JP2019112651A - 一液湿気硬化型組成物 - Google Patents
一液湿気硬化型組成物 Download PDFInfo
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- JP2019112651A JP2019112651A JP2019073015A JP2019073015A JP2019112651A JP 2019112651 A JP2019112651 A JP 2019112651A JP 2019073015 A JP2019073015 A JP 2019073015A JP 2019073015 A JP2019073015 A JP 2019073015A JP 2019112651 A JP2019112651 A JP 2019112651A
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Abstract
Description
(1) 末端にイソシアネート基を有するウレタンプレポリマーとカーボンブラックと充填材と可塑剤とからなる予備組成物と、
ヘキサメチレンジイソシアネートとトリメチロールプロパンとをイソシアネート基と水酸基との当量比が1.8以上2.2以下となるように反応させて得られる化合物(A)を含む接着付与剤と、
1,3−ジアセトキシ−1,1,3,3−テトラブチルジスタノキサンとエチルシリケートとをモル比が1:0.8〜1:1.2の範囲内で反応させて得られる化合物(C)と、ジブチル錫ビス(ペンタジオン)との何れか一方または両方を含む第1触媒と、
ジモルフォリノジエチルエーテルを含む第2触媒と、を含み、
前記化合物(A)の含有量をA質量部、
前記化合物(B)の含有量をB質量部、
前記化合物(C)の含有量をC質量部、
前記ジブチル錫ビス(ペンタジオン)の含有量をD質量部、
前記ジモルフォリノジエチルエーテルの含有量をE質量部としたとき、
前記予備組成物100質量部に対して下記式(1)〜(3)を満たし、
前記第2触媒は、さらにN,N−ジメチルアミノエチルモルフォリンを含み、
前記N,N−ジメチルアミノエチルモルフォリンの含有量をF質量部としたとき、前記予備組成物100質量部に対して下記式(4)を満たし、
前記予備組成物100質量部に対して下記式(5)、(6)を満たすことを特徴とする一液湿気硬化型組成物。
0.1≦(A+B)≦5 ・・・(1)
0.001≦(C+D)≦0.5 ・・・(2)
0.01≦E≦2 ・・・(3)
F≦2 ・・・(4)
F≦E ・・・(5)
0.5≦(E+F)≦2 ・・・(6)
(2) 前記接着付与剤が、ヘキサメチレンジイソシアネートのビュレット体またはイソシアヌレート体である化合物(B)を含む(1)に記載の一液湿気硬化型組成物。
予備組成物は、末端にイソシアネート基を有するウレタンプレポリマーとカーボンブラックとを含んでいる。
ウレタンプレポリマーは、分子内に複数のイソシアネート基を分子末端に含有するプレポリマーである。ウレタンプレポリマーは、取り扱いの観点から室温で液状であるものが好ましい。ウレタンプレポリマーの作製方法は、特に制限されるものではなく、従来より公知の方法が挙げられる。ウレタンプレポリマーは、例えば、ポリイソシアネート化合物とポリオール化合物とを、イソシアネート基(NCO基)がヒドロキシ基(OH基)に対して過剰となるように反応させることにより得られる反応生成物である。ウレタンプレポリマーは、一般に、0.5質量%以上10質量%以下のNCO基を分子末端に含有するものである。このイソシアネート基は、芳香族炭化水素、脂肪族炭化水素のいずれに結合していてもよい。
カーボンブラックは、特に限定されず、通常市販されているものを用いることができる。カーボンブラックとしては、例えば、米国材料試験協会規格における、N110、N220、N330、N550、N770等あるいはこれらの混合物が挙げられる。
接着付与剤は、ジイソシアネートとトリメチロールプロパン(TMP)またはグリセリンとをイソシアネート基と水酸基との当量比が1.8以上2.2以下となるように反応させて得られる化合物(A)と、ジイソシアネートのビュレット体またはイソシアヌレート体である化合物(B)との何れか一方または両方を含む。化合物(A)および化合物(B)は、3個以上のNCO基を有するポリイソシアネート化合物である。
(ジイソシアネート化合物)
ジイソシアネート化合物は、分子内にイソシアネート基(NCO基)を2個有するものであれば特に限定されない。ジイソシアネート化合物としては、具体的には、例えば、パラフェニレンジイソシアネート、トリレンジイソシアネート(TDI)、ナフタレンジイソシアネート(NDI)、4,4’ージフェニルメタンジイソシアネート(4,4’−MDI)、2,4’−ジフェニルメタンジイソシアネート(2,4’−MDI)、トリジンジイソシアネート(TODI)等の芳香族イソシアネート;テトラメチレンジイソシアネート、ヘキサメチレンジイソシアネート(HDI)、トリメチルヘキサメチレンジイソシアネート(TMHDI)、リジンジイソシアネート、ノルボルナンジイソシアネート(NBDI)、オクタデシルジイソシアネート等の脂肪族イソシアネート;トランスシクロヘキサン−1,4−ジイソシアネート、イソホロンジイソシアネート(IPDI)、ジシクロヘキシルメタンジイソシアネート(H12MDI)等の脂環式イソシアネート;キシレンジイソシアネート(XDI)、水素添加キシリレンジイソシアネート(HXDI)、テトラメチルキシリレンジイソシアネート(TMXDI)等のアリール脂肪族イソシアネート;上記各イソシアネートの変性イソシアネート等が挙げられる。これらは、それぞれ1種単独でまたは2種以上を組み合わせて使用することができる。
化合物(B)は、ジイソシアネートのビュレット体またはイソシアヌレート体である。ジイソシアネート化合物のビュレット体、イソシアヌレート体としては、例えば、ヘキサメチレンジイソシアネートのビュレット(以下、「HDIビュレット」ともいう。)体、ヘキサメチレンジイソシアネートのイソシアヌレート(以下、「HDIイソシアヌレート」ともいう。)体が挙げられる。HDIビュレット体は、例えば、下記式(I)で表される。HDIイソシアヌレート体は、例えば、下記式(II)で表される。
0.1≦(A+B)≦5 ・・・(1)
第1触媒は、1,3−ジアセトキシ−1,1,3,3−テトラブチルジスタノキサンとエチルシリケートとをモル比が1:0.8以上1:1.2以下の範囲内で反応させて得られる化合物(C)と、ジブチル錫ビス(ペンタジオン)との何れか一方または両方を含んでいる。
化合物(C)は、錫系触媒と珪酸エステル化合物との反応物である。第1触媒として、化合物(C)を含有することにより、本実施形態の組成物は、難接着な被着体に対して下地処理を行うことなく被着体を接着させることができ、難接着性塗板等の種々の被着体との接着性に優れる。
ジブチル錫ビス(ペンタジオン)は、6価の有機錫化合物であり錫系の金属触媒であり、下記式(IV)で表される。第1触媒として、ジブチル錫ビス(ペンタジオン)を含有することにより、本実施形態の組成物は、難接着な被着体に対して下地処理を行うことなく被着体を接着させることができ、難接着性塗板等の種々の被着体との接着性に優れる。
0.001≦(C+D)≦0.5 ・・・(2)
第2触媒は、アミン系触媒である下記式(V)で表されるジモルフォリノジエチルエーテル(DMDEE)を含有する。ジモルフォリノジエチルエーテルは、ウレタンプレポリマーのイソシアネート基と空気中の水分との反応を触媒するので、得られる組成物は硬化性、垂下性に優れる。また、ジモルフォリノジエチルエーテル(DMDEE)は、イソシアネート基と水以外の活性水素との反応を触媒しにくいので、得られる組成物は貯蔵安定性に優れる。
0.01≦E≦2 ・・・(3)
F≦2 ・・・(4)
F≦E ・・・(5)
0.1≦(E+F)≦2 ・・・(6)
数平均分子量5000のポリプロピレンエーテルトリオール200g(G−5000、商品名「EXCENOL5030」、旭硝子株式会社製)と、数平均分子量2000のポリプロピレンエーテルジオール600g(D−2000、商品名「EXCENOL2020」、旭硝子株式会社製)とをフラスコに投入して、100℃〜130℃に加熱し、脱気しながら攪拌して水分率が0.01%以下になるまで脱水した。その後、90℃まで冷却し、ジフェニルメタンジイソシアネート(MDI、商品名「スミジュール44S」、住化バイエルウレタン株式会社製)を、NCO基/OH基のモル比が1.8となる量を添加した後、約24時間、窒素雰囲気下で反応を進めNCO含有量が2.0%のウレタンプレポリマーを作製した。
このようにして得られたウレタンプレポリマー100質量部に、カーボンブラック(商品名:エルフテック8、キャボット社製)70質量部、炭酸カルシウム(重質炭酸カルシウム、商品名:SB青、白石カルシウム社製)20質量部、可塑剤(フタル酸ジイソノニル(DINP)、三菱化学社製)50質量部を添加し真空下でミキサーを用いて1時間混合し、予備組成物を得た。
HDI(商品名:デュラネート50M−HDI、NCO基:50質量%、旭化成ケミカルズ社製)100gを撹拌しながら、N2気流中でNCO基/OH基が2.0となるように、1,1,1−トリメチロールプロパン(三菱ガス化学社製)245gをメチルエチルケトン(MEK)に溶解させたものをHDIに滴下しながら反応させることで化合物(A)(NCO基:22.2質量%)を得た。
1,3−ジアセトキシ−1,1,3,3−テトラブチルジスタノキサン(大阪新薬社製)100gとエチルシリケート(テトラエトキシシラン、エルコート社製288gとを均一に混合して反応温度55℃以上65℃以下の条件下で24時間攪拌して反応させて、化合物(C)を得た。
表1〜5に示す各成分を同表に示す添加量(質量部)で配合し、これらを均一に混合して、表1〜5に示される実施例1〜14、比較例1〜32、33〜38の各一液湿気硬化型組成物(以下、単に組成物という。)を調整した。各々の実施例、比較例における各成分の添加量(質量部)を表1〜5に示す。
接着性評価用のガラス被着体にガラス用プライマー(商品名:MS−90、横浜ゴム社製)を塗布し、20℃で2分間放置した後、上記で得られた各組成物を3mm厚でビード状に塗布して試験体とした。この試験体を、20℃、60RH%の雰囲気下で3時間放置した後、40℃の温水に24時間浸漬させた。その後、この試験体に形成された各組成物の硬化物の一端を把持して180度剥離し、破壊状態を評価した。破壊状態の評価結果を表1〜5に示す。CFは硬化物の凝集破壊の面積率であり、AFは塗板/硬化物間の界面破壊の面積率であり、PSはプライマー組成物/硬化物間の界面破壊の面積率である。CFであれば良好と評価した。結果を表1〜5に示す。
接着性評価用のガラス被着体に上記で得られた各組成物を3mm厚でビード状に塗布して試験体とした。この試験体を、20℃、60RH%の雰囲気下に放置して、各組成物の表面に対してポリエチレンフィルムを密着させた後に引き上げてポリエチレンフィルムに対して各組成物が付着しなくなるまでの時間(皮張り時間)を測定した。皮張り時間が20分以上70分以下を○と評価し、70分を超え100分未満を△と評価し、それ以外は×と評価した。○、△であれば良好と判断した。結果を表1〜5に示す。
垂下性試験は、各組成物の形状維持性(チクソ性)を評価するものである。図1は、垂下性試験の一例を示す概念図である。図1に示すように、厚さ5mmのガラス板3に上記で得られた各組成物1を底辺6mm、高さ10mmの直角三角形ビードで帯状に押し出し、直ちにガラス板3に保持具4を取り付け90°の角度に保持し、20℃、65RH%の雰囲気下で30分放置後の各組成物2の頂点の垂れ下がりの距離hを測定した。距離hが0mmを良好と評価し、距離hが0mmを超え1.5mm以下を良と評価し、それ以外は劣ると評価した。結果を表1〜5に示す。
上記で得られた各組成物を密閉容器に充填して窒素置換し、40℃の雰囲気下で7日間放置し、その後、押出し粘度を測定して初期粘度に対する増粘率(%)を求めた。増粘率が20%以下を良好と評価し、20%を超え25%未満を良と評価し、25%以上を劣ると評価した。結果を表1〜5に示す。
接着性評価用のガラス被着体にガラス用プライマー(商品名:MS−90、横浜ゴム社製)を塗布し、20℃で2分間放置した後、上記で得られた各組成物を3mm厚でビード状に塗布して試験体とした。この試験体を、20℃、60RH%の雰囲気下で7日間放置した後、120℃の雰囲気下で5日間放置し、20℃まで徐冷した。その後、この試験体に形成された各組成物の硬化物の一端を把持して180度剥離し、破壊状態を評価した。破壊状態の評価結果を表1〜5に示す。CFは硬化物の凝集破壊の面積率であり、AFは塗板/硬化物間の界面破壊の面積率であり、PSはプライマー組成物/硬化物間の界面破壊の面積率である。CFであれば良好と評価した。結果を表1〜5に示す。
上記で得られた各組成物の硬化物を厚さ2mmのダンベル状試験片(ダンベル状3号形)に切り出し、JIS K6251−1993に準拠して、破断伸び(%)を測定した。破断伸びが300%以上を良好と評価し、270%以上300%未満を良と評価し、それ以外は劣ると評価した。結果を表1〜5に示す。
塗板1(酸エポキシ系塗板)、塗板2(酸エポキシ系塗板)、塗板3(アクリルメラミン系塗板)の表面をホワイトガソリンで洗浄した後に、それぞれプライマーを用いず直接に上記で得られた各組成物を3mm厚でビード状に塗布して試験体とした。この試験体を、20℃、60RH%の雰囲気下で7日間放置した後、40℃の温水に7日間浸漬させた。その後、20℃の雰囲気下で、この試験体に形成された各組成物の硬化物の一端を把持して180度剥離し、破壊状態を評価した。破壊状態の評価結果を表1〜5に示す。CFは硬化物の凝集破壊の面積率であり、AFは塗板/硬化物間の界面破壊の面積率であり、PSはプライマー組成物/硬化物間の界面破壊の面積率である。CFであれば良好と評価した。結果を表1〜5に示す。
・予備組成物:上記で調製して得られた組成物
・化合物(A):接着付与剤、上記で合成して得られた化合物
・化合物(B):接着付与剤、HDIビュレット体、商品名「タケネートD−165N」、三井化学社製
・化合物(C):第1触媒、上記で合成して得られた化合物
・ジブチル錫ビス(ペンタジオン):第1触媒、商品名「ネオスタンU−810」、日東化成工業社製
・ジモルフォリノジエチルエーテル:第2触媒、商品名「DMDEE」、サンアプロ社製
・N,N−ジメチルアミノエチルモルフォリン:第2触媒、商品名「X−DM」、エアープロダクツ社製
・TDIイソシアヌレート体:商品名「デスモジュールIL 1351」、バイエル社製
・ジブチル錫ジラウレート:商品名「ネオスタンU−100」、日東化成工業社製
Claims (2)
- 末端にイソシアネート基を有するウレタンプレポリマーとカーボンブラックと充填材と可塑剤とからなる予備組成物と、
ヘキサメチレンジイソシアネートとトリメチロールプロパンとをイソシアネート基と水酸基との当量比が1.8以上2.2以下となるように反応させて得られる化合物(A)を含む接着付与剤と、
1,3−ジアセトキシ−1,1,3,3−テトラブチルジスタノキサンとエチルシリケートとをモル比が1:0.8〜1:1.2の範囲内で反応させて得られる化合物(C)と、ジブチル錫ビス(ペンタジオン)との何れか一方または両方を含む第1触媒と、
ジモルフォリノジエチルエーテルを含む第2触媒と、を含み、
前記化合物(A)の含有量をA質量部、
前記化合物(B)の含有量をB質量部、
前記化合物(C)の含有量をC質量部、
前記ジブチル錫ビス(ペンタジオン)の含有量をD質量部、
前記ジモルフォリノジエチルエーテルの含有量をE質量部としたとき、
前記予備組成物100質量部に対して下記式(1)〜(3)を満たし、
前記第2触媒は、さらにN,N−ジメチルアミノエチルモルフォリンを含み、
前記N,N−ジメチルアミノエチルモルフォリンの含有量をF質量部としたとき、前記予備組成物100質量部に対して下記式(4)を満たし、
前記予備組成物100質量部に対して下記式(5)、(6)を満たすことを特徴とする一液湿気硬化型組成物。
0.1≦(A+B)≦5 ・・・(1)
0.001≦(C+D)≦0.5 ・・・(2)
0.01≦E≦2 ・・・(3)
F≦2 ・・・(4)
F≦E ・・・(5)
0.5≦(E+F)≦2 ・・・(6) - 前記接着付与剤が、ヘキサメチレンジイソシアネートのビュレット体またはイソシアヌレート体である化合物(B)を含む請求項1に記載の一液湿気硬化型組成物。
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