CS197332B2 - Process for preparing monoazodyes - Google Patents

Process for preparing monoazodyes Download PDF

Info

Publication number: CS197332B2
Authority: CS; Czechoslovakia
Prior art keywords: group; formula; acid; acylamino group; reactive
Prior art date: 1966-12-01

Application number

CS852267A

Other languages

Czech (cs)

English (en)

Inventor

Montmollin Rene De

Original Assignee

Montmollin Rene De

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.)

1966-12-01

Filing date

1967-12-01

Publication date

1980-04-30

1967-12-01 Application filed by Montmollin Rene De filed Critical Montmollin Rene De

1975-01-21 Priority to CS75416A priority Critical patent/CS197333B2/cs

1980-04-30 Publication of CS197332B2 publication Critical patent/CS197332B2/cs

Links

238000004519 manufacturing process Methods 0.000 title description 3
239000000975 dye Substances 0.000 claims abstract description 43
238000005859 coupling reaction Methods 0.000 claims abstract description 19
230000008878 coupling Effects 0.000 claims abstract description 18
238000010168 coupling process Methods 0.000 claims abstract description 18
125000004442 acylamino group Chemical group 0.000 claims abstract description 11
125000005843 halogen group Chemical group 0.000 claims abstract description 8
125000003277 amino group Chemical group 0.000 claims abstract description 7
-1 propionylamino group Chemical group 0.000 claims abstract description 6
239000000835 fiber Substances 0.000 claims abstract description 5
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 claims abstract description 5
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 2
125000004432 carbon atom Chemical group C* 0.000 claims description 10
238000000034 method Methods 0.000 claims description 10
150000008049 diazo compounds Chemical class 0.000 claims description 8
150000001412 amines Chemical class 0.000 claims description 7
230000008569 process Effects 0.000 claims description 7
125000001424 substituent group Chemical group 0.000 claims description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
125000001931 aliphatic group Chemical group 0.000 claims description 5
125000000623 heterocyclic group Chemical group 0.000 claims description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
125000000542 sulfonic acid group Chemical group 0.000 claims description 3
125000003282 alkyl amino group Chemical group 0.000 claims description 2
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims description 2
230000010933 acylation Effects 0.000 claims 1
238000005917 acylation reaction Methods 0.000 claims 1
210000002268 wool Anatomy 0.000 abstract description 12
125000002252 acyl group Chemical group 0.000 abstract description 8
238000006243 chemical reaction Methods 0.000 abstract description 7
239000012433 hydrogen halide Substances 0.000 abstract description 5
229910000039 hydrogen halide Inorganic materials 0.000 abstract description 5
238000006193 diazotization reaction Methods 0.000 abstract description 3
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract description 3
239000004952 Polyamide Substances 0.000 abstract description 2
239000003795 chemical substances by application Substances 0.000 abstract description 2
239000010985 leather Substances 0.000 abstract description 2
229920002647 polyamide Polymers 0.000 abstract description 2
150000003918 triazines Chemical class 0.000 abstract description 2
239000000463 material Substances 0.000 abstract 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
229920002635 polyurethane Polymers 0.000 abstract 1
239000004814 polyurethane Substances 0.000 abstract 1
150000003230 pyrimidines Chemical class 0.000 abstract 1
239000002253 acid Substances 0.000 description 19
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
230000007935 neutral effect Effects 0.000 description 8
230000002378 acidificating effect Effects 0.000 description 7
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
150000001875 compounds Chemical class 0.000 description 5
239000001632 sodium acetate Substances 0.000 description 5
235000017281 sodium acetate Nutrition 0.000 description 5
239000000725 suspension Substances 0.000 description 5
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
238000004043 dyeing Methods 0.000 description 4
239000000203 mixture Substances 0.000 description 4
239000000047 product Substances 0.000 description 4
239000007858 starting material Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
SEMRCUIXRUXGJX-UHFFFAOYSA-N 6-aminonaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=CC2=CC(N)=CC=C21 SEMRCUIXRUXGJX-UHFFFAOYSA-N 0.000 description 3
150000008064 anhydrides Chemical class 0.000 description 3
238000003776 cleavage reaction Methods 0.000 description 3
230000007017 scission Effects 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
235000010288 sodium nitrite Nutrition 0.000 description 3
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 2
QGLWBTPVKHMVHM-KTKRTIGZSA-N (z)-octadec-9-en-1-amine Chemical compound CCCCCCCC\C=C/CCCCCCCCN QGLWBTPVKHMVHM-KTKRTIGZSA-N 0.000 description 2
HWKWYDXHMQQDQJ-UHFFFAOYSA-N 2,3-dibromopropanoyl chloride Chemical compound ClC(=O)C(Br)CBr HWKWYDXHMQQDQJ-UHFFFAOYSA-N 0.000 description 2
DPVIABCMTHHTGB-UHFFFAOYSA-N 2,4,6-trichloropyrimidine Chemical compound ClC1=CC(Cl)=NC(Cl)=N1 DPVIABCMTHHTGB-UHFFFAOYSA-N 0.000 description 2
OKAUOXITMZTUOJ-UHFFFAOYSA-N 7-aminonaphthalene-2-sulfonic acid Chemical compound C1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 OKAUOXITMZTUOJ-UHFFFAOYSA-N 0.000 description 2
KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical class NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
150000001805 chlorine compounds Chemical class 0.000 description 2
230000005494 condensation Effects 0.000 description 2
238000009833 condensation Methods 0.000 description 2
MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 2
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
238000001914 filtration Methods 0.000 description 2
150000002391 heterocyclic compounds Chemical class 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
239000011707 mineral Substances 0.000 description 2
239000000843 powder Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
239000000126 substance Substances 0.000 description 2
125000000565 sulfonamide group Chemical group 0.000 description 2
125000001174 sulfone group Chemical group 0.000 description 2
WMDBQMYVAIBBDH-IHWYPQMZSA-N (z)-2-chlorobut-2-enoic acid Chemical compound C\C=C(/Cl)C(O)=O WMDBQMYVAIBBDH-IHWYPQMZSA-N 0.000 description 1
CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
NGCRLFIYVFOUMZ-UHFFFAOYSA-N 2,3-dichloroquinoxaline-6-carbonyl chloride Chemical compound N1=C(Cl)C(Cl)=NC2=CC(C(=O)Cl)=CC=C21 NGCRLFIYVFOUMZ-UHFFFAOYSA-N 0.000 description 1
GVBHCMNXRKOJRH-UHFFFAOYSA-N 2,4,5,6-tetrachloropyrimidine Chemical compound ClC1=NC(Cl)=C(Cl)C(Cl)=N1 GVBHCMNXRKOJRH-UHFFFAOYSA-N 0.000 description 1
QGFWFWSBFMRDNP-UHFFFAOYSA-N 2,4,6-trichloro-5-nitropyrimidine Chemical compound [O-][N+](=O)C1=C(Cl)N=C(Cl)N=C1Cl QGFWFWSBFMRDNP-UHFFFAOYSA-N 0.000 description 1
IAJCAZVXGKGAQK-UHFFFAOYSA-N 2,4,6-trichloropyrimidine-5-carbonitrile Chemical compound ClC1=NC(Cl)=C(C#N)C(Cl)=N1 IAJCAZVXGKGAQK-UHFFFAOYSA-N 0.000 description 1
NBCOZXBHPKSFSA-UHFFFAOYSA-N 2,4-dichloro-6-methyl-5-nitropyrimidine Chemical compound CC1=NC(Cl)=NC(Cl)=C1[N+]([O-])=O NBCOZXBHPKSFSA-UHFFFAOYSA-N 0.000 description 1
ZPTJJFUQGKXOKC-UHFFFAOYSA-N 2,4-dichloropyrimidine-5-sulfonyl chloride Chemical compound ClC1=NC=C(S(Cl)(=O)=O)C(Cl)=N1 ZPTJJFUQGKXOKC-UHFFFAOYSA-N 0.000 description 1
NUYJCMGJLNVOML-UHFFFAOYSA-N 2,6-dichloropyrimidine-4-carbonyl chloride Chemical compound ClC(=O)C1=CC(Cl)=NC(Cl)=N1 NUYJCMGJLNVOML-UHFFFAOYSA-N 0.000 description 1
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
HMENQNSSJFLQOP-UHFFFAOYSA-N 2-bromoprop-2-enoic acid Chemical compound OC(=O)C(Br)=C HMENQNSSJFLQOP-UHFFFAOYSA-N 0.000 description 1
MONMFXREYOKQTI-UHFFFAOYSA-N 2-bromopropanoic acid Chemical compound CC(Br)C(O)=O MONMFXREYOKQTI-UHFFFAOYSA-N 0.000 description 1
IVIONYSRTCLTPZ-UHFFFAOYSA-N 2-chloro-1,3-benzothiazole-6-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=C2N=C(Cl)SC2=C1 IVIONYSRTCLTPZ-UHFFFAOYSA-N 0.000 description 1
VRHSKNLJTFSZHK-UHFFFAOYSA-N 2-chloro-2-sulfoacetic acid Chemical compound OC(=O)C(Cl)S(O)(=O)=O VRHSKNLJTFSZHK-UHFFFAOYSA-N 0.000 description 1
SZTBMYHIYNGYIA-UHFFFAOYSA-N 2-chloroacrylic acid Chemical compound OC(=O)C(Cl)=C SZTBMYHIYNGYIA-UHFFFAOYSA-N 0.000 description 1
ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 description 1
JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 1
DBIVLAVBOICUQX-UHFFFAOYSA-N 3-bromopropanamide Chemical compound NC(=O)CCBr DBIVLAVBOICUQX-UHFFFAOYSA-N 0.000 description 1
RCKMXYKAMYSKPY-UHFFFAOYSA-N 4,6-dichloro-2-phenyl-1h-triazine Chemical compound N1C(Cl)=CC(Cl)=NN1C1=CC=CC=C1 RCKMXYKAMYSKPY-UHFFFAOYSA-N 0.000 description 1
UEGNVVBWZPHEQQ-UHFFFAOYSA-N 6-(methylamino)naphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=CC2=CC(NC)=CC=C21 UEGNVVBWZPHEQQ-UHFFFAOYSA-N 0.000 description 1
YUNBHHWDQDGWHC-UHFFFAOYSA-N 6-aminonaphthalene-1-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC2=CC(N)=CC=C21 YUNBHHWDQDGWHC-UHFFFAOYSA-N 0.000 description 1
ZYSOYLBBCYWEMB-UHFFFAOYSA-N 7-aminonaphthalen-1-ol Chemical compound C1=CC=C(O)C2=CC(N)=CC=C21 ZYSOYLBBCYWEMB-UHFFFAOYSA-N 0.000 description 1
FYVOTMMSGKWFPK-UHFFFAOYSA-N 7-aminonaphthalene-1-sulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=CC(N)=CC=C21 FYVOTMMSGKWFPK-UHFFFAOYSA-N 0.000 description 1
239000004604 Blowing Agent Substances 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
UYUBBNXOJMZRQL-UHFFFAOYSA-N ClN1NC=CC(=N1)Cl Chemical group ClN1NC=CC(=N1)Cl UYUBBNXOJMZRQL-UHFFFAOYSA-N 0.000 description 1
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
241000510097 Megalonaias nervosa Species 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
229920000297 Rayon Polymers 0.000 description 1
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
229910000272 alkali metal oxide Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
125000003368 amide group Chemical group 0.000 description 1
MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 description 1
229940040526 anhydrous sodium acetate Drugs 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
150000005700 bromopyrimidines Chemical class 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
229940106681 chloroacetic acid Drugs 0.000 description 1
239000003086 colorant Substances 0.000 description 1
238000004040 coloring Methods 0.000 description 1
239000007859 condensation product Substances 0.000 description 1
238000007865 diluting Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
150000005694 halopyrimidines Chemical class 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 1
ILXYDRFJSVKZLV-UHFFFAOYSA-N oxosulfamic acid Chemical compound OS(=O)(=O)N=O ILXYDRFJSVKZLV-UHFFFAOYSA-N 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229920000151 polyglycol Polymers 0.000 description 1
239000010695 polyglycol Substances 0.000 description 1
UORVCLMRJXCDCP-UHFFFAOYSA-N propynoic acid Chemical compound OC(=O)C#C UORVCLMRJXCDCP-UHFFFAOYSA-N 0.000 description 1
239000002964 rayon Substances 0.000 description 1
230000009467 reduction Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000004044 response Effects 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000000758 substrate Substances 0.000 description 1
PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical compound [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
229920002994 synthetic fiber Polymers 0.000 description 1
239000012209 synthetic fiber Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- 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
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/002—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the linkage of the reactive group being alternatively specified
- C09B62/006—Azodyes
- C09B62/008—Monoazo dyes
- C09B62/0081—Monoazo dyes with coupling components containing an amino directing group
- 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
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/002—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the linkage of the reactive group being alternatively specified
- C09B62/006—Azodyes
- C09B62/008—Monoazo dyes

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Coloring (AREA)

CS852267A 1966-12-01 1967-12-01 Process for preparing monoazodyes CS197332B2 (en)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CS75416A CS197333B2 (cs)	1966-12-01	1975-01-21	Způsob přípravy monoazobarviv

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH1718266A CH487988A (de)	1966-12-01	1966-12-01	Verfahren zur Herstellung neuer Monoazofarbstoffe

Publications (1)

Publication Number	Publication Date
CS197332B2 true CS197332B2 (en)	1980-04-30

Family

ID=4423405

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS852267A CS197332B2 (en)	1966-12-01	1967-12-01	Process for preparing monoazodyes

Country Status (7)

Country	Link
BE (1)	BE707307A (de)
CH (1)	CH487988A (de)
CS (1)	CS197332B2 (de)
DE (1)	DE1644132C3 (de)
GB (1)	GB1179760A (de)
NL (1)	NL160314C (de)
SE (1)	SE324198B (de)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2459821A1 (fr) *	1979-06-26	1981-01-16	Sandoz Sa	Nouveaux composes monoazoiques utilisables comme colorants reactifs et leur preparation
EP0062607B1 (de) *	1981-03-27	1986-04-23	Ciba-Geigy Ag	Monoazofarbstoffe, deren Herstellung und Verwendung
EP0360735A1 (de) *	1988-08-26	1990-03-28	Ciba-Geigy Ag	Verfahren zum Trichromie-Färben oder -Bedrucken

1966
- 1966-12-01 CH CH1718266A patent/CH487988A/de not_active IP Right Cessation
1967
- 1967-11-22 DE DE1967C0043921 patent/DE1644132C3/de not_active Expired
- 1967-11-30 SE SE1645967A patent/SE324198B/xx unknown
- 1967-11-30 BE BE707307D patent/BE707307A/xx not_active IP Right Cessation
- 1967-11-30 NL NL6716325A patent/NL160314C/xx active
- 1967-12-01 GB GB5486367D patent/GB1179760A/en not_active Expired
- 1967-12-01 CS CS852267A patent/CS197332B2/cs unknown

Also Published As

Publication number	Publication date
CH487988A (de)	1970-03-31
NL160314C (nl)	1979-10-15
NL160314B (nl)	1979-05-15
DE1644132A1 (de)	1971-04-15
SE324198B (de)	1970-05-25
BE707307A (de)	1968-04-01
DE1644132C3 (de)	1978-08-31
DE1644132B2 (de)	1977-12-29
NL6716325A (de)	1968-06-04
GB1179760A (en)	1970-01-28

Publication	Publication Date	Title
US4474697A (en)	1984-10-02	Fluorotriazine-group-containing azo dyestuffs
DE3201114A1 (de)	1983-07-28	Disazoreaktivfarbstoffe
GB2036780A (en)	1980-07-02	Disazo dyestuffs
US3261826A (en)	1966-07-19	Monoazo triazine containing dyestuffs
US2951837A (en)	1960-09-06	New monoazo dyestuffs
US3697500A (en)	1972-10-10	Water-soluble disazo pyrazole dyestuffs containing fiber-reactive substituents
US3625935A (en)	1971-12-07	1:2-chromium complexes of a monoazo dyestuff and a disazo dyestuff
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