AU696642B2 - Improved method for the preparation of iodonium salts - Google Patents
Improved method for the preparation of iodonium salts Download PDFInfo
- Publication number
- AU696642B2 AU696642B2 AU28552/95A AU2855295A AU696642B2 AU 696642 B2 AU696642 B2 AU 696642B2 AU 28552/95 A AU28552/95 A AU 28552/95A AU 2855295 A AU2855295 A AU 2855295A AU 696642 B2 AU696642 B2 AU 696642B2
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- Australia
- Prior art keywords
- acid
- group
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- nyl
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- Prior art date
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- 238000000034 method Methods 0.000 title claims description 43
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title claims description 9
- -1 halohydrocarbon radicals Chemical class 0.000 claims description 101
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 67
- 239000002253 acid Substances 0.000 claims description 53
- 150000001450 anions Chemical group 0.000 claims description 27
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 26
- 150000007513 acids Chemical class 0.000 claims description 25
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
- 239000002904 solvent Substances 0.000 claims description 24
- 239000004215 Carbon black (E152) Substances 0.000 claims description 18
- 229930195733 hydrocarbon Natural products 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 16
- 125000001931 aliphatic group Chemical group 0.000 claims description 15
- KWKXNDCHNDYVRT-UHFFFAOYSA-N dodecylbenzene Chemical compound CCCCCCCCCCCCC1=CC=CC=C1 KWKXNDCHNDYVRT-UHFFFAOYSA-N 0.000 claims description 15
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- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 14
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- 125000003336 coronenyl group Chemical group C1(=CC2=CC=C3C=CC4=CC=C5C=CC6=CC=C1C1=C6C5=C4C3=C21)* 0.000 claims description 5
- 239000012955 diaryliodonium Substances 0.000 claims description 5
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
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- 125000005023 xylyl group Chemical group 0.000 claims description 4
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- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 3
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- 239000001257 hydrogen Substances 0.000 claims description 3
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- 238000004519 manufacturing process Methods 0.000 claims description 3
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- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 2
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- 238000006116 polymerization reaction Methods 0.000 claims description 2
- PNGLEYLFMHGIQO-UHFFFAOYSA-M sodium;3-(n-ethyl-3-methoxyanilino)-2-hydroxypropane-1-sulfonate;dihydrate Chemical compound O.O.[Na+].[O-]S(=O)(=O)CC(O)CN(CC)C1=CC=CC(OC)=C1 PNGLEYLFMHGIQO-UHFFFAOYSA-M 0.000 claims description 2
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- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims 1
- 150000003738 xylenes Chemical class 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 61
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
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- 239000000376 reactant Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- ZJMWRROPUADPEA-UHFFFAOYSA-N sec-butylbenzene Chemical compound CCC(C)C1=CC=CC=C1 ZJMWRROPUADPEA-UHFFFAOYSA-N 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 235000015096 spirit Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 125000005409 triarylsulfonium group Chemical group 0.000 description 1
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/32—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of salts of sulfonic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
- C07C17/12—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms in the ring of aromatic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
- C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C309/06—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing halogen atoms, or nitro or nitroso groups bound to the carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/292,149 US5426222A (en) | 1994-08-17 | 1994-08-17 | Method for the preparation of iodonium salts |
| US292149 | 1994-08-17 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2855295A AU2855295A (en) | 1996-02-29 |
| AU696642B2 true AU696642B2 (en) | 1998-09-17 |
Family
ID=23123448
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU28552/95A Ceased AU696642B2 (en) | 1994-08-17 | 1995-08-15 | Improved method for the preparation of iodonium salts |
Country Status (6)
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999048945A1 (fr) * | 1998-03-20 | 1999-09-30 | Nippon Soda Co., Ltd. | Composition photodurcissable contenant un sel d'iodonium |
| US6969576B2 (en) * | 2001-11-30 | 2005-11-29 | Sandia National Laboratories | Photosensitive dissolution inhibitors and resists based on onium salt carboxylates |
| US6858378B1 (en) * | 2002-04-17 | 2005-02-22 | Sandia National Laboratories | Photoimageable composition |
| US6632960B2 (en) * | 2002-06-21 | 2003-10-14 | Goldschmidt Ag | Diaryliodonium salt catalysts made from iodotoluene and a method for preparing them |
| US20060216642A1 (en) * | 2005-03-23 | 2006-09-28 | Fuji Photo Film Co., Ltd. | Lithographic printing plate precursor and lithographic printing method |
| JP5062996B2 (ja) * | 2005-09-20 | 2012-10-31 | 富士フイルム株式会社 | ジアリールヨードニウム塩の製造方法及びジアリールヨードニウム塩 |
| JP7129167B2 (ja) * | 2017-01-20 | 2022-09-01 | 住友化学株式会社 | レジスト組成物及びレジストパターンの製造方法 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4513137A (en) * | 1981-04-09 | 1985-04-23 | The University Of Akron | Iodonium salts |
| US4554360A (en) * | 1983-03-29 | 1985-11-19 | Nippon Petrochemicals Company, Limited | Process for converting aromatic compounds |
| US4826635A (en) * | 1981-04-09 | 1989-05-02 | The University Of Akron | Composition and a process for the preparation of (hydroxy (organosulfonyloxy)iodo)arenes and their use in a regiospecific synthesis of diaryliodonium salts |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4038245A (en) * | 1976-05-21 | 1977-07-26 | The Dow Chemical Company | Char-forming polymer compositions |
| US4108747A (en) * | 1976-07-14 | 1978-08-22 | General Electric Company | Curable compositions and method for curing such compositions |
| US4310469A (en) * | 1978-12-29 | 1982-01-12 | General Electric Company | Diaryliodonium salts |
| US4348525A (en) * | 1981-04-09 | 1982-09-07 | The University Of Akron | Composition and a process for the preparation of [hydroxy(organosulfonyloxy)iodo]arenes and their use in a regiospecific synthesis of diaryliodonium salts |
| US4399071A (en) * | 1982-03-12 | 1983-08-16 | General Electric Company | Method for making diaryliodonium salts |
| US4518676A (en) * | 1982-09-18 | 1985-05-21 | Ciba Geigy Corporation | Photopolymerizable compositions containing diaryliodosyl salts |
| US4482679A (en) * | 1982-09-18 | 1984-11-13 | Ciba-Geigy Corporation | Heat-curable epoxy compositions containing diaryliodosyl salts |
| GB8332073D0 (en) * | 1983-12-01 | 1984-01-11 | Ciba Geigy Ag | Polymerisable compositions |
| US4786441A (en) * | 1987-08-24 | 1988-11-22 | International Business Machines Corporation | Preparation of iodonium and sulfonium triflates |
| US5066795A (en) * | 1989-02-10 | 1991-11-19 | Sagami Chemical Research Center | Perfluoroalkyl-containing compound |
| DE4142327A1 (de) * | 1991-12-20 | 1993-06-24 | Wacker Chemie Gmbh | Jodoniumsalze und verfahren zu deren herstellung |
| FR2688790B1 (fr) * | 1992-03-23 | 1994-05-13 | Rhone Poulenc Chimie | Compositions a base de polyorganosiloxanes a groupements fonctionnels reticulables et leur utilisation pour la realisation de revetements anti-adhesifs. |
-
1994
- 1994-08-17 US US08/292,149 patent/US5426222A/en not_active Expired - Fee Related
-
1995
- 1995-08-11 EP EP95305639A patent/EP0697387B1/en not_active Expired - Lifetime
- 1995-08-11 DE DE69502145T patent/DE69502145T2/de not_active Expired - Fee Related
- 1995-08-15 AU AU28552/95A patent/AU696642B2/en not_active Ceased
- 1995-08-16 JP JP7208794A patent/JPH08169853A/ja not_active Withdrawn
- 1995-08-17 KR KR1019950025259A patent/KR960007609A/ko not_active Ceased
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4513137A (en) * | 1981-04-09 | 1985-04-23 | The University Of Akron | Iodonium salts |
| US4826635A (en) * | 1981-04-09 | 1989-05-02 | The University Of Akron | Composition and a process for the preparation of (hydroxy (organosulfonyloxy)iodo)arenes and their use in a regiospecific synthesis of diaryliodonium salts |
| US4554360A (en) * | 1983-03-29 | 1985-11-19 | Nippon Petrochemicals Company, Limited | Process for converting aromatic compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| DE69502145D1 (de) | 1998-05-28 |
| DE69502145T2 (de) | 1998-12-03 |
| EP0697387A3 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1996-03-27 |
| EP0697387A2 (en) | 1996-02-21 |
| AU2855295A (en) | 1996-02-29 |
| EP0697387B1 (en) | 1998-04-22 |
| US5426222A (en) | 1995-06-20 |
| JPH08169853A (ja) | 1996-07-02 |
| KR960007609A (ko) | 1996-03-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |