CH626647A5 - Process for preparing azo dyes - Google Patents

Process for preparing azo dyes Download PDF

Info

Publication number: CH626647A5
Authority: CH; Switzerland
Prior art keywords: lower alkyl; dye; formula; radical; cyanide
Prior art date: 1976-05-28

Application number

CH656777A

Other languages

German (de)

English (en)

Inventor

Peter Michael Quan

Peter John Duggan

Original Assignee

Ici Ltd

Priority date (The priority date 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 date listed.)

1976-05-28

Filing date

1977-05-27

Publication date

1981-11-30

1977-05-27 Application filed by Ici Ltd filed Critical Ici Ltd

1981-11-30 Publication of CH626647A5 publication Critical patent/CH626647A5/de

Links

239000000987 azo dye Substances 0.000 title claims description 14
238000004519 manufacturing process Methods 0.000 title description 2
239000000975 dye Substances 0.000 claims description 92
238000000034 method Methods 0.000 claims description 50
125000000217 alkyl group Chemical group 0.000 claims description 47
238000006243 chemical reaction Methods 0.000 claims description 46
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 29
125000004093 cyano group Chemical group *C#N 0.000 claims description 28
229910052739 hydrogen Inorganic materials 0.000 claims description 26
239000001257 hydrogen Substances 0.000 claims description 26
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims description 20
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 20
239000000203 mixture Substances 0.000 claims description 18
229910052751 metal Inorganic materials 0.000 claims description 17
239000002184 metal Substances 0.000 claims description 17
239000003444 phase transfer catalyst Substances 0.000 claims description 17
229910052736 halogen Inorganic materials 0.000 claims description 16
150000002367 halogens Chemical class 0.000 claims description 16
150000002431 hydrogen Chemical group 0.000 claims description 16
-1 phenylazo Chemical group 0.000 claims description 15
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 14
229910052802 copper Inorganic materials 0.000 claims description 14
239000010949 copper Substances 0.000 claims description 14
DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 claims description 14
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 11
125000003545 alkoxy group Chemical group 0.000 claims description 11
239000002904 solvent Substances 0.000 claims description 11
125000004432 carbon atom Chemical group C* 0.000 claims description 10
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims description 10
239000005749 Copper compound Substances 0.000 claims description 9
150000001880 copper compounds Chemical class 0.000 claims description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 claims description 8
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
238000002360 preparation method Methods 0.000 claims description 7
150000003242 quaternary ammonium salts Chemical class 0.000 claims description 7
125000004442 acylamino group Chemical group 0.000 claims description 6
230000003197 catalytic effect Effects 0.000 claims description 6
125000005843 halogen group Chemical group 0.000 claims description 5
125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
241000251730 Chondrichthyes Species 0.000 claims description 4
229910052783 alkali metal Inorganic materials 0.000 claims description 4
239000012736 aqueous medium Substances 0.000 claims description 4
125000003118 aryl group Chemical group 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
150000004714 phosphonium salts Chemical class 0.000 claims description 4
150000001450 anions Chemical class 0.000 claims description 3
125000003710 aryl alkyl group Chemical group 0.000 claims description 3
125000004429 atom Chemical group 0.000 claims description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
125000001424 substituent group Chemical group 0.000 claims description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
125000005036 alkoxyphenyl group Chemical group 0.000 claims description 2
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
125000005037 alkyl phenyl group Chemical group 0.000 claims description 2
125000005422 alkyl sulfonamido group Chemical group 0.000 claims description 2
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
239000007864 aqueous solution Substances 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
229910052799 carbon Inorganic materials 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
125000004122 cyclic group Chemical group 0.000 claims description 2
125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
125000005059 halophenyl group Chemical group 0.000 claims description 2
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
125000003386 piperidinyl group Chemical group 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims 1
150000001875 compounds Chemical class 0.000 claims 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
125000001624 naphthyl group Chemical group 0.000 claims 1
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
MGDAAGXPGBSVIO-UHFFFAOYSA-M tributyl(octyl)azanium;bromide Chemical compound [Br-].CCCCCCCC[N+](CCCC)(CCCC)CCCC MGDAAGXPGBSVIO-UHFFFAOYSA-M 0.000 description 12
238000010992 reflux Methods 0.000 description 11
238000001914 filtration Methods 0.000 description 10
125000001246 bromo group Chemical group Br* 0.000 description 8
239000000243 solution Substances 0.000 description 8
244000172533 Viola sororia Species 0.000 description 7
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
239000012071 phase Substances 0.000 description 6
239000000376 reactant Substances 0.000 description 6
238000001256 steam distillation Methods 0.000 description 6
238000003756 stirring Methods 0.000 description 6
239000007900 aqueous suspension Substances 0.000 description 5
KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 5
239000000460 chlorine Substances 0.000 description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
239000000463 material Substances 0.000 description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 4
125000000751 azo group Chemical group [*]N=N[*] 0.000 description 4
JBIROUFYLSSYDX-UHFFFAOYSA-M benzododecinium chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 JBIROUFYLSSYDX-UHFFFAOYSA-M 0.000 description 4
239000002609 medium Substances 0.000 description 4
239000000126 substance Substances 0.000 description 4
239000004753 textile Substances 0.000 description 4
238000004809 thin layer chromatography Methods 0.000 description 4
NZDXSXLYLMHYJA-UHFFFAOYSA-M 4-[(1,3-dimethylimidazol-1-ium-2-yl)diazenyl]-n,n-dimethylaniline;chloride Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1N=NC1=[N+](C)C=CN1C NZDXSXLYLMHYJA-UHFFFAOYSA-M 0.000 description 3
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
235000011114 ammonium hydroxide Nutrition 0.000 description 3
125000000129 anionic group Chemical group 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
229920000728 polyester Polymers 0.000 description 3
229910052700 potassium Inorganic materials 0.000 description 3
150000003254 radicals Chemical class 0.000 description 3
239000001044 red dye Substances 0.000 description 3
150000003839 salts Chemical group 0.000 description 3
239000004094 surface-active agent Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 3
238000012546 transfer Methods 0.000 description 3
KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
QAQSNXHKHKONNS-UHFFFAOYSA-N 1-ethyl-2-hydroxy-4-methyl-6-oxopyridine-3-carboxamide Chemical compound CCN1C(O)=C(C(N)=O)C(C)=CC1=O QAQSNXHKHKONNS-UHFFFAOYSA-N 0.000 description 2
GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
101150065749 Churc1 gene Proteins 0.000 description 2
102100038239 Protein Churchill Human genes 0.000 description 2
244000154870 Viola adunca Species 0.000 description 2
235000005811 Viola adunca Nutrition 0.000 description 2
235000013487 Viola odorata Nutrition 0.000 description 2
235000002254 Viola papilionacea Nutrition 0.000 description 2
229910001870 ammonium persulfate Inorganic materials 0.000 description 2
239000003945 anionic surfactant Substances 0.000 description 2
239000002585 base Substances 0.000 description 2
VJGNLOIQCWLBJR-UHFFFAOYSA-M benzyl(tributyl)azanium;chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CC1=CC=CC=C1 VJGNLOIQCWLBJR-UHFFFAOYSA-M 0.000 description 2
239000001045 blue dye Substances 0.000 description 2
238000009835 boiling Methods 0.000 description 2
230000015556 catabolic process Effects 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
238000006731 degradation reaction Methods 0.000 description 2
OCTAKUVKMMLTHX-UHFFFAOYSA-M di(icosyl)-dimethylazanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCCCC OCTAKUVKMMLTHX-UHFFFAOYSA-M 0.000 description 2
WLCFKPHMRNPAFZ-UHFFFAOYSA-M didodecyl(dimethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCC WLCFKPHMRNPAFZ-UHFFFAOYSA-M 0.000 description 2
ZCPCLAPUXMZUCD-UHFFFAOYSA-M dihexadecyl(dimethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCC ZCPCLAPUXMZUCD-UHFFFAOYSA-M 0.000 description 2
239000006185 dispersion Substances 0.000 description 2
238000004043 dyeing Methods 0.000 description 2
MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 2
QPFQQVUSISSKRU-UHFFFAOYSA-M hexadecyl(tripropyl)phosphanium;bromide Chemical group [Br-].CCCCCCCCCCCCCCCC[P+](CCC)(CCC)CCC QPFQQVUSISSKRU-UHFFFAOYSA-M 0.000 description 2
239000002736 nonionic surfactant Substances 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
ZXUCBXRTRRIBSO-UHFFFAOYSA-L tetrabutylazanium;sulfate Chemical compound [O-]S([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC.CCCC[N+](CCCC)(CCCC)CCCC ZXUCBXRTRRIBSO-UHFFFAOYSA-L 0.000 description 2
PLAZTCDQAHEYBI-UHFFFAOYSA-N 2-nitrotoluene Chemical compound CC1=CC=CC=C1[N+]([O-])=O PLAZTCDQAHEYBI-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
241000974482 Aricia saepiolus Species 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
229910021595 Copper(I) iodide Inorganic materials 0.000 description 1
VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 description 1
JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical class [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
239000000654 additive Substances 0.000 description 1
239000003513 alkali Substances 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
125000005078 alkoxycarbonylalkyl group Chemical group 0.000 description 1
239000002168 alkylating agent Substances 0.000 description 1
229940100198 alkylating agent Drugs 0.000 description 1
SWLVFNYSXGMGBS-UHFFFAOYSA-N ammonium bromide Chemical compound [NH4+].[Br-] SWLVFNYSXGMGBS-UHFFFAOYSA-N 0.000 description 1
229940077484 ammonium bromide Drugs 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
229940073608 benzyl chloride Drugs 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
QXJJQWWVWRCVQT-UHFFFAOYSA-K calcium;sodium;phosphate Chemical compound [Na+].[Ca+2].[O-]P([O-])([O-])=O QXJJQWWVWRCVQT-UHFFFAOYSA-K 0.000 description 1
125000002091 cationic group Chemical group 0.000 description 1
RLGQACBPNDBWTB-UHFFFAOYSA-N cetyltrimethylammonium ion Chemical compound CCCCCCCCCCCCCCCC[N+](C)(C)C RLGQACBPNDBWTB-UHFFFAOYSA-N 0.000 description 1
230000000536 complexating effect Effects 0.000 description 1
239000007859 condensation product Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
150000003983 crown ethers Chemical class 0.000 description 1
HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
229940008406 diethyl sulfate Drugs 0.000 description 1
239000000986 disperse dye Substances 0.000 description 1
GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 1
JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
239000004744 fabric Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
238000000227 grinding Methods 0.000 description 1
239000000383 hazardous chemical Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000001072 heteroaryl group Chemical group 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
125000002346 iodo group Chemical group I* 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
QLPMKRZYJPNIRP-UHFFFAOYSA-M methyl(trioctyl)azanium;bromide Chemical compound [Br-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC QLPMKRZYJPNIRP-UHFFFAOYSA-M 0.000 description 1
XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 1
ZEOQPNRYUCROGZ-UHFFFAOYSA-N n,n-dibutylbutan-1-amine;hydrobromide Chemical compound [Br-].CCCC[NH+](CCCC)CCCC ZEOQPNRYUCROGZ-UHFFFAOYSA-N 0.000 description 1
AJDUTMFFZHIJEM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 description 1
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-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
239000001048 orange dye Substances 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
125000000962 organic group Chemical group 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
125000000913 palmityl 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])[H] 0.000 description 1
239000002245 particle Substances 0.000 description 1
230000002572 peristaltic effect Effects 0.000 description 1
WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
125000004437 phosphorous atom Chemical group 0.000 description 1
229920000570 polyether Polymers 0.000 description 1
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
239000000047 product Substances 0.000 description 1
125000001453 quaternary ammonium group Chemical group 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000012552 review Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
RUQIYMSRQQCKIK-UHFFFAOYSA-M sodium;2,3-di(propan-2-yl)naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(C(C)C)C(C(C)C)=CC2=C1 RUQIYMSRQQCKIK-UHFFFAOYSA-M 0.000 description 1
125000000542 sulfonic acid group Chemical group 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
230000007704 transition Effects 0.000 description 1
SWGJCIMEBVHMTA-UHFFFAOYSA-K trisodium;6-oxido-4-sulfo-5-[(4-sulfonatonaphthalen-1-yl)diazenyl]naphthalene-2-sulfonate Chemical compound [Na+].[Na+].[Na+].C1=CC=C2C(N=NC3=C4C(=CC(=CC4=CC=C3O)S([O-])(=O)=O)S([O-])(=O)=O)=CC=C(S([O-])(=O)=O)C2=C1 SWGJCIMEBVHMTA-UHFFFAOYSA-K 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1
239000001043 yellow dye Substances 0.000 description 1

Classifications

- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/16—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using dispersed, e.g. acetate, dyestuffs
- D06P1/18—Azo dyes
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/095—Amino naphthalenes
- C09B29/0955—Amino naphthalenes containing water solubilizing groups
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/40—Preparation of azo dyes from other azo compounds by substituting hetero atoms by radicals containing other hetero atoms
- C09B43/42—Preparation of azo dyes from other azo compounds by substituting hetero atoms by radicals containing other hetero atoms by substituting radicals containing hetero atoms for —CN radicals
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/34—Material containing ester groups
- D06P3/52—Polyesters
- D06P3/54—Polyesters using dispersed dyestuffs

Landscapes

Chemical & Material Sciences (AREA)
Dispersion Chemistry (AREA)
Engineering & Computer Science (AREA)
Textile Engineering (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Coloring (AREA)

CH656777A 1976-05-28 1977-05-27 Process for preparing azo dyes CH626647A5 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB2228376A GB1578732A (en)	1976-05-28	1976-05-28	Process for the manufacture of cyano azo dyes

Publications (1)

Publication Number	Publication Date
CH626647A5 true CH626647A5 (en)	1981-11-30

Family

ID=10176874

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH656777A CH626647A5 (en)	1976-05-28	1977-05-27	Process for preparing azo dyes

Country Status (10)

Country	Link
JP (1)	JPS52146432A (it)
BE (1)	BE854903A (it)
BR (1)	BR7703412A (it)
CH (1)	CH626647A5 (it)
DE (1)	DE2724117A1 (it)
ES (1)	ES459246A1 (it)
FR (1)	FR2352864A1 (it)
GB (1)	GB1578732A (it)
IT (1)	IT1078992B (it)
NL (1)	NL7705742A (it)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2846438C2 (de)	1978-10-25	1987-05-07	Bayer Ag, 5090 Leverkusen	Verfahren zur Herstellung von Cyanazofarbstoffen
CH654589A5 (de) *	1983-12-02	1986-02-28	Ciba Geigy Ag	Farbstoffmischungen.
DE3511728A1 (de) *	1985-03-30	1986-10-02	Cassella Ag, 6000 Frankfurt	Wasserunloesliche rote monoazofarbstoffe, ihre herstellung und verwendung
DE3533980A1 (de) *	1985-09-24	1987-03-26	Cassella Ag	Monoazofarbstoffe, ihre herstellung und verwendung
DE4417699A1 (de) *	1994-05-20	1995-11-23	Cassella Ag	Wasserunlösliche rote Monoazofarbstoffe, ihre Herstellung und ihre Verwendung
CN119505564B (zh) *	2025-01-15	2025-04-18	浙江博澳新材料股份有限公司	一种制备偶氮型分散染料的方法

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1290915B (de) *	1966-02-17	1969-03-20	Bayer Ag	Verfahren zum Faerben und Bedrucken von Fasermaterialien aus aromatischen Polyestern und Celluloseacetaten
DE2310745C3 (de) *	1973-03-03	1981-11-05	Bayer Ag, 5090 Leverkusen	Verfahren zur Herstellung von Azoverbindungen

1976
- 1976-05-28 GB GB2228376A patent/GB1578732A/en not_active Expired
1977
- 1977-05-23 BE BE177795A patent/BE854903A/xx not_active IP Right Cessation
- 1977-05-25 NL NL7705742A patent/NL7705742A/xx not_active Application Discontinuation
- 1977-05-27 DE DE19772724117 patent/DE2724117A1/de not_active Withdrawn
- 1977-05-27 CH CH656777A patent/CH626647A5/de not_active IP Right Cessation
- 1977-05-27 IT IT2409677A patent/IT1078992B/it active
- 1977-05-27 FR FR7716327A patent/FR2352864A1/fr active Granted
- 1977-05-27 JP JP6207077A patent/JPS52146432A/ja active Pending
- 1977-05-28 ES ES459246A patent/ES459246A1/es not_active Expired
- 1977-06-26 BR BR7703412A patent/BR7703412A/pt unknown

Also Published As

Publication number	Publication date
BR7703412A (pt)	1978-01-10
GB1578732A (en)	1980-11-05
IT1078992B (it)	1985-05-08
FR2352864B1 (it)	1981-12-24
ES459246A1 (es)	1978-03-16
DE2724117A1 (de)	1978-03-23
FR2352864A1 (fr)	1977-12-23
JPS52146432A (en)	1977-12-06
BE854903A (fr)	1977-11-23
NL7705742A (nl)	1977-11-30

Legal Events

Date	Code	Title	Description
1986-01-31	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
EP0555179A1 (de)	1993-08-11	Azofarbstoffe
CH626647A5 (en)	1981-11-30	Process for preparing azo dyes
EP0894830B1 (de)	2011-08-24	Dispersionsfarbstoffe
EP0284560B1 (de)	1992-03-04	Dispersionsfarbstoffe, enthaltend eine Tricyanovinylgruppierung
DE2036505C3 (de)	1978-10-05	Kationische Farbstoffe, Verfahren zu deren Herstellung und deren Verwendung
DE1058178B (de)	1959-05-27	Verfahren zur Herstellung von Phthalocyaninpigmenten
DE2013791A1 (en)	1971-10-14	Yellow basic hydrazone dyes for polyacry-lonitrile etc
DE2122232B2 (de)	1974-04-25	Anthrachinonverbindungen, Verfahren zu deren Herstellung und deren Verwendung
EP0434609B1 (de)	1994-09-21	Verfahren zum Färben von Polyacrylnitrilmaterialien
DE1544357A1 (de)	1970-05-06	Verfahren zur Herstellung von Farbstoffen fuer Cellulosematerialien
CH654589A5 (de)	1986-02-28	Farbstoffmischungen.
DE2318783C2 (de)	1985-02-28	Anthrachinonfarbstoffe, Verfahren zu deren Herstellung und Verwendung derselben
CH625265A5 (en)	1981-09-15	Process for the preparation of novel water-soluble azo dyes
CH661519A5 (de)	1987-07-31	Monoazoverbindungen.
DE2500237B1 (de)	1976-05-26	Anthrachinoide dispersionsfarbstoffe, deren herstellung und deren verwendung
DE2539634C2 (de)	1984-03-22	Monoazoverbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung
DE2724116A1 (de)	1978-03-23	Verfahren zur herstellung von azofarbstoffen
CH371862A (de)	1963-09-15	Mineralzahn mit einem Kern aus keramischer Hartmasse
EP0073965B1 (de)	1984-10-10	Neue Farbstoffe der Phthalocyaninreihe, deren Herstellung und Verwendung
DE1931789B2 (de)	1975-04-24	Dispersionsfarbstoffe, Verfahren zu deren Herstellung und deren Verwendung
DE2849995B2 (de)	1980-09-04	Monoazofarbstoffe, Verfahren zu deren Herstellung und ihre Verwendung
DE2341109A1 (de)	1974-02-28	Verfahren zur herstellung von azoverbindungen
DE2935011A1 (de)	1980-03-20	Disperse monoazofarbstoffe und verfahren zu ihrer herstellung sowie ihre verwendung zum faerben von synthetischen textilmaterialien
DE1644122C3 (de)	1977-03-10	Sulfonsäure- und carbonsäuregruppenfreie wasserunlösliche Monoazofarbstoffe und Verfahren zu ihrer Herstellung
DE1644252C (de)	1973-04-26	In Wasser schwerlösliche Farbstoffe der Anthrachinon Azoreihe, Verfahren zu ihrer Herstellung und ihre Verwendung