JP7076644B2 - シリコーン-ポリエステルコポリマー、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-ポリエステルコポリマー、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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- JP7076644B2 JP7076644B2 JP2021531849A JP2021531849A JP7076644B2 JP 7076644 B2 JP7076644 B2 JP 7076644B2 JP 2021531849 A JP2021531849 A JP 2021531849A JP 2021531849 A JP2021531849 A JP 2021531849A JP 7076644 B2 JP7076644 B2 JP 7076644B2
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- polyester
- silicone
- sealant
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- 238000000034 method Methods 0.000 title claims description 86
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- 150000003961 organosilicon compounds Chemical class 0.000 claims description 50
- 125000004432 carbon atom Chemical group C* 0.000 claims description 47
- 238000006459 hydrosilylation reaction Methods 0.000 claims description 44
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- 239000003054 catalyst Substances 0.000 claims description 39
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- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 8
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- 229910019142 PO4 Inorganic materials 0.000 description 7
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 7
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/42—Block-or graft-polymers containing polysiloxane sequences
- C08G77/445—Block-or graft-polymers containing polysiloxane sequences containing polyester sequences
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/16—Catalysts
- C08G18/22—Catalysts containing metal compounds
- C08G18/24—Catalysts containing metal compounds of tin
- C08G18/244—Catalysts containing metal compounds of tin tin salts of carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/16—Catalysts
- C08G18/22—Catalysts containing metal compounds
- C08G18/24—Catalysts containing metal compounds of tin
- C08G18/244—Catalysts containing metal compounds of tin tin salts of carboxylic acids
- C08G18/246—Catalysts containing metal compounds of tin tin salts of carboxylic acids containing also tin-carbon bonds
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- C—CHEMISTRY; METALLURGY
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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62/783,697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。
各Yは、独立して選択されたポリエステル部分であり、各Zは、式[R1 hSiO(4-h)/2]dを有する、独立して選択されたシロキサン部分である。これらの部分では、各R1は、1~18個の炭素原子を有する独立して選択された置換または非置換ヒドロカルビル基であり、各R2は、1~18個の炭素原子を有する独立して選択された置換または非置換ヒドロカルビル基であり、各D1は、2~18個の炭素原子を有する独立して選択された二価の炭化水素基であり、各下付き文字aは、独立して0~2であり、各下付き文字bは、独立して0または1であり、下付き文字cは、1~150であり、各下付き文字dは、1~1000であり、各下付き文字eは、独立して1または2であり、各下付き文字fは、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であり、下付き文字gは、>1であり、下付き文字hは、下付き文字dによって示される各部分において0~2から独立して選択され、各下付き文字jは、独立して≧0かつ<2であり、各下付き文字oは、独立して>0かつ<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であり、下付き文字tは、≧0であり、下付き文字uは、>0である。
各Yは、独立して選択されたポリエステル部分であり、各Zは、式[R1 hSiO(4-h)/2]dを有する独立して選択されたシロキサン部分であり、式中、各R1は、1~18個の炭素原子を有する独立して選択された置換または非置換ヒドロカルビル基であり、各R2は、1~18個の炭素原子を有する独立して選択された置換または非置換ヒドロカルビル基であり、各D1は、2~18個の炭素原子を有する独立して選択された二価の炭化水素基であり、各下付き文字aは、独立して0~2であり、各下付き文字bは、独立して0または1であり、下付き文字cは、1~150であり、各下付き文字dは、1~1000であり、各下付き文字eは、独立して1または2であり、各下付き文字fは、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であり、下付き文字hは、下付き文字dによって示される各部分において0~2から独立して選択され、各下付き文字jは、独立して≧0かつ<2であり、各下付き文字oは、独立して>0かつ<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であり、下付き文字tは、≧0であり、下付き文字uは、>0である。
式中、各X、Y、Z、および下付き文字cは、上記で定義されている。これらの構造に示されるように、各シロキサン部分Zは、直鎖状か、または分岐状であり得る。特定の実施形態において、ポリエステル部分Yおよびシロキサン部分Zの両方が、分岐状であることができるため、シリコーン-ポリエステルコポリマーは、以下の構造のうちの1つを有し得る:
式中、各X、Y、Z、および下付き文字cは、上で定義されている。
式中、各X、Y、A、R1、下付き文字c、および下付き文字dは、上で定義されている。
式中、各R1は、上で定義されたとおりであり、下付き文字d’は、1~999である。
式中、各Y、R1、下付き文字c、および下付き文字dは、上で定義されたとおりである。したがって、利用されるシロキサンポリエステル化合物は、シリコーン-ポリエステルコポリマーの所望の構造に基づいて、例えば、分子量、各Yの特定の構造(すなわち、各Y内の単位)、下付き文字dによって表されるシロキサン単位の重合度などに基づいて選択され得る。
式中、R17は、水素原子または一価の有機基(例えば、4~15個の炭素原子、代替的に9~12個の炭素原子のアルキル基などの分岐状または直鎖状の一価の炭化水素基)を表す。これらまたは他の実施形態において、可塑剤は、平均して分子ごとに環状炭化水素における炭素原子に各々結合した上記の式の少なくとも2個の基を有する。かかる例において、可塑剤は以下の一般式を有し得る。
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、0.94mol)をその中に配置する。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℃に保つ。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、0.71mol)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℃に保つ。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、ブレンドを得、次いで、それを均一な混合物が取得されるまで撹拌した。反応が完了したと見なされるまで(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(118.1g)を含有する4つ口フラスコにポリエステル化合物(85.8g、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(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、シリコーンポリエステルコポリマーと称した。
硬化生成物
室温で固体である実施例1のシリコーン-ポリエステルコポリマー30gを、65℃のオーブン内のポリプロピレン製歯科用カップの中で2時間温める。次いで、0.03gのDBTDLおよび0.15gのZ-6020を添加して混合物を得る。その混合物を、FlackTek Speed Mixer DAC150.1 FVZを用いて、3500rpmで1分間混合する。次いで、その混合物を、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%、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用い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が分析される。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。ドッグボーン試験片はまた、60℃または80℃の加熱空気循環オーブンである特定の時間エージングし、引張試験を行ってその安定性を測定する。
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を用いて実行する。サンプルをTzeroアルミニウムパンに量り入れ(約10mgのサンプル)、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、ASTMD5895に準拠したコーティング用のGardco BK6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の重りを適用してコーティング層に針を配置し、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て、タックフリータイムを決定する。
実施例3は、実施例1のシリコーン-ポリエステルコポリマーを利用する。配合する前、プレミックス溶液0。Z-6020およびDBTDLを、1オンスのガラスバイアルにおいて組み合わせる。この溶液を、明澄なストロー溶液(straw solution)が取得されるまで、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-ポリエステルコポリマーは、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-ポリエステルコポリマーが冷却されるにつれてシリコーン-ポリエステルコポリマー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行する。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-ポリエステルコポリマー、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、混合ジャーに添加し、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任意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、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行する: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 (10)
- 式Xg[ZjYo]cを有するシリコーン-ポリエステルコポリマーであって、式中、各Xは、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は、1~18個の炭素原子を有する独立して選択された置換または非置換ヒドロカルビル基であり、各R2は、1~18個の炭素原子を有する独立して選択された置換または非置換ヒドロカルビル基であり、各D1は、2~18個の炭素原子を有する独立して選択された二価の炭化水素基であり、各下付き文字aは、独立して0~2から選択され、各下付き文字bは、独立して0または1であり、下付き文字cは、1~150であり、各下付き文字dは、1~1000であり、各下付き文字eは、独立して1または2であり、各下付き文字fは、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であり、下付き文字gは、>1であり、下付き文字hは、下付き文字dによって示される各部分において0~2から独立して選択され、各下付き文字jは、独立して≧0かつ<2であり、各下付き文字oは、独立して>0かつ<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であり、下付き文字tは、≧0であり、下付き文字uは、>0である、シリコーン-ポリエステルコポリマー。 - 式:[XA]g[ZjYo]cを有するシリコーン-ポリエステルコポリマーであって、式中、各Xは、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R 1 は、1~18個の炭素原子を有する独立して選択された置換または非置換ヒドロカルビル基であり、各R 2 は、1~18個の炭素原子を有する独立して選択された置換または非置換ヒドロカルビル基であり、各D 1 は、2~18個の炭素原子を有する独立して選択された二価の炭化水素基であり、各下付き文字aは、独立して0~2から選択され、各下付き文字bは、独立して0または1であり、下付き文字cは、1~150であり、各下付き文字dは、1~1000であり、各下付き文字eは、独立して1または2であり、各下付き文字fは、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であり、下付き文字gは、>1であり、下付き文字hは、下付き文字dによって示される各部分において0~2から独立して選択され、各下付き文字jは、独立して≧0かつ<2であり、各下付き文字oは、独立して>0かつ<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であり、下付き文字tは、≧0であり、下付き文字uは、>0であり、各シリコーン部分Xは、Aを介して、1つのポリエステル部分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は、独立して、-D2-O-C(=O)-NH-、および-D2-NH-C(=O)-NH-から選択され、式中、D2は、二価の基である、シリコーン-ポリエステルコポリマー。 - 少なくとも1つのYが、前記ポリエステル部分に加えて、かつ前記ポリエステル部分とは異なる、少なくとも1つの部分をさらに含み、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、ポリアクリレート部分、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、ポリビニリジエン部分、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、ポリエステルケトン部分、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1または2に記載のシリコーン-ポリエステルコポリマー。
- シリコーン-ポリエステルコポリマーを調製する方法であって、前記方法が、
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エステル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-ポリエステルコポリマーを得ることを含み、
前記シリコーン-ポリエステルコポリマーが、請求項1~4のいずれか一項に記載のシリコーン-ポリエステルコポリマーである、方法。 - シリコーン-ポリエステルコポリマーを調製する方法であって、前記方法が、
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エステル化合物とを反応させて、前記シリコーン-ポリエステルコポリマーを得ることと、を含み、
前記シリコーン-ポリエステルコポリマーが、請求項1~4のいずれか一項に記載のシリコーン-ポリエステルコポリマーである、方法。 - シーラントであって、
シリコーン-ポリエステルコポリマーと、
縮合反応触媒と、を含み、
前記シリコーン-ポリエステルコポリマーが、請求項1~4のいずれか一項に記載のシリコーン-ポリエステルコポリマーである、シーラント。 - 請求項7に記載のシーラントの硬化生成物。
- 複合物品を調製する方法であって、前記方法が、
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7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、前記方法が、
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7に記載のシーラントである、方法。
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