KR960007609A - 요오도늄 염의 개선된 제조방법 - Google Patents
요오도늄 염의 개선된 제조방법 Download PDFInfo
- Publication number
- KR960007609A KR960007609A KR1019950025259A KR19950025259A KR960007609A KR 960007609 A KR960007609 A KR 960007609A KR 1019950025259 A KR1019950025259 A KR 1019950025259A KR 19950025259 A KR19950025259 A KR 19950025259A KR 960007609 A KR960007609 A KR 960007609A
- Authority
- KR
- South Korea
- Prior art keywords
- acid
- dibenzanthracenyl
- phenyl
- substituent
- mixture
- 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.)
- Ceased
Links
- 238000004519 manufacturing process Methods 0.000 title claims abstract 4
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 title claims abstract 3
- 238000000034 method Methods 0.000 claims abstract 11
- 239000002253 acid Substances 0.000 claims abstract 9
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical class OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims abstract 2
- -1 hydrocarbon radical Chemical class 0.000 claims 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 14
- FMMWHPNWAFZXNH-UHFFFAOYSA-N Benz[a]pyrene Chemical compound C1=C2C3=CC=CC=C3C=C(C=C3)C2=C2C3=CC=CC2=C1 FMMWHPNWAFZXNH-UHFFFAOYSA-N 0.000 claims 4
- 239000004215 Carbon black (E152) Substances 0.000 claims 4
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- 229930195733 hydrocarbon Natural products 0.000 claims 4
- 239000000203 mixture Substances 0.000 claims 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- 150000001555 benzenes Chemical group 0.000 claims 3
- 150000001875 compounds Chemical class 0.000 claims 3
- 239000012044 organic layer Substances 0.000 claims 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 claims 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 3
- KGHMWBNEMFNJFZ-UHFFFAOYSA-N Dibenzo[a,e]pyrene Chemical compound C1=C2C3=CC=CC=C3C=C(C=3C4=CC=CC=3)C2=C2C4=CC=CC2=C1 KGHMWBNEMFNJFZ-UHFFFAOYSA-N 0.000 claims 2
- 125000001931 aliphatic group Chemical group 0.000 claims 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims 2
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims 2
- 239000004327 boric acid Substances 0.000 claims 2
- OCKPCBLVNKHBMX-UHFFFAOYSA-N butylbenzene Chemical compound CCCCC1=CC=CC=C1 OCKPCBLVNKHBMX-UHFFFAOYSA-N 0.000 claims 2
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 claims 2
- 125000003336 coronenyl group Chemical group C1(=CC2=CC=C3C=CC4=CC=C5C=CC6=CC=C1C1=C6C5=C4C3=C21)* 0.000 claims 2
- 125000001624 naphthyl group Chemical group 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 claims 2
- JSJCPYAIAMNCBN-UHFFFAOYSA-N 5-methylheptoxybenzene Chemical compound CCC(C)CCCCOC1=CC=CC=C1 JSJCPYAIAMNCBN-UHFFFAOYSA-N 0.000 claims 1
- UPVOVYXEOKLFQE-UHFFFAOYSA-N 5-methylheptylbenzene Chemical compound CCC(C)CCCCC1=CC=CC=C1 UPVOVYXEOKLFQE-UHFFFAOYSA-N 0.000 claims 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 1
- MURVXRLYSCSZAV-UHFFFAOYSA-N [dimethyl(2-phenylpropyl)silyl]oxy-dimethyl-(2-phenylpropyl)silane Chemical compound C=1C=CC=CC=1C(C)C[Si](C)(C)O[Si](C)(C)CC(C)C1=CC=CC=C1 MURVXRLYSCSZAV-UHFFFAOYSA-N 0.000 claims 1
- 125000003158 alcohol group Chemical group 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 150000004996 alkyl benzenes Chemical class 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 150000001735 carboxylic acids Chemical group 0.000 claims 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- CRBREIOFEDVXGE-UHFFFAOYSA-N dodecoxybenzene Chemical compound CCCCCCCCCCCCOC1=CC=CC=C1 CRBREIOFEDVXGE-UHFFFAOYSA-N 0.000 claims 1
- KWKXNDCHNDYVRT-UHFFFAOYSA-N dodecylbenzene Chemical compound CCCCCCCCCCCCC1=CC=CC=C1 KWKXNDCHNDYVRT-UHFFFAOYSA-N 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical group C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 claims 1
- 150000005171 halobenzenes Chemical class 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- BCQZXOMGPXTTIC-UHFFFAOYSA-N halothane Chemical compound FC(F)(F)C(Cl)Br BCQZXOMGPXTTIC-UHFFFAOYSA-N 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- MBAKFIZHTUAVJN-UHFFFAOYSA-I hexafluoroantimony(1-);hydron Chemical compound F.F[Sb](F)(F)(F)F MBAKFIZHTUAVJN-UHFFFAOYSA-I 0.000 claims 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- 239000010410 layer Substances 0.000 claims 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- 210000002445 nipple Anatomy 0.000 claims 1
- 150000002825 nitriles Chemical group 0.000 claims 1
- QDYGCAOQFANHSG-UHFFFAOYSA-N octadecoxybenzene Chemical compound CCCCCCCCCCCCCCCCCCOC1=CC=CC=C1 QDYGCAOQFANHSG-UHFFFAOYSA-N 0.000 claims 1
- ZPIRTVJRHUMMOI-UHFFFAOYSA-N octoxybenzene Chemical compound CCCCCCCCOC1=CC=CC=C1 ZPIRTVJRHUMMOI-UHFFFAOYSA-N 0.000 claims 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- VXNSQGRKHCZUSU-UHFFFAOYSA-N octylbenzene Chemical compound [CH2]CCCCCCCC1=CC=CC=C1 VXNSQGRKHCZUSU-UHFFFAOYSA-N 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 claims 1
- JGTNAGYHADQMCM-UHFFFAOYSA-N perfluorobutanesulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F JGTNAGYHADQMCM-UHFFFAOYSA-N 0.000 claims 1
- DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 claims 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000001388 picenyl group Chemical group C1(=CC=CC2=CC=C3C4=CC=C5C=CC=CC5=C4C=CC3=C21)* 0.000 claims 1
- 239000003880 polar aprotic solvent Substances 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000001725 pyrenyl group Chemical group 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 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 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 125000000542 sulfonic acid group Chemical group 0.000 claims 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 claims 1
- ZYLUTTJKFBSYOL-UHFFFAOYSA-N tetracosylbenzene Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCC1=CC=CC=C1 ZYLUTTJKFBSYOL-UHFFFAOYSA-N 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- 239000008096 xylene Substances 0.000 claims 1
- 125000005023 xylyl group Chemical group 0.000 claims 1
- 125000005520 diaryliodonium group Chemical group 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 1
- 239000008199 coating composition Substances 0.000 abstract 1
- 239000012955 diaryliodonium Substances 0.000 abstract 1
- 238000006116 polymerization reaction Methods 0.000 abstract 1
- 230000005855 radiation Effects 0.000 abstract 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 abstract 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 |
|---|---|---|---|
| US292,149 | 1994-08-17 | ||
| US08/292,149 US5426222A (en) | 1994-08-17 | 1994-08-17 | Method for the preparation of iodonium salts |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR960007609A true KR960007609A (ko) | 1996-03-22 |
Family
ID=23123448
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019950025259A Ceased KR960007609A (ko) | 1994-08-17 | 1995-08-17 | 요오도늄 염의 개선된 제조방법 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US5426222A (enExample) |
| EP (1) | EP0697387B1 (enExample) |
| JP (1) | JPH08169853A (enExample) |
| KR (1) | KR960007609A (enExample) |
| AU (1) | AU696642B2 (enExample) |
| DE (1) | DE69502145T2 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999048945A1 (en) * | 1998-03-20 | 1999-09-30 | Nippon Soda Co., Ltd. | Photocurable composition containing iodonium salt compound |
| 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 |
Family Cites Families (15)
| 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 |
| 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 |
| US4513137A (en) * | 1981-04-09 | 1985-04-23 | The University Of Akron | Iodonium 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 |
| US4482679A (en) * | 1982-09-18 | 1984-11-13 | Ciba-Geigy Corporation | Heat-curable epoxy compositions containing diaryliodosyl salts |
| US4518676A (en) * | 1982-09-18 | 1985-05-21 | Ciba Geigy Corporation | Photopolymerizable compositions containing diaryliodosyl salts |
| JPS59181225A (ja) * | 1983-03-29 | 1984-10-15 | Nippon Petrochem Co Ltd | 芳香族炭化水素の変換方法 |
| 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
Also Published As
| Publication number | Publication date |
|---|---|
| DE69502145D1 (de) | 1998-05-28 |
| JPH08169853A (ja) | 1996-07-02 |
| EP0697387B1 (en) | 1998-04-22 |
| DE69502145T2 (de) | 1998-12-03 |
| AU696642B2 (en) | 1998-09-17 |
| AU2855295A (en) | 1996-02-29 |
| US5426222A (en) | 1995-06-20 |
| EP0697387A2 (en) | 1996-02-21 |
| EP0697387A3 (enExample) | 1996-03-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0109 | Patent application |
Patent event code: PA01091R01D Comment text: Patent Application Patent event date: 19950817 |
|
| PG1501 | Laying open of application | ||
| A201 | Request for examination | ||
| PA0201 | Request for examination |
Patent event code: PA02012R01D Patent event date: 20000714 Comment text: Request for Examination of Application Patent event code: PA02011R01I Patent event date: 19950817 Comment text: Patent Application |
|
| E902 | Notification of reason for refusal | ||
| PE0902 | Notice of grounds for rejection |
Comment text: Notification of reason for refusal Patent event date: 20021009 Patent event code: PE09021S01D |
|
| E601 | Decision to refuse application | ||
| PE0601 | Decision on rejection of patent |
Patent event date: 20021226 Comment text: Decision to Refuse Application Patent event code: PE06012S01D Patent event date: 20021009 Comment text: Notification of reason for refusal Patent event code: PE06011S01I |