JP2021515815A - 水性防曇樹脂、水性防曇塗料組成物及びその製造方法 - Google Patents
水性防曇樹脂、水性防曇塗料組成物及びその製造方法 Download PDFInfo
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Abstract
Description
R1とイソシアネート基はジイソシアネート系化合物を形成し、R1はジイソシアネート系化合物の母体構造であり、
R2はヒドロキシル(OH)とカルボキシル(COOH)を同時に含む化合物であり、
R3、R4、R5、R6はそれぞれH及びCH3から選ばれる1種であり、
R7は−O−N+H(C2H5OH)3、−O−N+H(C2H5)3、−O−K+又は−O−Na+のうちの1種である。)
(1)ジブチル錫ジラウレート又はp−トルエンスルホン酸を触媒とし、ヒドロキシル及びカルボキシルを含むR2化合物とR1を含むジイソシアネート系化合物を40〜60℃で0.5〜2時間反応させて化合物1を得るステップと、
(2)窒素保護下において、イソオクチルアクリレート、メタクリルアミド又はアクリルアミド、メタクリル酸メチル又はアクリル酸メチル、アクリル酸又はメタクリル酸、2−アクリルアミド−2−メチルプロパンスルホン酸、N,N−ジメチルアクリルアミド、メタクリル酸ヒドロキシエチル又はアクリル酸ヒドロキシエチル、アゾビスイソブチロニトリルを60〜90℃で4〜8時間反応させて化合物2を得るステップと、
(3)化合物1と化合物2を60〜90℃で0.5〜4時間反応させ、さらにトリエタノールアミン、トリエチルアミン、水酸化カリウム又は水酸化ナトリウムである塩基性化合物を添加して60〜90℃で0.1〜0.5時間反応させ、塩基性化合物をスルホン酸基及びカルボキシルの一部と反応させて塩を形成し、水性防曇樹脂を得るステップと、を含む。
さらに、ステップ(1)では、ヒドロキシル及びカルボキシルを含むR2化合物と、R1を含むジイソシアネート系化合物とのモル比は1:2〜2.5であり、触媒の質量はヒドロキシル及びカルボキシルを含むR2化合物とR1を含むジイソシアネート系化合物との全質量の0.2〜1%である。
の構造を形成し、具体的には水性防曇樹脂の構造式に示される。上記ジイソシアネート系化合物中のいくつかの物質は複数種の異性体を含み、R1は対応する構造に対応する母体構造である。R1がトルエンジイソシアネートの母体構造であることを例に説明する。トルエンジイソシアネートは
の2種の異性体を含み、対応するR1は
である。
(1)ジブチル錫ジラウレート又はp−トルエンスルホン酸を触媒とし、ヒドロキシル及びカルボキシルを含むR2化合物とR1を含むジイソシアネート系化合物を40〜60℃で0.5〜2時間反応させて化合物1を得るステップと、
(2)窒素保護下において、イソオクチルアクリレート、メタクリルアミド又はアクリルアミド、メタクリル酸メチル又はアクリル酸メチル、アクリル酸又はメタクリル酸、2−アクリルアミド−2−メチルプロパンスルホン酸、N,N−ジメチルアクリルアミド、メタクリル酸ヒドロキシエチル又はアクリル酸ヒドロキシエチル、アゾビスイソブチロニトリルを60〜90℃で4〜8時間反応させて化合物2を得るステップと、
(3)化合物1と化合物2を60〜90℃で0.5〜4時間反応させ、さらにトリエタノールアミン又はトリエチルアミン、水酸化カリウム又は水酸化ナトリウムである塩基性化合物を添加して60〜90℃で0.1〜0.5時間反応させ、塩基性化合物をスルホン酸基及びカルボキシルの一部と反応させて塩を形成し、水性防曇樹脂を得るステップと、を含む。
前記界面活性剤は少なくとも水溶性ドデシル硫酸ナトリウム及びスルホコハク酸ナトリウムジオクチルエステルのうちの1種である。
実施例1
(1)ジブチル錫ジラウレートを触媒とし、ジメチロールプロピオン酸とトルエンジイソシアネートモノマーを40℃で0.5時間反応させ、化合物1を得た。ジメチロールプロピオン酸とトルエンジイソシアネートモノマーとのモル比は1:2であり、触媒の使用量は上記2種の原料の全質量の0.2%であった。
(1)ジブチル錫ジラウレートを触媒とし、乳酸とイソホロンジイソシアネートモノマーを60℃で2時間反応させ、化合物1を得た。乳酸とイソホロンジイソシアネートモノマーとのモル比は1:2.5であり、触媒の使用量は上記2種の原料の全質量の0.5%であった。
(1)p−トルエンスルホン酸を触媒とし、ジメチロールプロピオン酸とヘキサメチレンジイソシアネートモノマーを50℃で1時間反応させ、化合物1を得た。ジメチロールプロピオン酸とヘキサメチレンジイソシアネートモノマーとのモル比は1:2.2であり、触媒の使用量は上記2種の原料の全質量の1%であった。
(1)ジブチル錫ジラウレートを触媒とし、ジメチロールプロピオン酸とジフェニルメタンジイソシアネートモノマーを50℃で1.5時間反応させ、化合物1を得た。ジメチロールプロピオン酸と、イソホロンジイソシアネートモノマーとのモル比は1:2.2であり、触媒の使用量は上記2種の原料の全質量の0.4%であった。
(1)ジブチル錫ジラウレートを触媒とし、ジメチロールプロピオン酸とトルエンジイソシアネートモノマーを50℃で0.3時間反応させ、化合物1を得た。ジメチロールプロピオン酸とトルエンジイソシアネートモノマーとのモル比は1:1.5であり、触媒の使用量は上記2種の原料の全質量の0.1%であった。
(1)ジブチル錫ジラウレートを触媒とし、ジメチロールプロピオン酸とトルエンジイソシアネートモノマーを35℃で0.5時間反応させ、化合物1を得た。ジメチロールプロピオン酸とトルエンジイソシアネートモノマーとのモル比は1:2であり、触媒の使用量は上記2種の原料の全質量の0.2%であった。
以下の水性防曇塗料組成物の実施例5〜8と比較例1〜2の各成分の含有量は表1に示され、ここで、塗料組成物の含有量はそれぞれ重量部である。
Claims (12)
- 水性防曇樹脂であって、以下の構造式を有することを特徴とする水性防曇樹脂。
R1とイソシアネート基はジイソシアネート系化合物を形成し、R1はジイソシアネート系化合物の母体構造であり、
R2はヒドロキシル(OH)とカルボキシル(COOH)を同時に含む化合物であり、
R3、R4、R5、R6はそれぞれH及びCH3から選ばれる1種であり、
R7は−O−N+H(C2H5OH)3、−O−N+H(C2H5)3、−O−K+又は−O−Na+のうちの1種である。) - 前記ジイソシアネート系化合物はトルエンジイソシアネート、ジフェニルメタンジイソシアネート、ヘキサメチレンジイソシアネート、イソホロンジイソシアネート又はジシクロヘキシルメタンジイソシアネートのうちの1種であり、前記R2は乳酸又はジメチロールプロピオン酸であることを特徴とする請求項1に記載の水性防曇樹脂。
- 前記R1はイソホロンジイソシアネートの母体構造、前記R2はジメチロールプロピオン酸、R3、R4、R6はCH3、R5はH、R7は−O−N+H(C2H5OH)3であることを特徴とする請求項2に記載の水性防曇樹脂。
- 前記水性防曇樹脂の数平均分子量は50000−100000であることを特徴とする請求項1に記載の水性防曇樹脂。
- 請求項1に記載の水性防曇樹脂の製造方法であって、
(1)ジブチル錫ジラウレート又はp−トルエンスルホン酸を触媒とし、ヒドロキシル及びカルボキシルを含むR2化合物とR1を含むジイソシアネート系化合物を40〜60℃で0.5〜2時間反応させて化合物1を得る;
(2)窒素保護下において、イソオクチルアクリレート、メタクリルアミド又はアクリルアミド、メタクリル酸メチル又はアクリル酸メチル、アクリル酸又はメタクリル酸、2−アクリルアミド−2−メチルプロパンスルホン酸、N,N−ジメチルアクリルアミド、メタクリル酸ヒドロキシエチル又はアクリル酸ヒドロキシエチル、アゾビスイソブチロニトリルを60〜90℃で4〜8時間反応させて化合物2を得る;
(3)前記化合物1と前記化合物2を60〜90℃で0.5〜4時間反応させ、さらにトリエタノールアミン、トリエチルアミン、水酸化カリウム又は水酸化ナトリウムである塩基性化合物を添加して60〜90℃で0.1〜0.5時間反応させ、塩基性化合物をスルホン酸基及びカルボキシルの一部と反応させて塩を形成し、水性防曇樹脂を得るステップと、を含むことを特徴とする水性防曇樹脂の製造方法。 - 前記ジイソシアネート系化合物はトルエンジイソシアネート又はジフェニルメタンジイソシアネート又はヘキサメチレンジイソシアネート又はイソホロンジイソシアネート又はジシクロヘキシルメタンジイソシアネートであり、前記ヒドロキシル及びカルボキシルを含むR2化合物は乳酸又はジメチロールプロピオン酸であることを特徴とする請求項5に記載の水性防曇樹脂の製造方法。
- 前記ステップ(1)では、前記ヒドロキシル及びカルボキシルを含むR2化合物と、R1を含むジイソシアネート系化合物とのモル比は1:2〜2.5であり、前記触媒の質量はヒドロキシル及びカルボキシルを含むR2化合物とR1を含むジイソシアネート系化合物との全質量の0.2〜1%であることを特徴とする請求項5に記載の水性防曇樹脂の製造方法。
- 前記ステップ(2)では、前記イソオクチルアクリレート、メタクリルアミド又はアクリルアミド、メタクリル酸メチル又はアクリル酸メチル、アクリル酸又はメタクリル酸、2−アクリルアミド−2−メチルプロパンスルホン酸、N,N−ジメチルアクリルアミド、メタクリル酸ヒドロキシエチル又はアクリル酸ヒドロキシエチルのモル比は1:0.1〜0.4:0.8〜1:0.1〜0.4:0.4〜0.8:0.1〜0.4:0.6〜1.2であり、前記アゾビスイソブチロニトリルの使用量はほかの反応原料の全質量の0.1〜0.5%であることを特徴とする請求項5に記載の水性防曇樹脂の製造方法。
- 前記ステップ(3)では、前記化合物2と前記化合物1とのモル比は1:0.2〜0.8、前記塩基性化合物と前記化合物2とのモル比は1:0.5〜1.2であることを特徴とする請求項5に記載の水性防曇樹脂の製造方法。
- 請求項1に記載の水性防曇樹脂30〜60重量部、架橋剤5〜20重量部、界面活性剤5〜10重量部、レベリング剤0.1〜1重量部、希釈剤20〜60重量部を含むことを特徴とする水性防曇塗料組成物。
- 前記架橋剤は水性ポリカルボジイミド、前記レベリング剤はアクリル酸官能基を含むポリエーテル変性シリコーン、前記希釈剤は脱イオン水又は蒸留水であることを特徴とする請求項10に記載の水性防曇塗料組成物。
- 請求項10に記載の水性防曇塗料組成物の製造方法であって、
前記水性防曇樹脂30〜60重量部、架橋剤5〜20重量部、界面活性剤5〜10重量部、レベリング剤0.1〜1重量部、希釈剤20〜60重量部を均一に混合して前記水性防曇塗料組成物を得ることを特徴とする水性防曇塗料組成物の製造方法。
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