JP2012201611A - スルホニウム化合物 - Google Patents
スルホニウム化合物 Download PDFInfo
- Publication number
- JP2012201611A JP2012201611A JP2011066229A JP2011066229A JP2012201611A JP 2012201611 A JP2012201611 A JP 2012201611A JP 2011066229 A JP2011066229 A JP 2011066229A JP 2011066229 A JP2011066229 A JP 2011066229A JP 2012201611 A JP2012201611 A JP 2012201611A
- Authority
- JP
- Japan
- Prior art keywords
- pentafluorophenyl
- tetrakis
- group
- borate
- sulfonium
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- -1 Sulfonium compound Chemical class 0.000 title claims abstract description 38
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 239000003999 initiator Substances 0.000 abstract description 11
- 229920000647 polyepoxide Polymers 0.000 abstract description 10
- 238000006116 polymerization reaction Methods 0.000 abstract description 10
- 239000003822 epoxy resin Substances 0.000 abstract description 9
- 150000001875 compounds Chemical class 0.000 abstract description 8
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 abstract description 6
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 abstract description 5
- 125000000217 alkyl group Chemical group 0.000 abstract description 3
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 17
- LWNGJAHMBMVCJR-UHFFFAOYSA-N (2,3,4,5,6-pentafluorophenoxy)boronic acid Chemical compound OB(O)OC1=C(F)C(F)=C(F)C(F)=C1F LWNGJAHMBMVCJR-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 6
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical class [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 6
- QWELZSJGAPVFPR-UHFFFAOYSA-N 4-but-3-ynylsulfanylphenol Chemical compound OC1=CC=C(SCCC#C)C=C1 QWELZSJGAPVFPR-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 238000001879 gelation Methods 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 239000003505 polymerization initiator Substances 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- QSLPNSWXUQHVLP-UHFFFAOYSA-N $l^{1}-sulfanylmethane Chemical compound [S]C QSLPNSWXUQHVLP-UHFFFAOYSA-N 0.000 description 2
- QASBCTGZKABPKX-UHFFFAOYSA-N 4-(methylsulfanyl)phenol Chemical compound CSC1=CC=C(O)C=C1 QASBCTGZKABPKX-UHFFFAOYSA-N 0.000 description 2
- 150000001463 antimony compounds Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 238000010538 cationic polymerization reaction Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 238000005342 ion exchange Methods 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 230000037048 polymerization activity Effects 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 229920001187 thermosetting polymer Polymers 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- QAEDNLDMOUKNMI-UHFFFAOYSA-O (4-hydroxyphenyl)-dimethylsulfanium Chemical compound C[S+](C)C1=CC=C(O)C=C1 QAEDNLDMOUKNMI-UHFFFAOYSA-O 0.000 description 1
- IUXHPSPHPKXTPA-ONEGZZNKSA-N (e)-1-bromobut-1-ene Chemical compound CC\C=C\Br IUXHPSPHPKXTPA-ONEGZZNKSA-N 0.000 description 1
- AVMHMVJVHYGDOO-NSCUHMNNSA-N (e)-1-bromobut-2-ene Chemical compound C\C=C\CBr AVMHMVJVHYGDOO-NSCUHMNNSA-N 0.000 description 1
- AVMHMVJVHYGDOO-UHFFFAOYSA-N 1-bromobut-2-ene Chemical compound CC=CCBr AVMHMVJVHYGDOO-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- JFNIDIDTWDBBFR-UHFFFAOYSA-N 4-(2-phenylethylsulfanyl)phenol Chemical compound C1=CC(O)=CC=C1SCCC1=CC=CC=C1 JFNIDIDTWDBBFR-UHFFFAOYSA-N 0.000 description 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- ZCJVVPFWJYOXJN-UHFFFAOYSA-N CO[S+](CCC1=CC=CC=C1)C1=CC=CC=C1 Chemical compound CO[S+](CCC1=CC=CC=C1)C1=CC=CC=C1 ZCJVVPFWJYOXJN-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- BQKYMSMPQVMZOQ-UHFFFAOYSA-O OC1=CC=C(C=C1)[S+](C)CC#CC Chemical compound OC1=CC=C(C=C1)[S+](C)CC#CC BQKYMSMPQVMZOQ-UHFFFAOYSA-O 0.000 description 1
- MHXHJAIFSRQDHP-UHFFFAOYSA-N O[S+](CCC1=CC=CC=C1)C1=CC=CC=C1 Chemical compound O[S+](CCC1=CC=CC=C1)C1=CC=CC=C1 MHXHJAIFSRQDHP-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 229940058905 antimony compound for treatment of leishmaniasis and trypanosomiasis Drugs 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- YTKRILODNOEEPX-NSCUHMNNSA-N crotyl chloride Chemical compound C\C=C\CCl YTKRILODNOEEPX-NSCUHMNNSA-N 0.000 description 1
- SFSPUVKCNQHXPP-UHFFFAOYSA-N disodium dioxido-(2,3,4,5,6-pentafluorophenoxy)borane Chemical compound [Na+].B(OC1=C(C(=C(C(=C1F)F)F)F)F)([O-])[O-].[Na+] SFSPUVKCNQHXPP-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 1
- NBADVBNRRHVIAO-UHFFFAOYSA-N phenylsulfanol Chemical compound OSC1=CC=CC=C1 NBADVBNRRHVIAO-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- LJZPPWWHKPGCHS-UHFFFAOYSA-N propargyl chloride Chemical compound ClCC#C LJZPPWWHKPGCHS-UHFFFAOYSA-N 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- SSTZGACKDAVIGZ-UHFFFAOYSA-N sulfanium;bromide Chemical compound [SH3+].[Br-] SSTZGACKDAVIGZ-UHFFFAOYSA-N 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- XDLNRRRJZOJTRW-UHFFFAOYSA-N thiohypochlorous acid Chemical compound ClS XDLNRRRJZOJTRW-UHFFFAOYSA-N 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Epoxy Resins (AREA)
Abstract
Description
4−(メチルチオ)フェノール 7.02g(50ミリモル)と臭化プロパルギル 6.2g (52.5ミリモル)に水 80mlを加え、30℃で90分反応させて4−ヒドロキシフェニルプロパルギルメチルスルホニウム ブロマイドの水溶液を得た。これを室温まで冷却し、酢酸エチル 50mlを加え、テトラキス(ペンタフルオロフェニル)ほう酸ナトリウム塩の10%水溶液 350g(50ミリモル)を滴下し、室温で2時間塩交換反応を行った。
融点 129〜131℃
IR (KBr)cm-1
3599,1646,1516,1464,1279,1182,1085,979,757
NMR(δ値)
8.20〜8.28(1H,d,HO),
6.98〜7.90(4H,m,芳香環) 4.30〜4.40(2H,d,プロパルギルメチレン), 3.15〜3.20(3H,d,CH3S),
2.38(1H,s,プロパルギルメチン)
原料の臭化プロパルギルを臭化2−ブテニル 7.09gに代えた以外は実施例1に準じて実施し、洗浄、乾燥後、白色の4−ヒドロキシフェニル−2−ブテニルメチルスルホニウム テトラキス(ペンタフルオロフェニル)ボレート 33.1g(収率 77.0%)を得た。
融点 98〜101℃
IR (KBr)cm-1
3594,1646,1602,1516,1464,1279,1090,979,756
NMR(δ値)
6.97〜7.85(4H,dd,芳香環),
3.95〜4.15(2H,d,αCH2), 3.00(3H,s,CH3S), 1.62〜1.77(2H,d,末端メチル)
本発明の化合物を重合開始剤として使用した硬化試験例を記載する。実施例1で得られた化合物0.1gをエピコート828(ジャパンエポキシレジン株式会社製 エポキシ樹脂の商品名)10gを混合してJISK7071(1988)の手法に準じてゲル化時間を測定した。結果は表1に記載する。
Claims (1)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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JP2011066229A JP5727830B2 (ja) | 2011-03-24 | 2011-03-24 | スルホニウム化合物 |
Applications Claiming Priority (1)
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JP2011066229A JP5727830B2 (ja) | 2011-03-24 | 2011-03-24 | スルホニウム化合物 |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2012201611A true JP2012201611A (ja) | 2012-10-22 |
JP2012201611A5 JP2012201611A5 (ja) | 2014-05-08 |
JP5727830B2 JP5727830B2 (ja) | 2015-06-03 |
Family
ID=47182964
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JP2011066229A Active JP5727830B2 (ja) | 2011-03-24 | 2011-03-24 | スルホニウム化合物 |
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JP (1) | JP5727830B2 (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2016143474A1 (ja) * | 2015-03-10 | 2016-09-15 | 横浜ゴム株式会社 | カチオン重合開始剤およびエポキシ樹脂組成物 |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH06122705A (ja) * | 1992-08-25 | 1994-05-06 | Nippon Soda Co Ltd | 重合開始剤組成物 |
JPH06345726A (ja) * | 1993-06-15 | 1994-12-20 | Nippon Soda Co Ltd | 新規スルホニウム塩化合物および重合開始剤 |
FR2727416A1 (fr) * | 1994-11-24 | 1996-05-31 | Rhone Poulenc Chimie | Nouveaux amorceurs cationiques thermoactivables, de polymerisation et/ou de reticulation et compositions monomeres et/ou polymeres fonctionnels les mettant en oeuvre |
JPH09176112A (ja) * | 1995-12-28 | 1997-07-08 | Toyo Ink Mfg Co Ltd | 感エネルギー線酸発生剤、感エネルギー線酸発生剤組成物および硬化性組成物 |
JPH1180324A (ja) * | 1997-09-02 | 1999-03-26 | Toshiba Corp | 含浸熱硬化性樹脂組成物および回転電機絶縁コイル |
JP2008122501A (ja) * | 2006-11-09 | 2008-05-29 | Sumitomo Chemical Co Ltd | ポジ型感放射線性樹脂組成物 |
JP2008303167A (ja) * | 2007-06-07 | 2008-12-18 | Sony Chemical & Information Device Corp | 新規なスルホニウムボレート錯体 |
-
2011
- 2011-03-24 JP JP2011066229A patent/JP5727830B2/ja active Active
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH06122705A (ja) * | 1992-08-25 | 1994-05-06 | Nippon Soda Co Ltd | 重合開始剤組成物 |
JPH06345726A (ja) * | 1993-06-15 | 1994-12-20 | Nippon Soda Co Ltd | 新規スルホニウム塩化合物および重合開始剤 |
FR2727416A1 (fr) * | 1994-11-24 | 1996-05-31 | Rhone Poulenc Chimie | Nouveaux amorceurs cationiques thermoactivables, de polymerisation et/ou de reticulation et compositions monomeres et/ou polymeres fonctionnels les mettant en oeuvre |
JPH09176112A (ja) * | 1995-12-28 | 1997-07-08 | Toyo Ink Mfg Co Ltd | 感エネルギー線酸発生剤、感エネルギー線酸発生剤組成物および硬化性組成物 |
JPH1180324A (ja) * | 1997-09-02 | 1999-03-26 | Toshiba Corp | 含浸熱硬化性樹脂組成物および回転電機絶縁コイル |
JP2008122501A (ja) * | 2006-11-09 | 2008-05-29 | Sumitomo Chemical Co Ltd | ポジ型感放射線性樹脂組成物 |
JP2008303167A (ja) * | 2007-06-07 | 2008-12-18 | Sony Chemical & Information Device Corp | 新規なスルホニウムボレート錯体 |
Non-Patent Citations (1)
Title |
---|
JPN6015008790; 鳥羽泰正: '「オニウムボレートを用いた光重合開始剤系の構築」' 高分子論文集 VOL.59,NO.8, 2002, PP.449-459 * |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2016143474A1 (ja) * | 2015-03-10 | 2016-09-15 | 横浜ゴム株式会社 | カチオン重合開始剤およびエポキシ樹脂組成物 |
CN107406581A (zh) * | 2015-03-10 | 2017-11-28 | 横滨橡胶株式会社 | 阳离子聚合引发剂和环氧树脂组合物 |
JPWO2016143474A1 (ja) * | 2015-03-10 | 2017-12-21 | 横浜ゴム株式会社 | カチオン重合開始剤およびエポキシ樹脂組成物 |
TWI671326B (zh) * | 2015-03-10 | 2019-09-11 | 日商橫浜橡膠股份有限公司 | 陽離子聚合起始劑及環氧樹脂組成物 |
CN107406581B (zh) * | 2015-03-10 | 2019-09-27 | 横滨橡胶株式会社 | 阳离子聚合引发剂和环氧树脂组合物 |
JP2020019973A (ja) * | 2015-03-10 | 2020-02-06 | 横浜ゴム株式会社 | カチオン重合開始剤およびエポキシ樹脂組成物 |
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