JP2013216825A - 光硬化性組成物 - Google Patents
光硬化性組成物 Download PDFInfo
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- JP2013216825A JP2013216825A JP2012090303A JP2012090303A JP2013216825A JP 2013216825 A JP2013216825 A JP 2013216825A JP 2012090303 A JP2012090303 A JP 2012090303A JP 2012090303 A JP2012090303 A JP 2012090303A JP 2013216825 A JP2013216825 A JP 2013216825A
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Abstract
【解決手段】炭素−炭素二重結合を1分子あたり平均して1個以上有し、数平均分子量が1万以上、かつ分子量分布が1.6以下である有機重合体と、1分子中に2個以上のメルカプト基を有する化合物、さらには光重合開始剤を組み合わせた光硬化性組成物により上記課題を解決できる。
【選択図】なし
Description
(1)(A)炭素−炭素二重結合を1分子あたり1個以上有し、数平均分子量1万以上、分子量分布が1.6以下の有機重合体、(B)1分子中に2個以上のメルカプト基を有する化合物、(C)光重合開始剤を含有する光硬化性組成物、
(2)(A)成分の炭素−炭素二重結合が、アリル基および/またはメタリル基であることを特徴とする、(1)に記載の光硬化性組成物、
(3)さらに(D)シランカップリング剤、および(E)縮合触媒を含有することを特徴とする、(1)もしくは(2)に記載の光硬化性組成物、
(4)さらに(F)反応性ケイ素基を分子末端に有する有機重合体、および(E)縮合触媒を含有することを特徴とする、(1)〜(3)のいずれかに記載の光硬化性組成物。
(5)(E)硬化触媒が、光酸発生剤であることを特徴とする、(3)または(4)に記載の光硬化性組成物、
(6)(A)成分がポリエーテル系重合体、ポリシロキサン系重合体、ビニル系重合体からなる群のなかから選ばれる少なくともひとつであることを特徴とする(1)〜(5)のいずれかに記載の光硬化性組成物、
(7)(A)成分がポリオキシアルキレン系重合体、ポリイソブチレン系重合体、(メタ)アクリル系重合体からなる群のなかから選ばれる少なくともひとつであることを特徴とする(1)〜(6)のいずれかに記載の光硬化性組成物、
(8)(A)成分が分子中に分岐鎖を有することを特徴とする(1)〜(7)のいずれかに記載の光硬化性組成物、
(9)(F)成分がポリエーテル系重合体、ポリシロキサン系重合体、ビニル系重合体からなる群のなかから選ばれる少なくともひとつであることを特徴とする(1)〜(8)のいずれかに記載の光硬化性組成物、
(10)(F)成分がポリオキシアルキレン系重合体、ポリイソブチレン系重合体、(メタ)アクリル系重合体からなる群のなかから選ばれる少なくともひとつであることを特徴とする(1)〜(9)のいずれかに記載の光硬化性組成物、
(11)(G)充填剤を含有することを特徴とする、(1)〜(10)のいずれかに記載の光硬化性組成物、
に関する。
例えば、ポリシロキサン、ポリエーテル、ビニル系重合体が挙げられる。ビニル系重合体としては、炭化水素系重合体である、ポリイソブチレン、水素添加ポリイソプレン、水素添加ポリブタジエン、および(メタ)アクリル系モノマー、アクリロニトリル系モノマー、芳香族ビニル系モノマー、フッ素含有ビニル系モノマー及びケイ素含有ビニル系モノマーからなる群から選ばれるモノマーを主として重合して製造される重合体等が挙げられる。
その中でも、重合体の主鎖が、一般式(2)で示される繰り返し単位を有するものが低粘度の光硬化性組成物が得られることから好ましい。
一般式(2):
−R5−O− (2)
(式中、R5は2価のアルキレン基)。
{H2C=C(R6)−R7−O}dR8 (3)
(式中、R6は水素又はメチル基、R7は炭素数1 〜20の2価の炭化水素基であって、1個以上のエーテル基が含まれていてもよい、R8は重合体残基であり、dは正の整数である。)で示される重合体が挙げられる。R7は具体的には、−CH2−、−CH2CH2−、−CH2CH2CH2−、−CH2CH(CH3)CH2−、−CH2CH2CH2CH2−,−CH2CH2OCH2CH2−、または−CH2CH2OCH2CH2CH2−などを挙げることができる。合成上の容易さからは−CH2−が好ましい。
{H2C=C(R6)−R7−OC(=O)}dR8 (4)
(式中、R6,R7,R8及びdは上記と同じ)で示されるエステル結合を有する重合体が挙げられる。
{H2C=C(R6)}dR8 (5)
(式中、R6、R8及びdは上記と同じ)で示される重合体も挙げられる。さらに、次の一般式(6):
{H2C =C(R6)−R7−OC(=O)O }dR8 (6)
(式中、R6、R7、R8及びdは上記と同じ)で示されるカーボネート結合を有する重合体も挙げられる。
縮合触媒としては特に制限はなく、各種のものを用いることができる。例えば、テトラブチルチタネート、テトラプロピルチタネート、チタンテトラアセチルアセトナート、ビスアセチルアセトナトジイソプロポキシチタンなどのチタン化合物;ジブチル錫ジラウレート、ジブチル錫マレエート、ジブチル錫フタレート、ジブチル錫ジオクテート、ジブチル錫ジエチルヘキサノレート、ジブチル錫ジメチルマレエート、ジブチル錫ジエチルマレエート、ジブチル錫ジブチルマレエート、ジブチル錫ジオクチルマレエート、ジブチル錫ジトリデシルマレエート、ジブチル錫ジベンジルマレエート、ジブチル錫ジアセテート、ジオクチル錫ジエチルマレエート、ジオクチル錫ジオクチルマレエート、ジブチル錫ジメトキサイド、ジブチル錫ジノニルフェノキサイド、ジブテニル錫オキサイド、ジブチル錫ジアセチルアセトナート、ジブチル錫ジエチルアセトアセトナート、ジブチル錫オキサイドとシリケート化合物との反応物、ジブチル錫オキサイドとフタル酸エステルとの反応物などの4価の有機錫化合物;アルミニウムトリスアセチルアセトナート、アルミニウムトリスエチルアセトアセテート、ジイソプロポキシアルミニウムエチルアセトアセテートなどの有機アルミニウム化合物類;ジルコニウムテトラアセチルアセトナートなどのジルコニウム化合物類が挙げられる。
本発明においては、スルホン酸誘導体を使用することができる。例えば、ジスルホン類、ジスルホニルジアゾメタン類、ジスルホニルメタン類、スルホニルベンゾイルメタン類、トリフルオロメチルスルホネート誘導体などのイミドスルホネート類、ベンゾインスルホネート類、1−オキシ−2−ヒドロキシ−3−プロピルアルコールのスルホネート類、ピロガロールトリスルホネート類、ベンジルスルホネート類を挙げることができる。
一般式(2):
−R5−O− (2)
(式中、R5は2価のアルキレン基)。
またさらに、下記一般式(1)で表される反応性ケイ素基は、活性が特に高く、非常に良好な硬化性が得られることから特に好ましい。
(式中、R1は置換および/または非置換の炭素数1〜20のアルキル基、炭素数6〜20のアリール基、炭素数7〜20のアラルキル基、またはR2 3SiO−で表わされるトリオルガノシロキシ基を示し、3個のR2は炭素数1〜20の炭化水素基であり、それらは同じでもよく、異なっていてもよい。R3は水素、または炭素数1〜6の炭化水素基である。Xは水酸基または加水分解性基を示す。Wは−O−,−O−CO−N(R4)−,−N(R4)−CO−O−,−N(R4)−CO−N(R4)−,−S−CO−NH−,−NH−CO−S−から選択される結合基を示し、R4は水素、ハロゲン置換されていてもよい環状、直鎖状または分岐鎖状の炭素数1〜18のアルキル基もしくは炭素−炭素二重結合、または炭素数6〜18のアリール基を示す。aは0,1または2、bは1,2または3、a+b=3であるとする条件を満たす。R1、R3、X、W、R4のそれぞれについて、それらが複数存在するとき、それらは同じでもよく、異なっていてもよい。)。
炭酸カルシウムは、重質炭酸カルシウム、膠質炭酸カルシウム等、特に制限なく従来公知のものを使用できる。この中でも特に、脂肪酸もしくはその塩、または樹脂酸もしくはその塩で処理された炭酸カルシウムを用いた場合、油面鋼板への接着性が良好になる傾向があり好ましい。
(合成例1)
分子量約2,000のポリオキシプロピレンジオールを開始剤とし、亜鉛ヘキサシアノコバルテートグライム錯体触媒にてプロピレンオキシドの重合を行い、数平均分子量が29,000(送液システムとして東ソー製HLC−8120GPCを用い、カラムは東ソー製TSK−GEL Hタイプを用い、溶媒はTHFを用いて測定したポリスチレン換算分子量)のポリオキシプロピレングリコールを得た。続いてこの水酸基末端ポリオキシプロピレングリコールの水酸基に対して1.2倍当量のNaOMeのメタノール溶液を添加してメタノールを留去し、さらに1.1当量の3−クロロ−1−プロペンを添加することにより、末端がアリル基であり、1分子あたりのアリル基が平均2.0個、数平均分子量が29,500である直鎖状のアリル基含有ポリオキシプロピレン重合体(重合体P−1)を得た。
分子量約3,000のポリオキシプロピレントリオールを開始剤とし、亜鉛ヘキサシアノコバルテートグライム錯体触媒にてプロピレンオキシドの重合を行い、数平均分子量が28,000(合成例1と同様の方法で算出)のポリオキシプロピレントリオールを得た。続いてこの水酸基末端ポリオキシプロピレントリオールの水酸基に対して1.2倍当量のNaOMeのメタノール溶液を添加してメタノールを留去し、さらに1.1当量の3−クロロ−1−プロペンを添加することにより、末端がアリル基であり、1分子あたりのアリル基が平均2.7個、数平均分子量が29,000である分岐状のアリル基含有ポリオキシプロピレン重合体(重合体P−2)を得た。
分子量約3,000のポリオキシプロピレントリオールを開始剤とし、亜鉛ヘキサシアノコバルテートグライム錯体触媒にてプロピレンオキシドの重合を行い、数平均分子量が16,000(合成例1と同様の方法で算出)のポリオキシプロピレントリオールを得た。続いてこの水酸基末端ポリオキシプロピレントリオールの水酸基に対して1.2倍当量のNaOMeのメタノール溶液を添加してメタノールを留去し、さらに1.1当量の3−クロロ−1−プロペンを添加することにより、末端がアリル基であり、1分子あたりのアリル基が平均2.7個、数平均分子量が16,500である分岐状のアリル基含有ポリオキシプロピレン重合体(重合体P−3)を得た。
分子量約2,000のポリオキシプロピレンジオールを開始剤とし、亜鉛ヘキサシアノコバルテートグライム錯体触媒にてプロピレンオキシドの重合を行い、数平均分子量が14,500(合成例1と同様の方法で算出)のポリオキシプロピレングリコールを得た。続いてこの水酸基末端ポリオキシプロピレングリコールの水酸基に対して1.2倍当量のNaOMeのメタノール溶液を添加してメタノールを留去し、さらに1.1当量の3−クロロ−1−プロペンを添加することにより、末端がアリル基であり、1分子あたりのアリル基が平均2.0個、数平均分子量が15,000である直鎖状のアリル基含有ポリオキシプロピレン重合体(重合体P−4)を得た。
分子量約4,400(合成例1と同様の方法で算出)のポリオキシプロピレンジオールの水酸基に対して1.2倍当量のNaOMeのメタノール溶液を添加してメタノールを留去し、さらに1.1当量の3−クロロ−1−プロペンを添加することにより、末端がアリル基であり、1分子あたりのアリル基が平均2.0個、数平均分子量が4,500である直鎖状のアリル基含有ポリオキシプロピレン重合体(重合体P−5)を得た。
以下に有機重合体(F)の合成例を示す。
分子量約2,000のポリオキシプロピレンジオールを開始剤とし、亜鉛ヘキサシアノコバルテートグライム錯体触媒にてプロピレンオキシドの重合を行い、数平均分子量が29,100(合成例1と同様の方法で算出した)のポリオキシプロピレングリコールを得た。続いてこの水酸基末端ポリオキシプロピレングリコールの水酸基に対して1.2倍当量のNaOMeのメタノール溶液を添加してメタノールを留去し、さらに1.1当量の3−クロロ−1−プロペンを添加して末端の水酸基をアリル基に変換した。次に得られたアリル基末端ポリオキシプロピレン重合体100重量部に対して白金ジビニルジシロキサン錯体(白金換算で3重量%のイソプロパノール溶液)36ppmを加え撹拌しながら、ジメトキシメチルシランをアリル基に対して0.9当量滴下した。その混合溶液を90℃で2時間反応させた後、未反応のジメトキシメチルシランを減圧下留去することにより、末端がジメトキシメチルシリル基であり、1分子あたりのケイ素基が平均1.5個、数平均分子量が29,600である直鎖状の反応性ケイ素基含有ポリオキシプロピレン重合体(重合体Q)を得た。
以下に実施例および比較例を示す。
(A)、(B)、(C)、(D)、(E)、(F)、(G)成分を表1に示す割合で混合し光硬化性樹脂組成物を調整した。
得られた光硬化性樹脂組成物を用いて下記の評価を行った。
●硬化性;
鋼板上に、光硬化性樹脂組成物を長さ50mm、幅20mm、厚み3mmで塗布した。塗布後、光を照射した(フュージョンUVランプシステム CY‐110Q‐G(LH10‐10)、照度1000mJ/cm2、積算光量700mW/cm2/1回あたり)。指触により光硬化性樹脂組成物が硬化しているかを判定し、硬化に要する光照射の回数を評価した。
●引張試験
厚さ3mmのシート状組成物に光を照射したのち、23℃湿度50%で3日間、更に50℃オーブンで4日間養生した後、JIS3号ダンベルを打ち抜き、引張り速度200mm/minにおける機械特性をオートグラフで測定した。
●接着性
冷間圧延鋼板(JISG3141記載のダル仕上げタイプ)および、防錆油を塗布した同冷間圧延鋼板へ、光硬化性組成物をビード状に塗布した。続いて光を照射し(フュージョンUVランプシステム CY‐110Q‐G(LH10‐10)、照度1000mJ/cm2、積算光量700mW/cm2/1回あたり)23℃湿度50%で7日間養生した後、硬化物を引き剥がして接着状態を観察した。剥離抵抗の大きさを3段階(大、中、小)で評価し、また、鋼板側へ接着剤が残った場合をCF(凝集破壊)、残らなかった場合をAF(界面破壊)とした。
得られた評価結果を表1に示す。
Claims (11)
- (A)炭素−炭素二重結合を1分子あたり1個以上有し、数平均分子量1万以上、分子量分布が1.6以下の有機重合体、(B)1分子中に2個以上のメルカプト基を有する化合物、(C)光重合開始剤、を含有する光硬化性組成物。
- (A)成分の炭素−炭素二重結合が、アリル基および/またはメタリル基であることを特徴とする、請求項1に記載の光硬化性組成物。
- さらに(D)シランカップリング剤、および(E)縮合触媒を含有することを特徴とする、請求項1、2に記載の光硬化性組成物。
- さらに(F)反応性ケイ素基を分子末端に有する有機重合体、および(E)縮合触媒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光硬化性組成物。
- (E)硬化触媒が、光酸発生剤であることを特徴とする、請求項3または4に記載の光硬化性組成物。
- (A)成分がポリエーテル系重合体、ポリシロキサン系重合体、ビニル系重合体からなる群のなかから選ばれる少なくともひとつであることを特徴とする請求項1〜5のいずれかに記載の光硬化性組成物。
- (A)成分がポリオキシアルキレン系重合体、ポリイソブチレン系重合体、(メタ)アクリル系重合体からなる群のなかから選ばれる少なくともひとつであることを特徴とする請求項1〜6のいずれかに記載の光硬化性組成物。
- (A)成分が分子中に分岐鎖を有することを特徴とする請求項1〜7のいずれかに記載の光硬化性組成物。
- (F)成分がポリエーテル系重合体、ポリシロキサン系重合体、ビニル系重合体からなる群のなかから選ばれる少なくともひとつであることを特徴とする請求項1〜8のいずれかに記載の光硬化性組成物。
- (F)成分がポリオキシアルキレン系重合体、ポリイソブチレン系重合体、(メタ)アクリル系重合体からなる群のなかから選ばれる少なくともひとつであることを特徴とする請求項1〜9のいずれかに記載の光硬化性組成物。
- (G)充填剤を含有することを特徴とする、請求項1〜10のいずれかに記載の光硬化性組成物。
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