JP6835481B2 - 可視および赤外放射に対して透過性の複合材ならびに組成物ならびにその複合材を製造するための方法 - Google Patents
可視および赤外放射に対して透過性の複合材ならびに組成物ならびにその複合材を製造するための方法 Download PDFInfo
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- JP6835481B2 JP6835481B2 JP2016095887A JP2016095887A JP6835481B2 JP 6835481 B2 JP6835481 B2 JP 6835481B2 JP 2016095887 A JP2016095887 A JP 2016095887A JP 2016095887 A JP2016095887 A JP 2016095887A JP 6835481 B2 JP6835481 B2 JP 6835481B2
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- BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 description 1
- 238000003856 thermoforming Methods 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 150000003567 thiocyanates Chemical class 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- GWIKYPMLNBTJHR-UHFFFAOYSA-M thiosulfonate group Chemical group S(=S)(=O)[O-] GWIKYPMLNBTJHR-UHFFFAOYSA-M 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
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Description
R8、R9、R10、R11、R12およびR13は、水素、および末端ビニル基を有するアルケニル置換基から独立に選ばれ、ここで、R8、R9、R10、R11、R12およびR13のうちの少なくとも2つは水素ではなく;
R’はC2〜C10炭化水素架橋であり;
rは1〜10の範囲の整数であり;
mは約70mol%〜約90mol%の範囲であり;
nは0mol%〜約30mol%であり;
oは0mol%〜約30mol%であり;および
n+oは約10mol%〜約30mol%である。)の化合物にすることができる。
上の式6は、末端不飽和炭化水素モノマーの一例としてのポリブタジエンを示す。一例として、式6のポリブタジエンポリマーの重量平均分子量は、約1400〜約5200g/molの範囲を取ることができる。m、nおよびoの値をみて分かる通り、ポリブタジエンは、(「n」で示す)trans−1,4−ブタジエンの形態の約0mol%〜約30mol%のポリマー単位、および(「o」で示す)cis−1,4−ブタジエンの形態の約0mol%〜約30mol%のポリマー単位を含む。ポリブタジエンは、ポリマー上で末端ビニル分枝基を生じる単位の大部分(約70mol%〜約90mol%)を含む。
(式中、R20、R21、R22およびR23は、水素、C2〜C8末端不飽和アルケニル基およびC2〜C8末端不飽和アルキニル基から独立に選ぶことができて、ここで、R20、R21、R22およびR23のうちの2つ、3つまたは4つすべてが水素ではない。)の任意のモノマーが含まれる。一例として、アルケニル基およびアルキニル基は、内部の不飽和を持たず、末端炭素に位置するただ1つの二重または三重結合をそれぞれ有する直鎖炭化水素鎖基である。一例として、置換シランモノマーは、例えば、テトラビニルシランまたはテトラアリルシランにすることができる。
式中、αは吸収係数、λは波長、kは複素屈折率(n+ik)の虚部である。2.5ミクロン〜25ミクロンの赤外波長での吸収係数を求めるための反射率および透過値はいずれもSOC−100 Hemispherical Directional Reflectometerを用いて集められた。反射値および透過値を用い、クラマース・クローニッヒの関係を用いて材料の複素屈折率を求めた。複素屈折率のk値から、吸収係数(cmあたりで測定される材料内の固有減衰)を計算した。SOC−100内で測定される各波長について、アルファ値を求めた。これらの値から、8000nm〜12000nmの赤外波長バンドについて平均アルファ値を計算した。例えば、アルファ値は、8000nm〜12000nmで1000nm刻みで求めることができて、値が平均されて平均吸収係数が得られる。
1,2,4−トリビニルシクロヘキサン(0.2g、1.23mmol)および1,6−ヘキサンジチオール(0.28g、1.85mmol)を合わせてよくボルテックスした。膜をより速く硬化するために、2,2−ジメトキシ−2−フェニルアセトフェノン(DMPA)などの光開始剤を少量(0.025質量%)加えた。チオレン混合物を、テフロンスペーサー(0.13mm厚)と共に2枚のガラススライド(75mm×50mm;厚さ1mm)の間に置き、クリップで固定した。膜をUVに3回暴露した(Hバルブ(5×60秒))。膜をガラススライドから注意深く除去して透明な膜を得た。
2−[2,4−ビス(2−メルカプトエチル)シクロヘキシル]エタンチオール(0.150g、0.57mmol;あらかじめ合成)および4,4’−メチレンビス(4−シクロヘキシルイソシアネート)(0.225g、0.86mmol、Sigma Aldrich)を合わせてよくボルテックスした。混合物にテトラヒドロフラン(937μL)を加え、混合物を再びボルテックスした。反応を進めるために、テトラヒドロフランに分散させたトリエチルアミンをバイアルに加えた(187μL、テトラヒドロフラン中の1%トリエチルアミン)。ガラス基板上に溶液をドロップキャスティングして膜を調製し、ガラス皿で基板を覆って溶媒をゆっくりと蒸発させると、透明な膜が残った。
2−[2,4−ビス(2−メルカプトエチル)シクロヘキシル]エタンチオール(0.100g、0.38mmol;あらかじめ合成)および1,6−ジイソシアナトヘキサン(0.095g、0.57mmol、Sigma Aldrich)を合わせてよくボルテックスした。混合物にテトラヒドロフラン(565μL)を加え、混合物を再びボルテックスした。テトラヒドロフランに分散させた触媒トリエチルアミンをバイアルに加えた(20μL、THF中の1%トリエチルアミン)。ガラス基板上に溶液をドロップキャスティングして膜を調製し、溶媒を蒸発させると、透明な膜が残った。
2−[2,4−ビス(2−メルカプトエチル)シクロヘキシル]エタンチオール(0.35g、1.33mmol;あらかじめ合成)、1,6−ジイソシアナトヘキサン(0.150g、0.89mmol、Sigma Aldrich)および4,4’−メチレンビス(4−シクロヘキシルイソシアネート)(0.234g、0.89mmol、Sigma Aldrich)を合わせてよくボルテックスした。混合物に2−ブタノン(2.02mL)を加え、混合物を再びボルテックスした。反応を触媒するために、2−ブタノンに分散させたトリエチルアミンをバイアルに加えた(180μL、2−ブタノン中の1%トリエチルアミン)。ガラス基板上に溶液をドロップキャスティングして膜を調製し、溶媒を蒸発させると、透明な膜が残った。
シンチレーションバイアル内で2−[2,4−ビス(2−メルカプトエチル)シクロヘキシル]エタンチオール(0.5g、1.89mmol;あらかじめ合成)およびテトラビニルシラン(0.19g、1.39mmol、Sigma Aldrich)を合わせ、ボルテックスを用いて混合した。膜をより速く硬化するために、2,2−ジメトキシ−2−フェニルアセトフェノン(DMPA)などの光開始剤を少量(0.025質量%)加えることができる。チオレン混合物を、テフロンスペーサー(0.13mm厚)と共に2枚のガラススライド(75mm×50mm;厚さ1mm)の間に置き、クリップで固定する。膜をUVに3回暴露した(Hバルブ(5×60秒))。膜をガラススライドから注意深く除去して透明な膜を得た。
ヘキサンジチオール(0.979g、6.51mmol)を1,6−ヘプタジイン(0.300g、3.26mmol)と合わせてよくボルテックスした。DMPA(0.32mg)を加え、混合物を再びボルテックスした。混合物を、テフロンスペーサー(0.13mm厚)と共に2枚のガラススライド(75mm×50mm)の間に置き、クリップで固定した。膜をUVに3回暴露した(H2バルブ(5×60秒))。膜をガラススライドから注意深く除去して透明な膜を得た。
2−[2,4−ビス(2−メルカプトエチル)シクロヘキシル]エタンチオール(0.614g、3.78mmol)を1,2,4−トリビニルシクロヘキサン(0.750g、3.78mmol)と合わせてよくボルテックスした。DMPA(0.34mg)を加え、混合物を再びボルテックスした。混合物を、テフロンスペーサー(0.13mm厚)と共に2枚のガラススライド(75mm×50mm)の間に置き、クリップで固定した。膜をUVに3回暴露した(H2バルブ(5×60秒))。膜をガラススライドから注意深く除去して透明な膜を得た。
2−[2,4−ビス(2−メルカプトエチル)シクロヘキシル]エタンチオール(1.15g、4.34mmol)を1,6−ヘプタジイン(0.300g、3.26mmol)と合わせてよくボルテックスした。DMPA(0.36mg)を加え、混合物を再びボルテックスした。混合物を、テフロンスペーサー(0.13mm厚)と共に2枚のガラススライド(75mm×50mm)の間に置き、クリップで固定した。膜をUVに3回暴露した(H2バルブ(5×60秒))。膜をガラススライドから注意深く除去して透明な膜を得た。
ポリブタジエンおよび1,6−ヘキサンジチオールから構成されるチオレン膜の合成
ポリブタジエン(0.49g;Mn=2900、80%ビニル)を1,6−ヘキサンジチオール(0.54g、3.62mmol)と合わせてよくボルテックスした。膜をより速く硬化するために、2,2−ジメトキシ−2−フェニルアセトフェノン(DMPA)などの光開始剤を少量(0.025質量%)加えることができる。混合物を、2枚のガラススライド(75mm×50mm)とテフロンスペーサー(0.13mm厚)の間に置き、クリップで固定した。膜をUVに3回暴露した(Hバルブ(5×60秒))。膜をガラススライドから注意深く除去して透明な膜を得た。
赤外透明充填材として10%(w/w)BaF2を用いる、ポリブタジエンおよび1,6−ヘキサンジチオールから構成されるチオレン膜の合成
ポリブタジエン(0.24g;Mn=2900、90%ビニル)を、それ自体に結合した配位子を有するフッ化バリウム(BaF2)ナノ粒子と合わせて凝集物(0.056g)を減らし、高速ミキサーを用いて2回(FlackTek(2300rpm、3×60秒))、または完全に混合されるまで混合した。配位子強化フッ化バリウム粒子は、Intelligent Material Solutions,Inc.(ニュージャージー州プリンストン)から入手した。1,6−ヘキサンジチオール(0.27g、1.80mmol)を混合物に加えてよくボルテックスした。膜をより速く硬化するために、2,2−ジメトキシ−2−フェニルアセトフェノン(DMPA)などの光開始剤を少量(0.025質量%)加えることができる。混合物を、2枚のガラススライド(75mm×50mm)とテフロンスペーサー(0.13mm厚)の間に置き、クリップで固定した。膜をUVに3回暴露した(2フィート離れたHバルブ(5×60秒))。膜をガラススライドから注意深く除去して、8〜12ミクロンの範囲の波長において89.2%の平均可視透明度および平均α値=62.6cm−1を持つ半透明な膜を得た。
実施例1−α=33.3cm−1
実施例2−α=125.6cm−1
実施例3−α=213.9cm−1
実施例4−α=182.2cm−1
実施例5−α=100.6cm−1
実施例6−α=83.2cm−1
実施例7−α=127.7cm−1
実施例8−α=131.6cm−1
実施例9−α=59.1cm−1。
mは約70mol%〜約90mol%の範囲であり;および
nおよびoはそれぞれ0mol%〜約30mol%の範囲であり、ここで、n+oは約10mol%〜約30mol%の範囲である。)の化合物である組成物。
R1、R2、R3、R4、R5およびR6は、水素、−SHおよび−R’SHから独立に選ばれ、ここで、R’はC1〜C10炭化水素架橋であり、R1、R2、R3、R4、R5およびR6のうちの少なくとも2つは水素ではなく;および
R7はC2〜C10炭化水素架橋である。)の化合物から選ばれる組成物。
(式中:
R1、R2、R3、R4、R5およびR6は、水素、−SHおよび−R’SHから独立に選ばれ、ここで、R’はC1〜C10炭化水素架橋であり、R1、R2、R3、R4、R5およびR6のうちの少なくとも2つは水素ではない。)の化合物である組成物。
R8、R9、R10、R11、R12およびR13は、水素、および末端ビニル基を有するアルケニル置換基から独立に選ばれ、ここで、R8、R9、R10、R11、R12およびR13のうちの少なくとも2つは水素ではなく;
R’はC2〜C10炭化水素架橋であり;および
rは1〜10の範囲の整数である。)の化合物である組成物。
2 層
4 コポリマーマトリックス
6 粒子状充填材
8 膜
10 パネル
20 レンズカバー
22 赤外カメラ
Claims (18)
- チオール末端炭化水素モノマー、ならびに、i)末端不飽和炭化水素モノマー、ii)イソシアネート官能化炭化水素モノマーおよびiii)2つ以上のC2〜C8末端不飽和アルケニル基またはC2〜C8末端不飽和アルキニル基で置換されたシランモノマーの化合物から選ばれる少なくとも1つの別のモノマーから製造されるコポリマーと;
前記コポリマー中に分散した粒子状充填材と;
溶媒とを含み、
ただし、前記末端不飽和炭化水素モノマーがポリブタジエンである場合、前記ポリブタジエンは、cis−1,4−ブタジエンの形態の0mol%〜30mol%のポリマー単位を含み、
前記粒子状充填材は、IR透明であり、透過型電子顕微鏡法(TEM)を用いる直接画像化によって測定して10nm〜250nmの範囲の平均一次粒径を有し、
前記コポリマーは、4ミクロン〜12ミクロンのIR波長帯内で透過性がある、組成物。 - 前記少なくとも1つの別のモノマーが前記末端不飽和炭化水素モノマーである、請求項1に記載の組成物。
- 前記末端不飽和炭化水素モノマーが、12個以上の炭素原子を有し、かつ複数の不飽和基を含むモノマーであり、前記チオール末端炭化水素モノマーが、2つ以上の末端チオール基を有する置換または非置換の直鎖、分岐鎖または環状のC3〜C36飽和炭化水素である、請求項2に記載の組成物。
- 前記末端不飽和炭化水素モノマーが、内部が飽和しており、かつ2つ以上の末端ビニル基またはアルキニル基を有する置換または非置換の直鎖、分岐鎖または環状のC3〜C36炭化水素であり、ここで、「内部」は分子の末端位置以外の位置を意味する、請求項6に記載の組成物。
- 前記少なくとも1つの別のモノマーが、2つ以上のC2〜C8末端不飽和アルケニル基またはC2〜C8末端不飽和アルキニル基で置換されたシランモノマーである、請求項6に記載の組成物。
- 前記少なくとも1つの別のモノマーが、前記イソシアネート官能化炭化水素モノマーである、請求項1に記載の組成物。
- 前記チオール末端炭化水素モノマーが、2つ以上の末端チオール基を有する置換または非置換の直鎖、分岐鎖または環状のC3〜C36飽和炭化水素モノマーである、請求項10に記載の組成物。
- 前記イソシアネート官能化炭化水素モノマーが、2つ以上の末端イソシアネート基を有する置換または非置換の直鎖、分岐鎖または環状のC3〜C36飽和炭化水素モノマーである、請求項10に記載の組成物。
- 可塑化添加剤をさらに含む、請求項1から13のいずれか一項に記載の組成物。
- 前記粒子状充填材が、ゲルマニウム、CaF2、NaCl、KCl、KBr、ダイヤモンド、Si、CsI、MgO、MgF2、LiF、BaF2、臭化ヨウ化タリウム(ThBrI)および臭化塩化タリウム(ThBrCl)から選ばれる少なくとも1つの材料を含む、請求項1から14のいずれか一項に記載の組成物。
- 前記粒子状充填材が、これと結合した1つまたは複数の配位子を含む、請求項1から15のいずれか一項に記載の組成物。
- 前記配位子が、炭化水素部分を有するチオール、飽和または不飽和アルキルアミンおよび飽和または不飽和アルキルカルボン酸から選ばれる、請求項16に記載の組成物。
- 前記粒子状充填材が、前記組成物の全乾燥重量に基づいて、5質量%〜95質量%の範囲の量で存在する、請求項1から17のいずれか一項に記載の組成物。
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EP3121216B1 (en) | 2022-05-04 |
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US20170022389A1 (en) | 2017-01-26 |
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