DE4014649A1 - Neue mehrfunktionelle verbindungen mit (alpha)-diazo-ss-ketoester- und sulfonsaeureester-einheiten, verfahren zu ihrer herstellung und deren verwendung - Google Patents
Neue mehrfunktionelle verbindungen mit (alpha)-diazo-ss-ketoester- und sulfonsaeureester-einheiten, verfahren zu ihrer herstellung und deren verwendungInfo
- Publication number
- DE4014649A1 DE4014649A1 DE4014649A DE4014649A DE4014649A1 DE 4014649 A1 DE4014649 A1 DE 4014649A1 DE 4014649 A DE4014649 A DE 4014649A DE 4014649 A DE4014649 A DE 4014649A DE 4014649 A1 DE4014649 A1 DE 4014649A1
- Authority
- DE
- Germany
- Prior art keywords
- groups
- radical
- ester
- sulfonic acid
- aliphatic
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 19
- 238000004519 manufacturing process Methods 0.000 title description 11
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 title description 7
- 239000000203 mixture Substances 0.000 claims description 127
- -1 cycloaliphatic Chemical group 0.000 claims description 119
- 239000002904 solvent Substances 0.000 claims description 108
- 150000003459 sulfonic acid esters Chemical class 0.000 claims description 78
- 150000002148 esters Chemical class 0.000 claims description 49
- 125000001931 aliphatic group Chemical group 0.000 claims description 40
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 40
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 31
- 150000001875 compounds Chemical class 0.000 claims description 28
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 26
- 239000002253 acid Substances 0.000 claims description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- 230000007935 neutral effect Effects 0.000 claims description 21
- 125000005842 heteroatom Chemical group 0.000 claims description 19
- 125000003118 aryl group Chemical group 0.000 claims description 18
- 229910052760 oxygen Inorganic materials 0.000 claims description 18
- 239000003153 chemical reaction reagent Substances 0.000 claims description 17
- 238000002360 preparation method Methods 0.000 claims description 17
- 230000005855 radiation Effects 0.000 claims description 17
- 238000001816 cooling Methods 0.000 claims description 12
- 239000011541 reaction mixture Substances 0.000 claims description 12
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
- 125000000468 ketone group Chemical group 0.000 claims description 10
- 239000001301 oxygen Substances 0.000 claims description 10
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 9
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 238000012546 transfer Methods 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- HSVFKFNNMLUVEY-UHFFFAOYSA-N sulfuryl diazide Chemical compound [N-]=[N+]=NS(=O)(=O)N=[N+]=[N-] HSVFKFNNMLUVEY-UHFFFAOYSA-N 0.000 claims description 6
- 125000002837 carbocyclic group Chemical group 0.000 claims description 5
- 238000001035 drying Methods 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- 125000003368 amide group Chemical group 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 238000006467 substitution reaction Methods 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 229930194542 Keto Natural products 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 239000002274 desiccant Substances 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 150000003512 tertiary amines Chemical class 0.000 claims description 2
- 125000002648 azanetriyl group Chemical group *N(*)* 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 214
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 57
- 239000000243 solution Substances 0.000 description 53
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 51
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 48
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 40
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 39
- 239000000047 product Substances 0.000 description 38
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 36
- 239000003921 oil Substances 0.000 description 36
- 150000003254 radicals Chemical class 0.000 description 36
- 239000012074 organic phase Substances 0.000 description 35
- 150000001298 alcohols Chemical class 0.000 description 33
- 239000000741 silica gel Substances 0.000 description 32
- 229910002027 silica gel Inorganic materials 0.000 description 32
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 29
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 25
- 238000004440 column chromatography Methods 0.000 description 25
- 229910052938 sodium sulfate Inorganic materials 0.000 description 25
- 235000011152 sodium sulphate Nutrition 0.000 description 25
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 24
- 238000003756 stirring Methods 0.000 description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
- 239000003480 eluent Substances 0.000 description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 18
- NDLIRBZKZSDGSO-UHFFFAOYSA-N tosyl azide Chemical compound CC1=CC=C(S(=O)(=O)[N-][N+]#N)C=C1 NDLIRBZKZSDGSO-UHFFFAOYSA-N 0.000 description 18
- 238000004140 cleaning Methods 0.000 description 17
- RUUJECRHYIYRSH-UHFFFAOYSA-N (5-ethyl-2,2-dimethyl-1,3-dioxan-5-yl)methanol Chemical compound CCC1(CO)COC(C)(C)OC1 RUUJECRHYIYRSH-UHFFFAOYSA-N 0.000 description 16
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 16
- 229940086542 triethylamine Drugs 0.000 description 16
- OWULJVXJAZBQLL-UHFFFAOYSA-N 4-azidosulfonylbenzoic acid Chemical compound OC(=O)C1=CC=C(S(=O)(=O)N=[N+]=[N-])C=C1 OWULJVXJAZBQLL-UHFFFAOYSA-N 0.000 description 15
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 13
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 13
- 239000008346 aqueous phase Substances 0.000 description 12
- 229910002092 carbon dioxide Inorganic materials 0.000 description 12
- 239000012230 colorless oil Substances 0.000 description 12
- 239000001569 carbon dioxide Substances 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 125000006239 protecting group Chemical group 0.000 description 9
- MBENEXSAQJBPKP-UHFFFAOYSA-N (2,2,5-trimethyl-1,3-dioxan-5-yl)methanol Chemical compound CC1(C)OCC(C)(CO)CO1 MBENEXSAQJBPKP-UHFFFAOYSA-N 0.000 description 8
- 235000011187 glycerol Nutrition 0.000 description 8
- AGNTUZCMJBTHOG-UHFFFAOYSA-N 3-[3-(2,3-dihydroxypropoxy)-2-hydroxypropoxy]propane-1,2-diol Chemical compound OCC(O)COCC(O)COCC(O)CO AGNTUZCMJBTHOG-UHFFFAOYSA-N 0.000 description 7
- 238000000746 purification Methods 0.000 description 7
- 229920006395 saturated elastomer Polymers 0.000 description 7
- JYKSTGLAIMQDRA-UHFFFAOYSA-N tetraglycerol Chemical compound OCC(O)CO.OCC(O)CO.OCC(O)CO.OCC(O)CO JYKSTGLAIMQDRA-UHFFFAOYSA-N 0.000 description 7
- ICVIFRMLTBUBGF-UHFFFAOYSA-N 2,2,6,6-tetrakis(hydroxymethyl)cyclohexan-1-ol Chemical compound OCC1(CO)CCCC(CO)(CO)C1O ICVIFRMLTBUBGF-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 238000011161 development Methods 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 6
- 238000010792 warming Methods 0.000 description 6
- LXACKIJAKIAGST-UHFFFAOYSA-N 5-(benzamidomethyl)thiophene-2-sulfonic acid Chemical compound S1C(S(=O)(=O)O)=CC=C1CNC(=O)C1=CC=CC=C1 LXACKIJAKIAGST-UHFFFAOYSA-N 0.000 description 5
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 5
- 239000005909 Kieselgur Substances 0.000 description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
- 230000003197 catalytic effect Effects 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 239000005457 ice water Substances 0.000 description 5
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 235000011181 potassium carbonates Nutrition 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 238000004809 thin layer chromatography Methods 0.000 description 5
- CGNOMSJAJQUXAT-UHFFFAOYSA-N 2,2-dimethyl-1,3-dioxan-5-ol Chemical compound CC1(C)OCC(O)CO1 CGNOMSJAJQUXAT-UHFFFAOYSA-N 0.000 description 4
- WUCVLFKANBQSOT-UHFFFAOYSA-N 2-[4-[1,1-bis[4-(2-hydroxyethoxy)phenyl]ethyl]phenoxy]ethanol Chemical compound C=1C=C(OCCO)C=CC=1C(C=1C=CC(OCCO)=CC=1)(C)C1=CC=C(OCCO)C=C1 WUCVLFKANBQSOT-UHFFFAOYSA-N 0.000 description 4
- CEPMBESUVXXFST-UHFFFAOYSA-N 3-chloropropane-1-sulfonic acid Chemical compound OS(=O)(=O)CCCCl CEPMBESUVXXFST-UHFFFAOYSA-N 0.000 description 4
- 239000005977 Ethylene Substances 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 230000027455 binding Effects 0.000 description 4
- 238000009739 binding Methods 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
- 125000004185 ester group Chemical group 0.000 description 4
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 230000035945 sensitivity Effects 0.000 description 4
- 150000005846 sugar alcohols Polymers 0.000 description 4
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- LAAXRTRBMYAAFB-UHFFFAOYSA-N (e)-2-diazonio-1-[2-[4-[1-[4-[2-[(e)-2-diazonio-3-oxidopent-2-enoyl]oxyethoxy]phenyl]-1-[4-(2-hydroxyethoxy)phenyl]ethyl]phenoxy]ethoxy]-1-oxopent-2-en-3-olate Chemical compound C1=CC(OCCOC([O-])=C([N+]#N)C(=O)CC)=CC=C1C(C)(C=1C=CC(OCCOC([O-])=C([N+]#N)C(=O)CC)=CC=1)C1=CC=C(OCCO)C=C1 LAAXRTRBMYAAFB-UHFFFAOYSA-N 0.000 description 3
- BPXVHIRIPLPOPT-UHFFFAOYSA-N 1,3,5-tris(2-hydroxyethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound OCCN1C(=O)N(CCO)C(=O)N(CCO)C1=O BPXVHIRIPLPOPT-UHFFFAOYSA-N 0.000 description 3
- HUHXLHLWASNVDB-UHFFFAOYSA-N 2-(oxan-2-yloxy)oxane Chemical compound O1CCCCC1OC1OCCCC1 HUHXLHLWASNVDB-UHFFFAOYSA-N 0.000 description 3
- SSRZDWMVPYKSSG-UHFFFAOYSA-N 5-[cyclohexyl(hydroxy)methylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione Chemical compound O=C1OC(C)(C)OC(=O)C1=C(O)C1CCCCC1 SSRZDWMVPYKSSG-UHFFFAOYSA-N 0.000 description 3
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- WDJHALXBUFZDSR-UHFFFAOYSA-N acetoacetic acid Chemical group CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- YJMNLPRMBFMFDL-UHFFFAOYSA-N n-diazo-2-methylbenzenesulfonamide Chemical compound CC1=CC=CC=C1S(=O)(=O)N=[N+]=[N-] YJMNLPRMBFMFDL-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- 125000001400 nonyl 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])C([H])([H])[H] 0.000 description 3
- 239000012071 phase Substances 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
- GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical class [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- KTXGPIUERQJKOE-UHFFFAOYSA-N (e)-1-cyclohexyl-3-[[2-[(z)-3-cyclohexyl-2-diazonio-3-oxidoprop-2-enoyl]oxy-3,3-bis[[(e)-3-cyclohexyl-2-diazonio-3-oxidoprop-2-enoyl]oxymethyl]-1-(hydroxymethyl)cyclohexyl]methoxy]-2-diazonio-3-oxoprop-1-en-1-olate Chemical compound C1CCC(COC(=O)C(=[N+]=[N-])C(=O)C2CCCCC2)(COC(=O)C(=[N+]=[N-])C(=O)C2CCCCC2)C(OC(=O)C(=[N+]=[N-])C(=O)C2CCCCC2)C1(CO)COC(=O)C(=[N+]=[N-])C(=O)C1CCCCC1 KTXGPIUERQJKOE-UHFFFAOYSA-N 0.000 description 2
- VJMOQOBZDJNHQA-UHFFFAOYSA-N (z)-1-cyclohexyl-2-diazonio-3-oxo-3-[[1,3,3-tris[[(e)-3-cyclohexyl-2-diazonio-3-oxidoprop-2-enoyl]oxymethyl]-2-hydroxycyclohexyl]methoxy]prop-1-en-1-olate Chemical compound C1CCC(COC(=O)C(\[N+]#N)=C(\[O-])C2CCCCC2)(COC(=O)C(\[N+]#N)=C(\[O-])C2CCCCC2)C(O)C1(COC(=O)C(\[N+]#N)=C(\[O-])C1CCCCC1)COC(=O)C(\[N+]#N)=C(\[O-])C1CCCCC1 VJMOQOBZDJNHQA-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- 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 2
- AEXZBOQRKJEZMT-UHFFFAOYSA-N 2-[3-(2-hydroxyethyl)-5-[2-(4-methyl-3-oxopentanoyl)oxyethyl]-2,4,6-trioxo-1,3,5-triazinan-1-yl]ethyl 4-methyl-3-oxopentanoate Chemical compound CC(C)C(=O)CC(=O)OCCN1C(=O)N(CCO)C(=O)N(CCOC(=O)CC(=O)C(C)C)C1=O AEXZBOQRKJEZMT-UHFFFAOYSA-N 0.000 description 2
- CGBAPPTZYRUHEM-UHFFFAOYSA-N 2-diazoethenone Chemical class [N-]=[N+]=C=C=O CGBAPPTZYRUHEM-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
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- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000005840 aryl radicals Chemical group 0.000 description 1
- 125000005325 aryloxy aryl group Chemical group 0.000 description 1
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- CVXBEEMKQHEXEN-UHFFFAOYSA-N carbaryl Chemical compound C1=CC=C2C(OC(=O)NC)=CC=CC2=C1 CVXBEEMKQHEXEN-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- 150000003857 carboxamides Chemical group 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 229960001701 chloroform Drugs 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125797 compound 12 Drugs 0.000 description 1
- 229940125833 compound 23 Drugs 0.000 description 1
- 229940125846 compound 25 Drugs 0.000 description 1
- 229940125851 compound 27 Drugs 0.000 description 1
- 229940127204 compound 29 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 229940125877 compound 31 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- LOGSONSNCYTHPS-UHFFFAOYSA-N cyclopentane-1,3-dione Chemical class O=C1CCC(=O)C1 LOGSONSNCYTHPS-UHFFFAOYSA-N 0.000 description 1
- 230000005595 deprotonation Effects 0.000 description 1
- 238000010537 deprotonation reaction Methods 0.000 description 1
- WOWBFOBYOAGEEA-UHFFFAOYSA-N diafenthiuron Chemical compound CC(C)C1=C(NC(=S)NC(C)(C)C)C(C(C)C)=CC(OC=2C=CC=CC=2)=C1 WOWBFOBYOAGEEA-UHFFFAOYSA-N 0.000 description 1
- POCFBDFTJMJWLG-UHFFFAOYSA-N dihydrosinapic acid methyl ester Natural products COC(=O)CCC1=CC(OC)=C(O)C(OC)=C1 POCFBDFTJMJWLG-UHFFFAOYSA-N 0.000 description 1
- 229910000396 dipotassium phosphate Inorganic materials 0.000 description 1
- 235000019797 dipotassium phosphate Nutrition 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002085 enols Chemical group 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 238000005562 fading Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- GXHFUVWIGNLZSC-UHFFFAOYSA-N meldrum's acid Chemical compound CC1(C)OC(=O)CC(=O)O1 GXHFUVWIGNLZSC-UHFFFAOYSA-N 0.000 description 1
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 1
- MIOOVIILBQHHNK-UHFFFAOYSA-N methyl 3-cyclohexyl-3-oxopropanoate Chemical compound COC(=O)CC(=O)C1CCCCC1 MIOOVIILBQHHNK-UHFFFAOYSA-N 0.000 description 1
- 150000005217 methyl ethers Chemical class 0.000 description 1
- 238000001393 microlithography Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- BHQIGUWUNPQBJY-UHFFFAOYSA-N n-diazomethanesulfonamide Chemical compound CS(=O)(=O)N=[N+]=[N-] BHQIGUWUNPQBJY-UHFFFAOYSA-N 0.000 description 1
- MSYOIOMHZVPPIY-UHFFFAOYSA-N n-diazonaphthalene-2-sulfonamide Chemical compound C1=CC=CC2=CC(S(=O)(=O)N=[N+]=[N-])=CC=C21 MSYOIOMHZVPPIY-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 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 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 150000002905 orthoesters Chemical class 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- DRINJBFRTLBHNF-UHFFFAOYSA-N propane-2-sulfonyl chloride Chemical compound CC(C)S(Cl)(=O)=O DRINJBFRTLBHNF-UHFFFAOYSA-N 0.000 description 1
- HNDXKIMMSFCCFW-UHFFFAOYSA-N propane-2-sulphonic acid Chemical class CC(C)S(O)(=O)=O HNDXKIMMSFCCFW-UHFFFAOYSA-N 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 125000004079 stearyl 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])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])[H] 0.000 description 1
- 238000013517 stratification Methods 0.000 description 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
- 238000012549 training Methods 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 1
- UAIFZYSPVVBOPN-UHFFFAOYSA-N trimethyl(prop-1-en-2-yloxy)silane Chemical compound CC(=C)O[Si](C)(C)C UAIFZYSPVVBOPN-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/63—Esters of sulfonic acids
- C07C309/64—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/63—Esters of sulfonic acids
- C07C309/64—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
- C07C309/65—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/63—Esters of sulfonic acids
- C07C309/64—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
- C07C309/67—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of an unsaturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/63—Esters of sulfonic acids
- C07C309/72—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/73—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/63—Esters of sulfonic acids
- C07C309/72—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/77—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing carboxyl groups bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/30—Only oxygen atoms
- C07D251/32—Cyanuric acid; Isocyanuric acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/30—Hetero atoms other than halogen
- C07D333/34—Sulfur atoms
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/016—Diazonium salts or compounds
- G03F7/0163—Non ionic diazonium compounds, e.g. diazosulphonates; Precursors thereof, e.g. triazenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/56—Ring systems containing bridged rings
- C07C2603/58—Ring systems containing bridged rings containing three rings
- C07C2603/70—Ring systems containing bridged rings containing three rings containing only six-membered rings
- C07C2603/74—Adamantanes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Indole Compounds (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4014649A DE4014649A1 (de) | 1990-05-08 | 1990-05-08 | Neue mehrfunktionelle verbindungen mit (alpha)-diazo-ss-ketoester- und sulfonsaeureester-einheiten, verfahren zu ihrer herstellung und deren verwendung |
| EP91106918A EP0456073B1 (de) | 1990-05-08 | 1991-04-29 | Mehrfunktionelle Verbindungen mit alpha-Diazo-beta-ketoester- und Sulfonsäureester-Einheiten und Verfahren zu ihrer Herstellung. |
| DE59106750T DE59106750D1 (de) | 1990-05-08 | 1991-04-29 | Mehrfunktionelle Verbindungen mit alpha-Diazo-beta-ketoester- und Sulfonsäureester-Einheiten und Verfahren zu ihrer Herstellung. |
| US07/694,386 US5191069A (en) | 1990-05-08 | 1991-05-01 | Polyfunctional compounds containing α-diazo-β-keto ester units and sulfonate units |
| KR1019910007328A KR920021502A (ko) | 1990-05-08 | 1991-05-07 | α-디아조-β-케토 에스테르 단위 및 설포네이트 단위를 함유하는 다작용성 화합물, 이의 제조방법 및 이의 용도 |
| JP3131954A JPH04225948A (ja) | 1990-05-08 | 1991-05-08 | α‐ジアゾ‐β‐ケトエステル単位およびスルホン酸エステル単位を含む新規な多官能性化合物、それらの調製方法およびそれらの使用 |
| TW080104078A TW201729B (enExample) | 1990-05-08 | 1991-05-25 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4014649A DE4014649A1 (de) | 1990-05-08 | 1990-05-08 | Neue mehrfunktionelle verbindungen mit (alpha)-diazo-ss-ketoester- und sulfonsaeureester-einheiten, verfahren zu ihrer herstellung und deren verwendung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE4014649A1 true DE4014649A1 (de) | 1991-11-14 |
Family
ID=6405904
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE4014649A Withdrawn DE4014649A1 (de) | 1990-05-08 | 1990-05-08 | Neue mehrfunktionelle verbindungen mit (alpha)-diazo-ss-ketoester- und sulfonsaeureester-einheiten, verfahren zu ihrer herstellung und deren verwendung |
| DE59106750T Expired - Fee Related DE59106750D1 (de) | 1990-05-08 | 1991-04-29 | Mehrfunktionelle Verbindungen mit alpha-Diazo-beta-ketoester- und Sulfonsäureester-Einheiten und Verfahren zu ihrer Herstellung. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE59106750T Expired - Fee Related DE59106750D1 (de) | 1990-05-08 | 1991-04-29 | Mehrfunktionelle Verbindungen mit alpha-Diazo-beta-ketoester- und Sulfonsäureester-Einheiten und Verfahren zu ihrer Herstellung. |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US5191069A (enExample) |
| EP (1) | EP0456073B1 (enExample) |
| JP (1) | JPH04225948A (enExample) |
| KR (1) | KR920021502A (enExample) |
| DE (2) | DE4014649A1 (enExample) |
| TW (1) | TW201729B (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4014648A1 (de) * | 1990-05-08 | 1991-11-14 | Hoechst Ag | Positiv arbeitendes strahlungsempfindiches gemisch und strahlungsempfindliches aufzeichnungsmaterial fuer die belichtung mit duv-strahlung |
| DE19647395A1 (de) * | 1996-11-15 | 1998-05-20 | Basf Ag | Verfahren zur Herstellung von cyclischen Acetalen oder Ketalen |
| TW550439B (en) * | 1997-07-01 | 2003-09-01 | Ciba Sc Holding Ag | New oxime sulfonates as latent acids and compositions and photoresists comprising said oxime sulfonates |
| DE19744748A1 (de) | 1997-10-10 | 1999-04-15 | Basf Ag | Polyurethan-Zweikomponentensysteme, die Reaktivverdünner enthalten |
| KR100320773B1 (ko) | 1999-05-31 | 2002-01-17 | 윤종용 | 포토레지스트 조성물 |
| CA2893843C (en) | 2012-12-21 | 2018-09-04 | Gilead Sciences, Inc. | Polycyclic-carbamoylpyridone compounds and their pharmaceutical use |
| WO2014150267A1 (en) | 2013-03-15 | 2014-09-25 | Momentive Specialty Chemicals Inc. | Amino-formaldehyde resins and applications thereof |
| DK3019503T3 (da) | 2013-07-12 | 2017-11-20 | Gilead Sciences Inc | Polycykliske-carbamoylpyridon-forbindelser og anvendelse deraf til behandling af hiv-infektioner |
| NO2865735T3 (enExample) | 2013-07-12 | 2018-07-21 | ||
| TWI677489B (zh) | 2014-06-20 | 2019-11-21 | 美商基利科學股份有限公司 | 多環型胺甲醯基吡啶酮化合物之合成 |
| NO2717902T3 (enExample) | 2014-06-20 | 2018-06-23 | ||
| TW201613936A (en) | 2014-06-20 | 2016-04-16 | Gilead Sciences Inc | Crystalline forms of(2R,5S,13aR)-8-hydroxy-7,9-dioxo-n-(2,4,6-trifluorobenzyl)-2,3,4,5,7,9,13,13a-octahydro-2,5-methanopyrido[1',2':4,5]pyrazino[2,1-b][1,3]oxazepine-10-carboxamide |
| CA3223390A1 (en) | 2021-08-17 | 2023-02-23 | Colin Brown | Methods and compositions for identifying methylated cytosines |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4339522A (en) * | 1979-06-18 | 1982-07-13 | International Business Machines Corporation | Ultra-violet lithographic resist composition and process |
| US4556513A (en) * | 1982-12-03 | 1985-12-03 | Meiji Seika Kaisha, Ltd. | Process for the production of antibiotic 1-oxadethiacephalosporins, and intermediate |
| US4683296A (en) * | 1983-03-07 | 1987-07-28 | Bristol-Myers Company | Carbapenem intermediates |
| US4622283A (en) * | 1983-10-07 | 1986-11-11 | J. T. Baker Chemical Company | Deep ultra-violet lithographic resist composition and process of using |
| US4601969A (en) * | 1985-03-28 | 1986-07-22 | International Business Machines Corporation | High contrast, high resolution deep ultraviolet lithographic resist composition with diazo carbonyl compound having alpha phosphoryl substitution |
| US4624908A (en) * | 1985-04-15 | 1986-11-25 | J. T. Baker Chemical Company | Deep ultra-violet lithographic resist composition and process of using |
| US4735885A (en) * | 1985-12-06 | 1988-04-05 | Allied Corporation | Deep UV photoresist composition with 1,3-disubstituted-5-diazobarbituric acids |
| GB8707515D0 (en) * | 1987-03-30 | 1987-05-07 | Fujisawa Pharmaceutical Co | Amino acid derivatives |
| EP0319325A3 (en) * | 1987-12-04 | 1990-12-27 | Wako Pure Chemical Industries, Ltd. | Photosensitive material and process for forming pattern using the same |
| DE3844739C2 (de) * | 1987-12-10 | 1995-09-07 | Toshiba Kawasaki Kk | Siliziumhaltiges lichtempfindliches Gemisch |
| JP2615742B2 (ja) * | 1988-01-22 | 1997-06-04 | 松下電器産業株式会社 | 感光性化合物を用いたレジスト |
| JPH01265066A (ja) * | 1988-04-15 | 1989-10-23 | Hitachi Ltd | α−ジアゾアセト酢酸エステル及びその製造方法 |
| DE3900736A1 (de) * | 1989-01-12 | 1990-07-26 | Hoechst Ag | Positiv arbeitendes strahlungsempfindliches gemisch enthaltend einen mehrfunktionellen (alpha)-diazo-(beta)-ketoester, verfahren zu dessen herstellung und strahlungsempfindliches aufzeichnungsmaterial enthaltend dieses gemisch |
| DE4014648A1 (de) * | 1990-05-08 | 1991-11-14 | Hoechst Ag | Positiv arbeitendes strahlungsempfindiches gemisch und strahlungsempfindliches aufzeichnungsmaterial fuer die belichtung mit duv-strahlung |
-
1990
- 1990-05-08 DE DE4014649A patent/DE4014649A1/de not_active Withdrawn
-
1991
- 1991-04-29 DE DE59106750T patent/DE59106750D1/de not_active Expired - Fee Related
- 1991-04-29 EP EP91106918A patent/EP0456073B1/de not_active Expired - Lifetime
- 1991-05-01 US US07/694,386 patent/US5191069A/en not_active Expired - Fee Related
- 1991-05-07 KR KR1019910007328A patent/KR920021502A/ko not_active Withdrawn
- 1991-05-08 JP JP3131954A patent/JPH04225948A/ja active Pending
- 1991-05-25 TW TW080104078A patent/TW201729B/zh active
Also Published As
| Publication number | Publication date |
|---|---|
| EP0456073B1 (de) | 1995-10-25 |
| US5191069A (en) | 1993-03-02 |
| DE59106750D1 (de) | 1995-11-30 |
| EP0456073A3 (en) | 1991-12-04 |
| KR920021502A (ko) | 1992-12-18 |
| JPH04225948A (ja) | 1992-08-14 |
| EP0456073A2 (de) | 1991-11-13 |
| TW201729B (enExample) | 1993-03-11 |
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