JPWO2017018361A1 - 耐酸性を有する塩基または/およびラジカル発生剤、ならびに該塩基または/およびラジカル発生剤を含有する硬化性樹脂組成物 - Google Patents
耐酸性を有する塩基または/およびラジカル発生剤、ならびに該塩基または/およびラジカル発生剤を含有する硬化性樹脂組成物 Download PDFInfo
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- JPWO2017018361A1 JPWO2017018361A1 JP2017530848A JP2017530848A JPWO2017018361A1 JP WO2017018361 A1 JPWO2017018361 A1 JP WO2017018361A1 JP 2017530848 A JP2017530848 A JP 2017530848A JP 2017530848 A JP2017530848 A JP 2017530848A JP WO2017018361 A1 JPWO2017018361 A1 JP WO2017018361A1
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 113
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- 125000001424 substituent group Chemical group 0.000 claims abstract description 57
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- 150000001350 alkyl halides Chemical class 0.000 description 12
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- 239000000758 substrate Substances 0.000 description 12
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 11
- 229910015900 BF3 Inorganic materials 0.000 description 11
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 11
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 11
- 238000006116 polymerization reaction Methods 0.000 description 11
- 239000000376 reactant Substances 0.000 description 11
- 150000003440 styrenes Chemical class 0.000 description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 10
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- 159000000003 magnesium salts Chemical class 0.000 description 10
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- XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 description 9
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- OEBXWWBYZJNKRK-UHFFFAOYSA-N 1-methyl-2,3,4,6,7,8-hexahydropyrimido[1,2-a]pyrimidine Chemical compound C1CCN=C2N(C)CCCN21 OEBXWWBYZJNKRK-UHFFFAOYSA-N 0.000 description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 8
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- 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 6
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 6
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- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 4
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- HGROHYJKYOVLRM-UHFFFAOYSA-N (3-chlorophenoxy)boronic acid Chemical compound OB(O)OC1=CC=CC(Cl)=C1 HGROHYJKYOVLRM-UHFFFAOYSA-N 0.000 description 3
- SZCWBURCISJFEZ-UHFFFAOYSA-N (3-hydroxy-2,2-dimethylpropyl) 3-hydroxy-2,2-dimethylpropanoate Chemical compound OCC(C)(C)COC(=O)C(C)(C)CO SZCWBURCISJFEZ-UHFFFAOYSA-N 0.000 description 3
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- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 1
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- ZQZCOBSUOFHDEE-UHFFFAOYSA-N tetrapropyl silicate Chemical compound CCCO[Si](OCCC)(OCCC)OCCC ZQZCOBSUOFHDEE-UHFFFAOYSA-N 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 229950003937 tolonium Drugs 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- WYXIGTJNYDDFFH-UHFFFAOYSA-Q triazanium;borate Chemical compound [NH4+].[NH4+].[NH4+].[O-]B([O-])[O-] WYXIGTJNYDDFFH-UHFFFAOYSA-Q 0.000 description 1
- GQIUQDDJKHLHTB-UHFFFAOYSA-N trichloro(ethenyl)silane Chemical compound Cl[Si](Cl)(Cl)C=C GQIUQDDJKHLHTB-UHFFFAOYSA-N 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- JCVQKRGIASEUKR-UHFFFAOYSA-N triethoxy(phenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC=C1 JCVQKRGIASEUKR-UHFFFAOYSA-N 0.000 description 1
- CNQDVAWRPXCHEG-UHFFFAOYSA-K trilithium;trichloride Chemical compound [Li+].[Li+].[Li+].[Cl-].[Cl-].[Cl-] CNQDVAWRPXCHEG-UHFFFAOYSA-K 0.000 description 1
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- XHGIFBQQEGRTPB-UHFFFAOYSA-N tris(prop-2-enyl) phosphate Chemical compound C=CCOP(=O)(OCC=C)OCC=C XHGIFBQQEGRTPB-UHFFFAOYSA-N 0.000 description 1
- JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- ROVRRJSRRSGUOL-UHFFFAOYSA-N victoria blue bo Chemical compound [Cl-].C12=CC=CC=C2C(NCC)=CC=C1C(C=1C=CC(=CC=1)N(CC)CC)=C1C=CC(=[N+](CC)CC)C=C1 ROVRRJSRRSGUOL-UHFFFAOYSA-N 0.000 description 1
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000005050 vinyl trichlorosilane Substances 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
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Abstract
Description
(1)一般式(A)で示される化合物(以下、本発明の化合物と略記する場合がある。)。
一般式(A):
(式中、4個のR1は、それぞれ独立して水素原子またはフッ素原子を表し、4個のR2は、それぞれ独立してフッ素原子またはトリフルオロメチル基を表し、R3、R6、R7およびR10は、それぞれ独立して水素原子または炭素数1〜12のアルキル基を表し、R4およびR5は、それぞれ独立して水素原子または炭素数1〜12のアルキル基を表すか、あるいはR4とR5が互いに結合して、炭素数2〜4のアルキレン基を表し、R8およびR9は、それぞれ独立して水素原子;炭素数1〜12のアルキル基;または炭素数1〜6のアルキル基、炭素数1〜6のアルコキシ基、炭素数1〜6のアルキルチオ基、炭素数2〜12のジアルキルアミノ基、ハロゲン原子およびニトロ基からなる群から選ばれる置換基を有していてもよい炭素数6〜14のアリール基を表すか、あるいはR8とR9が互いに結合して、炭素数2〜4のアルキレン基を表す。ただし、R3〜R10の8個の基のうちの2〜3個は水素原子であり、該8個の基のうちの2個が水素原子の場合には、残りのうちの3〜6個の基は炭素数1〜12のアルキル基であり、該8個の基のうちの3個が水素原子の場合には、残りのうちの4〜5個の基は炭素数1〜12のアルキル基である。)
本発明の化合物は、一般式(A)で示されるものである。
一般式(A):
(式中、4個のR1は、それぞれ独立して水素原子またはフッ素原子を表し、4個のR2は、それぞれ独立してフッ素原子またはトリフルオロメチル基を表し、R3、R6、R7およびR10は、それぞれ独立して水素原子または炭素数1〜12のアルキル基を表し、R4およびR5は、それぞれ独立して水素原子または炭素数1〜12のアルキル基を表すか、あるいはR4とR5が互いに結合して、炭素数2〜4のアルキレン基を表し、R8およびR9は、それぞれ独立して水素原子;炭素数1〜12のアルキル基;または炭素数1〜6のアルキル基、炭素数1〜6のアルコキシ基、炭素数1〜6のアルキルチオ基、炭素数2〜12のジアルキルアミノ基、ハロゲン原子およびニトロ基からなる群から選ばれる置換基を有していてもよい炭素数6〜14のアリール基を表すか、あるいはR8とR9が互いに結合して、炭素数2〜4のアルキレン基を表す。ただし、R3〜R10の8個の基のうちの2〜3個は水素原子であり、該8個の基のうちの2個が水素原子の場合には、残りのうちの3〜6個の基は炭素数1〜12のアルキル基であり、該8個の基のうちの3個が水素原子の場合には、残りのうちの4〜5個の基は炭素数1〜12のアルキル基である。)
1.R1:水素原子、R2:フッ素原子
2.R1:水素原子、R2:トリフルオロメチル基
3.R1:フッ素原子、R2:フッ素原子
言い換えれば、R1:フッ素原子、R2:トリフルオロメチル基の組み合わせは、好ましい組み合わせから除かれる。
一般式(B):
(式中、4個のR1および4個のR2は、上記に同じ。)
一般式(B'):
(式中、4個のR1'は、すべて同一であって、水素原子またはフッ素原子を表し、4個のR2'は、すべて同一であって、フッ素原子またはトリフルオロメチル基を表す。ただし、R1'がフッ素原子であり、且つR2'がトリフルオロメチル基である組み合わせを除く。)
1.R1':水素原子、R2':フッ素原子
2.R1':水素原子、R2':トリフルオロメチル基
3.R1':フッ素原子、R2':フッ素原子
一般式(C):
(式中、R3〜R10は、上記に同じ。)
一般式(C'):
(式中、R3'〜R7'およびR10'は、それぞれ独立して水素原子または炭素数1〜6のアルキル基を表し、R8'およびR9'は、それぞれ独立して炭素数2〜8のアルキル基;または炭素数1〜3のアルキル基、炭素数1〜3のアルコキシ基、ハロゲン原子およびニトロ基からなる群から選ばれる置換基を有していてもよいフェニル基を表す。ただし、R3'〜R10'の8個の基のうちの2〜3個は水素原子であり、該8個の基のうちの2個が水素原子の場合には、残りのうちの3〜6個の基はアルキル基であり、該8個の基のうちの3個が水素原子の場合には、残りのうちの4〜5個の基はアルキル基である。)
一般式(A'):
(式中、4個のR1、4個のR2およびR3'〜R10'は、上記に同じ。)
一般式(A''):
(式中、4個のR1'、4個のR2'およびR3'〜R10'は、上記に同じ。)
式(1)〜(5):
上述した本発明の化合物は、例えば下記[S-1]で表されるスキームで示される方法により製造することができる。すなわち、一般式(A)で示される化合物は、例えば下記式[I]で示されるトリフルオロボランに対して、下記一般式[II]で示されるグリニヤール反応剤を反応させて、下記一般式[III]で示されるテトラフェニルボレートのマグネシウム塩を得た後、該マグネシウム塩に対して、下記一般式[IV]で示されるビグアニジニウム塩を反応させて塩交換反応を行うことにより製造することができる。なお、下記一般式[IV]で示されるビグアニジニウム塩は、後述する方法のほかに、一般式[V]で示されるビグアニジニウム塩と下記一般式[IX]で示されるハロゲン化水素との反応により製造することができる。
1.一般式[IV]におけるR7およびR10の両方が水素原子であり、且つR8とR9とで炭素数2〜4のアルキレン基を形成していない化合物(下記一般式[IVa]で示される化合物):下記一般式[VI]で示されるグアニジン誘導体またはイミダゾリジン誘導体と下記一般式[VII]で示されるカルボジイミド誘導体を反応させて、下記一般式[VIII]で示される化合物を得、次いで、該一般式[VIII]で示される化合物と下記一般式[IX]で示されるハロゲン化水素とを反応させる方法
2.一般式[IV]におけるR7およびR10のいずれか一方が水素原子以外であり、他方が水素原子であり、且つR8とR9とで炭素数2〜4のアルキレン基を形成していない化合物(下記一般式[IVb]で示される化合物):下記一般式[VI]で示されるグアニジン誘導体またはイミダゾリジン誘導体と下記一般式[VII]で示されるカルボジイミド誘導体を反応させて、下記一般式[VIII]で示される化合物を得、次いで、該一般式[VIII]で示される化合物を塩基の存在下で、下記一般式[X]で示されるハロゲン化アルキルを反応させて、下記一般式[XI]で示される化合物を得た後、該一般式[XI]で示される化合物と下記一般式[IX]で示されるハロゲン化水素とを反応させる方法
3.一般式[IV]におけるR7およびR10の両方が水素原子以外の化合物、あるいは一般式[IV]におけるR8とR9とで炭素数2〜4のアルキレン基を形成している化合物(下記一般式[IVc]で示される化合物):下記一般式[VI]で示されるグアニジン誘導体またはイミダゾリジン誘導体と下記一般式[XII]で示される化合物とを反応させる方法
(上記スキーム中、R7aおよびR10aは、それぞれ独立して炭素数1〜12のアルキル基を表し、R8aおよびR9aは、それぞれ独立して水素原子;炭素数1〜12のアルキル基;または炭素数1〜6のアルキル基、炭素数1〜6のアルコキシ基、炭素数1〜6のアルキルチオ基、炭素数2〜12のジアルキルアミノ基、ハロゲン原子およびニトロ基からなる群から選ばれる置換基を有していてもよい炭素数6〜14のアリール基を表し、(i)R7bおよびR10bは、それぞれ独立して炭素数1〜12のアルキル基を表し、且つR8bおよびR9bは、それぞれ独立して水素原子;炭素数1〜12のアルキル基;または炭素数1〜6のアルキル基、炭素数1〜6のアルコキシ基、炭素数1〜6のアルキルチオ基、炭素数2〜12のジアルキルアミノ基、ハロゲン原子およびニトロ基からなる群から選ばれる置換基を有していてもよい炭素数6〜14のアリール基を表すか、あるいは(ii)R7bおよびR10bは、それぞれ独立して水素原子または炭素数1〜12のアルキル基を表し、且つR8bおよびR9bは、互いに結合して、炭素数2〜4のアルキレン基を表し、R3〜R6、X2およびX2−は、上記に同じ。ただし、一般式[IVa]において、R3〜R6、R8aおよびR9aの6個の基のうちの0〜1個は水素原子であり、該6個の基のうちのすべてが水素原子でない場合(該6個の基のうちの0個が水素原子の場合)には、3〜6個の基は炭素数1〜12のアルキル基であり、該6個の基のうちの1個が水素原子の場合には、残りのうちの4〜5個の基は炭素数1〜12のアルキル基であり、一般式[IVb]において、R3〜R6およびR7a〜R10aの7個の基のうちの1〜2個は水素原子であり、該7個の基のうちの1個が水素原子の場合には、残りのうちの3〜6個の基は炭素数1〜12のアルキル基であり、該7個の基のうちの2個が水素原子の場合には、残りのうちの4〜5個の基は炭素数1〜12のアルキル基であり、一般式[IVc]において、R3〜R6およびR7b〜R10bの8個の基のうちの2〜3個は水素原子であり、該8個の基のうちの2個が水素原子の場合には、残りのうちの3〜6個の基は炭素数1〜12のアルキル基であり、該8個の基のうちの3個が水素原子の場合には、残りのうちの4〜5個の基は炭素数1〜12のアルキル基である。)
本発明の塩基発生剤は、本発明の化合物(上記一般式(A)で示される化合物)を含んでなるものであり、例えば紫外線、可視光線、赤外線、X線等の光(活性エネルギー線)を照射したり加熱することによって塩基を発生するものである。
本発明の塩基硬化性樹脂組成物は、本発明の化合物(上記一般式(A)で示される化合物)と塩基硬化性樹脂原料とを含んでなるものであり、本発明の化合物(塩基発生剤)から発生する塩基の作用によって重合反応、架橋反応等を生じて硬化する性質を有するものである。
本発明のラジカル発生剤は、本発明の化合物(上記一般式(A)で示される化合物)を含んでなるものであり、例えば紫外線、可視光線、赤外線、X線等の光(活性エネルギー線)を照射したり加熱することによってラジカルを発生するものである。
本発明のラジカル硬化性樹脂組成物は、本発明の化合物(上記一般式(A)で示される化合物)とラジカル反応性化合物とを含んでなるものであり、本発明の化合物(ラジカル発生剤)から発生するラジカルの作用によって重合反応、架橋反応等を生じて硬化する性質を有するものである。
1,1,3,3-テトラメチルグアニジン12.2g(106mmol;和光純薬工業(株)製)に、N,N'-ジシクロヘキシルカルボジイミド10.9g(53mmol;和光純薬工業(株)製)を加え、100℃で2時間加熱攪拌した。反応終了後、反応液を減圧濃縮して、1,1,3,3-テトラメチルグアニジンを除去した後、得られた残渣に、アセトン20mLおよび水2mLを加え、ドライアイスを投入し、得られた固体をろ取することにより、1,2-ジシクロヘキシル-4,4,5,5-テトラメチルビグアニド炭酸塩8.44g(白色粉末、収率:45%)を得た。以下に、1H-NMRおよび13C-NMRの測定結果と、1,2-ジシクロヘキシル-4,4,5,5-テトラメチルビグアニド炭酸塩の構造を示す。
1H-NMR(400MHz,D2O)δ(ppm):1.22-1.80(40H,brm),2.86(24H,s),3.02(4H,m).
13C-NMR(400MHz,CD3OD)δ(ppm):26.1,34.1,40.1,52.4,158.0,161.2,164.4.
1,1,3,3-テトラメチルグアニジン11.9g(10.3mmol;和光純薬工業(株)製)に、N,N'-ジイソプロピルカルボジイミド13.1g(10.3mmol;和光純薬工業(株)製)を加え、100℃で2時間加熱攪拌した。反応終了後、反応液にヘキサンを加え、5℃まで冷却し、得られた固体を脱液することにより、1,2-ジイソプロピル-4,4,5,5-テトラメチルビグアニド9.88g(白色粉末、収率:39%)を得た。以下に、1H-NMRの測定結果と、1,2-ジイソプロピル-4,4,5,5-テトラメチルビグアニドの構造を示す。
1H-NMR(400MHz,CDCl3)δ(ppm):1.10(12H,d),2.78(13H,s),3.38(2H,q).
1,1,3,3-テトラメチルグアニジン3.18g(27.6mmol;和光純薬工業(株)製)に、ビス(2,6-ジイソプロピルフェニル)カルボジイミド13.1g(27.6mmol;東京化成工業(株)製)を加え、室温で30分攪拌した。反応終了後、反応液にヘキサンを加え、5℃まで冷却し、得られた固体を脱液することにより、1,2-ビス(2,6-ジイソプロピルフェニル)-4,4,5,5-テトラメチルビグアニド10.20g(白色粉末、収率:77%)を得た。以下に、1H-NMRの測定結果と、1,2-ビス(2,6-ジイソプロピルフェニル)-4,4,5,5-テトラメチルビグアニドの構造を示す。
1H-NMR(400MHz,CDCl3)δ(ppm):1.00-1.29(24H,m),2.81(12H,s),3.42-3.45(4H,m),4.85-4.95(1H,brs),7.07-7.26(6H,m).
独国特許出願公開第102006010034号明細書に記載の方法に従って、テトラキス(テトラメチルグアニジノ)ホスホニウムクロリドを合成した。以下に、テトラキス(テトラメチルグアニジノ)ホスホニウムクロリドの構造を示す。
2-クロロ-1,3-ジメチルイミダゾリニウムクロリド3.38g(20mmol;和光純薬工業(株)製)にジクロロメタン20mLとテトラヒドロフラン(THF)20mLを加え、5℃に冷却した後、1,1,3,3-テトラメチルグアニジン4.6g(40mmol;和光純薬工業(株)製)を加え、60℃で1.5時間攪拌した。反応終了後、反応液にアセトン30mLを加え、析出した固体をろ過によって除去した。得られた有機層を減圧濃縮することにより、1,3-ジメチル-2-(N',N',N'',N''-テトラメチルグアニジノ)-4,5-ジヒドロ-3H-イミダゾリウムクロリド4.76g(白色粉末、収率:96%)を得た。以下に、1H-NMRの測定結果と、1,3-ジメチル-2-(N',N',N'',N''-テトラメチルグアニジノ)-4,5-ジヒドロ−3H-イミダゾリウムクロリドの構造式を示す。
1H-NMR(400MHz,D2O)δ(ppm):2.86(6H,s),3.04(12H,s),3.88(4H,d).
1,8-ジアザビシクロ[5,4,0]ウンデカ-7-エン15.1g(100mmol;和光純薬工業(株)製)に酢酸エチル30mLを加え、10℃に冷却した後、ベンジルブロミド17.1g(100mmol;和光純薬工業(株)製)を加え、室温で3時間攪拌した。反応終了後、析出した固体をろ取することにより、2,3,4,6,7,8,9,10-オクタヒドロ-1-(フェニルメチル)-ピリミド[1,2-a]アゼピニウムブロミド25.2g(白色粉末、収率:78%)を得た。以下に、1H-NMRの測定結果と、2,3,4,6,7,8,9,10-オクタヒドロ-1-(フェニルメチル)-ピリミド[1,2-a]アゼピニウムブロミドの構造式を示す。
1H-NMR(400MHz,DMSO-d6)δ(ppm):1.49-1.58(2H,m),1.61-1.71(4H,m),2.01-2.11(2H,m),2.88-2.96(m,2H),3.45-3.60(4H,m),3.65-3.75(2H,m),4.86(2H,s),7.29-7.38(3H,m),7.40-7.48(2H,m).
合成例2で得られた1,2-ジイソプロピル-4,4,5,5-テトラメチルビグアニド1.00g(4.1mmol;和光純薬工業(株)製)と60%水素化ナトリウム0.3g(4.1mmol;和光純薬工業(株)製)を無水テトラヒドロフラン20mLに溶解させ、50℃で1時間攪拌した。次いで、反応液を室温まで冷却した後、反応液にヨウ化メチル0.63g(4.5mmol;和光純薬工業(株)製)を加え、室温で1時間反応させた。反応終了後、反応液にヘキサンを加えた後、セライトろ過し、得られたろ液を減圧濃縮することにより、1,2-ジイソプロピル-1,4,4,5,5-ペンタメチルビグアニド0.82g(微黄色油状物、収率:78%)を得た。以下に、1H-NMRの測定結果と、1,2-ジイソプロピル-1,4,4,5,5-ペンタメチルビグアニドの構造式を示す。
1H-NMR(400MHz,CDCl3)δ(ppm):1.04(12H,s),2.83(15H,s),3.03(1H,brs),4.45(1H,brs).
トリフルオロボラン・ジエチルエーテル錯体7.09g(50mmol;和光純薬工業(株)製)をテトラヒドロフラン5mLに溶解させた溶液に、マグネシウム粉末5.34g(200mmol;和光純薬工業(株)製)を加えた後、3-ブロモフルオロベンゼン38.5g(200mmol;東京化成工業(株)製)のテトラヒドロフラン溶液(30mL)を滴下し、還流下で1時間反応させた。次いで、反応液を室温まで冷却した後、合成例1で得られた1,2-ジシクロヘキシル-4,4,5,5-テトラメチルビグアニド炭酸塩20.14g(26mmol)を3.5%塩酸に溶解させた溶液(55mL、53mmol)を滴下し、室温で30分攪拌した。反応終了後、反応液に酢酸エチルを加えて抽出し、抽出後の有機層を水で洗浄した後、有機層を減圧濃縮し、得られた残渣をシリカゲルカラムクロマトグラフィーで精製することにより、1,2-ジシクロヘキシル-4,4,5,5-テトラメチルビグアニジウム テトラキス(3-フルオロフェニル)ボレート9.40g(白色粉末、収率:25%)を得た。以下に、1H-NMRの測定結果と、1,2-ジシクロヘキシル-4,4,5,5-テトラメチルビグアニジウム テトラキス(3-フルオロフェニル)ボレートの構造を示す。
1H-NMR(400MHz,CDCl3)δ(ppm):1.06-1.24(10H,m),1.58-1.60(2H,m),1.70-1.78(8H,m),2.72(12H,s),3.05-3.15(2H,m),4.25-4.35(2H,brs),6.59-6.64(4H,m),6.95-6.99(4H,m),7.04-7.10(4H,m),7.11-7.13(4H,m).
実施例1で用いた3-ブロモフルオロベンゼン(東京化成工業(株)製)の代わりに、1-ブロモ-3,5-ジフルオロベンゼン(和光純薬工業(株)製)を用いた以外は、実施例1と同様の操作を行うことにより、1,2-ジシクロヘキシル-4,4,5,5-テトラメチルビグアニジウム テトラキス(3,5-ジフルオロフェニル)ボレート1.13g(白色粉末、収率:39%)を得た。以下に、1H-NMRの測定結果と、1,2-ジシクロヘキシル-4,4,5,5-テトラメチルビグアニジウム テトラキス(3,5-ジフルオロフェニル)ボレートの構造を示す。
1H-NMR(400MHz,CDCl3)δ(ppm):1.07-1.31(10H,m),1.63-1.85(10H,m),2.85(12H,s),3.20-3.30(2H,m),3.35-3.50(2H,brs),6.36-6.42(4H,m),6.72-6.75(8H,m).
実施例1で用いた3-ブロモフルオロベンゼン(東京化成工業(株)製)の代わりに、3-ブロモトリフルオロメチルベンゼン(和光純薬工業(株)製)を用いた以外は、実施例1と同様の操作を行うことにより、1,2-ジシクロヘキシル-4,4,5,5-テトラメチルビグアニジウム テトラキス(3-トリフルオロフェニル)ボレート0.64g(微黄色粉末、収率:10%)を得た。以下に、1H-NMRの測定結果と、1,2-ジシクロヘキシル-4,4,5,5-テトラメチルビグアニジウム テトラキス(3-トリフルオロメチルフェニル)ボレートの構造を示す。
1H-NMR(400MHz,CDCl3)δ(ppm):1.07-1.32(10H,m),1.55-1.63(2H,m),1.70-1.74(4H,m),1.82-1.84(4H,m),2.59(12H,s),3.20-3.35(2H,brm),4.45-4.60(2H,brs),7.16-7.22(8H,m),7.45-7.55(4H,m),7.55-7.65(4H,m).
実施例1で用いた1,2-ジシクロヘキシル-4,4,5,5-テトラメチルビグアニド炭酸塩の代わりに、合成例2で得られた1,2-ジイソプロピル-4,4,5,5-テトラメチルビグアニドを用いた以外は、実施例1と同様の操作を行うことにより、1,2-ジイソプロピル-4,4,5,5-テトラメチルビグアニジウム テトラキス(3-フルオロフェニル)ボレート2.20g(微黄色油状物、収率:77%)を得た。以下に、1H-NMRの測定結果と、1,2-ジイソプロピル-4,4,5,5-テトラメチルビグアニジウム テトラキス(3-フルオロフェニル)ボレートの構造を示す。
1H-NMR(400MHz,CDCl3)δ(ppm):1.08(12H,s),2.70(12H,s),3.40-3.50(2H,m),5.05-5.25(2H,brs),6.58-6.63(4H,m),6.95-7.11(12H,m).
実施例1で用いた1,2-ジシクロヘキシル-4,4,5,5-テトラメチルビグアニド炭酸塩の代わりに、合成例3で得られた1,2-ビス(2,6-ジイソプロピルフェニル)-4,4,5,5-テトラメチルビグアニドを用いた以外は、実施例1と同様の操作を行うことにより、1,2-ビス(2,6-ジイソプロピルフェニル)-4,4,5,5-テトラメチルビグアニジウム テトラキス(3-フルオロフェニル)ボレート0.18g(無色油状物、収率:8%)を得た。以下に、1H-NMRの測定結果と、1,2-ビス(2,6-ジイソプロピルフェニル)-4,4,5,5-テトラメチルビグアニジウム テトラキス(3-フルオロフェニル)ボレートの構造を示す。
1H-NMR(400MHz,CDCl3)δ(ppm):1.00-1.05(6H,m),1.14(6H,d),1.20-1.30(6H,m),1.37-1.39(6H,d),2.74(12H,s),2.99-3.06(2H,m),3.20-3.25(2H,m),5.75-5.85(1H,brs),6.10-6.20(1H,brd),6.41-6.64(6H,m),6.91-6.97(6H,m),7.14-7.16(6H,m),7.29-7.34(4H,m).
合成例1で得られた1,2-ジシクロヘキシル-4,4,5,5-テトラメチルビグアニド炭酸塩1.41g(2.0mmol)を10%塩酸(1.5mL、4.0mmol)に溶解させた溶液に、20%リチウムトリフェニル(n-ブチル)ボレート水溶液6.12g(4.0mmol;北興化学工業(株)製)を加え、室温で30分間攪拌した。反応終了後、反応液に酢酸エチルを加えて抽出し、抽出後の有機層を水で洗浄した後、有機層を減圧濃縮することにより、1,2-ジシクロヘキシル-4,4,5,5-テトラメチルビグアニジウム トリフェニル(n-ブチル)ボレート1.83g(白色粉末、収率:73%)を得た。以下に、1H-NMRの測定結果と、1,2-ジシクロヘキシル-4,4,5,5-テトラメチルビグアニジウム トリフェニル(n-ブチル)ボレートの構造を示す。
1H-NMR(400MHz,CDCl3)δ(ppm):0.81(3H,t),1.02(2H,m),1.03-1.14(12H,brm),1.27-1.30(2H,m),1.50-1.70(10H,brm),2.75(12H,s),2.76-2.78(3H,brm),4.37(1H,brs),6.87(3H,t),7.04-7.08(6H,m),7.44-7.46(6H,m).
トリフルオロボラン・ジエチルエーテル錯体1.42g(10mmol;和光純薬工業(株)製)をテトラヒドロフラン5mLに溶解させた溶液に、マグネシウム粉末1.09g(45mmol;和光純薬工業(株)製)を加えた後、3-ブロモフルオロベンゼン5.25g(30mmol;東京化成工業(株)製)のテトラヒドロフラン溶液(15mL)を滴下し、還流下で1時間反応させた。その後、反応液に1-ブロモブタン2.05g(15mmol;和光純薬工業(株)製)のテトラヒドロフラン溶液(15mL)を滴下し、還流下で1時間反応させた。次いで、反応液を室温まで冷却した後、合成例1で得られた1,2-ジシクロヘキシル-4,4,5,5-テトラメチルビグアニド炭酸塩5.29g(7.5mmol)を3.5%塩酸に溶解させた溶液(16mL、15mmol)を滴下し、室温で30分攪拌した。反応終了後、反応液に酢酸エチルを加えて抽出し、抽出後の有機層を水で洗浄した後、有機層を減圧濃縮し、得られた残渣をシリカゲルカラムクロマトグラフィーで精製することにより、1,2-ジシクロヘキシル-4,4,5,5-テトラメチルビグアニジウム トリス(3-フルオロフェニル)(n-ブチル)ボレート4.03g(微黄色油状物、収率:59%)を得た。以下に、1H-NMRの測定結果と、1,2-ジシクロヘキシル-4,4,5,5-テトラメチルビグアニジウム トリス(3-フルオロフェニル)(n-ブチル)ボレートの構造を示す。
1H-NMR(400MHz,CDCl3)δ(ppm):0.82-0.94(4H,m),1.07-1.29(16H,m),1.71-1.77(9H,m),2.73(12H,s),3.00-3.10(2H,brm),4.60-4.70(2H,brs),6.59-6.64(3H,m),6.90-7.11(9H,m).
実施例1で用いた3-ブロモフルオロベンゼン(東京化成工業(株)製)の代わりに、2-ブロモフルオロベンゼン(和光純薬工業(株)製)を用いた以外は、実施例1と同様の操作を行うことにより、1,2-ジシクロヘキシル-4,4,5,5-テトラメチルビグアニジウム テトラキス(2-フルオロフェニル)ボレート0.18g(白色粉末、収率:3%)を得た。以下に、1H-NMRの測定結果と、1,2-ジシクロヘキシル-4,4,5,5-テトラメチルビグアニジウム テトラキス(2-フルオロフェニル)ボレートの構造を示す。
1H-NMR(400MHz,CDCl3)δ(ppm):0.97-1.15(10H,m),1.52-1.71(10H,m),2.75(12H,s),2.85-2.95(2H,brs),4.26-4.28(2H,brm),6.65-6.70(4H,m),6.89-7.08(8H,m),7.35-7.45(4H,m).
実施例1で用いた3-ブロモフルオロベンゼン(東京化成工業(株)製)の代わりに、4-ブロモフルオロベンゼン(和光純薬工業(株)製)を用いた以外は、実施例1と同様の操作を行うことにより、1,2-ジシクロヘキシル-4,4,5,5-テトラメチルビグアニジウム テトラキス(4-フルオロフェニル)ボレート1.05g(白色粉末、収率:73%)を得た。以下に、1H-NMRの測定結果と、1,2-ジシクロヘキシル-4,4,5,5-テトラメチルビグアニジウム テトラキス(4-フルオロフェニル)ボレートの構造を示す。
1H-NMR(400MHz,(CD3)2CO)δ(ppm):1.10-1.14(6H,m),1.29-1.34(8H,m),1.55-1.65(2H,m),1.73-1.75(4H,m),2.93(12H,s),3.55-3.70(2H,m),6.50-6.60(2H,brs),6.67-6.72(8H,m),7.17-7.21(8H,m).
実施例1で用いた3-ブロモフルオロベンゼン(東京化成工業(株)製)の代わりに、3-ブロモクロロベンゼン(和光純薬工業(株)製)を用いた以外は、実施例1と同様の操作を行うことにより、1,2-ジシクロヘキシル-4,4,5,5-テトラメチルビグアニジウム テトラキス(3-クロロフェニル)ボレート2.66g(無色油状物、収率:48%)を得た。以下に、1H-NMRの測定結果と、1,2-ジシクロヘキシル-4,4,5,5-テトラメチルビグアニジウム テトラキス(3-クロロフェニル)ボレートの構造を示す。
1H-NMR(400MHz,CDCl3)δ(ppm):1.05-1.23(10H,m),1.60-1.67(2H,m),1.69-1.77(8H,m),2.67(12H,s),3.10-3.20(2H,brm),4.50-4.60(2H,brs),6.90-6.93(4H,m),7.00-7.04(4H,m),7.16-7.24(8H,m).
合成例1で得られた1,2-ジシクロヘキシル-4,4,5,5-テトラメチルビグアニド炭酸塩39.8mg(0.057mmol)のメタノール溶液(2.0mL)に、35%塩酸(0.01mL、0.114mmol)を加えた後、テトラキス[3,5-ビス(トリフルオロメチル)フェニル]ホウ酸ナトリウム水和物0.72g(0.113mmol;東京化成工業(株)製)を加え、室温で30分間攪拌した。反応終了後、反応液に酢酸エチルを加えて抽出し、抽出後の有機層を水で洗浄した後、有機層を減圧濃縮することにより、1,2-ジシクロヘキシル-4,4,5,5-テトラメチルビグアニジウム テトラキス[3,5-ビス(トリフルオロメチル)フェニル]ボレート98.2mg(褐色油状物、収率:73%)を得た。以下に、1H-NMRの測定結果と、1,2-ジシクロヘキシル-4,4,5,5-テトラメチルビグアニジウム テトラキス[3,5-ビス(トリフルオロメチル)フェニル]ボレートの構造を示す。
1H-NMR(400MHz,CDCl3)δ(ppm):1.15-1.31(10H,m),1.55-1.73(6H,m),1.87-1.90(4H,d),2.79(12H,s),3.25-3.40(2H,m),4.30-4.40(2H,brs),7.53(4H,s),7.69(8H,s).
合成例1で得られた1,2-ジシクロヘキシル-4,4,5,5-テトラメチルビグアニド炭酸塩0.71mg(2.0mmol)のメタノール溶液(2.0mL)に、35%塩酸(0.4mL、4.0mmol)を加えた後、リチウムテトラキス(ペンタフルオロフェニル)ボレート1.37g(2.0mmol;東ソー・ファインケム(株)製)を加え、室温で30分間攪拌した。反応終了後、反応液に酢酸エチルを加えて抽出し、抽出後の有機層を水で洗浄した後、有機層を減圧濃縮することにより、1,2-ジシクロヘキシル-4,4,5,5-テトラメチルビグアニジウム テトラキス(ペンタフルオロベンゼン)ボレート1.89g(褐色アモルファス、収率:94%)を得た。以下に、1H-NMRの測定結果と、1,2-ジシクロヘキシル-4,4,5,5-テトラメチルビグアニジウム テトラキス(ペンタフルオロベンゼン)ボレートの構造を示す。
1H-NMR(400MHz,CDCl3)δ(ppm):1.14-1.33(10H,m),1.64-1.67(2H,m),1.74-1.77(4H,m),1.89-1.92(4H,m),2.87(12H,s),3.22-3.44(2H,m),4.40-4.55(2H,brs).
実施例1で用いた1,2-ジシクロヘキシル-4,4,5,5-テトラメチルビグアニド炭酸塩の代わりに、1,5,7-トリアザビシクロ[4.4.0]デカ-5-エン(TBD)(東京化成工業(株)製)を用いた以外は、実施例1と同様の操作を行うことにより、1,5,7-トリアザビシクロ[4.4.0]デカ-5-エニウム テトラキス(3-フルオロフェニル)ボレート0.80g(白色粉末、収率:33%)を得た。以下に、1H-NMRの測定結果と、1,5,7-トリアザビシクロ[4.4.0]デカ-5-エニウム テトラキス(3-フルオロフェニル)ボレートの構造を示す。
1H-NMR(400MHz,CDCl3)δ(ppm):1.75-1.80(4H,m),2.76-2.79(4H,m),3.06-3.09(4H,m),3.30-3.40(2H,brs),6.65-6.69(4H,m),7.01-7.26(12H,m).
実施例1で用いた1,2-ジシクロヘキシル-4,4,5,5-テトラメチルビグアニド炭酸塩の代わりに、1,8-ジアザビシクロ[5.4.0]-7-ウンデセン(DBU)(和光純薬工業(株)製)を用いた以外は、実施例1と同様の操作を行うことにより、1,8-ジアザビシクロ[5.4.0]-7-ウンデセニウム テトラキス(3-フルオロフェニル)ボレート1.56g(白色粉末、収率:63%)を得た。以下に、1H-NMRの測定結果と、1,8-ジアザビシクロ[5.4.0]-7-ウンデセニウム テトラキス(3-フルオロフェニル)ボレートの構造を示す。
1H-NMR(400MHz,CDCl3)δ(ppm):1.49-1.67(8H,m),2.10-2.30(2H,m),2.75-2.95(2H,m),3.07-3.19(5H,m),6.60-6.63(4H,m),6.95-7.20(12H,m).
実施例1で用いた1,2-ジシクロヘキシル-4,4,5,5-テトラメチルビグアニド炭酸塩の代わりに、1,8-ビス(ジメチルアミノ)ナフタレン(東京化成工業(株)製)を用いた以外は、実施例1と同様の操作を行うことにより、8-ジメチルアミノ-1-ナフチルジメチルアンモニウム テトラキス(3-フルオロフェニル)ボレート1.68g(白色粉末、収率:61%)を得た。以下に、1H-NMRの測定結果と、8-ジメチルアミノ-1-ナフチルジメチルアンモニウム テトラキス(3-フルオロフェニル)ボレートの構造を示す。
1H-NMR(400MHz,(CD3)2CO)δ(ppm):3.33(13H,s),6.50-6.60(4H,m),6.94-7.07(12H,m),7.76(2H,t),8.09-8.14(4H,m).
実施例1で用いた1,2-ジシクロヘキシル-4,4,5,5-テトラメチルビグアニド炭酸塩の代わりに、7-メチル-1,5,7-トリアザビシクロ[4.4.0]デカ-5-エン(MTBD)(和光純薬工業(株)製)を用いた以外は、実施例1と同様の操作を行うことにより、7-メチル-1,5,7-トリアザビシクロ[4.4.0]デカ-5-エニウム テトラキス(3-フルオロフェニル)ボレート1.94g(微黄色粉末、収率:79%)を得た。以下に、1H-NMRの測定結果と、7-メチル-1,5,7-トリアザビシクロ[4.4.0]デカ-5-エニウム テトラキス(3-フルオロフェニル)ボレートの構造を示す。
1H-NMR(400MHz,CDCl3)δ(ppm):1.65-1.68(2H,m),1.76-1.79(2H,m),2.28(3H,s),2.75-2.85(2H,m),2.90-3.10(6H,m),4.05-4.15(1H,brs),6.59-6.63(4H,m),6.95-7.26(12H,m).
実施例1で用いた1,2-ジシクロヘキシル-4,4,5,5-テトラメチルビグアニド炭酸塩の代わりに、2-エチル-4-メチルイミダゾール(和光純薬工業(株)製)を用いた以外は、実施例1と同様の操作を行うことにより、2-エチル-4-メチルイミダゾリウム テトラキス(3-フルオロフェニル)ボレート0.85g(白色粉末、収率:37%)を得た。以下に、1H-NMRの測定結果と、2-エチル-4-メチルイミダゾリウム テトラキス(3-フルオロフェニル)ボレートの構造を示す。
1H-NMR(400MHz,(CD3)2CO)δ(ppm):1.42(3H,t),2.36(3H,s),3.11(2H,q),6.50-6.60(4H,m),6.90-7.10(12H,m),7.30(1H,s),12.50-13.00(2H,brs).
実施例1で用いた1,2-ジシクロヘキシル-4,4,5,5-テトラメチルビグアニド炭酸塩の代わりに、1,1,3,3-テトラメチルグアニジン(和光純薬工業(株)製)を用いた以外は、実施例1と同様の操作を行うことにより、1,1,3,3-テトラメチルグアニジウム テトラキス(3-フルオロフェニル)ボレート0.80g(白色粉末、収率:35%)を得た。以下に、1H-NMRの測定結果と、1,1,3,3-テトラメチルグアニジウム テトラキス(3-フルオロフェニル)ボレートの構造を示す。
1H-NMR(400MHz,(CD3)2CO)δ(ppm):3.11(12H,s),6.55-6.62(4H,m),6.92-7.10(12H,m),7.30-7.42(2H,brs).
実施例1で用いた1,2-ジシクロヘキシル-4,4,5,5-テトラメチルビグアニド炭酸塩および3.5%塩酸の代わりに、合成例4で得られたテトラキス(テトラメチルグアニジノ)ホスホニウムクロリドを用いた以外は、実施例1と同様の操作を行うことにより、テトラキス(テトラメチルグアニジノ)ホスホニウム テトラキス(3-フルオロフェニル)ボレート2.78g(黄色油状物、収率:70%)を得た。以下に、1H-NMRの測定結果と、テトラキス(テトラメチルグアニジノ)ホスホニウム テトラキス(3-フルオロフェニル)ボレートの構造を示す。
1H-NMR(400MHz,CDCl3)δ(ppm):2.74(48H,s),6.56-6.61(4H,m),6.97-7.19(12H,m).
実施例1で用いた1,2-ジシクロヘキシル-4,4,5,5-テトラメチルビグアニド炭酸塩および3.5%塩酸の代わりに、合成例5で得られた1,3-ジメチル-2-(N',N',N'',N''-テトラメチルグアニジノ)-4,5-ジヒドロ-3H-イミダゾリウムクロリドを用いた以外は、実施例1と同様の操作を行うことにより、1,3-ジメチル-2-(N',N',N'',N''-テトラメチルグアニジノ)-4,5-ジヒドロ-3H-イミダゾリウム テトラキス(3-フルオロフェニル)ボレート0.04g(白色粉末、収率:31%)を得た。以下に、1H-NMRの測定結果と、1,3-ジメチル-2-(N',N',N'',N''-テトラメチルグアニジノ)-4,5-ジヒドロ-3H-イミダゾリウム テトラキス(3-フルオロフェニル)ボレートの構造を示す。
1H-NMR(400MHz,(CD3)2CO)δ(ppm):2.86(12H,s),2.98(12H,s),3.68-3.74(4H,m),6.48-6.62(4H,m),6.90-7.10(12H,m).
実施例1で用いた1,2-ジシクロヘキシル-4,4,5,5-テトラメチルビグアニド炭酸塩および3.5%塩酸の代わりに、合成例6で得られた2,3,4,6,7,8,9,10-オクタヒドロ-1-(フェニルメチル)-ピリミド[1,2-a]アゼピニウムブロミドを用いた以外は、実施例1と同様の操作を行うことにより、2,3,4,6,7,8,9,10-オクタヒドロ-1-(フェニルメチル)-ピリミド[1,2-a]アゼピニウム テトラキス(3-フルオロフェニル)ボレート2.61g(白色粉末、収率:58%)を得た。以下に、1H-NMRの測定結果と、2,3,4,6,7,8,9,10-オクタヒドロ-1-(フェニルメチル)-ピリミド[1,2-a]アゼピニウム テトラキス(3-フルオロフェニル)ボレートの構造を示す。
1H-NMR(400MHz,CDCl3)δ(ppm):1.30-1.40(2H,m),1.45-1.50(2H,m),1.55-1.60(2H,m),1.65-1.73(2H,m),2.36-2.43(2H,m),2.95-3.10(4H,m),3.13-3.23(2H,m),4.26(2H,s),6.55-6.65(4H,m),6.88-7.07(10H,m),7.09-7.18(4H,m),7.30-7.40(3H,m).
実施例1で用いた1,2-ジシクロヘキシル-4,4,5,5-テトラメチルビグアニド炭酸塩および3.5%塩酸の代わりに、1,1-ジメチルビグアニジウム塩酸塩を用いた以外は、実施例1と同様の操作を行うことにより、1,1-ジメチルビグアニジウム テトラキス(3-フルオロフェニル)ボレート1.77g(黄色油状物、収率:48%)を得た。以下に、1H-NMRの測定結果と、1,1-ジメチルビグアニジウム テトラキス(3-フルオロフェニル)ボレートの構造を示す。
1H-NMR(400MHz,(CD3)2CO)δ(ppm):3.10(6H,s),6.40-6.50(4H,brs),6.55-6.60(4H,m),6.92-7.10(14H,m).
実施例1で用いた1,2-ジシクロヘキシル-4,4,5,5-テトラメチルビグアニド炭酸塩の代わりに、1,2-ジイソプロピル-1,4,4,5,5-ペンタメチルビグアニドを用いた以外は、実施例1と同様の操作を行うことにより、1,2-ジイソプロピル-1,4,4,5,5-ペンタメチルビグアニジウム テトラキス(3-フルオロフェニル)ボレート0.23g(白色粉末、収率:13%)を得た。以下に、1H-NMRの測定結果と、1,1,3,3-テトラメチルグアニジウム テトラキス(3-フルオロフェニル)ボレートの構造を示す。
1H-NMR(400MHz,CDCl3)δ(ppm):1.06(6H,d,J=6.4Hz),1.09(6H,d,J=6.4Hz),2.48(3H,s),2.67(12H,s),3.25-3.35(1H,m),3.90-4.00(1H,m),4.50-4.60(1H,brs),6.57-6.62(4H,m),6.95-7.06(8H,m),7.07-7.13(4H,m).
実施例1〜5で得られた化合物(塩基発生剤)および比較例1〜13で得られた化合物をそれぞれ10mgずつ秤量し、これらの化合物に、酢酸3mLおよび1,2-ジクロロエタン3mLを加え、室温で3時間攪拌した後、溶媒を減圧下で留去し、得られた残渣について、1H-NMRを測定した。実施例1〜5および比較例1〜13の各化合物固有の1H-NMRと、安定性試験後の各化合物の1H-NMRの測定結果を比較し、ホウ素ユニットの分解の有無を確認した。安定性試験後において、ホウ素ユニットの分解率が25%未満の場合を「○」、ホウ素ユニットの分解率が25%以上の場合を「×」、未実施の場合を「−」と評価した。安定性試験の結果を表1に示す。なお、本発明の化合物に係るテトラフェニルボレート構造とは、ホウ素原子と4つの置換フェニル基とが結合している構造を指し、その構造のうちのホウ素原子と1つのフェニル基との結合を「ホウ素ユニット」と称する。また、1つのテトラフェニルボレート構造は、4つのホウ素ユニットを有しているため、1つのテトラフェニルボレート構造(4つのホウ素ユニットすべて)の分解率を100%とした場合に、ホウ素ユニットの分解率25%とは、1つのホウ素ユニットが完全に分解していることを意味する。
実施例1〜5で得られた化合物(塩基発生剤)または比較例1〜13で得られた化合物10mgおよび増感剤として9-アントリルメチル N,N-ジエチルカルバメート(商品名:WPBG-018;和光純薬工業(株)製)2mgをそれぞれ秤量し、これらの化合物および増感剤をジペンタエリスリトールヘキサアクリレート(商品名:KAYARAD DPHA;日本化薬(株)製)100mgに加え、100℃に加温してこれらの化合物および増感剤を溶解させた。また、評価例1として、増感剤として9-アントリルメチル N,N-ジエチルカルバメート(商品名:WPBG-018;和光純薬工業(株)製)2mgを秤量し、該増感剤のみをジペンタエリスリトールヘキサアクリレート(商品名:KAYARAD DPHA;日本化薬(株)製)100mgに加え、100℃に加温して該増感剤を溶解させた。各溶液をガラス板上に塗布して膜とし、得られた塗布膜に対して、240nm〜440nmの波長の光(活性エネルギー線)を照射する紫外線照射光源装置REX-250(朝日分光(株)製)を用い、室温で10秒間紫外線(活性エネルギー線)を照射して該塗布膜を硬化させた。塗布膜の硬度を鉛筆硬度試験法にて評価し、塗布膜が硬化して硬度が2H以上となった場合を「○」、塗布膜が硬化せず、硬度が2H未満となった場合を「×」と評価した。評価結果を表2に示す。
実施例1〜5で得られた化合物(塩基発生剤)または比較例1〜13で得られた化合物10mgおよび増感剤として2-イソプロピルチオキサントン1mgをそれぞれ秤量し、これらの化合物および増感剤をビスフェノールA型ジグリシジルエーテルオリゴマー(商品名:jER(登録商標)828;三菱化学(株)製)100mgに加え、加温してこれらの化合物および増感剤を溶解させた後、多価カルボン酸(商品名:CF-1069;32.4%PGMEA溶液、重量平均分子量14800、分散度1.85、酸価115mgKOH/g;和光純薬工業(株)製)100mgを混合した。各溶液をガラス板上に塗布して膜とし、得られた塗布膜を150℃に加熱して該塗布膜を硬化させた。塗布膜(硬化膜)の硬度を鉛筆硬度試験法にて評価し、加熱開始から所定時間経過後の硬度を測定した。塗布膜の硬度が2H以上となった場合を「塗布膜が硬化した」と定義し、加熱を開始してから塗布膜が硬化するまでの時間を評価した。実験例3では、光(活性エネルギー線)照射を行っておらず、また、塗布膜を硬化させる際のベーク温度(150℃)では、実施例1〜5で得られた化合物(塩基発生剤)または比較例1〜13で得られた化合物から塩基は発生しない。すなわち、実験例3では、実施例1〜5で得られた化合物(塩基発生剤)または比較例1〜13で得られた化合物から塩基を発生させるような操作を行っていない。それ故、実施例1〜5で得られた化合物(塩基発生剤)または比較例1〜13で得られた化合物が共存する多価カルボン酸に対して安定性が高いほど、すなわち、実施例1〜5で得られた化合物(塩基発生剤)または比較例1〜13で得られた化合物の耐酸性が高いほど、該化合物は多価カルボン酸に起因する分解を引き起こし難く、分解に伴って塩基が発生したり、多価カルボン酸を活性化する可能性は低い。また、実験例3の塗布膜は、該化合物から塩基が発生し難いほど、硬化する時間は長くなる。従って、加熱を開始してから塗布膜が硬化するまでの時間が長ければ長いほど、実施例1〜5で得られた化合物(塩基発生剤)または比較例1〜13で得られた化合物は、多価カルボン酸等の酸性を示す化合物に対して耐酸性が高く、酸性を示す化合物を含有する樹脂組成物に対して安定性が高いことを意味する。加熱開始から15分以下で塗布膜が硬化した場合を「××」、16〜30分で塗布膜が硬化した場合を「×」、31分以上経過しても塗布膜が硬化しなかった場合を「○」と評価した。評価結果を表3に示す。
実施例1〜5で得られた化合物(塩基発生剤)または比較例1〜13で得られた化合物10mgおよび増感剤として2-イソプロピルチオキサントン2mgをそれぞれ秤量し、これらの化合物および増感剤をビスフェノールA型ジグリシジルエーテルオリゴマー(商品名:jER(登録商標)828;三菱化学(株)製)100mgに加え、加温してこれらの化合物および増感剤を溶解させた後、多価カルボン酸(商品名:CF-1069;32.4%PGMEA溶液、重量平均分子量14800、分子量分布1.85、酸価115mgKOH/g;和光純薬工業(株)製)100mgを混合した。各溶液をガラス板上に塗布して膜とし、得られた塗布膜に対して、240nm〜440nmの波長の光(活性エネルギー線)を照射する紫外線照射光源装置REX-250(朝日分光(株)製)を用い、波長365nmで1.0J/cm2の紫外線(活性エネルギー線)を照射し、次いで、塗布膜を150℃に加熱することで該塗布膜を硬化させた。塗布膜の硬度を鉛筆硬度試験法にて評価し、加熱開始から所定時間経過後の硬度を測定した。塗布膜の硬度が2H以上となった場合を「塗布膜が硬化した」と定義し、加熱を開始してから塗布膜が硬化するまでの時間を評価した。実験例4では、光(活性エネルギー線)照射を行っており、また、光(活性エネルギー線)の照射量はすべて同じである。それ故、実施例1〜5で得られた化合物(塩基発生剤)または比較例1〜13で得られた化合物の光(活性エネルギー線)に対する感受性が高いほど、該化合物から塩基が発生し易く、また、該塩基の塩基性が高いほど、塗布膜が硬化し易い。従って、加熱を開始してから塗布膜が硬化するまでの時間が短ければ短いほど、実施例1〜5で得られた化合物(塩基発生剤)または比較例1〜13で得られた化合物は、光(活性エネルギー線)照射下において塩基を発生し易く、塗布膜に対する硬化性能が高いことを意味する。加熱開始から5分以内で塗布膜が硬化した場合を「◎」、6〜15分で塗布膜が硬化した場合を「○」、40分以上経過後に塗布膜が硬化した場合を「×」と評価した。評価結果を表4に示す。
実施例1で得られた化合物(塩基発生剤)または比較例8、9および12〜18で得られた化合物10mgならびに増感剤として2-イソプロピルチオキサントン2mgをそれぞれ秤量し、これらの化合物および増感剤をビスフェノールA型ジグリシジルエーテルオリゴマー(商品名:jER(登録商標)828;三菱化学(株)製)100mgに加え、加温してこれらの化合物および増感剤を溶解させた後、多価チオール(商品名:KarenzMT(商標登録)PE1;昭和電工(株)製)70mgを混合した。各溶液をガラス板上に塗布して膜とし、得られた塗布膜を120℃に加熱して該塗布膜を硬化させた。塗布膜(硬化膜)の硬度を鉛筆硬度試験法にて評価し、加熱開始から所定時間経過後の硬度を測定した。塗布膜の硬度が2H以上となった場合を「塗布膜が硬化した」と定義し、加熱を開始してから塗布膜が硬化するまでの時間を評価した。実験例5では、光(活性エネルギー線)照射を行っておらず、また、塗布膜を硬化させる際のベーク温度(120℃)では、実施例1で得られた化合物(塩基発生剤)または比較例8、9および12〜18で得られた化合物から塩基は発生しない。すなわち、実験例5では、実施例1で得られた化合物(塩基発生剤)または比較例8、9および12〜18で得られた化合物から塩基を発生させるような操作を行っていない。それ故、実施例1で得られた化合物(塩基発生剤)または比較例8、9および12〜18で得られた化合物が共存する多価チオールに対して安定性が高いほど、すなわち、実施例1で得られた化合物(塩基発生剤)または比較例8、9および12〜18で得られた化合物の耐酸性が高いほど、分解に伴って塩基が発生したり、多価チオールを活性化する可能性は低い。また、実験例5の塗布膜は、該化合物から塩基が発生し難いほど、硬化する時間は長くなる。従って、加熱を開始してから塗布膜が硬化するまでの時間が長ければ長いほど、実施例1で得られた化合物(塩基発生剤)または比較例8、9および12〜18で得られた化合物は、多価チオールを含有する樹脂組成物に対して安定性が高いことを意味する。加熱開始から120分未満で塗布膜が硬化した場合を「×」、120分以上経過しても塗布膜が硬化しなかった場合を「○」と評価した。評価結果を表6に示す。
実施例1で得られた化合物(塩基発生剤)または比較例8、9および12〜18で得られた化合物10mgならびに増感剤として2-イソプロピルチオキサントン2mgをそれぞれ秤量し、これらの化合物および増感剤をビスフェノールA型ジグリシジルエーテルオリゴマー(商品名:jER(登録商標)828;三菱化学(株)製)100mgに加え、加温してこれらの化合物および増感剤を溶解させた後、多価チオール(商品名:KarenzMT(商標登録)PE1;昭和電工(株)製)70mgを混合した。各溶液をガラス板上に塗布して膜とし、得られた塗布膜に対して、240nm〜440nmの波長の光(活性エネルギー線)を照射する紫外線照射光源装置REX-250(朝日分光(株)製)を用い、波長365nmで1.0J/cm2の紫外線(活性エネルギー線)を照射し、次いで、塗布膜を120℃に加熱することで該塗布膜を硬化させた。塗布膜の硬度を鉛筆硬度試験法にて評価し、加熱開始から所定時間経過後の硬度を測定した。塗布膜の硬度が2H以上となった場合を「塗布膜が硬化した」と定義し、加熱を開始してから塗布膜が硬化するまでの時間を評価した。実験例6では、光(活性エネルギー線)照射を行っており、また、光(活性エネルギー線)の照射量はすべて同じである。それ故、実施例1で得られた化合物(塩基発生剤)または比較例8、9および12〜18で得られた化合物の光(活性エネルギー線)に対する感受性が高いほど、該化合物から塩基が発生し易く、また、該塩基の塩基性が高いほど、塗布膜が硬化し易い。従って、加熱を開始してから塗布膜が硬化するまでの時間が短ければ短いほど、実施例1で得られた化合物(塩基発生剤)または比較例8、9および12〜18で得られた化合物は、光(活性エネルギー線)照射下において塩基を発生し易く、塗布膜に対する硬化性能が高いことを意味する。加熱開始から30分以内に塗布膜が硬化した場合を「○」、30分以上経過しても塗布膜が硬化しなかった場合を「×」と評価した。評価結果を表7に示す。
実施例1で得られた化合物(塩基発生剤)10mgおよび増感剤として2-イソプロピルチオキサントン2mgをそれぞれ秤量し、該化合物および増感剤、ビスフェノールA型ジグリシジルエーテルオリゴマー(商品名:jER(登録商標)828;三菱化学(株)製)100mg、ならびに多価カルボン酸(商品名:Joncryl(商標登録)682;OH等量138;BASFジャパン(株)製)100mgを、γ-ブチロラクトン(和光純薬工業(株)製)300mgに溶解させた。この溶液をポリカーボネート板上に塗布して膜とし、得られた塗布膜の一部に対して、240nm〜440nmの波長の光(活性エネルギー線)を照射する紫外線照射光源装置REX-250(朝日分光(株)製)を用い、波長365nmで1.0J/cm2の紫外線(活性エネルギー線)を照射し、次いで、塗布膜を150℃で10分間加熱することで該塗布膜を硬化させた。得られた硬化膜を1重量%炭酸ナトリウム水溶液に1分間浸漬し、現像できていることを目視で確認した。
Claims (15)
- 一般式(A)で示される化合物。
一般式(A):
(式中、4個のR1は、それぞれ独立して水素原子またはフッ素原子を表し、4個のR2は、それぞれ独立してフッ素原子またはトリフルオロメチル基を表し、R3、R6、R7およびR10は、それぞれ独立して水素原子または炭素数1〜12のアルキル基を表し、R4およびR5は、それぞれ独立して水素原子または炭素数1〜12のアルキル基を表すか、あるいはR4とR5が互いに結合して、炭素数2〜4のアルキレン基を表し、R8およびR9は、それぞれ独立して水素原子;炭素数1〜12のアルキル基;または炭素数1〜6のアルキル基、炭素数1〜6のアルコキシ基、炭素数1〜6のアルキルチオ基、炭素数2〜12のジアルキルアミノ基、ハロゲン原子およびニトロ基からなる群から選ばれる置換基を有していてもよい炭素数6〜14のアリール基を表すか、あるいはR8とR9が互いに結合して、炭素数2〜4のアルキレン基を表す。ただし、R3〜R10の8個の基のうちの2〜3個は水素原子であり、該8個の基のうちの2個が水素原子の場合には、残りのうちの3〜6個の基は炭素数1〜12のアルキル基であり、該8個の基のうちの3個が水素原子の場合には、残りのうちの4〜5個の基は炭素数1〜12のアルキル基である。) - 前記一般式(A)におけるR3〜R10の8個の基のうちの2個が、水素原子であり、且つ残りのうちの4〜6個の基が、炭素数1〜12のアルキル基である、請求項1に記載の化合物。
- 前記一般式(A)におけるR3〜R6が、すべて炭素数1〜6のアルキル基である、請求項1に記載の化合物。
- 前記一般式(A)における4個のR1が、すべて水素原子またはすべてフッ素原子であり、且つ4個のR2が、すべてフッ素原子である、請求項1に記載の化合物。
- 前記一般式(A)における4個のR1が、すべて水素原子であり、且つ4個のR2が、すべてトリフルオロメチル基である、請求項1に記載の化合物。
- 請求項1に記載の化合物を含んでなる塩基または/およびラジカル発生剤。
- 請求項1に記載の化合物を含んでなる塩基発生剤。
- 活性エネルギー線の照射によって塩基または/およびラジカルを発生するものである、請求項8に記載の塩基発生剤。
- 活性エネルギー線の照射によって塩基を発生するものである、請求項9に記載の塩基発生剤。
- 請求項1に記載の化合物と、塩基硬化性樹脂原料または/およびラジカル反応性化合物とを含有することを特徴とする塩基または/およびラジカル硬化性樹脂組成物。
- 請求項1に記載の化合物と塩基硬化性樹脂原料とを含有することを特徴とする塩基硬化性樹脂組成物。
- 前記塩基硬化性樹脂原料が、エポキシ系化合物と多価カルボン酸の混合物である、請求項12または13に記載の組成物。
- 前記塩基硬化性樹脂原料が、エポキシ系化合物と多価チオールの混合物である、請求項12または13に記載の組成物。
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KR102474260B1 (ko) * | 2018-05-07 | 2022-12-05 | 갓코호우징 도쿄리카다이가쿠 | 광반응성 조성물, 반응 생성물 및 반응 생성물의 제조방법 |
WO2020004488A1 (ja) * | 2018-06-26 | 2020-01-02 | 日東電工株式会社 | シーラントシート |
JP7345107B2 (ja) | 2019-04-15 | 2023-09-15 | パナソニックIpマネジメント株式会社 | 光硬化性組成物 |
CN110845414A (zh) * | 2019-11-27 | 2020-02-28 | 济宁康盛彩虹生物科技有限公司 | 一种n-双(二甲胺基)-1,3-二甲基咪唑啉制备方法及用途 |
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JP2012193279A (ja) * | 2011-03-16 | 2012-10-11 | Toyobo Co Ltd | 熱硬化性樹脂組成物 |
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KR102557854B1 (ko) | 2023-07-20 |
EP3327002B1 (en) | 2020-08-19 |
US20190002403A1 (en) | 2019-01-03 |
JP6822401B2 (ja) | 2021-01-27 |
CN107848963B (zh) | 2020-11-03 |
TWI701255B (zh) | 2020-08-11 |
KR20180034386A (ko) | 2018-04-04 |
CN107848963A (zh) | 2018-03-27 |
TW201714887A (zh) | 2017-05-01 |
WO2017018361A1 (ja) | 2017-02-02 |
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EP3327002A1 (en) | 2018-05-30 |
US10428015B2 (en) | 2019-10-01 |
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