BE1010726A5

BE1010726A5 - Sulfonates d'oximes et leur utilisation comme acides sulfoniques latents.

Sulfonates d'oximes et leur utilisation comme acides sulfoniques latents. Download PDF

Info

Publication number: BE1010726A5
Authority: BE; Belgium
Prior art keywords: residue; alkyl; phenyl; sep; substituted
Prior art date: 1995-10-31

Application number

BE9600924A

Other languages

English (en)

French (fr)

Original Assignee

Ciba Geigy Ag

Priority date

1995-10-31

Filing date

1996-10-31

Publication date

1998-12-01

1996-10-31 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1998-12-01 Application granted granted Critical

1998-12-01 Publication of BE1010726A5 publication Critical patent/BE1010726A5/fr

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-1 Sulfonates oximes Chemical class 0.000 title claims abstract description 238
239000002253 acid Substances 0.000 title claims abstract description 63
150000001875 compounds Chemical class 0.000 claims abstract description 104
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 100
229920002120 photoresistant polymer Polymers 0.000 claims abstract description 36
125000005561 phenanthryl group Chemical group 0.000 claims abstract description 28
125000001589 carboacyl group Chemical group 0.000 claims abstract description 25
238000002360 preparation method Methods 0.000 claims abstract description 18
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims abstract description 14
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims abstract description 13
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 8
125000002947 alkylene group Chemical group 0.000 claims abstract description 6
125000006678 phenoxycarbonyl group Chemical group 0.000 claims abstract description 5
239000000203 mixture Substances 0.000 claims description 107
125000001424 substituent group Chemical group 0.000 claims description 62
230000005855 radiation Effects 0.000 claims description 44
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 42
125000000217 alkyl group Chemical group 0.000 claims description 36
125000001624 naphthyl group Chemical group 0.000 claims description 32
239000002966 varnish Substances 0.000 claims description 32
125000004432 carbon atom Chemical group C* 0.000 claims description 31
125000001072 heteroaryl group Chemical group 0.000 claims description 25
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 24
229920000642 polymer Polymers 0.000 claims description 23
229910052740 iodine Inorganic materials 0.000 claims description 22
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims description 21
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 18
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
238000004132 cross linking Methods 0.000 claims description 15
238000000034 method Methods 0.000 claims description 15
238000004090 dissolution Methods 0.000 claims description 14
229910052757 nitrogen Inorganic materials 0.000 claims description 14
125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 12
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 12
230000000694 effects Effects 0.000 claims description 12
IFVTZJHWGZSXFD-UHFFFAOYSA-N biphenylene Chemical group C1=CC=C2C3=CC=CC=C3C2=C1 IFVTZJHWGZSXFD-UHFFFAOYSA-N 0.000 claims description 11
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 10
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
239000003112 inhibitor Substances 0.000 claims description 10
239000000463 material Substances 0.000 claims description 10
150000003254 radicals Chemical class 0.000 claims description 10
NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 8
125000005843 halogen group Chemical group 0.000 claims description 8
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
125000004957 naphthylene group Chemical group 0.000 claims description 8
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 8
238000007639 printing Methods 0.000 claims description 8
125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 7
BZOYSERZNRJPDQ-UHFFFAOYSA-N [(3,6-dimethoxyfluoren-9-ylidene)amino] 4-methylbenzenesulfonate Chemical compound C12=CC=C(OC)C=C2C2=CC(OC)=CC=C2C1=NOS(=O)(=O)C1=CC=C(C)C=C1 BZOYSERZNRJPDQ-UHFFFAOYSA-N 0.000 claims description 7
239000000654 additive Substances 0.000 claims description 7
125000003118 aryl group Chemical group 0.000 claims description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 6
125000005605 benzo group Chemical group 0.000 claims description 6
229910052799 carbon Inorganic materials 0.000 claims description 6
239000003795 chemical substances by application Substances 0.000 claims description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
125000005146 naphthylsulfonyl group Chemical group C1(=CC=CC2=CC=CC=C12)S(=O)(=O)* 0.000 claims description 6
JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical group O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 5
125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
PLBYSHJEOLBAIR-UHFFFAOYSA-N [(1,6-dimethoxyfluoren-9-ylidene)amino] 4-methylbenzenesulfonate Chemical compound C1=CC=C(OC)C2=C1C1=CC(OC)=CC=C1C2=NOS(=O)(=O)C1=CC=C(C)C=C1 PLBYSHJEOLBAIR-UHFFFAOYSA-N 0.000 claims description 4
125000001188 haloalkyl group Chemical group 0.000 claims description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 4
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
229910052717 sulfur Inorganic materials 0.000 claims description 4
125000001544 thienyl group Chemical group 0.000 claims description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
VBHIRACIRQVMMY-UHFFFAOYSA-N [(1,6-dimethoxyfluoren-9-ylidene)amino] 4-dodecylbenzenesulfonate Chemical compound C1=CC(CCCCCCCCCCCC)=CC=C1S(=O)(=O)ON=C1C2=C(OC)C=CC=C2C2=CC(OC)=CC=C21 VBHIRACIRQVMMY-UHFFFAOYSA-N 0.000 claims description 3
239000000976 ink Substances 0.000 claims description 3
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 3
KZKRRZFCAYOXQE-UHFFFAOYSA-N 1$l^{2}-azinane Chemical compound C1CC[N]CC1 KZKRRZFCAYOXQE-UHFFFAOYSA-N 0.000 claims description 2
125000006091 1,3-dioxolane group Chemical group 0.000 claims description 2
CPEONABTMRSIKA-UHFFFAOYSA-N 1,4$l^{2}-oxazinane Chemical compound C1COCC[N]1 CPEONABTMRSIKA-UHFFFAOYSA-N 0.000 claims description 2
125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 2
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 2
125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 2
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
FCAMERFAJMFLNM-UHFFFAOYSA-N [[cyano-(3,4-dimethoxyphenyl)methylidene]amino] propane-2-sulfonate Chemical compound COC1=CC=C(C(=NOS(=O)(=O)C(C)C)C#N)C=C1OC FCAMERFAJMFLNM-UHFFFAOYSA-N 0.000 claims description 2
125000004429 atom Chemical group 0.000 claims description 2
229910002091 carbon monoxide Inorganic materials 0.000 claims description 2
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 2
125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 2
125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims 1
QHTNOPQHRPSGML-UHFFFAOYSA-N 2-(9H-fluoren-1-ylsulfanyl)ethanol Chemical compound OCCSC1=CC=CC=2C3=CC=CC=C3CC1=2 QHTNOPQHRPSGML-UHFFFAOYSA-N 0.000 claims 1
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 1
OOPSDYCQTALYFH-UHFFFAOYSA-N [[cyano-(4-methylsulfanylphenyl)methylidene]amino] propane-2-sulfonate Chemical compound CSC1=CC=C(C(=NOS(=O)(=O)C(C)C)C#N)C=C1 OOPSDYCQTALYFH-UHFFFAOYSA-N 0.000 claims 1
LEVJVKGPFAQPOI-UHFFFAOYSA-N phenylmethanone Chemical compound O=[C]C1=CC=CC=C1 LEVJVKGPFAQPOI-UHFFFAOYSA-N 0.000 claims 1
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 90
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 78
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 57
239000000243 solution Substances 0.000 description 32
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
238000006243 chemical reaction Methods 0.000 description 26
238000004458 analytical method Methods 0.000 description 24
239000013078 crystal Substances 0.000 description 24
239000000047 product Substances 0.000 description 24
229920005989 resin Polymers 0.000 description 24
239000011347 resin Substances 0.000 description 24
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
238000002844 melting Methods 0.000 description 22
230000008018 melting Effects 0.000 description 22
239000012043 crude product Substances 0.000 description 21
238000010521 absorption reaction Methods 0.000 description 20
239000000126 substance Substances 0.000 description 20
239000007787 solid Substances 0.000 description 19
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 16
239000002904 solvent Substances 0.000 description 16
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
239000011230 binding agent Substances 0.000 description 15
238000000576 coating method Methods 0.000 description 15
239000000470 constituent Substances 0.000 description 14
238000011161 development Methods 0.000 description 13
239000011248 coating agent Substances 0.000 description 12
238000001953 recrystallisation Methods 0.000 description 12
238000001228 spectrum Methods 0.000 description 12
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 11
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
OHZRRBNQINJVRP-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-2-hydroxyiminoacetonitrile Chemical compound COC1=CC=C(C(=NO)C#N)C=C1OC OHZRRBNQINJVRP-UHFFFAOYSA-N 0.000 description 10
238000001723 curing Methods 0.000 description 10
239000010408 film Substances 0.000 description 10
238000010438 heat treatment Methods 0.000 description 10
239000003921 oil Substances 0.000 description 10
QSLPNSWXUQHVLP-UHFFFAOYSA-N $l^{1}-sulfanylmethane Chemical compound [S]C QSLPNSWXUQHVLP-UHFFFAOYSA-N 0.000 description 9
229920000877 Melamine resin Polymers 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 9
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 8
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 8
238000001035 drying Methods 0.000 description 8
239000003480 eluent Substances 0.000 description 8
229910052943 magnesium sulfate Inorganic materials 0.000 description 8
235000019341 magnesium sulphate Nutrition 0.000 description 8
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 8
229920001225 polyester resin Polymers 0.000 description 8
125000006239 protecting group Chemical group 0.000 description 8
239000000741 silica gel Substances 0.000 description 8
229910002027 silica gel Inorganic materials 0.000 description 8
WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 8
UJNAXQMROWKSIE-UHFFFAOYSA-N 3,6-dimethoxyfluoren-9-one Chemical compound C1=C(OC)C=C2C3=CC(OC)=CC=C3C(=O)C2=C1 UJNAXQMROWKSIE-UHFFFAOYSA-N 0.000 description 7
229920000178 Acrylic resin Polymers 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 7
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 7
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 7
230000015572 biosynthetic process Effects 0.000 description 7
150000002148 esters Chemical class 0.000 description 7
150000002923 oximes Chemical class 0.000 description 7
239000003208 petroleum Substances 0.000 description 7
239000002244 precipitate Substances 0.000 description 7
230000035945 sensitivity Effects 0.000 description 7
229910052710 silicon Inorganic materials 0.000 description 7
239000010703 silicon Substances 0.000 description 7
UUBKTKYSBIWUFZ-UHFFFAOYSA-N 2-hydroxyimino-2-(4-methylsulfanylphenyl)acetonitrile Chemical compound CSC1=CC=C(C(=NO)C#N)C=C1 UUBKTKYSBIWUFZ-UHFFFAOYSA-N 0.000 description 6
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 6
150000007513 acids Chemical class 0.000 description 6
RLSSMJSEOOYNOY-UHFFFAOYSA-N m-methyl-PhOH Natural products CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 6
229910052753 mercury Inorganic materials 0.000 description 6
239000000178 monomer Substances 0.000 description 6
IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 6
229920001568 phenolic resin Polymers 0.000 description 6
239000000049 pigment Substances 0.000 description 6
230000008569 process Effects 0.000 description 6
239000000758 substrate Substances 0.000 description 6
238000003786 synthesis reaction Methods 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
238000005481 NMR spectroscopy Methods 0.000 description 5
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
125000003545 alkoxy group Chemical group 0.000 description 5
229920000180 alkyd Polymers 0.000 description 5
229920003180 amino resin Polymers 0.000 description 5
238000001816 cooling Methods 0.000 description 5
239000000975 dye Substances 0.000 description 5
238000003818 flash chromatography Methods 0.000 description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
230000007246 mechanism Effects 0.000 description 5
JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 5
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 5
ODCCUFNTRJQXHK-UHFFFAOYSA-N n-(3,6-dimethoxyfluoren-9-ylidene)hydroxylamine Chemical compound C1=C(OC)C=C2C3=CC(OC)=CC=C3C(=NO)C2=C1 ODCCUFNTRJQXHK-UHFFFAOYSA-N 0.000 description 5
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 5
QWVGKYWNOKOFNN-UHFFFAOYSA-N o-methyl phenol Natural products CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 5
239000005011 phenolic resin Substances 0.000 description 5
239000000843 powder Substances 0.000 description 5
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
238000003756 stirring Methods 0.000 description 5
238000002211 ultraviolet spectrum Methods 0.000 description 5
TYFKBXOEBSNUGH-UHFFFAOYSA-N 2-[3,4-bis(methylsulfanyl)phenyl]-2-hydroxyiminoacetonitrile Chemical compound CSC1=CC=C(C(=NO)C#N)C=C1SC TYFKBXOEBSNUGH-UHFFFAOYSA-N 0.000 description 4
VLBSKIZWQATQRK-UHFFFAOYSA-N 4-dodecylbenzenesulfonyl chloride Chemical compound CCCCCCCCCCCCC1=CC=C(S(Cl)(=O)=O)C=C1 VLBSKIZWQATQRK-UHFFFAOYSA-N 0.000 description 4
JAGRUUPXPPLSRX-UHFFFAOYSA-N 4-prop-1-en-2-ylphenol Chemical compound CC(=C)C1=CC=C(O)C=C1 JAGRUUPXPPLSRX-UHFFFAOYSA-N 0.000 description 4
ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
150000001241 acetals Chemical class 0.000 description 4
150000003863 ammonium salts Chemical class 0.000 description 4
239000004202 carbamide Substances 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
238000005119 centrifugation Methods 0.000 description 4
230000008859 change Effects 0.000 description 4
238000009833 condensation Methods 0.000 description 4
229920001577 copolymer Polymers 0.000 description 4
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
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 4
238000004817 gas chromatography Methods 0.000 description 4
239000011521 glass Substances 0.000 description 4
150000002367 halogens Chemical class 0.000 description 4
FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 4
WTDHULULXKLSOZ-UHFFFAOYSA-N hydroxylamine hydrochloride Substances Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 4
WCYJQVALWQMJGE-UHFFFAOYSA-M hydroxylammonium chloride Chemical compound [Cl-].O[NH3+] WCYJQVALWQMJGE-UHFFFAOYSA-M 0.000 description 4
BLLFVUPNHCTMSV-UHFFFAOYSA-N methyl nitrite Chemical compound CON=O BLLFVUPNHCTMSV-UHFFFAOYSA-N 0.000 description 4
GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 4
239000012452 mother liquor Substances 0.000 description 4
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 4
229920003986 novolac Polymers 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
239000003973 paint Substances 0.000 description 4
150000002989 phenols Chemical class 0.000 description 4
239000004848 polyfunctional curative Substances 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
238000000926 separation method Methods 0.000 description 4
STLZYIISXRSPML-UHFFFAOYSA-N (4-methylsulfanylphenyl)methyl methanesulfonate Chemical compound CSC1=CC=C(COS(C)(=O)=O)C=C1 STLZYIISXRSPML-UHFFFAOYSA-N 0.000 description 3
GQRXDRJNCURJKY-UHFFFAOYSA-N 1,6-dimethoxyfluoren-9-one Chemical compound C12=CC(OC)=CC=C2C(=O)C2=C1C=CC=C2OC GQRXDRJNCURJKY-UHFFFAOYSA-N 0.000 description 3
KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 3
KNGQSQMWQHAQCZ-UHFFFAOYSA-N 4-(chloromethyl)-1,2-bis(methylsulfanyl)benzene Chemical compound CSC1=CC=C(CCl)C=C1SC KNGQSQMWQHAQCZ-UHFFFAOYSA-N 0.000 description 3
FUGYGGDSWSUORM-UHFFFAOYSA-N 4-hydroxystyrene Chemical group OC1=CC=C(C=C)C=C1 FUGYGGDSWSUORM-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
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WGKLOLBTFWFKOD-UHFFFAOYSA-N tris(2-nonylphenyl) phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC WGKLOLBTFWFKOD-UHFFFAOYSA-N 0.000 description 1
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