JP6938794B2 - 光解離性β−ジカルボニル化合物 - Google Patents
光解離性β−ジカルボニル化合物 Download PDFInfo
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- JP6938794B2 JP6938794B2 JP2020541717A JP2020541717A JP6938794B2 JP 6938794 B2 JP6938794 B2 JP 6938794B2 JP 2020541717 A JP2020541717 A JP 2020541717A JP 2020541717 A JP2020541717 A JP 2020541717A JP 6938794 B2 JP6938794 B2 JP 6938794B2
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- -1 quaternary ammonium halide Chemical class 0.000 claims description 125
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- 229910052723 transition metal Inorganic materials 0.000 claims description 33
- 150000003624 transition metals Chemical class 0.000 claims description 31
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- 150000003839 salts Chemical class 0.000 claims description 10
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- 235000019270 ammonium chloride Nutrition 0.000 description 6
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- 230000002028 premature Effects 0.000 description 1
- BOQSSGDQNWEFSX-UHFFFAOYSA-N propan-2-yl 2-methylprop-2-enoate Chemical compound CC(C)OC(=O)C(C)=C BOQSSGDQNWEFSX-UHFFFAOYSA-N 0.000 description 1
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical class CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000006894 reductive elimination reaction Methods 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 239000003340 retarding agent Substances 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 238000007761 roller coating Methods 0.000 description 1
- ORIHZIZPTZTNCU-YVMONPNESA-N salicylaldoxime Chemical compound O\N=C/C1=CC=CC=C1O ORIHZIZPTZTNCU-YVMONPNESA-N 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- YJHHPIHPAJYNFT-UHFFFAOYSA-N silabenzene Chemical compound C1=CC=[SiH]C=C1 YJHHPIHPAJYNFT-UHFFFAOYSA-N 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 125000005372 silanol group Chemical group 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- MBDNRNMVTZADMQ-UHFFFAOYSA-N sulfolene Chemical compound O=S1(=O)CC=CC1 MBDNRNMVTZADMQ-UHFFFAOYSA-N 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical class CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 150000003623 transition metal compounds Chemical class 0.000 description 1
- XTTGYFREQJCEML-UHFFFAOYSA-N tributyl phosphite Chemical compound CCCCOP(OCCCC)OCCCC XTTGYFREQJCEML-UHFFFAOYSA-N 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- IEKWPPTXWFKANS-UHFFFAOYSA-K trichlorocobalt Chemical compound Cl[Co](Cl)Cl IEKWPPTXWFKANS-UHFFFAOYSA-K 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical class CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- ZTWTYVWXUKTLCP-UHFFFAOYSA-N vinylphosphonic acid Chemical class OP(O)(=O)C=C ZTWTYVWXUKTLCP-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000012991 xanthate Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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Description
X1及びX2は、独立して、共有結合、O、S、−N(R4)−、−[C(R4)2]y−、−CO−又は−CO−O−であり、式中、R4はH又は1〜18Cアルキルであり、下付き文字y=1、2、又は3であり、
R1、R2は、独立して、任意に置換された1〜18Cヒドロカルビルであり、
R3はH、又は任意に置換された1〜18Cヒドロカルビルであり、
式中、R1+R2、又はR1+R3、又はR2+R3は、任意に一緒になって5員環又は6員環を形成し、
RPhotoは、光解離性基である]、
を含むレドックス開始剤系と、を含む。
[MLp]n+A−[式中、Mはレドックスサイクルに関与する遷移金属であり、
Lは配位子であり、A−はアニオンであり、nは1〜7、好ましくは1〜3の整数値を有する遷移金属上の形式電荷であり、pは1〜9、好ましくは1〜2の数値を有する遷移金属上の配位子の数である]を有する。
i.最大100重量部、好ましくは85〜99.5重量部の(メタ)アクリル酸エステル、
ii.0〜15重量部、好ましくは0.5〜15重量部の酸官能性エチレン性不飽和モノマー、
iii.0〜15重量部の非酸官能性エチレン性不飽和極性モノマー、
iv.0〜5重量部のビニルモノマー、
v.i〜ivに対して、0〜100重量部、好ましくは50〜100重量部の多官能性(メタ)アクリレート、
及び
vi.i〜vの全モノマー100部に対して、約0.1重量%〜約5.0重量%、の量のレドックス開始剤系(錯体、酸化剤及び光解離性還元剤を含む)。
a)50重量部超、好ましくは75重量部超、最も好ましくは80重量部超の、(メタ)アクリレートエステルモノマー単位、
b)1〜10重量部、好ましくは、1〜5重量部、最も好ましくは、1〜3重量部の、ペンダントフリーラジカル重合性官能基を有するモノマー単位と、
c)0〜20重量部のその他の極性モノマー単位と、を含み、モノマー単位の合計は100重量部である、ペンダント重合性基を有する反応性オリゴマーを含んでもよい。
−[MUnsatd]o[Mester]p[Mpolar]q−、II
(式中、
[MUnsatd]は、ペンダントフリーラジカル重合性官能基を有するモノマー単位を表し、下付き文字「o」はその重量部(parts be weight)であり、
[Mester]は、(メタ)アクリレートエステルモノマー単位を表し、下付き文字「p」はその重量部を表し、
[Mpolar]は、極性モノマー単位を表し、下付き文字「q」はその重量部を表す)によって表すことができる。
20〜80重量部の多官能性(メタ)アクリレートモノマー及び/又は多官能性(メタ)アクリレート反応性オリゴマーと、
0〜の重量部範囲の(メタ)アクリレート希釈剤と、
20〜75重量%のシリカ(官能化の有無にかかわらず、それ自体)と、
重合性組成物の重合性成分の100重量部を基準として、約0.1重量%〜約5.0重量%のレドックス開始剤系と、を含んでもよい。
〜[MEster]a−[MOH]b−[MPolar]c−[MSilyl]e−[MPoly]d〜、
(式中、
−[MEster]−は、共重合された(メタ)アクリレートエステルモノマー単位を表し、下付き文字aは、50重量部よりも大きく、
−[MOH]−は、ペンダントヒドロキシ基を有する共重合された(メタ)アクリロイルモノマー単位を表し、下付き文字bは0〜20重量部を表し、
[MPolar]は、任意の極性モノマー単位を表し、下付き文字cは0〜20、好ましくは1〜10重量部であり、
[MSilyl]は、シリル官能性モノマー単位を表し、下付き文字eは0〜10、好ましくは1〜5重量部であり、
[MPoly]は、重合性基シラン官能性モノマー単位を含むモノマー単位を表し、下付き文字dは1〜10重量部を表す)のものである。波線符号は、連続するポリマー鎖を表す。下付き文字a〜eの合計は100重量部である。かかる反応性オリゴマーは、出願人の同時係属米国特許出願公開第2015/0284601号(Yurtら、参照により本明細書に援用する)及び国際公開第2014/078115号(Behlingら)に更に記載されている。Yurtの‘601号に教示されるように、オリゴマーは、MOHモノマーのペンダントヒドロキシ基の官能化によって、重合性基(MPoly単位)で官能化される。Yurtの‘601号組成物の第2の構成成分は、C2〜C4アルキレンオキシド単位と、1〜3個の末端重合性基、例えば(メタ)アクリレート基とを含む。
材料
材料及びそれらの供給元は、表1に列挙されたとおりであった。特に記載のない限り、他の全ての試薬はSigma−Aldrich Company(St.Louis,Missouri)などのファインケミカル業者から入手したか、又は入手可能であり、あるいは公知の方法で合成することができる。
以下の実施例は、それぞれ表2及び3に記載のベース樹脂と促進剤との10:1混合物からなる。ベース樹脂は、アクリルモノマー、遷移金属塩、及び任意にハロゲン化アンモニウム塩からなる。全ての成分をDAC混合カップ(FlackTek Inc.,Landrum,SC)に添加し、均質になるまで混合することによって、ベース樹脂を調製した。
実施例45〜52(EX45〜EX52)を、1.50gの適用可能なベース樹脂(表2)及び0.15gの促進剤(表3)を小型ガラスバイアルに添加し、均質性を確保するために約30秒間振盪することによって調製した。その後直ちに、混合配合物の1滴を、ガラス顕微鏡スライド(75×38×1.0mm、Fisher Scientific,Pittsburgh,PAから)上に置き、顕微鏡カバーガラス(22×22mm、Fisher Scientific,Pittsburgh,PA)で被覆した。適用可能な場合、365nmのLEDランプを備えたLX−400器具(Lumen Dynamics,Mississauga,Ontario,Canada)を使用して、カバーガラスの表面から約1cmにランプを30秒間保持して、サンプルを照射した。硬化時間は、カバーガラスを手でそれ以上移動させることができない点として定義した。
反応性オリゴマーAを、概して、以下の手順に従って調製した:2EHA(12g)、50gのCHA、30gのBA、5gのAcm、3gのHPA、0.1gのVAZO−52、0.1gのTDDM、及び100gのEtOAcを、ガラス瓶に添加した。内容物を混合し、窒素で4分間バブリングした後、密閉し、60℃にて24時間、Launder−Ometer回転水槽中に置いた。24時間後、サンプルを、GPCを用いて分析して、Mw及び多分散指数を決定した。第2の工程では、0.52gのIEM及び40gのMEKを瓶に添加した。瓶をポリテトラフルオロエチレンテープで封止し、60℃の温度に達するように設計されたIRランプ加熱ローラー上で24時間圧延した。得られたポリマーの重量平均分子量は、従来のゲル浸透クロマトグラフィー(GPC)法により決定されるとき、約298kDであった。GPC装置は、Waters Corporation(Milford,Massachusetts)から入手し、高圧液体クロマトグラフィーポンプ(Model 1515HPLC)、オートサンプラー(Model 717)、UV検出器(Model 2487)、及び屈折率検出器(Model 2410)を含んでいた。クロマトグラフは、Varian Inc.(Palo Alto,California)から入手可能な、2個の5ミクロンPLgel MIXED−Dカラムを装備していた。最終的な決定を、ポリスチレン標準を参照することにより行った。
重なり剪断試験法サンプル調製
選択された接着剤組成物(EtOAc/MEK溶液中)を、RL1シリコーン処理ポリエステル剥離ライナーの張り側上にコーティングし、70℃の溶媒オーブン内で30分間乾燥した。1”×4”×0.064”(2.5cm×10.2cm×0.16cm)のアルミニウム基材を、末端1”(2.54cm)をスコッチ・ブライトハンドパッド汎用No.7447(3M)で擦った後、イソプロパノールで洗浄し、空気乾燥することによって調整した。接着剤組成物の1/2”×1”(1.3cm×2.5cm)の部分を、1つの基材の擦られた端部に適用した。剥離ライナーを除去し、組成物をDバルブマイクロ波源(Heraeus Noblelight America,Gaithersburg,MD)からのUVに曝露させた。各サンプルに適用された放射線の量は、EIT PowerPuck II放射計(EIT,Inc.,Sterling,VA)によって測定した場合、UVAでは2.0J/cm2、UVBでは0.5J/cm2、UVCでは0.2J/cm2、及びUVVでは2.1J/cm2であった。第2の基材を、照射サンプルに適用することで、結合を閉鎖した(結合面積1/2”×1”(1.3cm×2.5cm))。このアセンブリは、指圧を適用することによってウェットアウトされた。接着部を大型バインダークリップではさみ、試験前に室温で18〜24時間静置した。
動的重なり剪断試験を、MODEL 55R1122 INSTRON引張試験機(Instron,Norwood,MA)を使用して、周囲温度にて実施した。試験片をグリップに載せ、0.1”(0.25cm)/分でクロスヘッドを操作し、試験片に荷重をかけ、損傷した。破断時応力をpsi単位で記録し、パスカル(又はキロパスカル)に変換した。各サンプルの3つの試験片を試験し、平均結果を計算した。
Claims (10)
- エチレン性不飽和重合性成分と、
a)レドックスサイクルに関与する遷移金属錯体、
b)酸化剤、
c)下記式の光解離性還元剤:
R1及びR2は、それぞれ独立して、任意に置換された1〜18Cヒドロカルビルであり、
R3はH、又は任意に置換された1〜18Cヒドロカルビルであるか、又は
式中、R1 、R2、及びR3 のうちのいずれか2つが一緒になって2価の基を形成することにより5員環又は6員環を形成し、
ただし、R 1 及びR 2 が一緒になって5員環を形成する場合、X 1 又はX 2 のうちの少なくとも1つは、共有結合であり、
RPhotoは、光解離性基である]、
を含むレドックス開始剤系と、
任意に、四級アンモニウムハライドと、を含む、重合性組成物。 - 前記光解離性基RPhotoが、フェナシル基、2−アルキルフェナシル基、エチレン架橋フェナシル基、p−ヒドロキシフェナシル基、ベンゾイン基、o−又はp−ニトロベンジル基、o−ニトロ−2−フェネチルオキシカルボニル基、クマリン−4−イルメチル基、ベンジル基、o−又はp−ヒドロキシベンジル基、o−又はp−ヒドロキシナフチル基、2,5−ジヒドロキシベンジル基、9−フェニルチオキサンチル、9−フェニルキサンチル基、アントラキノン−2−イル基、8−ハロ−7−ヒドロキシキノリン−2−イルメチル基、及びピバロイルグリコール基から選択される、請求項1に記載の重合性組成物。
- 前記遷移金属錯体が、式:
[MLp]n+A−[式中、Mはレドックスサイクルに関与する遷移金属であり、Lは配位子であり、A−はアニオンであり、nは1〜7、好ましくは1〜3の整数値を有する遷移金属上の形式電荷であり、pは1〜9、好ましくは1〜2の数値を有する遷移金属上の配位子の数である]のものである、請求項1又は2に記載の重合性組成物。 - 前記レドックス開始剤系の酸化剤が、過硫酸及びその塩、過酸化物、ヒドロ過酸化物、遷移金属、過ホウ酸及びその塩、過マンガン酸及びその塩、過リン酸及びその塩、並びにこれらの混合物から選択される、請求項1〜3のいずれか一項に記載の重合性組成物。
- 前記エチレン性不飽和重合性成分が、
i.85〜100重量部の(メタ)アクリル酸エステルと、
ii.0〜15重量部の酸官能性エチレン性不飽和モノマーと、
iii.0〜10重量部の非酸官能性エチレン性不飽和極性モノマーと、
iv.0〜5部のビニルモノマーと、
v.0〜5部の多官能性(メタ)アクリレートと、
vi.i)〜v)の100重量部を基準として、0.1〜10重量部の前記レドックス開始剤系と、
を含む、請求項1〜4のいずれか一項に記載の重合性組成物。 - 前記遷移金属錯体の酸化剤に対するモル比が、1:1000〜1:5である、請求項1〜5のいずれか一項に記載の重合性組成物。
- 前記酸化剤及び還元剤が、前記重合性組成物の前記エチレン性不飽和重合性成分の総重量を基準として、0.01〜10重量部の量で存在する、請求項1〜6のいずれか一項に記載の重合性組成物。
- 前記エチレン性不飽和重合性成分が、
i.最大100重量部の(メタ)アクリル酸エステルと、
ii.0〜15重量部、好ましくは0.5〜15重量部の酸官能性エチレン性不飽和モノマーと、
iii.0〜15重量部の非酸官能性エチレン性不飽和極性モノマーと、
iv.0〜5部のビニルモノマーと、
v.100部のi〜ivに対して、0〜100部の多官能性(メタ)アクリレートと、
vii.i〜vの全モノマー100部に対して、約0.1重量%〜約5.0重量%の量の前記レドックス開始剤系(前記遷移金属錯体、酸化剤及び光解離性還元剤を含む)と、
を含む、請求項1〜7のいずれか一項に記載の重合性組成物。 - 前記i〜ivの100重量部を基準として、50重量部超の多官能性(メタ)アクリレートを含む、請求項8に記載の重合性組成物。
- 前記重合性組成物の前記エチレン性不飽和重合性成分の100重量部に対して、1〜35重量部の強靭化剤を更に含む、請求項1〜9のいずれか一項に記載の重合性組成物。
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