CH606346A5 - Fibre reactive disazo dyes - Google Patents

Fibre reactive disazo dyes

Info

Publication number: CH606346A5
Authority: CH; Switzerland
Prior art keywords: disulfonic acid; aliphatic; aminobenzene; amino; compound
Prior art date: 1975-01-08

Application number

CH16675A

Other languages

German (de)

English (en)

Inventor

Henri Dr Riat

Karl Dr Seitz

Original Assignee

Ciba Geigy Ag

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.)

1975-01-08

Filing date

1975-01-08

Publication date

1978-10-31

1975-01-08 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1975-01-08 Priority to CH16675A priority Critical patent/CH606346A5/de

1976-01-05 Priority to DE19762600164 priority patent/DE2600164A1/de

1976-01-05 Priority to FR7600091A priority patent/FR2297233A1/fr

1976-01-06 Priority to CA243,008A priority patent/CA1052776A/fr

1976-01-07 Priority to GB528/76A priority patent/GB1512151A/en

1976-01-07 Priority to ES444104A priority patent/ES444104A1/es

1976-01-07 Priority to BR7600054A priority patent/BR7600054A/pt

1976-01-07 Priority to BE163346A priority patent/BE837355A/fr

1976-01-07 Priority to CS7698A priority patent/CS194735B2/cs

1976-01-07 Priority to AR261851A priority patent/AR209137A1/es

1976-01-07 Priority to IT47537/76A priority patent/IT1053285B/it

1976-01-08 Priority to JP51001168A priority patent/JPS5929621B2/ja

1978-02-27 Priority to US05/881,447 priority patent/US4228071A/en

1978-10-31 Publication of CH606346A5 publication Critical patent/CH606346A5/de

Links

239000000975 dye Substances 0.000 title claims abstract description 45
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title claims abstract description 25
239000000835 fiber Substances 0.000 title abstract description 5
-1 s-triazinyl Chemical group 0.000 claims abstract description 53
230000008878 coupling Effects 0.000 claims description 26
238000010168 coupling process Methods 0.000 claims description 26
238000005859 coupling reaction Methods 0.000 claims description 26
238000000034 method Methods 0.000 claims description 21
150000004984 aromatic diamines Chemical class 0.000 claims description 18
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 16
150000001875 compounds Chemical class 0.000 claims description 13
238000009833 condensation Methods 0.000 claims description 12
230000005494 condensation Effects 0.000 claims description 12
MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 claims description 12
125000001931 aliphatic group Chemical group 0.000 claims description 11
125000003277 amino group Chemical group 0.000 claims description 9
125000003118 aryl group Chemical group 0.000 claims description 9
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
230000008569 process Effects 0.000 claims description 8
ILFIVTCNXZZSQT-UHFFFAOYSA-N 2-amino-5-[(4-aminobenzoyl)amino]benzene-1,4-disulfonic acid Chemical compound C1=CC(N)=CC=C1C(=O)NC1=CC(S(O)(=O)=O)=C(N)C=C1S(O)(=O)=O ILFIVTCNXZZSQT-UHFFFAOYSA-N 0.000 claims description 7
239000007859 condensation product Substances 0.000 claims description 7
238000002360 preparation method Methods 0.000 claims description 7
125000005843 halogen group Chemical group 0.000 claims description 6
239000007858 starting material Substances 0.000 claims description 6
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 claims description 4
GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 claims description 3
LDCCBULMAFILCT-UHFFFAOYSA-N 2-aminobenzene-1,4-disulfonic acid Chemical compound NC1=CC(S(O)(=O)=O)=CC=C1S(O)(=O)=O LDCCBULMAFILCT-UHFFFAOYSA-N 0.000 claims description 2
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
239000000987 azo dye Substances 0.000 claims 1
230000001419 dependent effect Effects 0.000 claims 1
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
239000000243 solution Substances 0.000 description 25
OATNQHYJXLHTEW-UHFFFAOYSA-N benzene-1,4-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(S(O)(=O)=O)C=C1 OATNQHYJXLHTEW-UHFFFAOYSA-N 0.000 description 22
239000002253 acid Substances 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
238000004043 dyeing Methods 0.000 description 10
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 10
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
239000000203 mixture Substances 0.000 description 8
239000004744 fabric Substances 0.000 description 7
229920000742 Cotton Polymers 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
235000002639 sodium chloride Nutrition 0.000 description 6
239000007864 aqueous solution Substances 0.000 description 5
238000007639 printing Methods 0.000 description 5
150000003254 radicals Chemical class 0.000 description 5
239000011780 sodium chloride Substances 0.000 description 5
235000010288 sodium nitrite Nutrition 0.000 description 5
WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 4
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
150000004985 diamines Chemical class 0.000 description 4
238000006193 diazotization reaction Methods 0.000 description 4
WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Natural products CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 3
229920003043 Cellulose fiber Polymers 0.000 description 3
230000002378 acidificating effect Effects 0.000 description 3
239000003513 alkali Substances 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
WOWBFOBYOAGEEA-UHFFFAOYSA-N diafenthiuron Chemical compound CC(C)C1=C(NC(=S)NC(C)(C)C)C(C(C)C)=CC(OC=2C=CC=CC=2)=C1 WOWBFOBYOAGEEA-UHFFFAOYSA-N 0.000 description 3
150000008049 diazo compounds Chemical class 0.000 description 3
230000007935 neutral effect Effects 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
239000001488 sodium phosphate Substances 0.000 description 3
210000002268 wool Anatomy 0.000 description 3
VOPSFYWMOIKYEM-UHFFFAOYSA-N 2,5-diaminobenzene-1,4-disulfonic acid Chemical compound NC1=CC(S(O)(=O)=O)=C(N)C=C1S(O)(=O)=O VOPSFYWMOIKYEM-UHFFFAOYSA-N 0.000 description 2
MFYSUUPKMDJYPF-UHFFFAOYSA-N 2-[(4-methyl-2-nitrophenyl)diazenyl]-3-oxo-n-phenylbutanamide Chemical compound C=1C=CC=CC=1NC(=O)C(C(=O)C)N=NC1=CC=C(C)C=C1[N+]([O-])=O MFYSUUPKMDJYPF-UHFFFAOYSA-N 0.000 description 2
LDQMZKBIBRAZEA-UHFFFAOYSA-N 4-amino-2-aminobenzoic acid Natural products NC1=CC=C(C(O)=O)C(N)=C1 LDQMZKBIBRAZEA-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 2
125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical group C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 2
238000009835 boiling Methods 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
229920002678 cellulose Polymers 0.000 description 2
239000001913 cellulose Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
239000003599 detergent Substances 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
238000002955 isolation Methods 0.000 description 2
239000000463 material Substances 0.000 description 2
UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
239000002562 thickening agent Substances 0.000 description 2
JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical group C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-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
IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
WCZNKVPCIFMXEQ-UHFFFAOYSA-N 2,3,5,6-tetramethylbenzene-1,4-diamine Chemical compound CC1=C(C)C(N)=C(C)C(C)=C1N WCZNKVPCIFMXEQ-UHFFFAOYSA-N 0.000 description 1
RDMFEHLCCOQUMH-UHFFFAOYSA-N 2,4'-Diphenyldiamine Chemical compound C1=CC(N)=CC=C1C1=CC=CC=C1N RDMFEHLCCOQUMH-UHFFFAOYSA-N 0.000 description 1
ZVDSMYGTJDFNHN-UHFFFAOYSA-N 2,4,6-trimethylbenzene-1,3-diamine Chemical compound CC1=CC(C)=C(N)C(C)=C1N ZVDSMYGTJDFNHN-UHFFFAOYSA-N 0.000 description 1
BAHPQISAXRFLCL-UHFFFAOYSA-N 2,4-Diaminoanisole Chemical compound COC1=CC=C(N)C=C1N BAHPQISAXRFLCL-UHFFFAOYSA-N 0.000 description 1
JVMSQRAXNZPDHF-UHFFFAOYSA-N 2,4-diaminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C(N)=C1 JVMSQRAXNZPDHF-UHFFFAOYSA-N 0.000 description 1
QGNJPFLIBOTDKU-UHFFFAOYSA-N 2,5-diaminobenzene-1,3-disulfonic acid Chemical compound NC1=CC(S(O)(=O)=O)=C(N)C(S(O)(=O)=O)=C1 QGNJPFLIBOTDKU-UHFFFAOYSA-N 0.000 description 1
HEAHMJLHQCESBZ-UHFFFAOYSA-N 2,5-diaminobenzenesulfonic acid Chemical compound NC1=CC=C(N)C(S(O)(=O)=O)=C1 HEAHMJLHQCESBZ-UHFFFAOYSA-N 0.000 description 1
UONVFNLDGRWLKF-UHFFFAOYSA-N 2,5-diaminobenzoic acid Chemical compound NC1=CC=C(N)C(C(O)=O)=C1 UONVFNLDGRWLKF-UHFFFAOYSA-N 0.000 description 1
UJJIPRCLIYLSHI-UHFFFAOYSA-N 2-[2-amino-5-[4-amino-3-(carboxymethoxy)phenyl]phenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(N)=CC=C1C1=CC=C(N)C(OCC(O)=O)=C1 UJJIPRCLIYLSHI-UHFFFAOYSA-N 0.000 description 1
IIQLVLWFQUUZII-UHFFFAOYSA-N 2-amino-5-(4-amino-3-carboxyphenyl)benzoic acid Chemical compound C1=C(C(O)=O)C(N)=CC=C1C1=CC=C(N)C(C(O)=O)=C1 IIQLVLWFQUUZII-UHFFFAOYSA-N 0.000 description 1
XTIDBJBGIGJGIZ-UHFFFAOYSA-N 2-amino-5-[(3-nitrobenzoyl)amino]benzene-1,4-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C(N)=CC(S(O)(=O)=O)=C1NC(=O)C1=CC=CC([N+]([O-])=O)=C1 XTIDBJBGIGJGIZ-UHFFFAOYSA-N 0.000 description 1
UDVUXXZHSPUHJC-UHFFFAOYSA-N 2-amino-5-[(4-nitrobenzoyl)amino]benzene-1,4-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C(N)=CC(S(O)(=O)=O)=C1NC(=O)C1=CC=C([N+]([O-])=O)C=C1 UDVUXXZHSPUHJC-UHFFFAOYSA-N 0.000 description 1
YRGYYQCOWUULNF-UHFFFAOYSA-N 2-hydroxy-4-methyl-6-oxo-1h-pyridine-3-carbonitrile Chemical compound CC1=CC(=O)NC(O)=C1C#N YRGYYQCOWUULNF-UHFFFAOYSA-N 0.000 description 1
OBCSAIDCZQSFQH-UHFFFAOYSA-N 2-methyl-1,4-phenylenediamine Chemical compound CC1=CC(N)=CC=C1N OBCSAIDCZQSFQH-UHFFFAOYSA-N 0.000 description 1
HUWXDEQWWKGHRV-UHFFFAOYSA-N 3,3'-Dichlorobenzidine Chemical compound C1=C(Cl)C(N)=CC=C1C1=CC=C(N)C(Cl)=C1 HUWXDEQWWKGHRV-UHFFFAOYSA-N 0.000 description 1
JRBJSXQPQWSCCF-UHFFFAOYSA-N 3,3'-Dimethoxybenzidine Chemical compound C1=C(N)C(OC)=CC(C=2C=C(OC)C(N)=CC=2)=C1 JRBJSXQPQWSCCF-UHFFFAOYSA-N 0.000 description 1
NUIURNJTPRWVAP-UHFFFAOYSA-N 3,3'-Dimethylbenzidine Chemical compound C1=C(N)C(C)=CC(C=2C=C(C)C(N)=CC=2)=C1 NUIURNJTPRWVAP-UHFFFAOYSA-N 0.000 description 1
MBDPTRRYRXXGCZ-UHFFFAOYSA-N 3-hydroxyquinoline-2-sulfonic acid Chemical class C1=CC=C2N=C(S(O)(=O)=O)C(O)=CC2=C1 MBDPTRRYRXXGCZ-UHFFFAOYSA-N 0.000 description 1
NHLAPJMCARJFOG-UHFFFAOYSA-N 3-methyl-1,4-dihydropyrazol-5-one Chemical compound CC1=NNC(=O)C1 NHLAPJMCARJFOG-UHFFFAOYSA-N 0.000 description 1
NXTNASSYJUXJDV-UHFFFAOYSA-N 3-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=CC(C(Cl)=O)=C1 NXTNASSYJUXJDV-UHFFFAOYSA-N 0.000 description 1
KGDFBLAMEFQDOK-UHFFFAOYSA-N 3-oxo-n-propan-2-ylbutanamide Chemical compound CC(C)NC(=O)CC(C)=O KGDFBLAMEFQDOK-UHFFFAOYSA-N 0.000 description 1
YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 1
YADSWTKOIHUSDX-UHFFFAOYSA-N 4,6-diaminobenzene-1,3-disulfonic acid Chemical compound NC1=CC(N)=C(S(O)(=O)=O)C=C1S(O)(=O)=O YADSWTKOIHUSDX-UHFFFAOYSA-N 0.000 description 1
IHDBZCJYSHDCKF-UHFFFAOYSA-N 4,6-dichlorotriazine Chemical compound ClC1=CC(Cl)=NN=N1 IHDBZCJYSHDCKF-UHFFFAOYSA-N 0.000 description 1
QYIMZXITLDTULQ-UHFFFAOYSA-N 4-(4-amino-2-methylphenyl)-3-methylaniline Chemical compound CC1=CC(N)=CC=C1C1=CC=C(N)C=C1C QYIMZXITLDTULQ-UHFFFAOYSA-N 0.000 description 1
FTEGMIZQLGXBNA-UHFFFAOYSA-N 4-(4-amino-3-methylnaphthalen-1-yl)-2-methylnaphthalen-1-amine Chemical compound C1=CC=CC2=C(N)C(C)=CC(C=3C4=CC=CC=C4C(N)=C(C)C=3)=C21 FTEGMIZQLGXBNA-UHFFFAOYSA-N 0.000 description 1
HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 1
ZWUBBMDHSZDNTA-UHFFFAOYSA-N 4-Chloro-meta-phenylenediamine Chemical compound NC1=CC=C(Cl)C(N)=C1 ZWUBBMDHSZDNTA-UHFFFAOYSA-N 0.000 description 1
KOGDFDWINXIWHI-OWOJBTEDSA-N 4-[(e)-2-(4-aminophenyl)ethenyl]aniline Chemical compound C1=CC(N)=CC=C1\C=C\C1=CC=C(N)C=C1 KOGDFDWINXIWHI-OWOJBTEDSA-N 0.000 description 1
NQHVJMJEWQQXBS-UHFFFAOYSA-N 4-ethoxybenzene-1,3-diamine Chemical compound CCOC1=CC=C(N)C=C1N NQHVJMJEWQQXBS-UHFFFAOYSA-N 0.000 description 1
PTMVFRKAMOUORT-UHFFFAOYSA-N 4-ethylbenzene-1,3-diamine Chemical compound CCC1=CC=C(N)C=C1N PTMVFRKAMOUORT-UHFFFAOYSA-N 0.000 description 1
DPIZKMGPXNXSGL-UHFFFAOYSA-N 4-nitro-1,3-phenylenediamine Chemical compound NC1=CC=C([N+]([O-])=O)C(N)=C1 DPIZKMGPXNXSGL-UHFFFAOYSA-N 0.000 description 1
SKDHHIUENRGTHK-UHFFFAOYSA-N 4-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=C(C(Cl)=O)C=C1 SKDHHIUENRGTHK-UHFFFAOYSA-N 0.000 description 1
XDVZFVQLRRGUKX-UHFFFAOYSA-N 5,5-diamino-2-[2-(2-sulfophenyl)ethenyl]cyclohexa-1,3-diene-1-sulfonic acid Chemical compound C1=CC(N)(N)CC(S(O)(=O)=O)=C1C=CC1=CC=CC=C1S(O)(=O)=O XDVZFVQLRRGUKX-UHFFFAOYSA-N 0.000 description 1
MOUMWCTZFHYCJY-UHFFFAOYSA-N 5-amino-1-phenylpyrazole-3-carboxylic acid Chemical compound NC1=CC(C(O)=O)=NN1C1=CC=CC=C1 MOUMWCTZFHYCJY-UHFFFAOYSA-N 0.000 description 1
FMKMKBLHMONXJM-UHFFFAOYSA-N 5-methyl-2-phenylpyrazol-3-amine Chemical compound N1=C(C)C=C(N)N1C1=CC=CC=C1 FMKMKBLHMONXJM-UHFFFAOYSA-N 0.000 description 1
IMZSHPUSPMOODC-UHFFFAOYSA-N 5-oxo-1-phenyl-4h-pyrazole-3-carboxylic acid Chemical compound O=C1CC(C(=O)O)=NN1C1=CC=CC=C1 IMZSHPUSPMOODC-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
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 1
239000004952 Polyamide Substances 0.000 description 1
BERPCVULMUPOER-UHFFFAOYSA-N Quinolinediol Chemical class C1=CC=C2NC(=O)C(O)=CC2=C1 BERPCVULMUPOER-UHFFFAOYSA-N 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
OXIKYYJDTWKERT-UHFFFAOYSA-N [4-(aminomethyl)cyclohexyl]methanamine Chemical compound NCC1CCC(CN)CC1 OXIKYYJDTWKERT-UHFFFAOYSA-N 0.000 description 1
230000009471 action Effects 0.000 description 1
125000004442 acylamino group Chemical group 0.000 description 1
150000001447 alkali salts Chemical class 0.000 description 1
239000012670 alkaline solution Substances 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
125000006267 biphenyl group Chemical group 0.000 description 1
239000006172 buffering agent Substances 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
238000001816 cooling Methods 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
125000004956 cyclohexylene group Chemical group 0.000 description 1
238000009792 diffusion process Methods 0.000 description 1
BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
229910000397 disodium phosphate Inorganic materials 0.000 description 1
235000019800 disodium phosphate Nutrition 0.000 description 1
238000001035 drying Methods 0.000 description 1
QELUYTUMUWHWMC-UHFFFAOYSA-N edaravone Chemical compound O=C1CC(C)=NN1C1=CC=CC=C1 QELUYTUMUWHWMC-UHFFFAOYSA-N 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
125000001475 halogen functional group Chemical group 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000005457 ice water Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
239000010985 leather Substances 0.000 description 1
239000002609 medium Substances 0.000 description 1
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 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
229910000403 monosodium phosphate Inorganic materials 0.000 description 1
235000019799 monosodium phosphate Nutrition 0.000 description 1
FLCPERRDPXWFDK-UHFFFAOYSA-N n-cyclohexyl-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1CCCCC1 FLCPERRDPXWFDK-UHFFFAOYSA-N 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
229920002635 polyurethane Polymers 0.000 description 1
239000004814 polyurethane Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
WLFXSECCHULRRO-UHFFFAOYSA-N pyridine-2,6-diol Chemical compound OC1=CC=CC(O)=N1 WLFXSECCHULRRO-UHFFFAOYSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
239000012048 reactive intermediate Substances 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
230000009467 reduction Effects 0.000 description 1
239000004627 regenerated cellulose Substances 0.000 description 1
238000010020 roller printing Methods 0.000 description 1
238000005185 salting out Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000000661 sodium alginate Substances 0.000 description 1
235000010413 sodium alginate Nutrition 0.000 description 1
229940005550 sodium alginate Drugs 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
LJRGBERXYNQPJI-UHFFFAOYSA-M sodium;3-nitrobenzenesulfonate Chemical compound [Na+].[O-][N+](=O)C1=CC=CC(S([O-])(=O)=O)=C1 LJRGBERXYNQPJI-UHFFFAOYSA-M 0.000 description 1
238000001694 spray drying Methods 0.000 description 1
PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
235000021286 stilbenes Nutrition 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
239000000725 suspension Substances 0.000 description 1
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
229910000406 trisodium phosphate Inorganic materials 0.000 description 1
235000019801 trisodium phosphate Nutrition 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
- C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
- C09B62/04—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a triazine ring
- C09B62/043—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a triazine ring containing two or more triazine rings linked together by a non-chromophoric link

Landscapes

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

CH16675A 1975-01-08 1975-01-08 Fibre reactive disazo dyes CH606346A5 (en)

Priority Applications (13)

Application Number	Priority Date	Filing Date	Title
CH16675A CH606346A5 (en)	1975-01-08	1975-01-08	Fibre reactive disazo dyes
DE19762600164 DE2600164A1 (de)	1975-01-08	1976-01-05	Faserreaktive disazofarbstoffe, deren herstellung und verwendung
FR7600091A FR2297233A1 (fr)	1975-01-08	1976-01-05	Colorants disazoiques reactifs sur fibres, leur procede de preparation et leur utilisation
CA243,008A CA1052776A (fr)	1975-01-08	1976-01-06	Colorants diazoiques reagissant avec les fibres
GB528/76A GB1512151A (en)	1975-01-08	1976-01-07	Fibre-reactive disazo dyestuffs their production and their use
ES444104A ES444104A1 (es)	1975-01-08	1976-01-07	Procedimiento para la preparacion de colorantes disazoicos fibrorreactivos.
BR7600054A BR7600054A (pt)	1975-01-08	1976-01-07	Processo para preparacao de disazocorantes reativos em relacao a fibras e suas aplicacoes
BE163346A BE837355A (fr)	1975-01-08	1976-01-07	Colorants disazoiques reactifs sur fibres, leur procede de preparation et leur utilisation
CS7698A CS194735B2 (en)	1975-01-08	1976-01-07	Process for preparing disazodyes reactive with fibres
AR261851A AR209137A1 (es)	1975-01-08	1976-01-07	Colorantes disazoicos reactivos con fibras su preparacion y composiciones que los contienen
IT47537/76A IT1053285B (it)	1975-01-08	1976-01-07	Disazocoloranti reattivi per le fibre e procedimento per la loro produzione ed applicazione
JP51001168A JPS5929621B2 (ja)	1975-01-08	1976-01-08	繊維反応性ジスアゾ染料およびその製法
US05/881,447 US4228071A (en)	1975-01-08	1978-02-27	Triazine containing fiber-reactive disazo dyestuffs

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH16675A CH606346A5 (en)	1975-01-08	1975-01-08	Fibre reactive disazo dyes

Publications (1)

Publication Number	Publication Date
CH606346A5 true CH606346A5 (en)	1978-10-31

Family

ID=4180755

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH16675A CH606346A5 (en)	1975-01-08	1975-01-08	Fibre reactive disazo dyes

Country Status (2)

Country	Link
BE (1)	BE837355A (fr)
CH (1)	CH606346A5 (fr)

1975
- 1975-01-08 CH CH16675A patent/CH606346A5/de not_active IP Right Cessation
1976
- 1976-01-07 BE BE163346A patent/BE837355A/fr unknown

Also Published As

Publication number	Publication date
BE837355A (fr)	1976-07-07

Legal Events

Date	Code	Title	Description
1984-09-28	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
DE2001960C3 (fr)	1977-02-24
CH628671A5 (de)	1982-03-15	Verfahren zur herstellung von reaktivfarbstoffen.
DE2500062C2 (de)	1986-02-20	Faserreaktive Tetrazofarbstoffe und ihre Verwendung
DE2600164A1 (de)	1976-07-15	Faserreaktive disazofarbstoffe, deren herstellung und verwendung
DE2601043A1 (de)	1976-07-22	Tetrareaktive disazofarbstoffe, deren herstellung und verwendung
EP0073178B1 (fr)	1985-05-29	Colorants réactifs, leur préparation et leur utilisation
DE2318412C2 (de)	1984-05-17	Azo-Reaktivfarbstoffe
EP0170612B1 (fr)	1989-05-24	Colorants réactifs, leur préparation et leur utilisation
CH599316A5 (en)	1978-05-31	Fibre-reactive azo dyes prepn.
CH606346A5 (en)	1978-10-31	Fibre reactive disazo dyes
EP0105027B1 (fr)	1987-05-06	Colorants réactifs, leur préparation et leur emploi
DE1298220B (de)	1969-06-26	Verfahren zur Herstellung faserreaktiver Monoazofarbstoffe
CH635859A5 (de)	1983-04-29	Azofarbstoffe sowie deren herstellung.
CH621358A5 (en)	1981-01-30	Process for preparing fibre-reactive dyes
EP0134197B1 (fr)	1988-06-01	Colorants réactifs disazoiques, leur préparation et leur utilisation
DE1136039B (de)	1962-09-06	Verfahren zur Herstellung von Disazofarbstoffen
EP0122881B1 (fr)	1986-08-13	Colorants réactifs, leur préparation et leur utilisation
CH606345A5 (en)	1978-10-31	Tetrakis:azo dyes contg. two fibre-reactive triazinyl gps.
DE2734679C2 (de)	1984-03-08	Faserreaktive Azofarbstoffe, deren Herstellung und Verwendung
DE2751293A1 (de)	1978-05-24	Faserreaktive azofarbstoffe, deren herstellung und verwendung
CH524671A (de)	1972-06-30	Verfahren zur Herstellung von neuen Monoazofarbstoffen
DE1419795C3 (de)	1974-03-21	Verfahren zur Herstellung von Disazoreaktivfarbstoffen
AT200686B (de)	1958-11-25	Verfahren zur Herstellung neuer, wasserlöslicher Disazofarbstoffe
DE2108402A1 (de)	1971-09-09	Neue Azoverbindungen, Verfahren zu deren Herstellung und Verwendung
DE1110788B (de)	1961-07-13	Verfahren zur Herstellung von Disazofarbstoffen