JP6783245B2 - メルカプト官能性ケイ素化合物含有反応性組成物 - Google Patents
メルカプト官能性ケイ素化合物含有反応性組成物 Download PDFInfo
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- JP6783245B2 JP6783245B2 JP2017553365A JP2017553365A JP6783245B2 JP 6783245 B2 JP6783245 B2 JP 6783245B2 JP 2017553365 A JP2017553365 A JP 2017553365A JP 2017553365 A JP2017553365 A JP 2017553365A JP 6783245 B2 JP6783245 B2 JP 6783245B2
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Description
(a)一般式(I)を有する少なくとも一つのメルカプト官能性ケイ素化合物:
式中Aは-OR3、-OCR2 2(CR2 2)fCR2 2OH、または
BはH、または
式中Zの各々は独立して-OR3、-OCR2 2(CR2 2)fCR2 2OH、
からなる群より選択され;
式中R1の各々は、1から10の炭素原子を有するアルキレン、5から12の炭素原子を有するシクロアルキレン、フェニレン、および6から10の炭素原子を有するアラルキルからなる群より独立して選択される二価の基;
式中R2の各々は、1から4の炭素原子を有するアルキルおよび水素からなる群より独立して選択される一価の基;
式中R3の各々は、水素、1から12の炭素原子を有するアルキル、5から12の炭素原子を有するシクロアルキル、フェニルおよびベンジルからなる群より独立して選択され;
式中下付文字fの各々は、独立して0から4の整数;そして
式中下付文字nは0から15の整数であり、但しnが0のとき、Bは
および/または一般式(II):
を有するその部分加水分解物または縮合物であり、式中A、B、ZおよびR1は上掲の定義を有し、n1は2から15の整数;および
(b)少なくとも一つのエポキシ基および/または少なくとも一つの(メタ)アクリレート基を有する反応性樹脂
を含む組成物が提供される。
(a)一般式(I)を有する少なくとも一つのメルカプト官能性ケイ素化合物:
式中Aは-OR3、-OCR2 2(CR2 2)fCR2 2OH、または
BはH、または
式中Zの各々は独立して-OR3、-OCR2 2(CR2 2)fCR2 2OH、
からなる群より選択され;
式中R1の各々は、1から10の炭素原子を有するアルキレン、5から12の炭素原子を有するシクロアルキレン、フェニレン、および6から10の炭素原子を有するアラルキルからなる群より独立して選択される二価の基;
式中R2の各々は、1から4の炭素原子を有するアルキルおよび水素からなる群より独立して選択される一価の基;
式中R3の各々は、水素、1から12の炭素原子を有するアルキル、5から12の炭素原子を有するシクロアルキル、フェニルおよびベンジルからなる群より独立して選択され;
式中下付文字fの各々は、独立して0から4の整数;そして
式中下付文字nは0から15の整数であり、但しnが0のとき、Bは
および/または一般式(II):
を有するその部分加水分解物または縮合物であり、式中A、BおよびR1は上掲の定義を有し、n1は2から15の整数;および
(b)少なくとも一つのエポキシ基および/または少なくとも一つの(メタ)アクリレート基を有する反応性樹脂
を含む組成物が提供される。
式中:
R4の各々は独立して、水素、または1から8の炭素原子、より特定的には1から6の炭素原子のアルキル基、7から12の炭素原子、より特定的には7から10の炭素原子のフェニル基またはアラルキルまたはアレーニル基;
R5の各々は1から12の炭素原子の二価の有機基または化学結合;
G1は1から2,000の炭素原子を含む二価または多価の有機基;そしてbは2から8の整数である。
式中zは0から12の整数;
式中zは0から12の整数;
式中Eは水素または式(IV)の基
に対する結合;そしてzは0から12の整数;
式中Eは水素または(IV)の基
に対する結合;そしてzは0から12の整数;
式中R6の各々は独立して水素またはメチル、好ましくは水素;
式中G2は1から2,000の炭素原子を含有する二価または多価の有機基であり、但しH2C=C(R6)C(=O)O-基の酸素はG2基の炭素原子に結合し;そして
式中dは2から8の整数である。
式中R3は水素またはメチル、好ましくは水素、G3は独立してパラフェニレンまたは二価のシクロヘキシル基、そしてkは1から10の整数である。ビスフェノールジグリシジルエーテルポリマーの(メタ)アクリレートは、ビスフェノールA、ビスフェノールF、およびビスフェノールSのジグリシジルエーテルポリマーのアクリレートを含み、そして特にkは5未満である。好ましくは、数平均分子量は400と3,000の間にある。
式中R6は水素またはメチル、R7は2から6の炭素原子のアルキレン基、R8は水素または1から12の炭素原子を有するアルキル基、Arは6から10の炭素原子を有する二価の芳香族基、そしてlは0から12の整数;
式中R6は水素またはメチル、R7は2から6の炭素原子のアルキレン基、そしてmは1から8の整数;および
式中R6は水素またはメチル、R7は2から6の炭素原子のアルキレン基;R9は独立して水素またはメチル、そしてmは1から8の整数である。
式中R6は水素原子またはメチル基を表し、G4は2から6の炭素原子、好ましくは2から4の炭素原子を有するアルキレン基、フェニレン基、ビフェニレン基、ナフチレン基のような二価の基を表し、pは独立して1から10、好ましくは1から5の整数、そしてqは独立して1から10、好ましくは1から5の整数である。
式中R9およびR10は独立して1から5の炭素原子を有するアルキル基を表し、Arはフェニレン基、ビフェニレン基、ナフチレン基その他のような6から10の炭素原子を有する二価の芳香族基を表し、そしてqは2から50、好ましくは2から20の整数を示す。
に対するモル当量比を0.001から15まで、より特定的には0.002から1、さらにより特定的には0.1から1の範囲で、または少なくとも一つの(メタ)アクリレート官能基を有する反応性樹脂(b)と、0.001から15まで、より特定的には0.002から1、さらにより特定的には0.1から1の範囲で反応させることによって形成される。
ここでAは-OR3、-OCR2 2(CR2 2)fCR2 2OHまたは
BはHまたは
式中Zの各々は独立して-OR3、-OCR2 2(CR2 2)fCR2 2OH、
からなる群より選択され、
式中R1の各々は、1から10の炭素原子を有するアルキレン、5から12の炭素原子を有するシクロアルキレン、フェニレン、および6から10の炭素原子を有するアラルキルからなる群より独立して選択される二価の基;
式中R2の各々は、1から4の炭素原子を有するアルキルおよび水素からなる群より独立して選択される一価の基;
式中R3の各々は、水素、1から12の炭素原子を有するアルキル、5から12の炭素原子を有するシクロアルキル、フェニルおよびベンジルからなる群より独立して選択され;
式中下付文字fの各々は、独立して0から4の整数;および
式中下付文字nは0から15の整数であり、但しnが0のとき、Bは
であり、そして
Q1の各々は水素、
式中R4、R5、R6、G1、G2、bおよびdの各々は上記で定義した前述の意味のいずれかを有し、そして少なくとも一つのQ1は
式中R4、R5、R6、G1、G2、bおよびdの各々は上記で定義した前述の意味のいずれかを有し、そしてQ2は
であり、式中Aは-OR3、-OCR2 2(CR2 2)fCR2 2OH、または
BはH、または
Zの各々は独立して-OR3、-OCR2 2(CR2 2)fCR2 2OH、
からなる群より選択され、
R1の各々は、1から10の炭素原子を有するアルキレン、5から12の炭素原子を有するシクロアルキレン、フェニレン、および6から10の炭素原子を有するアラルキルからなる群より独立して選択される二価の基;
R2の各々は、1から4の炭素原子を有するアルキルおよび水素からなる群より独立して選択される一価の基;
R3の各々は、水素、1から12の炭素原子を有するアルキル、5から12の炭素原子を有するシクロアルキル、フェニルおよびベンジルからなる群より独立して選択され;
E1は水素または硫黄原子と炭素原子の間の化学結合;
下付文字fの各々は、独立して0から4の整数;
下付文字nは0から15の整数、n1は2から15の整数であり、但し(i)nが0のときBは
であり、そして(ii)Q2についての構造中の一つのE1のみが化学結合である。
であり、式中R1、R2およびfは上記で定義したいずれかの意味を有し、そしてE1は硫黄原子と炭素原子の間の化学結合である。
であり、式中Aは-OR3または-OCR2 2(CR2 2)fCR2 2OH、Bは水素、Zは-OR3または-OCR2 2(CR2 2)fCR2 2OH、E1は化学結合、およびnは1であり、より好ましくはAが-OCR2 2(CR2 2)fCR2 2OHのときZは-OCR2 2(CR2 2)fCR2 2OHである。
であり、式中R1の各々は独立して-CH2-、-CH2CH2-または-CH2CH2CH2-;R2の各々は独立して水素またはメチル;R4は水素またはメチル、R5は化学結合、または-C(=O)-、-C(=O)O-、-CcH2c-または-CcH2cO-基であり、ここで下付文字cは1から4の整数、有利には1;G1は上記に前述したいずれかの意味を有し;そしてbおよびfは整数であって、bは2から8そしてfは0または1である。
a)薄膜反応器において、メルカプト官能性アルコキシシラン、ジオール、および触媒を含む薄膜反応媒体を反応させ、ジオール由来のメルカプト官能性シランおよびアルコール副生物をもたらし;
b)薄膜からアルコール副生物を蒸発させて反応を推進し;
c)式(I)のメルカプト官能性ケイ素化合物反応生成物を回収し;
d)任意選択的に、アルコール副生物を凝縮により回収し;および
e)任意選択的に、式(I)のメルカプト官能性ケイ素化合物生成物を中和して、その貯蔵安定性を改善する。
5リットルの丸底フラスコ中に、1190グラムの3-メルカプトプロピルトリエトキシシラン(Momentive PerformanceMaterials社から受け取った商品名Silquest登録商標A-1891のシラン)および1.27グラムの硫酸(500ppm)を入れた。フラスコは8キロパスカルの真空下に置き、50℃に加熱した。その撹拌混合物中に、添加漏斗を使用し3時間をかけて、1350グラムの2-メチル-1,3-プロパンジオールを滴下した。この混合物は、受器に材料が追加収集されなくなるまでストリッピングした。この撹拌混合物中に、エタノール中21%のナトリウムエトキシドを4.1グラム添加して、混合物を中和した。必要であれば追加のナトリウムエトキシドを添加して、pHを6.0と6.5の間とした。フラスコを高真空下に置いて、残存するすべてのエタノールを除去し、次いで混合物を室温まで放冷した。50グラムのセライト(Celite)を添加して混合物を20〜30分間撹拌し、次いで30マイクロメートルのフィルターパッドを介して濾過した。
試験に用いた基材は、ACT Test Panels社から入手可能な冷間圧延スチールAPR10184基材であった。
Cowles破砕ブレードを備えたミキサーにしっかりと固定された400mLのプラスチック製トリコーナービーカーに、顔料、樹脂、および溶媒、78.45グラムのn-ブチルアセテート溶媒(Aldrich社から入手)、31.68グラムのEpon 1001Fおよび60.72グラムのEpon 828樹脂(いずれもHexion/MSC社から入手)を破砕するため、250グラムの酸化ジルコニウム(ZrO)ビーズを入れた。ミキサーを高速に設定し、CowlesミルがすべてのEpon 1001F固体フレークを溶液中に十分に溶解するまで破砕した。
エポキシ樹脂混合物とアミン硬化剤を別個に調製した。
エポキシ樹脂混合物とアミン硬化剤を別個に調製した。
エポキシ樹脂混合物とアミン硬化剤を別個に調製した。
エポキシ樹脂混合物とアミン硬化剤を別個に調製した。
エポキシ樹脂混合物とアミン硬化剤を別個に調製した。
プライマーは、白色の単層被覆(モノコート)トップコートでコーティングするに先立ち、大気硬化条件の下で、24時間以上硬化した。
プライマーを大気条件下で24時間以上硬化した後、これらのプライマーは大気条件下または-25℃の温度条件下のいずれかにおいて、3日間以上、但し10日間以下の時間間隔を置くように調整した。
1)大気硬化、3日後にトップコート
2)-25℃で冷凍調整、3日後にトップコート
3)大気硬化、10日後にトップコート
-25℃で冷凍調整、10日後にトップコート。
以下は、プライマーの実施例4および5ならびに比較例I、IIおよびIII上に塗布された白色トップコートの処方に用いた例である。
プライマーは、白色のモノコートのトップコートでコーティングするに先立ち、大気硬化条件の下で、24時間以上硬化した。
プライマーを大気条件下で24時間以上硬化した後、これらのプライマーは大気条件下または-25℃の温度条件下のいずれかにおいて、3日間以上、但し10日間以下の時間間隔を置くように調整した。
4)大気硬化、3日後にトップコート
5)-25℃で冷凍調整、3日後にトップコート
6)大気硬化、10日後にトップコート
7)-25℃で冷凍調整、10日後にトップコート。
次いで実施例8Fの白色モノコートを、実施例11で列挙した時間に基づいて、2インチ×2インチの正方形に切断されている多数のプライミングされたパネル上にスプレー塗布して、白色トップコートでオーバーコートした。白色トップコートのスプレー塗布は、DeVilbiss社から入手可能なStartingLine HVLP重力供給式サイホン噴霧ハンドスプレーガンを用いて行った。コーティングは、25lb/in2の壁圧で噴霧した。このスプレー塗布技術は、おおよそ3.7ミルの厚みの乾燥白色トップコートコーティングがパネル上に塗布されるまで、おおよそ1,000インチ/分の速度でパネル上にスプレーを左右に掃引し、掃引当たりにパネルを上下におおよそ2インチずつ間欠的に移動させるものであった。
パネルが白色トップコートでコーティングされたら、次いでコーティング系を大気条件下で少なくとも24時間硬化した。その後、接着試験の前少なくとも一週間、パネルを-25℃の冷凍庫に入れ、または大気条件下で調整(コンディショニング)した。
パネルにクロスカット工具で切り込みを入れた後に破壊が生じた場合を除き、3M898テープを用いた2回のテープ引き剥がしの後に、ASTM3359方法Bの接着結果を報告した。接着試験用のゴバン目は2mm×2mmであった。
材料は50mLのプラスチック製ビーカー中で混合した。これらの材料は表5に示す添加順序で添加した。すべての材料がプラスチック製ビーカー中に添加されたら、ビーカー内にフィットする小型のブレードを用いて材料のブレンドを撹拌した。試料は、成分が共に完全にブレンドされるまで混合した。
2Silquest A-1100はMomentive Performance Materials社から入手したガンマ-アミノプロピルトリエトキシシラン
3DBTDL=Aldrich社から入手したジブチルスズジラウレート
4Epikure 3253は、MomentiveSpecialty Chemicals社から入手した三級アミン触媒
5乾燥時間の結果は、英国サリーGU5 9LJゴンシャルギルドフォードのMickle Laboratory Engineering Groupから入手可能なB.K.乾燥レコーダーを使用して得た
マグネチックス撹拌バー、水凝縮器(真空ポンプに接続)、滴下漏斗、内部温度計、および加熱マントルを備えた250mLの丸底フラスコに、122.2グラムの3-(トリエトキシシリル)-1-プロパンチオール(98.5%、0.505モル)、111mgのパラトルエンスルホン酸、および61.02グラムの2-メチル-2,4-ペンタンジオール(99%、0.511モル)を仕込んだ。この反応フラスコの内容物を33℃に加熱し、形成されたエタノールを除去するために真空(11mmHg)を適用した。2時間後に温度を60℃に上昇させて、反応を完了させ、残存するエタノールを除去した。2時間後に温度を60℃に上昇させて、反応を完了させ、残存するエタノールを除去した。135.6グラムの3-(2-メチル-2,4-ペンタンジオキシエトキシシリル)-1-プロパンチオール生成物(純度84%、0.431モル、収率99.2%)が得られた。
Claims (26)
- 組成物であって:
(a)一般式(I)を有する少なくとも一つのメルカプト官能性ケイ素化合物:
式中Aは-OR3、-OCR2 2(CR2 2)fCR2 2OH、または
BはH、または
式中Zの各々は独立して-OR3、-OCR2 2(CR2 2)fCR2 2OH、
からなる群より選択され、
式中R1の各々は、1から10の炭素原子を有するアルキレン、5から12の炭素原子を有するシクロアルキレン、フェニレン、および6から10の炭素原子を有するアラルキルからなる群より独立して選択される二価の基;
式中R2の各々は、1から4の炭素原子を有するアルキルおよび水素からなる群より独立して選択される一価の基;
式中R3の各々は、水素、1から12の炭素原子を有するアルキル、5から12の炭素原子を有するシクロアルキル、フェニル、およびベンジルからなる群より独立して選択され;
式中下付文字fの各々は、独立して0から4の整数;そして
式中下付文字nは0から15の整数、但しnが0のとき、Bは
および/または一般式(II):
を有する部分加水分解物またはその縮合物であり
式中A、B、R1およびZは上記に定義されており下付文字n1は2から15の整数;
(b)少なくとも一つのエポキシ基および/または少なくとも一つの(メタ)アクリレート基を有する反応性樹脂
を含む組成物。 - R1が-CH2-、-CH2CH2-、-CH2CH2CH2-、-CH2CH(CH3)CH2-、または-CH2CH(CH3)CH2CH2-からなる群より選択され、R2が水素、-CH3または-CH2CH3であり、fが0または1であり;そしてnが0、1、2または3である、請求項1の組成物。
- R1が-CH2CH2CH2-;R2が水素または-CH3から選択され;fが1;そしてnが0または1である、請求項1の組成物。
- 反応性樹脂成分(b)が、分子当たり少なくとも一つの1,2-エポキシ基と約100から約2,000グラム当量のエポキシド当量重量を有する少なくとも一つの有機化合物である、請求項1の組成物。
- 反応性樹脂成分(b)が、分子当たり少なくとも一つの(メタ)アクリレート基と約100から約12,000の範囲にある数平均分子量を有する有機化合物または有機化合物の混合物である、請求項1の組成物。
- さらに(c)硬化剤を含む、請求項1の組成物。
- 硬化剤(c)が、紫外放射線、ガンマ放射線、触媒、硬化架橋剤、およびこれらの組み合わせからなる群より選択される、請求項9の組成物。
- 反応性樹脂(b)がエポキシ樹脂であり、硬化剤(c)がジメチルプロピルアミン、ジメチルフェニルアミン、トリエチルアミンおよびこれらの組み合わせからなる群より選択される三級アミン触媒である、請求項9の組成物。
- 反応性樹脂(b)がエポキシ樹脂であり、硬化剤が(c)硬化架橋剤である、請求項9の組成物。
- 硬化架橋剤が、脂肪族第一級アミン、芳香族第一級アミン、脂肪族第二級アミン、芳香族第二級アミン、脂肪族第一級ポリアミン、芳香族第一級ポリアミン、脂肪族第二級ポリアミン、芳香族第二級ポリアミン、ポリアミド、アミドアミン、ケチミン、アルジミン、メルカプタン、イソシアネート、メラミンホルムアルデヒド樹脂、尿素ホルムアルデヒド樹脂、フェノールホルムアルデヒド樹脂、カルボン酸、カルボン酸無水物、またはこれらの組み合わせからなる群より選択される、請求項12の組成物。
- 反応性樹脂(b)が(メタ)アクリレート樹脂であり、硬化剤(c)が放射線活性開始剤と組み合わせての放射線である、請求項9の組成物。
- 請求項1の組成物を含む、成分(a)および(b)の反応生成物を含有するシリル化樹脂。
- 一般式(XII)〜(XIII)を有し:
式中Aは-OR3、-OCR2 2(CR2 2)fCR2 2OHまたは
BはHまたは
式中Zの各々は独立して-OR3、-OCR2 2(CR2 2)fCR2 2OH、
からなる群より選択され、
式中R1の各々は、1から10の炭素原子を有するアルキレン、5から12の炭素原子を有するシクロアルキレン、フェニレン、および6から10の炭素原子を有するアラルキルからなる群より独立して選択される二価の基;
式中R2の各々は、1から4の炭素原子を有するアルキルおよび水素からなる群より独立して選択される一価の基;
式中R3の各々は、水素、1から12の炭素原子を有するアルキル、5から12の炭素原子を有するシクロアルキル、フェニル、およびベンジルからなる群より独立して選択され;
式中下付文字fは独立して0から4の整数;
式中下付文字n1は2から15の整数;そして
式中下付文字nは0から15の整数、但しnが0のとき、Bは
であり、そして
Q1の各々は水素、
式中R4の各々は独立して、水素、または1から8の炭素原子のアルキル基、フェニル基、または7から12の炭素原子のアラルキルまたはアレーニル基;
式中R5の各々は1から12の炭素原子の二価の有機基または化学結合;
式中R6の各々は水素またはメチル、
式中G1は1から2,000の炭素原子を含有する二価または多価の有機基;
式中G2は1から2,000の炭素原子を含有する二価または多価の有機基、但しH2C=C(R6)C(=O)O-基の酸素はG2基の炭素原子に結合され;
式中bは2から8の整数、および
式中dは2から8の整数、但し少なくとも一つのQ1は
である、請求項15のシリル化樹脂。 - シリル化樹脂が一般式(XIV)〜(XV)を有し:
ここで式中R4の各々は独立して、水素、1から8の炭素原子、より特定的には1から6の炭素原子のアルキル基、フェニル基、または7から12の炭素原子、より特定的には7から10の炭素原子のアラルキルまたはアレーニル基;
式中R5の各々は1から12の炭素原子の二価の有機基または化学結合;
式中R6の各々は水素またはメチル、
式中G1は1から2,000の炭素原子を含有する二価または多価の有機基;
式中G2は1から2,000の炭素原子を含有する二価または多価の有機基、但し-CH2-CH(R6)C(=O)O-基の酸素はG2基の炭素原子に結合し;
式中bは2から8の整数、そして
式中dは2から8の整数であり、
またここでQ2の各々は独立して
式中Aは-OR3、-OCR2 2(CR2 2)fCR2 2OHまたは
BはHまたは
式中Zの各々は-OR3、-OCR2 2(CR2 2)fCR2 2OH、
からなる群より独立して選択され、
式中R1の各々は、1から10の炭素原子を有するアルキレン、5から12の炭素原子を有するシクロアルキレン、フェニレン、および6から10の炭素原子を有するアラルキルからなる群より独立して選択される二価の基;
式中R2の各々は、1から4の炭素原子を有するアルキルおよび水素からなる群より独立して選択される一価の基;
式中R3の各々は、水素、1から12の炭素原子を有するアルキル、5から12の炭素原子を有するシクロアルキル、フェニル、およびベンジルからなる群より独立して選択され;
式中E1は水素または硫黄原子と炭素原子の間の化学結合;
式中下付文字fの各々は独立して0から4の整数;
式中下付文字nは0から15の整数、n1は2から15の整数、但し(i)nが0のとき、Bは
であり、(ii)Q2についての構造中の一つのE1のみが化学結合である、請求項15のシリル化樹脂。 - Q2がA-Bであり、ここでAは-OR3、-OCR2 2(CR2 2)fCR2 2OHそしてBは
であり、式中R1の各々は、1から10の炭素原子を有するアルキレン、5から12の炭素原子を有するシクロアルキレン、フェニレン、および6から10の炭素原子を有するアラルキルからなる群より独立して選択される二価の基;
式中R2の各々は、1から4の炭素原子を有するアルキルおよび水素からなる群より独立して選択される一価の基;
式中R3の各々は、水素、1から12の炭素原子を有するアルキル、5から12の炭素原子を有するシクロアルキル、フェニルおよびベンジルからなる群より独立して選択され;
式中E1は水素または硫黄原子と炭素原子の間の化学結合;
式中下付文字fの各々は独立して0から4の整数である、請求項17のシリル化樹脂。 - さらにフィラーを含有する、請求項1の組成物。
- 請求項1の組成物を含有するコーティング。
- 請求項1の組成物を含有するシーラント。
- 請求項15のシリル化樹脂を含有するコーティング組成物。
- 請求項15のシリル化樹脂を含有するシーラント組成物。
- 請求項1の組成物を含有するプライマー。
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