JP2005529167A - モノ−およびビス−アシルホスフィンオキサイドのマルチマー形態 - Google Patents
モノ−およびビス−アシルホスフィンオキサイドのマルチマー形態 Download PDFInfo
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- JP2005529167A JP2005529167A JP2004511314A JP2004511314A JP2005529167A JP 2005529167 A JP2005529167 A JP 2005529167A JP 2004511314 A JP2004511314 A JP 2004511314A JP 2004511314 A JP2004511314 A JP 2004511314A JP 2005529167 A JP2005529167 A JP 2005529167A
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- phosphine
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- 150000001875 compounds Chemical class 0.000 claims abstract description 67
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 42
- 238000000034 method Methods 0.000 claims abstract description 20
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims abstract description 20
- 125000003118 aryl group Chemical group 0.000 claims abstract description 18
- 125000000732 arylene group Chemical group 0.000 claims abstract description 14
- 239000000539 dimer Substances 0.000 claims abstract description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 8
- 238000002360 preparation method Methods 0.000 claims abstract description 8
- 239000002253 acid Substances 0.000 claims abstract description 5
- AVUYXHYHTTVPRX-UHFFFAOYSA-N Tris(2-methyl-1-aziridinyl)phosphine oxide Chemical class CC1CN1P(=O)(N1C(C1)C)N1C(C)C1 AVUYXHYHTTVPRX-UHFFFAOYSA-N 0.000 claims abstract 4
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 claims abstract 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 40
- -1 dicarboxylic acid halide Chemical class 0.000 claims description 31
- 239000000543 intermediate Substances 0.000 claims description 23
- 238000004519 manufacturing process Methods 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 22
- 125000004122 cyclic group Chemical group 0.000 claims description 14
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 12
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 11
- 150000004820 halides Chemical class 0.000 claims description 6
- 229910052744 lithium Inorganic materials 0.000 claims description 6
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 claims description 5
- 229910052700 potassium Inorganic materials 0.000 claims description 5
- 229910052708 sodium Inorganic materials 0.000 claims description 5
- 230000003647 oxidation Effects 0.000 claims description 4
- 238000007254 oxidation reaction Methods 0.000 claims description 4
- GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 claims description 4
- 150000001266 acyl halides Chemical class 0.000 claims description 3
- 238000007363 ring formation reaction Methods 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract description 6
- 125000003545 alkoxy group Chemical group 0.000 abstract description 2
- 239000007795 chemical reaction product Substances 0.000 abstract description 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 229920001577 copolymer Polymers 0.000 description 12
- 229920005862 polyol Polymers 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- 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 8
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- 150000001735 carboxylic acids Chemical class 0.000 description 8
- 239000011248 coating agent Substances 0.000 description 8
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- 0 CC(C)(*C(Cl)=O)C(Cl)=O Chemical compound CC(C)(*C(Cl)=O)C(Cl)=O 0.000 description 7
- 239000000654 additive Substances 0.000 description 7
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- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 6
- QNVNLUSHGRBCLO-UHFFFAOYSA-N 5-hydroxybenzene-1,3-dicarboxylic acid Chemical compound OC(=O)C1=CC(O)=CC(C(O)=O)=C1 QNVNLUSHGRBCLO-UHFFFAOYSA-N 0.000 description 6
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 6
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000000600 sorbitol Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 5
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- 230000003287 optical effect Effects 0.000 description 5
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- 229910052717 sulfur Inorganic materials 0.000 description 5
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 4
- IJFXRHURBJZNAO-UHFFFAOYSA-N 3-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=CC(O)=C1 IJFXRHURBJZNAO-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 4
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- 150000008064 anhydrides Chemical class 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- 229920002635 polyurethane Polymers 0.000 description 4
- 239000004814 polyurethane Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
- BBCQSMSCEJBIRD-UHFFFAOYSA-N 3-fluorophthalic acid Chemical compound OC(=O)C1=CC=CC(F)=C1C(O)=O BBCQSMSCEJBIRD-UHFFFAOYSA-N 0.000 description 3
- DVIPPHSQIBKWSA-UHFFFAOYSA-N 4-chlorophthalic acid Chemical compound OC(=O)C1=CC=C(Cl)C=C1C(O)=O DVIPPHSQIBKWSA-UHFFFAOYSA-N 0.000 description 3
- MWRVRCAFWBBXTL-UHFFFAOYSA-N 4-hydroxyphthalic acid Chemical compound OC(=O)C1=CC=C(O)C=C1C(O)=O MWRVRCAFWBBXTL-UHFFFAOYSA-N 0.000 description 3
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 239000004952 Polyamide Substances 0.000 description 3
- 239000003570 air Substances 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 238000003818 flash chromatography Methods 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
- 239000011976 maleic acid Substances 0.000 description 3
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 3
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 3
- 229920002647 polyamide Polymers 0.000 description 3
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- 239000011734 sodium Substances 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 description 2
- MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 description 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
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- UTDGMRWXJVWFFX-UHFFFAOYSA-N 2,4,6-trimethylbenzene-1,3-dicarbonyl chloride Chemical compound CC1=CC(C)=C(C(Cl)=O)C(C)=C1C(Cl)=O UTDGMRWXJVWFFX-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- HCLJOFJIQIJXHS-UHFFFAOYSA-N 2-[2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOCCOC(=O)C=C HCLJOFJIQIJXHS-UHFFFAOYSA-N 0.000 description 2
- PTJWCLYPVFJWMP-UHFFFAOYSA-N 2-[[3-hydroxy-2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)COCC(CO)(CO)CO PTJWCLYPVFJWMP-UHFFFAOYSA-N 0.000 description 2
- GPNNOCMCNFXRAO-UHFFFAOYSA-N 2-aminoterephthalic acid Chemical compound NC1=CC(C(O)=O)=CC=C1C(O)=O GPNNOCMCNFXRAO-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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Abstract
Description
R2は、非置換または置換の、C3〜C6シクロアルキルまたはC5〜C14アリールであり、Qは、2〜3または4価のアリーレン残基であり、
nは、1〜4であり、mは、0〜2であり、n+mは、2、3または4である。)
Qは2〜3または4価のアリーレン残基であり、
nは1〜4であり、mは0〜2であり、n+mは2、3または4であり、
ただし、R1およびR3は、互いに異なる。)
ジ金属化ホスフィンR1P(M)2(n+m)当量をジ−またはポリ−カルボン酸ハロゲン化物
ジ金属化ホスフィン R1P(M)21当量をジカルボン酸ハロゲン化物
ジ金属化ホスフィン R1P(M)22当量をテトラカルボン酸ハロゲン化物
C1〜C12アルキルは、直鎖状または分岐状であって、例えば、C1〜C12アルキル、C1〜C8アルキル、C1〜C6アルキル、またはC1〜C4アルキルである。その例は、メチル、エチル、プロピル、イソプロピル、n−ブチル、sec−ブチル、イソブチル、tert−ブチル、ペンチル、ヘキシル、ヘプチル、2,4,4−トリメチルペンチル、2−エチルヘキシル、オクチル、ノニル、デシル、ウンデシルまたはドデシルである。
アルキル基は、1回またはそれ以上、O、SまたはN(C1〜C12アルキル)によって分断され得る。その基が、2個またはそれ以上のO、SまたはN(C1〜C12アルキル)によって分断されている場合は、O原子、S原子またはN(C1〜C12アルキル)基は、それぞれの場合、少なくとも1個のメチレン基によって互いに分離されている。したがって、O原子、S原子、またはN(C1〜C12アルキル)基は、直接的に連続しない。例えば、−CH2−O−CH3、−CH2CH2−O−CH2CH3、−[CH2CH2O]Z−CH3(ここで、zは、1〜9である。)、−(CH2CH2O)7CH2CH3、−CH2−CH(CH3)−O−CH2−CH2CH3、−CH2−CH(CH3)−O−CH2−CH3、−CH2SCH3または−CH2−N(CH3)2のような構造単位が生ずる。
テレフタル酸およびその誘導体、例えば、テトラフルオロ−またはテトラクロロフタル酸、3−フルオロフタル酸、4−(トリフルオロメチル)フタル酸、4−クロロ−または4,5−ジクロロフタル酸、4−メチルフタル酸のようなフタル酸およびその誘導体;
ヘミメリット酸、トリメリット酸およびピロメリット酸;
例えば、テトラフルオロイソフタル酸、4−ブロモイソフタル酸、4−ヒドロキシ−または5−ヒドロキシイソフタル酸、5−アミノイソフタル酸のようなイソフタル酸およびその誘導体;
トリメシン酸、5−メチル−1,3−ベンゼンジカルボン酸;
例えば、テトラフルオロ−またはテトラクロロテレフタル酸、2−ブロモテレフタル酸、2−アミノテレフタル酸、2,5−ジメチルテレフタル酸、2,5−ジクロロ−または2,5−ジブロモテレフタル酸のようなものである。
金属化ホスフィン R1P(M)2の製造は、例えば、適切なハロゲン化リン R1P(Hal)2〔その製造は公知であり、例えば、W.Davies.の J.Chem.Soc.(1935)、462およびJ.Chem.Soc.(1944)、276によって開示されている。〕を相応するアルカリ金属と反応させることによって行われる。金属(M)として適切なものは、リチウム、ナトリウムまたはカリウムであり、リチウムが好ましい。これらの金属の混合物もまた使用することができる。アルカリ金属4〜8モル当量が、有利に使用される。反応は、溶媒中で有利に行われる。特に、溶媒として、大気圧および室温で液状のエーテルを使用することができる。その例は、ジメチルエーテル、ジエチルエーテル、メチルプロピルエーテル、1,2−ジメトキシエタン、ビス(2−メトキシエチル)エーテル、ジオキサンまたはテトラヒドロフランである。テトラヒドロフランを使用することが好ましい。反応温度は、有利には、−60℃〜+120℃である。
適切なハロゲン置換カルボン酸は、例えば、3−フルオロ−または4−クロロフタル酸、2−フルオロイソフタル酸、2−フルオロまたは4−フルオロ安息香酸または4−クロロ安息香酸である。
本方法は、カルボン酸ハロゲン化物を、好ましくは、THF、ジオキサンまたはジエチルエーテルのような不活性溶媒中で、−20℃〜80℃の温度で、金属化ホスフィンと反応させることによって開始される.BAPOまたはMAPO化合物のダイマーまたはマルチマー形態を製造する本方法の重要な特徴は、ジ−またはポリ−カルボン酸塩化物に対する金属化ホスフィンのモル比をコントロールすることからなる。酸塩化物基の当量当たり、金属化ホスフィン基の約1当量が利用できるようにすることが望ましい。カルボン酸塩化物は、ホスフィンの過剰が維持されるように、好ましくは、ホスフィン中に滴下される。酸塩化物基の当量当たり、金属化ホスフィン基の約0.5当量を使用すると、環状ビスアシルホスフィンオキサイドが生成する。
式IおよびIIを有するMAPOおよびBAPO化合物も、式VIまたはVIIを有する環状BAPO化合物も、エチレン性不飽和化合物またはそのような化合物からなる混合物の光重合用の光開始剤として使用され得る。この使用は、また、他の光開始剤および/または他の添加剤と組み合わせて行われ得る。
トリメチロールプロパントリアクリレート、トリメタロールエタントリアクリレート、トリメチロールプロパントリメタクリレート、トリメチロールエタントリメタクリレート、テトラメチレングリコールジメタクリレート、トリエチレングリコールジメタクリレート、テトラエチレングリコールジアクリレート、ペンタエリスリトールジアクリレート、ペンタエリスリトールトリアクリレート、ペンタエリスリトールテトラアクリレート、ジペンタエリスリトールジアクリレート、ジペンタエリスリトールトリアクリレート、ジペンタエリスリトールテトラアクリレート、ジペンタエリスリトールペンタアクリレート、ジペンタエリスリトールヘキサアクリレート、トリペンタエリスリトールオクタアクリレート、ペンタエリスリトールジメタクリレート、ペンタエリスリトールトリメタクリレート、ジペンタエリスリトールジメタクリレート、ジペンタエリスリトールテトラメタクリレート、トリペンタエリスリトールオクタメタクリレート、ペンタエリスリトールジイタコネート、ジペンタエリスリトールトリスイタコネート、ジペンタエリスリトールペンタイタコネート、ジペンタエリスリトールヘキサイタコネート、エチレングリコールジアクリレート、1,3−ブタンジオールジアクリレート、1,3−ブタンジオールジメタアクリレート、1,4−ブタンジオールジイタコネート、ソルビトールトリアクリレート、ソルビトールテトラアクリレート、ペンタエリスリトール修飾トリアクリレート、ソルビトールテトラメタクリレート、ソルビトールペンタアクリレート、ソルビトールヘキサアクリレート、オリゴエステルアクリレートおよびメタクリレート、グリセロールジ−およびトリアクリレート、1,4−シクロヘキサンジアクリレート、分子量200〜1,500を有するポリエチレングリコールのビスアクリレートおよびビスメタクリレートまたはそれらの混合物。
2−(2′−ヒドロキシフェニル)ベンゾトリアゾール、2−ヒドロキシベンゾフェノン、非置換または置換安息香酸のエステル、アクリレート、立体障害型アミン、シュウ酸アミド、2−(2−ヒドロキシフェニル)−1,3,5−トリアジン、ホスファイトおよびホスホナイト。
トリエタノールアミン、N−メチルジエタノールアミン、エチルp−ジメチルアミノベンゾエートまたはミヒラーケトン、ベンゾフェノン、チオキサントン、特にイソプロピルチオキサントン、アントラキノンおよび3−アシルクマリン誘導体、テルフェニル、スチリルケトンおよび3−(アロイルメチレン)トリアゾール、カンファキノン、さらに、エオシン、ローダミンおよびエリスロシン染料。
光重合性組成物は、有利には、組成物に基づき、0.05〜20重量%の量、例えば0.05〜15重量%、好ましくは0.1〜5重量%の光開始剤からなる。光開始剤の量は、それらの混合物が使用される場合は、全ての加えられた光開始剤に基づく。
1.ダイマー・ビスシクロホスフィンオキサイド(BAPO)の製造
[フェニル−(2,4,6−トリメチル−ベンゾイル)−ホスフィノイル]−{2,4,6−トリメチル−3− [フェニル−(2,4,6−トリメチル−ベンゾイル)−ホスフィノアンカルボニル]−フェニル}−メタノン
1H−NMR(ppm)7.72〜7.80(m)、7.45〜7.47(m)、6.76(s)、6.62〜6.67(m)、2.11(s)、2.05(s)、1.96(s)および1.89〜1.92(d):CDCl3中で測定。
[3−(ベンジル−イソブチル−ホスフィノアンカルボニル)−2,4,6−トリメチル−フェニル]−(ベンジル−イソブチル−ホスフィノイル)−メタノン
1H−NMR(ppm)7.13〜7.28(m)、6.76(s)、3.14〜3.41(m)、2.01〜2.0(d)、1.60〜1.97(m)および0.89〜0.95(q):CDCl3中で測定。
2−オキソ−2−フェニル−2,5−イソホスフィンドール−1,3−ジオン
重量(g)、製品、説明
30.0 Ebecryl 605 エポキシアクリレート(UCB)
10.0 Ebecryl 710 アミノアクリレート(UCB)
5.0 Ebecryl 40 プロポキル化ペンタエリスリトール(UCB)
30.0 OTA 480 グリセロール誘導体に基づくアクリル化3官能オ
リゴマー(UCB)
24.0 TPGDA トリプロピレングリコールジアクリレート
0.5 Ebecryl 1360 シリコンヘキサアクリレート
0.5 Dow Corning 57 シリコン添加剤、ダウ・コーニング
100.0 全OPV処方
その結果を表1に示す。
基体 白色カード紙(400μm)
塗布装置 (エリクセン)
層厚さ 5μm
ランプ 1m.p. Hg120W/cm(IST)
硬化速度(m/分)
10%光開始剤 8%光開始剤
実施例1 90 50
実施例1.b 80 10
実施例2 30 15
基体 ボール紙
層厚 100μm
ランプ 1m.p.Hg120W/cm(IST)、TLK40/05
硬化速度 10m/分
装置 光沢:ハーズ−グロス(Byk−ガードナー)
光沢20°
10%光開始剤 8%光開始剤
実施例1 88.00 88.00
実施例1.b 88.00
実施例2 88.00 84.00
Claims (10)
- ジ金属化ホスフィンR1P(M)2(n+m)当量をジ−またはポリカルボン酸ハロゲン化物
1当量と反応させて、式IIIを有する中間体を形成させ、
その後、該中間体をさらなるカルボン酸ハロゲン化物(R2−CO−Hal)(n+m)当量と反応させて、式IVを有するビスアシルホスフィン中間体のダイマーおよびマルチマー形態を形成するか、
またはハロゲン化物R3−Hal(n+m)当量と反応させて、式Vを有するモノアシルホスフィン中間体のダイマーおよびマルチマー形態を形成するかのいずれかの後、
上記のホスフィンIVまたはVを酸化して、式IまたはII(式中、Mは、Li、NaまたはKであり、R1、R2およびR3;Q;nおよびmは、請求項1および2で定義されたとおりである。)を有するホスフィンオキサイドを形成することを特徴とする、式Iを有するBAPO化合物のダイマーおよびマルチマー形態ならびに式IIを有するMAPO化合物のダイマーおよびマルチマー形態の製造方法。 - Mが、Liであり、該方法を不活性雰囲気中において、−20〜80℃の温度で実施する請求項3、6または7のいずれかに記載の方法。
- nが1であり、mが1である請求項1、2または4のいずれかに記載の方法。
- (a)少なくとも1種のエチレン性不飽和光重合性化合物および
(b)光開始剤として、少なくとも1種の上記に定義された式I、II、VIまたはVIIを有する化合物
からなる光重合性組成物。
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WO2017145484A1 (ja) * | 2016-02-25 | 2017-08-31 | 富士フイルム株式会社 | 水性硬化性組成物、及び、水溶性光重合開始剤 |
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DE102004008304A1 (de) | 2004-02-20 | 2005-09-08 | Covion Organic Semiconductors Gmbh | Organische elektronische Vorrichtungen |
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US20080093776A1 (en) * | 2006-10-05 | 2008-04-24 | 3M Innovative Properties Company | Method of molding ultraviolet cured microstructures and molds |
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DE102012212429A1 (de) | 2012-07-16 | 2014-01-16 | Voco Gmbh | Dentalhandgerät, Verfahren und Verwendung desselben zum Aushärten lichthärtbaren Materials |
GB201213163D0 (en) | 2012-07-24 | 2012-09-05 | Lambson Ltd | Photopolymerisation processes and novel compounds therefor |
ES2720760T3 (es) * | 2012-10-01 | 2019-07-24 | Eth Zuerich | Un procedimiento para la preparación de acilofosfanos |
JP6016768B2 (ja) * | 2013-02-21 | 2016-10-26 | 富士フイルム株式会社 | インク組成物、インクジェット記録方法、及び、高分子開始剤 |
WO2015004566A2 (en) * | 2013-07-08 | 2015-01-15 | Basf Se | Liquid bisacylphosphine oxide photoinitiator |
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- 2003-06-03 BR BR0312133-0A patent/BR0312133A/pt not_active Application Discontinuation
- 2003-06-03 AU AU2003274653A patent/AU2003274653A1/en not_active Abandoned
- 2003-06-03 MX MXPA04011923A patent/MXPA04011923A/es not_active Application Discontinuation
- 2003-06-03 CA CA002489246A patent/CA2489246A1/en not_active Abandoned
- 2003-06-03 EP EP03740176A patent/EP1511754B1/en not_active Expired - Lifetime
- 2003-06-03 DE DE60322388T patent/DE60322388D1/de not_active Expired - Lifetime
- 2003-06-03 US US10/517,231 patent/US7196228B2/en not_active Expired - Fee Related
- 2003-06-03 CN CNB038134772A patent/CN1324037C/zh not_active Expired - Fee Related
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WO2017086224A1 (ja) * | 2015-11-20 | 2017-05-26 | 富士フイルム株式会社 | 光重合開始剤及びその製造方法、重合性組成物、インクジェット記録方法、並びに、アシルホスフィンオキシド化合物 |
JPWO2017086224A1 (ja) * | 2015-11-20 | 2018-10-11 | 富士フイルム株式会社 | 光重合開始剤及びその製造方法、重合性組成物、インクジェット記録方法、並びに、アシルホスフィンオキシド化合物 |
US10941307B2 (en) | 2015-11-20 | 2021-03-09 | Fujifilm Corporation | Photopolymerization initiator and producing method thereof, polymerizable composition, ink jet recording method, and acylphosphine oxide compound |
US11898046B2 (en) | 2015-11-20 | 2024-02-13 | Fujifilm Corporation | Photopolymerization initiator and producing method thereof, polymerizable composition, ink jet recording method, and acylphosphine oxide compound |
WO2017145484A1 (ja) * | 2016-02-25 | 2017-08-31 | 富士フイルム株式会社 | 水性硬化性組成物、及び、水溶性光重合開始剤 |
JPWO2017145484A1 (ja) * | 2016-02-25 | 2018-08-23 | 富士フイルム株式会社 | 水性硬化性組成物、及び、水溶性光重合開始剤 |
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Also Published As
Publication number | Publication date |
---|---|
EP1511754B1 (en) | 2008-07-23 |
AU2003274653A1 (en) | 2003-12-22 |
ATE402183T1 (de) | 2008-08-15 |
MXPA04011923A (es) | 2005-03-31 |
KR20050009744A (ko) | 2005-01-25 |
US20050245768A1 (en) | 2005-11-03 |
US7196228B2 (en) | 2007-03-27 |
WO2003104245A1 (en) | 2003-12-18 |
CA2489246A1 (en) | 2003-12-18 |
CN1324037C (zh) | 2007-07-04 |
BR0312133A (pt) | 2005-04-05 |
EP1511754A1 (en) | 2005-03-09 |
CN1659175A (zh) | 2005-08-24 |
DE60322388D1 (de) | 2008-09-04 |
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