンダー処理後の塗工紙の中空樹脂粒子層側の表面と、中空樹脂粒子層の切断面を、走査型電子顕微鏡により倍率2000倍で観察した。中空樹脂粒子層の切断面は、塗工紙を液体窒素に浸して凍結させた後、速やかに切断することにより得た。
○:表面の粒子が形状を維持している
×:表面の粒子がすべて潰れている
ウレタンプレポリマーが、カルボキシル基を有する実施例1〜20は、その体積平均粒子径を、1.2μm以上18μm以下に調整できたことがわかる。
Claims (16)
- 内部が中空であり、ウレタン・ウレア樹脂からなる中空樹脂粒子であって、
前記ウレタン・ウレア樹脂は、イソシアネート基を有するウレタンプレポリマーと、活性水素基を有する鎖伸長化合物との反応生成物であって、
前記ウレタンプレポリマーは、ポリイソシアネート成分とカルボキシル基を含有する活性水素基含有成分との反応生成物であり、
前記ポリイソシアネート成分および前記活性水素基含有成分のうち、少なくともいずれか一方が環構造を有する化合物を含有することを特徴とする、中空樹脂粒子。 - 前記活性水素基含有成分は、多価アルコールと、カルボキシル基および2つの活性水素基を有するカルボキシル基含有活性水素化合物とを含むことを特徴とする、請求項1に記載の中空樹脂粒子。
- 前記多価アルコールは、環構造を有することを特徴とする、請求項2に記載の中空樹脂粒子。
- 前記多価アルコールは、脂環構造および/または芳香環構造を有することを特徴とする、請求項3に記載の中空樹脂粒子。
- 前記活性水素基含有成分は、多価アルコールを含まず、カルボキシル基および2つの活性水素基を有するカルボキシル基含有活性水素化合物を含むことを特徴とする、請求項1に記載の中空樹脂粒子。
- ポリイソシアネート成分が、環構造を有するポリイソシアネートを含有することを特徴とする、請求項1に記載の中空樹脂粒子。
- 前記ポリイソシアネート成分は、環構造を有するジイソシアネートを含むことを特徴とする、請求項6に記載の中空樹脂粒子。
- 前記ポリイソシアネート成分は、脂環構造を有するジイソシアネートを含むことを特徴とする、請求項7に記載の中空樹脂粒子。
- 前記ジイソシアネートは、第2級イソシアネート基を含むことを特徴とする、請求項8に記載の中空樹脂粒子。
- 前記ポリイソシアネート成分および前記活性水素基含有成分の両方が環構造を有する化合物を含有することを特徴とする、請求項1に記載の中空樹脂粒子。
- 前記ウレタンプレポリマーのイソシアネート基の含有量が、10%質量以上であることを特徴とする、請求項1に記載の中空樹脂粒子。
- 前記ウレタン・ウレア樹脂が、架橋剤により架橋されていることを特徴とする、請求項1に記載の中空樹脂粒子。
- 前記架橋剤が、i)シランカップリング剤、ii)カルボジイミド基、オキサゾリン基、エポキシ基のうち、少なくとも1つを有する化合物、および、iii)メラミン化合物からなる群から選択される少なくとも1種であることを特徴とする、請求項12に記載の中空樹脂粒子。
- 内部が中空であり、カルボキシル基および環構造を有するウレタン・ウレア樹脂からなることを特徴とする、中空樹脂粒子。
- 支持層と、断熱層と、感熱記録層とを順に備え、
前記断熱層は、請求項1に記載の中空樹脂粒子を含むことを特徴とする、感熱記録材料。 - ポリイソシアネート成分とカルボキシル基を含有する活性水素基含有成分とを反応させて、イソシアネート基を有するウレタンプレポリマーを得る工程、
前記ウレタンプレポリマーと疎水性溶剤とを混合して混合液を調製し、その混合液に水を添加し、前記ウレタンプレポリマーにより前記疎水性溶剤を内包したウレタンプレポリマー液滴を得る工程、
前記ウレタンプレポリマーと、活性水素基を有する鎖伸長化合物とを反応させて、前記疎水性溶剤を内包したウレタン・ウレア樹脂からなる樹脂粒子を得る工程、および、
前記樹脂粒子おいて内包された前記疎水性溶剤を除去して、前記ウレタン・ウレア樹脂からなり、内部が中空である中空樹脂粒子を得る工程
を備え、
前記ポリイソシアネート成分および前記活性水素基含有成分のうち、少なくともいずれか一方が環構造を有する化合物を含有することを特徴とする、中空樹脂粒子の製造方法。
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WO2022073950A1 (en) | 2020-10-07 | 2022-04-14 | Basf Se | Novel polyurethanes and their use in pharmaceutical dosage forms |
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