BE525300A

BE525300A -

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Publication number: BE525300A
Authority: BE; Belgium
Prior art keywords: sep; residue; group; carboxylic; formula
Prior art date

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English (en)

French (fr)

Publication of BE525300A publication Critical patent/BE525300A/fr

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UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 45
239000002253 acid Substances 0.000 claims description 43
125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 30
-1 Carboxylic acid halides Chemical class 0.000 claims description 21
239000000049 pigment Substances 0.000 claims description 19
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
150000004820 halides Chemical class 0.000 claims description 12
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
150000001733 carboxylic acid esters Chemical group 0.000 claims description 11
238000000034 method Methods 0.000 claims description 11
150000001408 amides Chemical class 0.000 claims description 10
150000001412 amines Chemical class 0.000 claims description 10
125000003118 aryl group Chemical group 0.000 claims description 10
150000004985 diamines Chemical class 0.000 claims description 10
230000003381 solubilizing effect Effects 0.000 claims description 8
150000007513 acids Chemical class 0.000 claims description 7
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
238000006243 chemical reaction Methods 0.000 claims description 7
238000006193 diazotization reaction Methods 0.000 claims description 7
239000003795 chemical substances by application Substances 0.000 claims description 6
125000001424 substituent group Chemical group 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 5
125000003277 amino group Chemical group 0.000 claims description 5
150000004984 aromatic diamines Chemical class 0.000 claims description 5
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 5
150000001805 chlorine compounds Chemical class 0.000 claims description 5
239000003960 organic solvent Substances 0.000 claims description 5
150000002790 naphthalenes Chemical class 0.000 claims description 4
238000004043 dyeing Methods 0.000 claims description 3
125000002252 acyl group Chemical group 0.000 claims description 2
239000000463 material Substances 0.000 claims description 2
125000004185 ester group Chemical group 0.000 claims 1
125000001624 naphthyl group Chemical group 0.000 claims 1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 38
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 36
PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 31
239000000975 dye Substances 0.000 description 22
239000004305 biphenyl Substances 0.000 description 21
235000010290 biphenyl Nutrition 0.000 description 20
239000000243 solution Substances 0.000 description 19
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 18
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 16
238000002360 preparation method Methods 0.000 description 15
238000009833 condensation Methods 0.000 description 14
230000005494 condensation Effects 0.000 description 14
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
239000000203 mixture Substances 0.000 description 12
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 10
238000003756 stirring Methods 0.000 description 10
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
230000001034 aminogenic effect Effects 0.000 description 9
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
230000005012 migration Effects 0.000 description 8
238000013508 migration Methods 0.000 description 8
229920000915 polyvinyl chloride Polymers 0.000 description 8
239000004800 polyvinyl chloride Substances 0.000 description 8
239000002904 solvent Substances 0.000 description 8
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
150000001735 carboxylic acids Chemical class 0.000 description 6
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 6
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
238000005096 rolling process Methods 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
ALKYHXVLJMQRLQ-UHFFFAOYSA-N 3-Hydroxy-2-naphthoate Chemical compound C1=CC=C2C=C(O)C(C(=O)O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-N 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
230000002140 halogenating effect Effects 0.000 description 5
239000000047 product Substances 0.000 description 5
HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical group C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 4
238000009835 boiling Methods 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 4
239000007858 starting material Substances 0.000 description 4
229920002554 vinyl polymer Polymers 0.000 description 4
ZYECOAILUNWEAL-NUDFZHEQSA-N (4z)-4-[[2-methoxy-5-(phenylcarbamoyl)phenyl]hydrazinylidene]-n-(3-nitrophenyl)-3-oxonaphthalene-2-carboxamide Chemical compound COC1=CC=C(C(=O)NC=2C=CC=CC=2)C=C1N\N=C(C1=CC=CC=C1C=1)/C(=O)C=1C(=O)NC1=CC=CC([N+]([O-])=O)=C1 ZYECOAILUNWEAL-NUDFZHEQSA-N 0.000 description 3
CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 3
229920000297 Rayon Polymers 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
150000007942 carboxylates Chemical class 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
239000000839 emulsion Substances 0.000 description 3
GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthene Chemical compound C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 3
238000010348 incorporation Methods 0.000 description 3
VAMXMNNIEUEQDV-UHFFFAOYSA-N methyl anthranilate Chemical compound COC(=O)C1=CC=CC=C1N VAMXMNNIEUEQDV-UHFFFAOYSA-N 0.000 description 3
239000001054 red pigment Substances 0.000 description 3
OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 2
ZRHUHDUEXWHZMA-UHFFFAOYSA-N 1,4-dihydropyrazol-5-one Chemical compound O=C1CC=NN1 ZRHUHDUEXWHZMA-UHFFFAOYSA-N 0.000 description 2
HUWXDEQWWKGHRV-UHFFFAOYSA-N 3,3'-Dichlorobenzidine Chemical group C1=C(Cl)C(N)=CC=C1C1=CC=C(N)C(Cl)=C1 HUWXDEQWWKGHRV-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
SMEGJBVQLJJKKX-HOTMZDKISA-N [(2R,3S,4S,5R,6R)-5-acetyloxy-3,4,6-trihydroxyoxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O)OC(=O)C)O)O SMEGJBVQLJJKKX-HOTMZDKISA-N 0.000 description 2
229940081735 acetylcellulose Drugs 0.000 description 2
125000003545 alkoxy group Chemical group 0.000 description 2
239000012736 aqueous medium Substances 0.000 description 2
239000000987 azo dye Substances 0.000 description 2
150000001555 benzenes Chemical class 0.000 description 2
239000001058 brown pigment Substances 0.000 description 2
239000005018 casein Substances 0.000 description 2
BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 2
235000021240 caseins Nutrition 0.000 description 2
229920002678 cellulose Polymers 0.000 description 2
229920002301 cellulose acetate Polymers 0.000 description 2
WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 2
IQFVPQOLBLOTPF-HKXUKFGYSA-L congo red Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(/N=N/C3=CC=C(C=C3)C3=CC=C(C=C3)/N=N/C3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)N)=CC(S([O-])(=O)=O)=C21 IQFVPQOLBLOTPF-HKXUKFGYSA-L 0.000 description 2
230000027326 copulation Effects 0.000 description 2
TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
229940117389 dichlorobenzene Drugs 0.000 description 2
238000001035 drying Methods 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
125000000468 ketone group Chemical group 0.000 description 2
239000002609 medium Substances 0.000 description 2
229910052698 phosphorus Inorganic materials 0.000 description 2
239000011574 phosphorus Substances 0.000 description 2
238000006116 polymerization reaction Methods 0.000 description 2
229920001296 polysiloxane Polymers 0.000 description 2
BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
229920005989 resin Polymers 0.000 description 2
239000011347 resin Substances 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
238000009987 spinning Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
229920003002 synthetic resin Polymers 0.000 description 2
239000000057 synthetic resin Substances 0.000 description 2
RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
JHRMJWGBGBDNJE-UHFFFAOYSA-N 1,3-benzothiazole-2,4-diamine Chemical class C1=CC=C2SC(N)=NC2=C1N JHRMJWGBGBDNJE-UHFFFAOYSA-N 0.000 description 1
GWEHVDNNLFDJLR-UHFFFAOYSA-N 1,3-diphenylurea Chemical compound C=1C=CC=CC=1NC(=O)NC1=CC=CC=C1 GWEHVDNNLFDJLR-UHFFFAOYSA-N 0.000 description 1
NUMXHEUHHRTBQT-AATRIKPKSA-N 2,4-dimethoxy-1-[(e)-2-nitroethenyl]benzene Chemical compound COC1=CC=C(\C=C\[N+]([O-])=O)C(OC)=C1 NUMXHEUHHRTBQT-AATRIKPKSA-N 0.000 description 1
AQBLHXAPPAUPCH-UHFFFAOYSA-N 2-(4-aminophenyl)-1,3-benzothiazol-6-amine Chemical compound C1=CC(N)=CC=C1C1=NC2=CC=C(N)C=C2S1 AQBLHXAPPAUPCH-UHFFFAOYSA-N 0.000 description 1
HQOBDLCAOWRBOU-UHFFFAOYSA-N 2-hydroxy-9h-carbazole-1-carboxylic acid Chemical class C12=CC=CC=C2NC2=C1C=CC(O)=C2C(=O)O HQOBDLCAOWRBOU-UHFFFAOYSA-N 0.000 description 1
JSCNDCWUFHAJQL-UHFFFAOYSA-N 2-hydroxy-9h-carbazole-3-carboxylic acid Chemical compound N1C2=CC=CC=C2C2=C1C=C(O)C(C(=O)O)=C2 JSCNDCWUFHAJQL-UHFFFAOYSA-N 0.000 description 1
UAIUNKRWKOVEES-UHFFFAOYSA-N 3,3',5,5'-tetramethylbenzidine Chemical group CC1=C(N)C(C)=CC(C=2C=C(C)C(N)=C(C)C=2)=C1 UAIUNKRWKOVEES-UHFFFAOYSA-N 0.000 description 1
NUIURNJTPRWVAP-UHFFFAOYSA-N 3,3'-Dimethylbenzidine Chemical group C1=C(N)C(C)=CC(C=2C=C(C)C(N)=CC=2)=C1 NUIURNJTPRWVAP-UHFFFAOYSA-N 0.000 description 1
CKOFBUUFHALZGK-UHFFFAOYSA-N 3-[(3-aminophenyl)methyl]aniline Chemical compound NC1=CC=CC(CC=2C=C(N)C=CC=2)=C1 CKOFBUUFHALZGK-UHFFFAOYSA-N 0.000 description 1
XFXOLBNQYFRSLQ-UHFFFAOYSA-N 3-amino-2-naphthoic acid Chemical compound C1=CC=C2C=C(C(O)=O)C(N)=CC2=C1 XFXOLBNQYFRSLQ-UHFFFAOYSA-N 0.000 description 1
PHQKCVOZVPSTAF-UHFFFAOYSA-N 3-hydroxyanthracene-2-carboxylic acid Chemical compound C1=CC=C2C=C(C=C(C(C(=O)O)=C3)O)C3=CC2=C1 PHQKCVOZVPSTAF-UHFFFAOYSA-N 0.000 description 1
PBTGPULVUFUPNO-UHFFFAOYSA-N 3-hydroxydibenzofuran-2-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=C(O)C(C(=O)O)=C2 PBTGPULVUFUPNO-UHFFFAOYSA-N 0.000 description 1
HSWDRWISQZLYOO-UHFFFAOYSA-N 3-hydroxydibenzothiophene-2-carboxylic acid Chemical compound C(=O)(O)C1=CC2=C(SC3=C2C=CC=C3)C=C1O HSWDRWISQZLYOO-UHFFFAOYSA-N 0.000 description 1
YEEQJJCLPLPVCW-UHFFFAOYSA-N 5-(3-amino-4-chlorophenyl)sulfonyl-2-chloroaniline Chemical compound C1=C(Cl)C(N)=CC(S(=O)(=O)C=2C=C(N)C(Cl)=CC=2)=C1 YEEQJJCLPLPVCW-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
206010021703 Indifference Diseases 0.000 description 1
229920000877 Melamine resin Polymers 0.000 description 1
239000000020 Nitrocellulose Substances 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
239000004793 Polystyrene Substances 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
229920001807 Urea-formaldehyde Polymers 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
238000004026 adhesive bonding Methods 0.000 description 1
239000012670 alkaline solution Substances 0.000 description 1
229920003180 amino resin Polymers 0.000 description 1
229940040526 anhydrous sodium acetate Drugs 0.000 description 1
RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical class NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 1
150000007860 aryl ester derivatives Chemical group 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
238000010533 azeotropic distillation Methods 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
150000001649 bromium compounds Chemical class 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 description 1
238000005266 casting Methods 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920003086 cellulose ether Polymers 0.000 description 1
239000012320 chlorinating reagent Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
150000008422 chlorobenzenes Chemical class 0.000 description 1
125000000068 chlorophenyl group Chemical group 0.000 description 1
KBKDLNWEWQZIEW-UHFFFAOYSA-N chrysene-2,8-diamine Chemical compound C1=CC(N)=CC2=CC=C3C4=CC=C(N)C=C4C=CC3=C21 KBKDLNWEWQZIEW-UHFFFAOYSA-N 0.000 description 1
239000007859 condensation product Substances 0.000 description 1
238000001944 continuous distillation Methods 0.000 description 1
238000010411 cooking Methods 0.000 description 1
239000002537 cosmetic Substances 0.000 description 1
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
230000000694 effects Effects 0.000 description 1
229920001971 elastomer Polymers 0.000 description 1
125000002587 enol group Chemical group 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
239000004744 fabric Substances 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
239000000835 fiber Substances 0.000 description 1
IVJISJACKSSFGE-UHFFFAOYSA-N formaldehyde;1,3,5-triazine-2,4,6-triamine Chemical compound O=C.NC1=NC(N)=NC(N)=N1 IVJISJACKSSFGE-UHFFFAOYSA-N 0.000 description 1
239000003365 glass fiber Substances 0.000 description 1
150000002391 heterocyclic compounds Chemical class 0.000 description 1
VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
150000002466 imines Chemical class 0.000 description 1
JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000004922 lacquer Substances 0.000 description 1
238000010030 laminating Methods 0.000 description 1
238000003475 lamination Methods 0.000 description 1
IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical compound CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 1
OHZZTXYKLXZFSZ-UHFFFAOYSA-I manganese(3+) 5,10,15-tris(1-methylpyridin-1-ium-4-yl)-20-(1-methylpyridin-4-ylidene)porphyrin-22-ide pentachloride Chemical compound [Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Mn+3].C1=CN(C)C=CC1=C1C(C=C2)=NC2=C(C=2C=C[N+](C)=CC=2)C([N-]2)=CC=C2C(C=2C=C[N+](C)=CC=2)=C(C=C2)N=C2C(C=2C=C[N+](C)=CC=2)=C2N=C1C=C2 OHZZTXYKLXZFSZ-UHFFFAOYSA-I 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
FODZNORQIATQIP-UHFFFAOYSA-N methyl 2-amino-3,5-dichlorobenzoate Chemical compound COC(=O)C1=CC(Cl)=CC(Cl)=C1N FODZNORQIATQIP-UHFFFAOYSA-N 0.000 description 1
IGHVUURTQGBABT-UHFFFAOYSA-N methyl 2-amino-5-chlorobenzoate Chemical compound COC(=O)C1=CC(Cl)=CC=C1N IGHVUURTQGBABT-UHFFFAOYSA-N 0.000 description 1
WHMQTPBEFHEYJI-UHFFFAOYSA-N methyl 3-aminonaphthalene-2-carboxylate Chemical compound C1=CC=C2C=C(N)C(C(=O)OC)=CC2=C1 WHMQTPBEFHEYJI-UHFFFAOYSA-N 0.000 description 1
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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