CA1175811A - Diazonium sulfonates and uses thereof - Google Patents
Diazonium sulfonates and uses thereofInfo
- Publication number
- CA1175811A CA1175811A CA000390217A CA390217A CA1175811A CA 1175811 A CA1175811 A CA 1175811A CA 000390217 A CA000390217 A CA 000390217A CA 390217 A CA390217 A CA 390217A CA 1175811 A CA1175811 A CA 1175811A
- Authority
- CA
- Canada
- Prior art keywords
- trifluoromethylsulfonate
- diazonium
- diazography
- sulfonate
- formulation
- 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.)
- Expired
Links
- 239000012954 diazonium Substances 0.000 title claims abstract description 115
- -1 Diazonium sulfonates Chemical class 0.000 title claims abstract description 87
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims abstract description 107
- 239000000203 mixture Substances 0.000 claims abstract description 82
- 238000009472 formulation Methods 0.000 claims abstract description 40
- 150000001989 diazonium salts Chemical class 0.000 claims abstract description 26
- 150000001768 cations Chemical class 0.000 claims abstract description 13
- 239000000463 material Substances 0.000 claims description 64
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 claims description 61
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 55
- 239000002253 acid Substances 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 24
- 125000003118 aryl group Chemical group 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 21
- CIZVQWNPBGYCGK-UHFFFAOYSA-N benzenediazonium Chemical compound N#[N+]C1=CC=CC=C1 CIZVQWNPBGYCGK-UHFFFAOYSA-N 0.000 claims description 18
- 239000002904 solvent Substances 0.000 claims description 17
- 230000008569 process Effects 0.000 claims description 16
- 230000008878 coupling Effects 0.000 claims description 15
- 238000010168 coupling process Methods 0.000 claims description 15
- 238000005859 coupling reaction Methods 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 238000006116 polymerization reaction Methods 0.000 claims description 13
- 239000000178 monomer Substances 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 238000006149 azo coupling reaction Methods 0.000 claims description 10
- 150000002118 epoxides Chemical class 0.000 claims description 10
- 239000003112 inhibitor Substances 0.000 claims description 10
- 230000005855 radiation Effects 0.000 claims description 9
- 239000000758 substrate Substances 0.000 claims description 9
- 150000002596 lactones Chemical class 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 7
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- 125000005561 phenanthryl group Chemical group 0.000 claims description 7
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 238000000354 decomposition reaction Methods 0.000 claims description 6
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 claims description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims description 5
- 230000002378 acidificating effect Effects 0.000 claims description 5
- 125000005024 alkenyl aryl group Chemical group 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 239000000987 azo dye Substances 0.000 claims description 5
- 229920000642 polymer Polymers 0.000 claims description 5
- MTLLOVNAURGSIK-UHFFFAOYSA-M 2,5-dimethoxy-4-(4-methylphenyl)sulfanylbenzenediazonium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.COC1=CC([N+]#N)=C(OC)C=C1SC1=CC=C(C)C=C1 MTLLOVNAURGSIK-UHFFFAOYSA-M 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 4
- 125000001769 aryl amino group Chemical group 0.000 claims description 4
- 230000003197 catalytic effect Effects 0.000 claims description 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 4
- SNZXFRFQGXSSGN-UHFFFAOYSA-N phenylsulfanyloxysulfanylbenzene Chemical compound C=1C=CC=CC=1SOSC1=CC=CC=C1 SNZXFRFQGXSSGN-UHFFFAOYSA-N 0.000 claims description 4
- LBTBIJDNDZRVER-UHFFFAOYSA-M 2,4-dimethoxybenzenediazonium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.COC1=CC=C([N+]#N)C(OC)=C1 LBTBIJDNDZRVER-UHFFFAOYSA-M 0.000 claims description 3
- YWOQXKPQDUFZEM-UHFFFAOYSA-M 2,5-diethoxy-4-(4-methylphenyl)sulfanylbenzenediazonium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.CCOC1=CC([N+]#N)=C(OCC)C=C1SC1=CC=C(C)C=C1 YWOQXKPQDUFZEM-UHFFFAOYSA-M 0.000 claims description 3
- GMROFGKJUJLQIJ-UHFFFAOYSA-M 2,5-diethoxy-4-phenylsulfanylbenzenediazonium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.CCOC1=CC([N+]#N)=C(OCC)C=C1SC1=CC=CC=C1 GMROFGKJUJLQIJ-UHFFFAOYSA-M 0.000 claims description 3
- BRCTXLNLUGVRNN-UHFFFAOYSA-M 4-(4-chlorophenoxy)-2,5-diethoxybenzenediazonium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.CCOC1=CC([N+]#N)=C(OCC)C=C1OC1=CC=C(Cl)C=C1 BRCTXLNLUGVRNN-UHFFFAOYSA-M 0.000 claims description 3
- ICRLNNNKWMQRDM-UHFFFAOYSA-M 4-morpholin-4-yl-2,5-di(propan-2-yloxy)benzenediazonium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=C([N+]#N)C(OC(C)C)=CC(N2CCOCC2)=C1OC(C)C ICRLNNNKWMQRDM-UHFFFAOYSA-M 0.000 claims description 3
- 238000011161 development Methods 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- PNKZBZPLRKCVLI-UHFFFAOYSA-N (2-methylpropan-2-yl)oxybenzene Chemical compound CC(C)(C)OC1=CC=CC=C1 PNKZBZPLRKCVLI-UHFFFAOYSA-N 0.000 claims description 2
- UIQDRRQDSQRRLM-UHFFFAOYSA-N 1-(3-methylbutan-2-yloxy)naphthalene Chemical compound C1=CC=C2C(OC(C)C(C)C)=CC=CC2=C1 UIQDRRQDSQRRLM-UHFFFAOYSA-N 0.000 claims description 2
- CQTPIJQVFIVEGT-UHFFFAOYSA-N 1-[(2-methylpropan-2-yl)oxy]naphthalene Chemical compound C1=CC=C2C(OC(C)(C)C)=CC=CC2=C1 CQTPIJQVFIVEGT-UHFFFAOYSA-N 0.000 claims description 2
- QQIXXARXQNTKCP-UHFFFAOYSA-N 1-bromo-4-[(2-methylpropan-2-yl)oxy]naphthalene Chemical compound C1=CC=C2C(OC(C)(C)C)=CC=C(Br)C2=C1 QQIXXARXQNTKCP-UHFFFAOYSA-N 0.000 claims description 2
- HIDABGBTTZQWGE-UHFFFAOYSA-M 2,5-dimethoxy-4-morpholin-4-ylbenzenediazonium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=C([N+]#N)C(OC)=CC(N2CCOCC2)=C1OC HIDABGBTTZQWGE-UHFFFAOYSA-M 0.000 claims description 2
- HKMFVHIOGQPGRA-UHFFFAOYSA-M 2-chlorobenzenediazonium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.ClC1=CC=CC=C1[N+]#N HKMFVHIOGQPGRA-UHFFFAOYSA-M 0.000 claims description 2
- YYNFWYSHAJZVCX-UHFFFAOYSA-M 2-methoxybenzenediazonium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.COC1=CC=CC=C1[N+]#N YYNFWYSHAJZVCX-UHFFFAOYSA-M 0.000 claims description 2
- ITBWUATXCGWRFO-UHFFFAOYSA-M 3-methoxy-4-(4-methylphenyl)sulfanylbenzenediazonium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.COC1=CC([N+]#N)=CC=C1SC1=CC=C(C)C=C1 ITBWUATXCGWRFO-UHFFFAOYSA-M 0.000 claims description 2
- VYYLLSPKXPATCF-UHFFFAOYSA-M 4-chlorobenzenediazonium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.ClC1=CC=C([N+]#N)C=C1 VYYLLSPKXPATCF-UHFFFAOYSA-M 0.000 claims description 2
- FJIUFBGRMLBERH-UHFFFAOYSA-M 4-chloronaphthalene-1-diazonium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC=C2C(Cl)=CC=C([N+]#N)C2=C1 FJIUFBGRMLBERH-UHFFFAOYSA-M 0.000 claims description 2
- OAYHQIHRYRWYEO-UHFFFAOYSA-M 4-phenylmethoxybenzenediazonium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC([N+]#N)=CC=C1OCC1=CC=CC=C1 OAYHQIHRYRWYEO-UHFFFAOYSA-M 0.000 claims description 2
- NCUNVMIPCBLELH-UHFFFAOYSA-M 4-pyrrolidin-1-ylnaphthalene-1-diazonium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C12=CC=CC=C2C([N+]#N)=CC=C1N1CCCC1 NCUNVMIPCBLELH-UHFFFAOYSA-M 0.000 claims description 2
- PSFCVFPWIMGMGS-UHFFFAOYSA-M 6-morpholin-4-ylpyridine-3-diazonium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.N1=CC([N+]#N)=CC=C1N1CCOCC1 PSFCVFPWIMGMGS-UHFFFAOYSA-M 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 125000006267 biphenyl group Chemical group 0.000 claims description 2
- 230000000694 effects Effects 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- JMGWESOVQVAGNE-UHFFFAOYSA-N n-(2-ethylphenyl)-3-(2-methoxyethoxymethoxy)naphthalene-2-carboxamide Chemical compound CCC1=CC=CC=C1NC(=O)C1=CC2=CC=CC=C2C=C1OCOCCOC JMGWESOVQVAGNE-UHFFFAOYSA-N 0.000 claims description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 4
- 125000001475 halogen functional group Chemical group 0.000 claims 3
- QIZPASVBKOHLGL-UHFFFAOYSA-M 4-(2,6-dimethylmorpholin-4-yl)benzenediazonium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1C(C)OC(C)CN1C1=CC=C([N+]#N)C=C1 QIZPASVBKOHLGL-UHFFFAOYSA-M 0.000 claims 2
- NSSXACMFFBFQNE-UHFFFAOYSA-N 1-(1-butoxyethoxy)naphthalene Chemical compound C1=CC=C2C(OC(C)OCCCC)=CC=CC2=C1 NSSXACMFFBFQNE-UHFFFAOYSA-N 0.000 claims 1
- LQASNGDRTHETOK-UHFFFAOYSA-N 1-[(2-methylpropan-2-yl)oxy]-5-[2-[5-[(2-methylpropan-2-yl)oxy]naphthalen-1-yl]ethyl]naphthalene Chemical compound C1=CC=C2C(CCC3=C4C=CC=C(C4=CC=C3)OC(C)(C)C)=CC=CC2=C1OC(C)(C)C LQASNGDRTHETOK-UHFFFAOYSA-N 0.000 claims 1
- DAFULUFUWJEOSK-UHFFFAOYSA-N 2-naphthalen-1-yloxyoxane Chemical compound O1CCCCC1OC1=CC=CC2=CC=CC=C12 DAFULUFUWJEOSK-UHFFFAOYSA-N 0.000 claims 1
- RPCVBERUBAWVJL-UHFFFAOYSA-M 3-chloro-4-(4-methylphenyl)sulfanylbenzenediazonium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC(C)=CC=C1SC1=CC=C([N+]#N)C=C1Cl RPCVBERUBAWVJL-UHFFFAOYSA-M 0.000 claims 1
- XSFCTLSDHWDXHB-UHFFFAOYSA-M 4-(3,5-dimethylmorpholin-4-yl)benzenediazonium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.CC1COCC(C)N1C1=CC=C([N+]#N)C=C1 XSFCTLSDHWDXHB-UHFFFAOYSA-M 0.000 claims 1
- NKECHNXDSURVNO-UHFFFAOYSA-M 4-ethoxybenzenediazonium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.CCOC1=CC=C([N+]#N)C=C1 NKECHNXDSURVNO-UHFFFAOYSA-M 0.000 claims 1
- NBPYPSWYCWXMFB-UHFFFAOYSA-M 4-methyl-2-nitrobenzenediazonium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.CC1=CC=C([N+]#N)C([N+]([O-])=O)=C1 NBPYPSWYCWXMFB-UHFFFAOYSA-M 0.000 claims 1
- XRRQBISKMYDCQW-UHFFFAOYSA-M 4-nitrobenzenediazonium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.[O-][N+](=O)C1=CC=C([N+]#N)C=C1 XRRQBISKMYDCQW-UHFFFAOYSA-M 0.000 claims 1
- ZRHGSXSUDMCUMT-UHFFFAOYSA-M 6-(dimethylamino)pyridine-3-diazonium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.CN(C)C1=CC=C([N+]#N)C=N1 ZRHGSXSUDMCUMT-UHFFFAOYSA-M 0.000 claims 1
- QRXYLDGKSJHWPG-UHFFFAOYSA-M 9h-carbazole-2-diazonium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC=C2C3=CC=C([N+]#N)C=C3NC2=C1 QRXYLDGKSJHWPG-UHFFFAOYSA-M 0.000 claims 1
- 125000005605 benzo group Chemical group 0.000 claims 1
- 230000000379 polymerizing effect Effects 0.000 claims 1
- 238000005406 washing Methods 0.000 claims 1
- 150000003839 salts Chemical class 0.000 abstract description 23
- 239000003505 polymerization initiator Substances 0.000 abstract description 8
- 239000007795 chemical reaction product Substances 0.000 abstract description 4
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 33
- 239000000126 substance Substances 0.000 description 20
- 239000000306 component Substances 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 14
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 14
- 230000001235 sensitizing effect Effects 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 9
- 150000008049 diazo compounds Chemical class 0.000 description 9
- 239000010410 layer Substances 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- YKYOUMDCQGMQQO-UHFFFAOYSA-L cadmium dichloride Chemical compound Cl[Cd]Cl YKYOUMDCQGMQQO-UHFFFAOYSA-L 0.000 description 8
- 238000000576 coating method Methods 0.000 description 8
- 150000001450 anions Chemical class 0.000 description 7
- 239000011248 coating agent Substances 0.000 description 7
- BTZNPZMHENLISZ-UHFFFAOYSA-N fluoromethanesulfonic acid Chemical compound OS(=O)(=O)CF BTZNPZMHENLISZ-UHFFFAOYSA-N 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 238000001556 precipitation Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000011592 zinc chloride Substances 0.000 description 6
- 235000005074 zinc chloride Nutrition 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 150000002576 ketones Chemical class 0.000 description 5
- 229920003023 plastic Polymers 0.000 description 5
- 239000004033 plastic Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000000654 additive Substances 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 238000003384 imaging method Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000011159 matrix material Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- 239000012429 reaction media Substances 0.000 description 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 229920008347 Cellulose acetate propionate Polymers 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 3
- 239000012431 aqueous reaction media Substances 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 239000012964 benzotriazole Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000012018 catalyst precursor Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 150000004292 cyclic ethers Chemical class 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 230000033458 reproduction Effects 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- NKTOLZVEWDHZMU-UHFFFAOYSA-N 2,5-xylenol Chemical compound CC1=CC=C(C)C(O)=C1 NKTOLZVEWDHZMU-UHFFFAOYSA-N 0.000 description 2
- UYEMGAFJOZZIFP-UHFFFAOYSA-N 3,5-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC(O)=C1 UYEMGAFJOZZIFP-UHFFFAOYSA-N 0.000 description 2
- DBEQHSWUYRYJMT-UHFFFAOYSA-N 4-chlorobenzenediazonium Chemical compound ClC1=CC=C([N+]#N)C=C1 DBEQHSWUYRYJMT-UHFFFAOYSA-N 0.000 description 2
- NLGKUUBHOZCNAL-UHFFFAOYSA-N 4-ethoxybenzenediazonium Chemical compound CCOC1=CC=C([N+]#N)C=C1 NLGKUUBHOZCNAL-UHFFFAOYSA-N 0.000 description 2
- NJYDJNRTEZIUBS-UHFFFAOYSA-N 4-morpholin-4-ylbenzenediazonium Chemical compound C1=CC([N+]#N)=CC=C1N1CCOCC1 NJYDJNRTEZIUBS-UHFFFAOYSA-N 0.000 description 2
- DKJVSIITPZVTRO-UHFFFAOYSA-N 6,7-dihydroxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C=C(O)C(O)=CC2=C1 DKJVSIITPZVTRO-UHFFFAOYSA-N 0.000 description 2
- JAESEVUZBMTKFI-UHFFFAOYSA-N 6-(pyridin-2-ylamino)pyridine-3-diazonium Chemical compound N1=CC([N+]#N)=CC=C1NC1=CC=CC=N1 JAESEVUZBMTKFI-UHFFFAOYSA-N 0.000 description 2
- BKIPSJHDEMCBCE-UHFFFAOYSA-N 6-morpholin-4-ylpyridine-3-diazonium Chemical compound N1=CC([N+]#N)=CC=C1N1CCOCC1 BKIPSJHDEMCBCE-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
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- 239000012442 inert solvent Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 239000005453 ketone based solvent Substances 0.000 description 1
- 208000013469 light sensitivity Diseases 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 229960002900 methylcellulose Drugs 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- KOHNUEXAOQRRPI-UHFFFAOYSA-N n-benzyl-3-oxobutanamide Chemical compound CC(=O)CC(=O)NCC1=CC=CC=C1 KOHNUEXAOQRRPI-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- LGQLOGILCSXPEA-UHFFFAOYSA-L nickel sulfate Chemical class [Ni+2].[O-]S([O-])(=O)=O LGQLOGILCSXPEA-UHFFFAOYSA-L 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000012430 organic reaction media Substances 0.000 description 1
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 1
- 229960001553 phloroglucinol Drugs 0.000 description 1
- 238000006303 photolysis reaction Methods 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 229920000131 polyvinylidene Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- YRAXWUBIFFTPLB-UHFFFAOYSA-N pyridine-3-diazonium Chemical compound N#[N+]C1=CC=CN=C1 YRAXWUBIFFTPLB-UHFFFAOYSA-N 0.000 description 1
- 239000001397 quillaja saponaria molina bark Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229930182490 saponin Natural products 0.000 description 1
- 150000007949 saponins Chemical class 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000008542 thermal sensitivity Effects 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C1/00—Photosensitive materials
- G03C1/52—Compositions containing diazo compounds as photosensitive substances
- G03C1/54—Diazonium salts or diazo anhydrides
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C1/00—Photosensitive materials
- G03C1/52—Compositions containing diazo compounds as photosensitive substances
- G03C1/56—Diazo sulfonates
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
- Materials For Photolithography (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US20807280A | 1980-11-18 | 1980-11-18 | |
| US208,072 | 1980-11-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1175811A true CA1175811A (en) | 1984-10-09 |
Family
ID=22773066
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000390217A Expired CA1175811A (en) | 1980-11-18 | 1981-11-17 | Diazonium sulfonates and uses thereof |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS57114566A (enrdf_load_stackoverflow) |
| BE (1) | BE891173A (enrdf_load_stackoverflow) |
| CA (1) | CA1175811A (enrdf_load_stackoverflow) |
| DE (1) | DE3145406A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2494457A1 (enrdf_load_stackoverflow) |
| GB (1) | GB2090245A (enrdf_load_stackoverflow) |
| NL (1) | NL8105190A (enrdf_load_stackoverflow) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61223651A (ja) * | 1985-03-29 | 1986-10-04 | Kyowa Medetsukusu Kk | ビリルビンの定量方法 |
| DE4005212A1 (de) * | 1990-02-20 | 1991-08-22 | Basf Ag | Strahlungsempfindliches gemisch |
| DE4128265A1 (de) * | 1991-08-26 | 1993-03-04 | Bosch Siemens Hausgeraete | Verfahren und vorrichtung zur programmsteuerung in fernsehgeraeten |
-
1981
- 1981-11-16 FR FR8121367A patent/FR2494457A1/fr active Granted
- 1981-11-16 NL NL8105190A patent/NL8105190A/nl not_active Application Discontinuation
- 1981-11-16 GB GB8134470A patent/GB2090245A/en not_active Withdrawn
- 1981-11-16 DE DE19813145406 patent/DE3145406A1/de not_active Withdrawn
- 1981-11-17 CA CA000390217A patent/CA1175811A/en not_active Expired
- 1981-11-18 JP JP18389881A patent/JPS57114566A/ja active Pending
- 1981-11-18 BE BE0/206587A patent/BE891173A/fr not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE3145406A1 (de) | 1982-07-08 |
| FR2494457A1 (fr) | 1982-05-21 |
| FR2494457B3 (enrdf_load_stackoverflow) | 1983-08-26 |
| JPS57114566A (en) | 1982-07-16 |
| BE891173A (fr) | 1982-05-18 |
| GB2090245A (en) | 1982-07-07 |
| NL8105190A (nl) | 1982-06-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEC | Expiry (correction) | ||
| MKEX | Expiry |