JP2007045959A - 反応性紫外線吸収剤およびその製造方法 - Google Patents
反応性紫外線吸収剤およびその製造方法 Download PDFInfo
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- JP2007045959A JP2007045959A JP2005232844A JP2005232844A JP2007045959A JP 2007045959 A JP2007045959 A JP 2007045959A JP 2005232844 A JP2005232844 A JP 2005232844A JP 2005232844 A JP2005232844 A JP 2005232844A JP 2007045959 A JP2007045959 A JP 2007045959A
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Abstract
Description
(R1〜R4はそれぞれ独立して水素原子、水酸基、もしくは酸素原子を含有してもよい炭素数1〜18の脂肪族炭化水素基を表わし、Aはアリル基またはメタリル基を含有する基を表わす)
(R1〜R4はそれぞれ独立して水素原子、水酸基、もしくは酸素原子を含有してもよい炭素数1〜18の脂肪族炭化水素基を表わす)
(1)アリルクロライド、アリルブロマイド、メタリルクロライドなどのハロゲン化合物や、アリルグリシジルエーテル、メタリルグリシジルエーテルなどのエポキシ化合物などの基を持ったアリル化合物またはメタリル化合物を、一般式(2)で表わされる化合物と反応する方法。
(2)一般式(2)で表わされる化合物にアルキレンオキシドを反応させた後に、上記のハロゲン化合物やエポキシ化合物を反応させる方法。
(3)ヘキサメチレンジイソシアネートやトリレンジイソシアネートなどの2価イソシアネートを一般式(2)で表わされる化合物に反応させ、その後アリルアルコール、アリルアミン、メタリルアルコールなどのアリル化合物やメタリル化合物を反応させる方法。
(4)モノエポキシ化合物を一般式(2)で表わされる化合物に反応させ、反応後に生成した水酸基にアリルグリシジルエーテルやメタリルグリシジルエーテルなどを反応させる方法。
(5)ジエポキシ化合物を一般式(2)で表わされる化合物に反応させ、未反応のエポキシ基にアリルアルコール、アリルアミン、メタリルアルコールなどのアリル化合物やメタリル化合物を反応させる方法。
(6)ジカルボン酸化合物を一般式(2)で表わされる化合物に反応させ、未反応のカルボキシル基にアリルアルコール、アリルアミン、メタリルアルコールなどのアリル化合物やメタリル化合物を反応させる方法などが挙げられる。
これらの中でも、副生物が少なく製造しやすいことから、アリル基またはメタリル基を持ったエポキシ化合物を一般式(2)で表わされる化合物に反応させるのが好ましく、アリルグリシジルエーテルの使用がより好ましい。
(製造例1)
攪拌機、温度計および窒素導入管を備えた3,000cm3のステンレス製加圧反応装置に、2,4−ジヒドロキシベンゾフェノン1,070g(5モル)および触媒として水酸化ナトリウム10gを仕込み、反応装置内の雰囲気を窒素で置換後、アリルグリシジルエーテル570g(5モル)を90℃でフィードし、フィード終了後、90℃で5時間熟成した。熟成終了後、吸着剤を使用して触媒の水酸化ナトリウムを除去し、本発明の下記化合物Aを得た。
製造例1と同様の装置に、2,2’,4−トリヒドロキシ−4’−オクチルベンゾフェノン1,710g(5モル)および触媒として水酸化ナトリウム10gを仕込み、反応装置内の雰囲気を窒素で置換後、アリルグリシジルエーテル570g(5モル)を90℃でフィードし、フィード終了後、90℃で5時間熟成した。熟成終了後、吸着剤を使用して触媒の水酸化ナトリウムを除去し、本発明の下記化合物Bを得た。
製造例1と同様の装置に、2,4−ジヒドロキシ−4’−メトキシベンゾフェノン1,220g(5モル)および触媒として水酸化ナトリウム5gを仕込み、反応装置内の雰囲気を窒素で置換後、ヘキサメチレンジイソシアネート840g(5モル)を60℃でフィードし、フィード終了後、90℃で2時間熟成した。熟成終了後、メタリルアルコール360g(5モル)を90℃でフィードし、フィード終了後、90℃で3時間熟成した。その後、吸着剤を使用して触媒の水酸化ナトリウムを除去し、本発明の下記化合物Cを得た。
製造例1と同様の装置に、2,4−ジヒドロキシ−6−メチルベンゾフェノン1,140g(5モル)、コハク酸590g(5モル)および触媒として水酸化ナトリウム10gを仕込み、反応装置内の雰囲気を窒素で置換後180℃まで昇温した。その後、エステル化反応で出てくる水を除去しながら徐々に減圧を行い、1.3kPaまで減圧して、その減圧度のまま180℃で3時間熟成した。熟成終了後、80℃まで冷却および常圧に戻し、アリルアルコール290g(5モル)を添加し、再び180℃および1.3kPaの減圧度で3時間エステル化反応を行った。反応終了後、吸着剤を使用して触媒の水酸化ナトリウムを除去し、本発明の下記化合物Dを得た。
製造例1と同様の装置に、前記化合物A984g(3モル)、スルファミン酸291g(3モル)および触媒として尿素4gを仕込み、反応装置内の雰囲気を窒素で置換後120℃に昇温し、同温度で8時間反応させた後、ろ過にて触媒を除去し、本発明の下記化合物Eを得た。
製造例1と同様の装置に、前記化合物A984g(3モル)および触媒として水酸化カリウム3gを仕込み、反応装置内の雰囲気を窒素で置換後、エチレンオキシド1,980g(45モル)を120℃で3時間かけてフィードした。フィード終了後、120℃で2時間熟成し、反応終了後、吸着剤を使用して触媒の水酸化カリウムを除去し、本発明の下記化合物Fを得た。
製造例1と同様の装置に、2,4−ジヒドロキシ−4’−メチルベンゾフェノン1,140g(5モル)および触媒として水酸化ナトリウム10gを仕込み、反応装置内の雰囲気を窒素で置換後、アリルグリシジルエーテル570g(5モル)を90℃でフィードし、フィード終了後、90℃で5時間熟成した。熟成終了後120℃に昇温し、同温度でエチレンオキシド2,200g(50モル)を3時間かけてフィードし、120℃で2時間熟成させた。熟成後、吸着剤を使用して触媒の水酸化ナトリウムを除去し、スルファミン酸485g(5モル)および触媒として尿素11gを仕込み、120℃で8時間反応させた後、ろ過にて触媒を除去し、本発明の下記化合物Gを得た。
製造例1と同様の装置に、前記化合物A984g(3モル)および無水マレイン酸294g(3モル)を仕込み、反応装置内の雰囲気を窒素で置換後、80℃で6時間エステル化反応した後、水酸化カリウムで中和し、本発明の下記化合物Hを得た。
製造例1と同様の装置に、前記化合物A984g(3モル)を仕込み、40℃で五酸化二リン284g(2モル)を1時間かけて添加した後、80℃で2時間熟成した。このあと、水酸化ナトリウム水溶液で中和し、本発明の下記化合物Iを得た。なお、化合物Iは、リン酸モノエステルとリン酸ジエステルが1対1(モル比)の混合物であった。
本発明の反応性紫外線吸収剤(前記化合物A〜E)の樹脂改質剤として性能を見るために、スチレンの溶液重合を行い、得られた樹脂の耐候性を評価した。
<重合方法>
撹拌機、温度計および窒素導入管を備えた500mlのステンレス製加圧反応装置にキシレン100gを仕込み、系内を窒素ガスで置換した。別にスチレン150g、本発明の反応性紫外線吸収剤(化合物A〜E)をそれぞれ7.5g、過酸化ベンゾイル2gおよびジターシャリブチルパーオキサイド1gからなる5種の混合溶液を調製し、それぞれ反応温度130℃で上記5種の混合溶液を2時間かけて反応容器内に連続的に滴下した。滴下終了後、さらにキシレン10g、過酸化ベンゾイル0.5gおよびジターシャリブチルパーオキサイド0.5gからなる混合溶液をそれぞれ滴下し、130℃で2時間反応させ、その後冷却して5種の重合体溶液を得た。これらの重合体溶液から得られる試験片について以下の耐候性試験を行った。なお、比較例として本発明の反応性紫外線吸収剤を含まないスチレンホモポリマー溶液を同様の反応によって得た。また、得られたスチレンホモポリマー溶液(固形分150g)に対して、前記化合物Lを7.5g添加した重合体溶液についても以下の耐候性試験を行った。
上記で得た7種の重合体溶液を、50mm×70mmのガラス板に厚さ1mmになるように塗布および乾燥して成膜した7種の試験片を作成した。耐候性試験法としては、サンシャインウエザオメーター(スガ試験機(株)製WEL−SUN−HCH−B型)を用いて促進耐候性試験を行った。試験条件は、温度:63±3℃、サイクル:120分中18分降雨、時間は2,000hrである。耐候性試験後の各試験片を光沢計((株)村上色彩技術研究所製 GM26D型)を使用して光沢を測定して光沢保持率を求めた。測定角は60度で、光沢保持率は、光沢保持率(%)=[試験後の光沢/試験前の光沢]×100である。保持率が高いほど光沢が低下しにくく、耐候性に優れていることを示す。結果を表1に示す。
本発明の反応性紫外線吸収剤(前記化合物F〜I)と比較の乳化剤(前記化合物J、K)を使用し、アクリル酸ブチル/アクリル酸メチル/アクリル酸=49/49/2(質量比)の混合物を単量体としてそれぞれ乳化重合を行い、得られた6種の重合体の耐水性と耐候性を測定した。
<重合方法>
実施例1と同様の装置に、脱イオン水120gを仕込み、系内を窒素ガスで置換した。別に混合単量体(アクリル酸ブチル/アクリル酸メチル/アクリル酸=49/49/2(質量比))100gに前記化合物F〜Kの乳化重合用乳化剤4gをそれぞれ溶解し6種の単量体乳化液を得た。それぞれの単量体乳化液10gと過硫酸アンモニウム0.08gとを反応容器に加え60℃に昇温した。その後、残りの単量体乳化液を2時間かけてそれぞれの反応容器内に連続的に滴下し、滴下終了後同温度で2時間熟成して6種の重合体エマルションを得た。
上記6種の重合体エマルションをそれぞれ0.2mmの厚さのポリマーフィルムになるようにガラス板にそれぞれ塗布および乾燥して成膜し、得られた6種の試験片をそれぞれ50℃の水に浸漬した。それぞれについて、ポリマーフィルムが白化して、ポリマーフィルムを通して8ポイントの文字が判別できなくなるまでの時間を測定し、耐水性の評価とした。評価の基準は以下の通りである。結果を表2に示す。
○:24時間以上
△:5時間以上
×:1時間未満
上記乳化重合によって得た6種の重合体エマルションを、50mm×70mmのガラス板にそれぞれ厚さ0.2mmになるように塗布および乾燥して成膜して6種の試験片を作成した。耐候性試験法としては、サンシャインウエザオメーター(スガ試験機(株)製WEL−SUN−HCH−B型)を用いて促進耐候性試験を行った。試験条件は、温度:63±3℃、サイクル:120分中18分降雨、時間は2,000hrである。
耐候性試験後の各試験片を光沢計((株)村上色彩技術研究所製 GM26D型)を使用して光沢を測定して光沢保持率を求めた。測定角は60度で、光沢保持率は、光沢保持率(%)=[試験後の光沢/試験前の光沢]×100である。保持率が高いほど光沢が低下しにくく、耐候性に優れていることを示す。結果を表2に示す。
Claims (7)
- 一般式(1)のAが、アニオン性親水基および/またはポリエーテル鎖を含有する請求項1に記載の反応性紫外線吸収剤。
- 請求項3に記載の方法で得られた生成物に、さらに炭素数2〜4のアルキレンオキシドを反応させる請求項3に記載の反応性紫外線吸収剤の製造方法。
- 請求項3または4に記載の方法で得られた生成物に、さらにアニオン性親水基を付与させる請求項3または4に記載の反応性紫外線吸収剤の製造方法。
- 請求項1〜5のいずれか1項に記載の反応性紫外線吸収剤からなることを特徴とする乳化重合用反応性乳化剤。
- 請求項1〜5のいずれか1項に記載の反応性紫外線吸収剤を使用して得られたことを特徴とする重合物。
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JPH02289509A (ja) * | 1989-03-22 | 1990-11-29 | L'oreal Sa | ジオルガノポリシロキサン含有化粧品組成物 |
JPH0539327A (ja) * | 1991-08-02 | 1993-02-19 | Tokyo Keikaku:Kk | 水に良好に分散する紫外線吸収能を有する樹脂 |
JPH07207250A (ja) * | 1994-01-18 | 1995-08-08 | Asahi Denka Kogyo Kk | 反応性紫外線吸収剤及び感熱記録材料 |
JPH1077219A (ja) * | 1996-08-26 | 1998-03-24 | Basf Ag | 化粧品用薬剤及びその製法 |
JPH10212469A (ja) * | 1997-01-28 | 1998-08-11 | Dai Ichi Kogyo Seiyaku Co Ltd | 紫外線吸収剤 |
JP2000160072A (ja) * | 1998-11-24 | 2000-06-13 | Ricoh Co Ltd | 記録用インク |
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JPS4928589A (ja) * | 1972-07-12 | 1974-03-14 | ||
JPS4935367A (ja) * | 1972-07-31 | 1974-04-01 | ||
JPH01172486A (ja) * | 1987-12-28 | 1989-07-07 | Mitsubishi Petrochem Co Ltd | 反応性紫外線吸収剤 |
JPH02233638A (ja) * | 1989-03-06 | 1990-09-17 | Nippon Petrochem Co Ltd | アルケニルベンゾフェノンの製造方法 |
JPH02289509A (ja) * | 1989-03-22 | 1990-11-29 | L'oreal Sa | ジオルガノポリシロキサン含有化粧品組成物 |
JPH0539327A (ja) * | 1991-08-02 | 1993-02-19 | Tokyo Keikaku:Kk | 水に良好に分散する紫外線吸収能を有する樹脂 |
JPH07207250A (ja) * | 1994-01-18 | 1995-08-08 | Asahi Denka Kogyo Kk | 反応性紫外線吸収剤及び感熱記録材料 |
JPH1077219A (ja) * | 1996-08-26 | 1998-03-24 | Basf Ag | 化粧品用薬剤及びその製法 |
JPH10212469A (ja) * | 1997-01-28 | 1998-08-11 | Dai Ichi Kogyo Seiyaku Co Ltd | 紫外線吸収剤 |
JP2000160072A (ja) * | 1998-11-24 | 2000-06-13 | Ricoh Co Ltd | 記録用インク |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20140378572A1 (en) * | 2010-06-22 | 2014-12-25 | Coloplast A/S | Hydrophilic gels from polyalkylether-based photoinitiators |
US9212266B2 (en) | 2010-06-22 | 2015-12-15 | Coloplast A/S | Hydrophilic gels from polyalkylether-based photoinitiators |
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