JP2022514570A - シリコーン-ポリアクリレートコポリマー、それを含むシーラント、および関連する方法 - Google Patents
シリコーン-ポリアクリレートコポリマー、それを含むシーラント、および関連する方法 Download PDFInfo
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- JP2022514570A JP2022514570A JP2021535045A JP2021535045A JP2022514570A JP 2022514570 A JP2022514570 A JP 2022514570A JP 2021535045 A JP2021535045 A JP 2021535045A JP 2021535045 A JP2021535045 A JP 2021535045A JP 2022514570 A JP2022514570 A JP 2022514570A
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- silicone
- polyacrylate
- sealant
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- UBMUZYGBAGFCDF-UHFFFAOYSA-N trimethoxy(2-phenylethyl)silane Chemical compound CO[Si](OC)(OC)CCC1=CC=CC=C1 UBMUZYGBAGFCDF-UHFFFAOYSA-N 0.000 description 1
- JCGDCINCKDQXDX-UHFFFAOYSA-N trimethoxy(2-trimethoxysilylethyl)silane Chemical compound CO[Si](OC)(OC)CC[Si](OC)(OC)OC JCGDCINCKDQXDX-UHFFFAOYSA-N 0.000 description 1
- NMEPHPOFYLLFTK-UHFFFAOYSA-N trimethoxy(octyl)silane Chemical compound CCCCCCCC[Si](OC)(OC)OC NMEPHPOFYLLFTK-UHFFFAOYSA-N 0.000 description 1
- LFRDHGNFBLIJIY-UHFFFAOYSA-N trimethoxy(prop-2-enyl)silane Chemical compound CO[Si](OC)(OC)CC=C LFRDHGNFBLIJIY-UHFFFAOYSA-N 0.000 description 1
- AXNJHBYHBDPTQF-UHFFFAOYSA-N trimethoxy(tetradecyl)silane Chemical compound CCCCCCCCCCCCCC[Si](OC)(OC)OC AXNJHBYHBDPTQF-UHFFFAOYSA-N 0.000 description 1
- ASEGJSMHCHEQSA-UHFFFAOYSA-N trimethoxy(undec-10-enyl)silane Chemical compound CO[Si](OC)(OC)CCCCCCCCCC=C ASEGJSMHCHEQSA-UHFFFAOYSA-N 0.000 description 1
- MAFQBSQRZKWGGE-UHFFFAOYSA-N trimethoxy-[2-[4-(2-trimethoxysilylethyl)phenyl]ethyl]silane Chemical compound CO[Si](OC)(OC)CCC1=CC=C(CC[Si](OC)(OC)OC)C=C1 MAFQBSQRZKWGGE-UHFFFAOYSA-N 0.000 description 1
- SCRSFLUHMDMRFP-UHFFFAOYSA-N trimethyl-(methyl-octyl-trimethylsilyloxysilyl)oxysilane Chemical compound CCCCCCCC[Si](C)(O[Si](C)(C)C)O[Si](C)(C)C SCRSFLUHMDMRFP-UHFFFAOYSA-N 0.000 description 1
- LAGQNGWYNLUQRI-UHFFFAOYSA-N trioctylmethylammonium bis(trifluoromethylsulfonyl)imide Chemical compound FC(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F.CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC LAGQNGWYNLUQRI-UHFFFAOYSA-N 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- HQUQLFOMPYWACS-UHFFFAOYSA-N tris(2-chloroethyl) phosphate Chemical compound ClCCOP(=O)(OCCCl)OCCCl HQUQLFOMPYWACS-UHFFFAOYSA-N 0.000 description 1
- 239000002383 tung oil Substances 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
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Abstract
Description
本出願は、2018年12月21日に出願された米国仮特許出願第62/783,703号の優先権および全ての利点を主張し、その内容は参照により本明細書に組み込まれる。
ヒドロキシル官能性中間体
乾燥した4つ口フラスコを温度制御された発熱ブロック内に配置し、機械式撹拌機、温度計、滴下漏斗、および還流冷却器を取り付ける。フラスコをN2でパージし、1つの末端不飽和基および1つの末端ヒドロキシル基を有する有機化合物(ポリエステル化合物、750.0g、0.94モル)をその中に入れる。フラスコを加熱し、断続的なN2パージとともに真空下で2~3時間105℃に保持する。次いで、フラスコを85℃に冷却する。ヒドロシリル化触媒を追加した(5ppm、MMに溶解した0-0719の1重量%溶液)。エンドキャッピング有機ケイ素化合物(ETM、200.0g、0.71モル)を滴加する。温度が5~10℃上昇する断熱発熱が観察され、それに応じてエンドキャッピング有機ケイ素化合物の添加を調整することにより、反応温度を85℃に維持する。反応が完了したと見なされるまで(約5時間)、すなわち、検出可能なSiH濃度(FTIRまたは1H NMRによる)が2.5ppmを下回るまで、フラスコを85℃に加熱して保持する。次いで、フラスコの内容物を室温まで冷却し、N2流下でナルゲン容器に封入する。完成した材料は、ヒドロキシル官能性中間体と称する。
乾燥した4つ口フラスコを温度制御された発熱ブロック内に配置し、機械式撹拌機、温度計、滴下漏斗、および還流冷却器を取り付ける。次いで、フラスコに、ヒドロキシル官能性中間体(369.2g)、反応完了時に約2.5~3.00重量%の残留NCOを目標とする量で使用されるポリイソシアネート(IPDI、75.6g)、T-9(0.02g)を充填して、ブレンドを生成し、次いで、それを均一な混合物が得られるまで撹拌した。反応が完了したと見なされるまで(約2時間)、すなわち、目標の%NCOに到達するまで(IRで測定した場合)、混合物を80℃に加熱し保持する。次いで、混合物を室温に冷却して、イソシアネート官能性中間体を得る。
イソシアネート官能性中間体(49.2g)を含む4つ口フラスコに、ポリアクリレート化合物(155.8g、EtAcに溶解させた)を充填し、40℃に加熱する。次いで、フラスコにT-12(0.04g)を充填し、反応が完了したと見なされるまで(約10時間)、すなわち、FTIRでNCOが検出されなくなるまで、70℃に加熱して保持する。完了したら、反応混合物を冷却し、一口丸底フラスコに移し、真空下で揮発性物質をストリップする(回転蒸発器、80℃)。次いで、フラスコの内容物を室温まで冷却し、N2流下でナルゲン容器に封入する。完成した材料は、シリコーン-ポリアクリレートコポリマーと称する。
硬化生成物
実施例1のシリコーン-ポリアクリレートコポリマー30gを、80℃のオーブン内のポリプロピレン製歯科用カップ中で30分間温める。次いで、0.03gのDBTDLおよび0.15gのZ-6020を添加した。混合物を、FlackTek Speed Mixer DAC 150.1 FVZを用いて、3500rpmで1分間混合する。次いで、混合物を、サイズが15cm×15cm、深さが2mmのテフロン型にキャストする。次いで、キャストプレートを、環境管理された部屋(相対湿度50%および25℃)に保管し、7日間硬化させる。
ドッグボーン試験片(全長5cm、ネック長2cm)は、引張試験用に炭素鋼ダイを使用して硬化生成物から切り出される(打ち抜かれる)。次いで、そのドッグボーン試験片の引張特性を分析する。試験には、全容量100Nのロードセルを備えたMTS試験フレームを使用する。試験速度は、50.8cm/分である。歪みは、狭いネック部の長さにわたる変位として計算した。破断での応力は、ピーク応力を狭いネック部領域の初期断面積で割ることにより計算する。硬化生成物を、60℃または80℃の加熱空気循環オーブンで一定時間エージングし、引張試験を行って安定性を測定する。
示差走査熱量測定(DSC)のために、硬化生成物から小片を切り出す。DSCは、TA Instrument Discovery Series DSC2500を使用して実施する。試料をTzeroアルミニウムパンに量り入れ(約10mgの試料)、機器で分析する。温度は、最初に-180℃まで下げ(10℃/分で)、次いで200℃まで上げる(10℃/分で)。ランピングプロセスに追随していくために必要な熱を記録し、Tgは、熱容量の急激な変化として検出される。
タックフリータイムは、ASTM D5895に準拠したコーティング用のGardco BK 6トラック乾燥タイムレコーダーを使用し、厚さ150マイクロメートル、幅12mmのコーティング層をアルミニウムストリップ上にコーティングし、針の頂部に5gの重りを付けてコーティング層に針を置き、その針をコーティングを通過させながらドラッグする。そのトラックを一定時間放置した後に観察し、タックフリータイムを決める。
硬度は、Zwick Roell硬度テスターによって12.5Nの力を加えて測定する。OOスケールを利用する。
実施例3は、実施例1のシリコーン-ポリアクリレートコポリマーを利用する。配合する前に、Z-6020とDBTDLとのプレミックス溶液を、1オンスのガラスバイアル中で組み合わせる。この溶液を、明澄なストロー溶液(straw solution)が得られるまで、手動で振盪し、後に使用するために取っておく。シリコーン-ポリカーボネートポリマーを、流動性が得られるまで70℃のオーブンで温める。混合プロセス中の任意の時点で、シリコーン-ポリアクリレートコポリマーが冷却されるにつれて材料が増粘し始めた場合、2000rpmで30秒の追加の混合ステップを実施する。DAC 600.2 VAC SpeedMixerで使用するために設計された最大300の長い混合ジャーを天秤に配置し、風袋引きし、次いでシリコーン-ポリアクリレートコポリマー、DINP、およびVTMを添加する。これを800rpmで30秒間混合し、次いで1500rpmで30秒間混合する。次いで、CCを、混合ジャーに追加し、800rpmで30秒間混合し、ミキサーから取り出し、ジャーを手でこそぎ落とし、再度挿入して、1500rpmでさらに30秒間混合する。この混合ステップの後、CS-11を混合ジャーに量り入れ、ジャーをミキサーに戻し、1300rpmで30秒間混合する。次いで、ジャーを取り外し、手でこそぎ落して充填剤の粒子を再び取り込み、次いでミキサーに戻し、2000rpmで30秒間混合する。充填剤を組み込んだ後、予め調製しておいたプレミックス溶液を混合ジャーに添加し、次いで1300rpmで30秒間混合した後、ジャーを取り外し、手でこそぎ落とす。最後に、ジャーの蓋を中央に穴を有するものに交換して、閉じ込められた空気または揮発性物質を真空ステップのために混合ジャーから逃がす。最終の混合ステップを、次のプログラムに従って真空で実施する:すなわち、3.5psiの真空まで800rpmで37秒間の混合、3.5psiの真空を保持しながら1300rpmで40秒間の混合、および800rpmで35秒間混合して周囲の実験室条件まで真空を破壊する。次いで、シーラント混合物を、SEMCOカートリッジにパッケージし、試験のために取っておく。
実施例3の物性および硬化特性を、以下のそれぞれの手順に従って評価する。
Claims (24)
- 式Xg[ZjYo]cを有するシリコーン-ポリアクリレートコポリマーであって、式中、各Xが独立して、式(I)または(II)のうちの1つを有するシリコーン部分であり、
各R1が、1~18個の炭素原子を有する独立して選択される置換または非置換ヒドロカルビル基であり、各R2が、1~18個の炭素原子を有する独立して選択される置換または非置換ヒドロカルビル基であり、各D1が、2~18個の炭素原子を有する独立して選択される二価の炭化水素基であり、各下付き文字aが独立して、0~2から選択され、各下付き文字bが独立して、0または1であり、下付き文字cが、1~150であり、各下付き文字dが、1~1000であり、各下付き文字eが独立して、1または2であり、各下付き文字fが独立して、0または1であり、ただし、各X内において、fが1のとき、bは1であることを条件とし、下付き文字gが、>1であり、下付き文字hが独立して、下付き文字dによって示される各部分において0~2から選択され、各下付き文字jが独立して、≧0および<2であり、各下付き文字oが独立して、>0および<2であり、ただし、下付き文字cによって示される各部分においてj+o=2であることを条件とし、下付き文字tが、≧0であり、下付き文字uが、>0である、シリコーン-ポリアクリレートコポリマー。 - 前記シリコーン-ポリアクリレートコポリマーが、式:[XA]g[ZjYo]cを有し、式中、各シリコーン部分Xが、Aを介して、1つのポリアクリレート部分Yまたは1つのシロキサン部分Z(存在する場合)に結合され、各Aが独立して、共有結合、-D2-O-C(=O)-NH-、-D2-NH-C(=O)-NH-、-D2-NR3-CH2CH2C(=O)O-、および-D2-OC(=O)-CH2CH2NR3-から選択され、式中、D2が、二価の基であり、R3が、HまたはR1であり、R1が、上に定義される、請求項1に記載のシリコーン-ポリアクリレートコポリマー。
- jが、0であり、前記シリコーン-ポリアクリレートコポリマーが、式:X-A-Y1-A-Xを有し、式中、XおよびAが独立して選択され、かつ上に定義されており、Y1が、ポリアクリレート部分を含む、請求項2に記載のシリコーン-ポリアクリレートコポリマー。
- 少なくとも1つのYが、前記ポリアクリレート部分に加えて、かつ前記ポリアクリレート部分と異なる少なくとも1つの部分をさらに含む、請求項1~3のいずれか一項に記載のシリコーン-ポリアクリレートコポリマー。
- 前記部分が、アルキルアルミノキサン部分、アルキルゲルモキサン部分、ポリチオエステル部分、ポリエーテル部分、ポリチオエーテル部分、ポリエステル部分、ポリアクリロニトリル部分、ポリアクリルアミド部分、ポリカーボネート部分、エポキシ部分、ポリウレタン部分、ポリ尿素部分、ポリアセタール部分、ポリオレフィン部分、ポリビニルアルコール部分、ポリビニルエステル部分、ポリビニルエーテル部分、ポリビニルケトン部分、ポリイソブチレン部分、ポリクロロプレン部分、ポリイソプレン部分、ポリブタジエン部分、ポリビニリデン部分、ポリフルオロカーボン部分、ポリ塩素化炭化水素部分、ポリアルキン部分、ポリアミド部分、ポリイミド部分、ポリイミダゾール部分、ポリオキサゾール部分、ポリオキサジン部分、ポリオキシジアゾール部分、ポリチアゾール部分、ポリスルホン部分、ポリスルフィド部分、ポリケトン部分、ポリエーテルケトン部分、ポリ無水物部分、ポリアミン部分、ポリイミン部分、ポリホスファゼン部分、多糖部分、ポリペプチド部分、ポリイソシアネート部分、セルロース部分、およびそれらの組み合わせから選択される、請求項5に記載のシリコーン-ポリアクリレートコポリマー。
- (i)各R1が、メチルであり、(ii)各R2が、プロピルであり、(iii)各下付き文字aが、0であり、(iv)各D1が、C2H4であり、または(v)(i)~(iv)の任意の組み合わせである、請求項1~6のいずれか一項に記載のシリコーン-ポリアクリレートコポリマー。
- シリコーン-ポリアクリレートコポリマーを調製する方法であって、
ヒドロシリル化触媒の存在下で、平均して1超の不飽和基を有するポリアクリレート化合物とエンドキャッピング有機ケイ素化合物とを反応させて、前記シリコーン-ポリアクリレートコポリマーを得ることを含み、
前記シリコーン-ポリアクリレートコポリマーが、請求項1~7のいずれか一項に記載のシリコーン-ポリアクリレートコポリマーである、方法。 - 前記ポリアクリレート化合物および前記エンドキャッピング有機ケイ素化合物とともに、(i)鎖延長有機ケイ素化合物および(ii)平均して1超の不飽和基を有するハイブリダイズ化合物のうちの少なくとも1つを反応させることをさらに含む、請求項8に記載の方法。
- 前記ポリアクリレート化合物が、以下の式を有し、
Y[R4]i
式中、各R4が独立して、アクリレート基および2~14個の炭素原子を有する不飽和基から選択され、下付き文字iが、>1であり、Yが、ポリアクリレート部分である、請求項8または9に記載の方法。 - 前記鎖延長有機ケイ素化合物を反応させることをさらに含み、前記鎖延長有機ケイ素化合物が、(i)直鎖状水素化ケイ素官能性有機ケイ素化合物、(ii)分岐状水素化ケイ素官能性有機ケイ素化合物、または(iii)(i)および(ii)の両方を含む、請求項9または10に記載の方法。
- 請求項8~13のいずれか一項に記載の方法に従って調製されたシリコーン-ポリアクリレートコポリマー。
- シリコーン-ポリアクリレートコポリマーを調製する方法であって、
ヒドロシリル化触媒の存在下で、1つの末端不飽和基および1つの末端ヒドロキシル基を有する有機化合物を、エンドキャッピング有機ケイ素化合物と反応させて、ヒドロキシル官能性中間体を得ることと、
前記ヒドロキシル官能性中間体をポリイソシアネートと反応させて、イソシアネート官能性中間体を得ることと、
前記イソシアネート官能性中間体と、平均して1超のヒドロキシル基を有するポリアクリレート化合物と、任意に、平均して1超のヒドロキシル基を有するポリシロキサンとを反応させて、前記シリコーン-ポリアクリレートコポリマーを得ることと、を含み、
前記シリコーン-ポリアクリレートコポリマーが、請求項1~7のいずれか一項に記載のシリコーン-ポリアクリレートコポリマーである、方法。 - 請求項15または16に記載の方法に従って調製されたシリコーン-ポリアクリレートコポリマー。
- シーラントであって、
シリコーン-ポリアクリレートコポリマーと、
縮合反応触媒と、を含み、
前記シリコーン-ポリアクリレートコポリマーが、請求項1~8、14、および17のいずれか一項に記載のシリコーン-ポリアクリレートコポリマーである、シーラント。 - (i)充填剤、(ii)充填処理剤、(iii)架橋剤、(iv)表面改質剤、(v)乾燥剤、(vi)増量剤、(vii)殺生物剤、(viii)難燃剤、(ix)可塑剤、(x)末端遮断剤、(xi)接合剤、(xii)老化防止添加剤、(xiii)水放出剤、(xiv)顔料、(xv)レオロジー調整剤、(xvii)担体、(xii)粘着付与剤、(xiii)腐食阻害剤、(xix)触媒阻害剤、(xx)接着促進剤、(xxi)粘度調整剤、(xxii)UV吸収剤、(xxiii)抗酸化剤、(xxiv)光安定剤、または(xxv)(i)~(xxiv)の組み合わせをさらに含む、請求項18に記載のシーラント。
- 前記シーラントが、前記充填剤、前記架橋剤、前記増量剤、前記可塑剤、および前記接着促進剤を含む、請求項19に記載のシーラント。
- 請求項18~20のいずれか一項に記載のシーラントの硬化生成物。
- 基材と、前記基材上に配置された請求項21に記載の硬化生成物と、を含む複合物品。
- 複合物品を調製する方法であって、
基材上にシーラントを配置することと、
前記シーラントを硬化させて、前記基材上の硬化生成物を得、それにより前記複合物品を形成することと、を含み、
前記シーラントが、請求項18~20のいずれか一項に記載のシーラントである、方法。 - 2つの要素間に画定された空間を封止する方法であって、
前記空間にシーラントを適用することと、
前記空間内の前記シーラントを硬化させ、それにより前記空間を封止することと、を含み、
前記シーラントが、請求項18~20のいずれか一項に記載のシーラントである、方法。
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