CH619258A5 - Process for the preparation of fibre-reactive dyestuffs - Google Patents

Process for the preparation of fibre-reactive dyestuffs Download PDF

Info

Publication number: CH619258A5
Authority: CH; Switzerland
Prior art keywords: sep; formula; amino; anthraquinone; acid
Prior art date: 1975-12-09

Application number

CH1597575A

Other languages

German (de)

English (en)

Inventor

Henri Dr Riat

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.)

1975-12-09

Filing date

1975-12-09

Publication date

1980-09-15

1975-12-09 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1975-12-09 Priority to CH1597575A priority Critical patent/CH619258A5/de

1976-12-07 Priority to CA267,271A priority patent/CA1064915A/fr

1976-12-07 Priority to DE19762655449 priority patent/DE2655449A1/de

1976-12-07 Priority to IT5249976A priority patent/IT1066798B/it

1976-12-07 Priority to ES454015A priority patent/ES454015A1/es

1976-12-08 Priority to BR7608230A priority patent/BR7608230A/pt

1976-12-08 Priority to CS802476A priority patent/CS194247B2/cs

1976-12-08 Priority to FR7637036A priority patent/FR2334724A1/fr

1976-12-08 Priority to BE173042A priority patent/BE849161A/fr

1976-12-09 Priority to JP14718476A priority patent/JPS5269933A/ja

1976-12-09 Priority to GB5150976A priority patent/GB1547659A/en

1980-09-15 Publication of CH619258A5 publication Critical patent/CH619258A5/de

Links

238000000034 method Methods 0.000 title claims description 22
230000008569 process Effects 0.000 title claims description 14
238000002360 preparation method Methods 0.000 title claims description 4
239000000975 dye Substances 0.000 claims abstract description 45
239000007859 condensation product Substances 0.000 claims abstract description 21
PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims abstract description 19
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 claims abstract description 18
150000004056 anthraquinones Chemical class 0.000 claims abstract description 18
125000001424 substituent group Chemical group 0.000 claims abstract description 18
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 14
238000006243 chemical reaction Methods 0.000 claims abstract description 12
239000002253 acid Substances 0.000 claims description 91
-1 benzene radical Chemical class 0.000 claims description 44
UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 34
239000000985 reactive dye Substances 0.000 claims description 29
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 28
MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 claims description 24
230000008878 coupling Effects 0.000 claims description 20
238000010168 coupling process Methods 0.000 claims description 20
238000005859 coupling reaction Methods 0.000 claims description 20
229910052739 hydrogen Inorganic materials 0.000 claims description 17
239000001257 hydrogen Substances 0.000 claims description 17
125000000217 alkyl group Chemical group 0.000 claims description 13
VZCRCIVIAYWVEX-UHFFFAOYSA-N 4-[1-(naphthalen-1-yldiazenyl)naphthalen-2-yl]aniline Chemical compound NC1=CC=C(C=C1)C1=C(C2=CC=CC=C2C=C1)N=NC1=CC=CC2=CC=CC=C12 VZCRCIVIAYWVEX-UHFFFAOYSA-N 0.000 claims description 12
239000001000 anthraquinone dye Substances 0.000 claims description 12
230000005494 condensation Effects 0.000 claims description 11
238000009833 condensation Methods 0.000 claims description 11
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
125000004432 carbon atom Chemical group C* 0.000 claims description 9
229910052801 chlorine Inorganic materials 0.000 claims description 8
239000000460 chlorine Substances 0.000 claims description 8
239000001007 phthalocyanine dye Substances 0.000 claims description 8
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
239000007858 starting material Substances 0.000 claims description 7
FHXNIPOPDUIKEX-UHFFFAOYSA-N N-[5-amino-2-[1-(naphthalen-1-yldiazenyl)naphthalen-2-yl]phenyl]acetamide Chemical compound NC1=CC(=C(C=C1)C1=C(C2=CC=CC=C2C=C1)N=NC1=CC=CC2=CC=CC=C12)NC(C)=O FHXNIPOPDUIKEX-UHFFFAOYSA-N 0.000 claims description 6
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 6
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 6
125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 5
229910006069 SO3H Inorganic materials 0.000 claims description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 3
150000002367 halogens Chemical class 0.000 claims description 3
125000000468 ketone group Chemical group 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 claims description 2
150000003852 triazoles Chemical class 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims 3
125000001309 chloro group Chemical group Cl* 0.000 claims 1
IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 abstract description 7
125000003277 amino group Chemical group 0.000 abstract description 5
230000009257 reactivity Effects 0.000 abstract description 2
LZKGFGLOQNSMBS-UHFFFAOYSA-N 4,5,6-trichlorotriazine Chemical compound ClC1=NN=NC(Cl)=C1Cl LZKGFGLOQNSMBS-UHFFFAOYSA-N 0.000 abstract 1
RZSYLLSAWYUBPE-UHFFFAOYSA-L Fast green FCF Chemical compound [Na+].[Na+].C=1C=C(C(=C2C=CC(C=C2)=[N+](CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=2C(=CC(O)=CC=2)S([O-])(=O)=O)C=CC=1N(CC)CC1=CC=CC(S([O-])(=O)=O)=C1 RZSYLLSAWYUBPE-UHFFFAOYSA-L 0.000 abstract 1
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 39
239000000243 solution Substances 0.000 description 22
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 12
125000004435 hydrogen atom Chemical group [H]* 0.000 description 12
239000000203 mixture Substances 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
229920000742 Cotton Polymers 0.000 description 7
239000000987 azo dye Substances 0.000 description 7
238000004519 manufacturing process Methods 0.000 description 7
150000003254 radicals Chemical class 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
KPUYGBSCRCGTHQ-UHFFFAOYSA-N [5-amino-2-[1-(naphthalen-1-yldiazenyl)naphthalen-2-yl]phenyl]urea Chemical compound NC1=CC(=C(C=C1)C1=C(C2=CC=CC=C2C=C1)N=NC1=CC=CC2=CC=CC=C12)NC(=O)N KPUYGBSCRCGTHQ-UHFFFAOYSA-N 0.000 description 6
150000001875 compounds Chemical class 0.000 description 6
238000004043 dyeing Methods 0.000 description 6
230000007935 neutral effect Effects 0.000 description 6
150000001555 benzenes Chemical class 0.000 description 5
229910052802 copper Inorganic materials 0.000 description 5
239000010949 copper Substances 0.000 description 5
125000005843 halogen group Chemical group 0.000 description 5
229920003043 Cellulose fiber Polymers 0.000 description 4
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
239000004744 fabric Substances 0.000 description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
159000000000 sodium salts Chemical class 0.000 description 4
125000000542 sulfonic acid group Chemical group 0.000 description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
125000004442 acylamino group Chemical group 0.000 description 3
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 3
150000004982 aromatic amines Chemical class 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
150000008049 diazo compounds Chemical class 0.000 description 3
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 3
239000000835 fiber Substances 0.000 description 3
229910052731 fluorine Inorganic materials 0.000 description 3
239000011737 fluorine Substances 0.000 description 3
RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
230000004048 modification Effects 0.000 description 3
238000012986 modification Methods 0.000 description 3
210000002268 wool Anatomy 0.000 description 3
GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 2
JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 2
JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 2
DOPJNPGPZIJGEZ-UHFFFAOYSA-N 5-methylpyrazol-3-one Chemical compound CC1=CC(=O)N=N1 DOPJNPGPZIJGEZ-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
230000009471 action Effects 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
239000003513 alkali Substances 0.000 description 2
125000003545 alkoxy group Chemical group 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
125000000732 arylene group Chemical group 0.000 description 2
HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 2
LMIZORQOLSLQRY-UHFFFAOYSA-N benzene;naphthalene Chemical compound C1=CC=CC=C1.C1=CC=CC2=CC=CC=C21 LMIZORQOLSLQRY-UHFFFAOYSA-N 0.000 description 2
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 2
229960001506 brilliant green Drugs 0.000 description 2
HXCILVUBKWANLN-UHFFFAOYSA-N brilliant green cation Chemical compound C1=CC(N(CC)CC)=CC=C1C(C=1C=CC=CC=1)=C1C=CC(=[N+](CC)CC)C=C1 HXCILVUBKWANLN-UHFFFAOYSA-N 0.000 description 2
229920002678 cellulose Polymers 0.000 description 2
239000001913 cellulose Substances 0.000 description 2
239000003599 detergent Substances 0.000 description 2
238000006193 diazotization reaction Methods 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
239000000463 material Substances 0.000 description 2
SQYUJKVKVFILNB-UHFFFAOYSA-N methyl 2-amino-4-[(2,5-dichlorophenyl)carbamoyl]benzoate Chemical compound C1=C(N)C(C(=O)OC)=CC=C1C(=O)NC1=CC(Cl)=CC=C1Cl SQYUJKVKVFILNB-UHFFFAOYSA-N 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 2
RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 1
JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 1
ZRHUHDUEXWHZMA-UHFFFAOYSA-N 1,4-dihydropyrazol-5-one Chemical compound O=C1CC=NN1 ZRHUHDUEXWHZMA-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
KXSVVRDMKIHHMK-UHFFFAOYSA-N 1-amino-4-[4-(4-aminophenyl)anilino]anthracene-9,10-dione Chemical compound C1=CC(N)=CC=C1C(C=C1)=CC=C1NC1=CC=C(N)C2=C1C(=O)C1=CC=CC=C1C2=O KXSVVRDMKIHHMK-UHFFFAOYSA-N 0.000 description 1
125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
CDULGHZNHURECF-UHFFFAOYSA-N 2,3-dimethylaniline 2,4-dimethylaniline 2,5-dimethylaniline 2,6-dimethylaniline 3,4-dimethylaniline 3,5-dimethylaniline Chemical group CC1=CC=C(N)C(C)=C1.CC1=CC=C(C)C(N)=C1.CC1=CC(C)=CC(N)=C1.CC1=CC=C(N)C=C1C.CC1=CC=CC(N)=C1C.CC1=CC=CC(C)=C1N CDULGHZNHURECF-UHFFFAOYSA-N 0.000 description 1
DVXMQZHDVBYYEQ-UHFFFAOYSA-N 2,4,6-triaminopyridine-3-carbonitrile Chemical compound NC1=CC(N)=C(C#N)C(N)=N1 DVXMQZHDVBYYEQ-UHFFFAOYSA-N 0.000 description 1
VHYBUUMUUNCHCK-UHFFFAOYSA-N 2,4,6-tribromo-1,3,5-triazine Chemical compound BrC1=NC(Br)=NC(Br)=N1 VHYBUUMUUNCHCK-UHFFFAOYSA-N 0.000 description 1
LUZXGSRCYGQGQF-UHFFFAOYSA-N 2,5-dichloro-4-(5-methyl-3-oxo-1h-pyrazol-2-yl)benzenesulfonic acid Chemical compound N1C(C)=CC(=O)N1C1=CC(Cl)=C(S(O)(=O)=O)C=C1Cl LUZXGSRCYGQGQF-UHFFFAOYSA-N 0.000 description 1
LHIOGENQCVAALC-UHFFFAOYSA-N 2-amino-4-(trifluoromethyl)benzenesulfonic acid Chemical compound NC1=CC(C(F)(F)F)=CC=C1S(O)(=O)=O LHIOGENQCVAALC-UHFFFAOYSA-N 0.000 description 1
VRLPHBSFRWMMPW-UHFFFAOYSA-N 2-amino-4-chloro-5-methylbenzenesulfonic acid Chemical compound CC1=CC(S(O)(=O)=O)=C(N)C=C1Cl VRLPHBSFRWMMPW-UHFFFAOYSA-N 0.000 description 1
BDCJBCKISOZMBR-UHFFFAOYSA-N 2-amino-4-methoxybenzenesulfonic acid Chemical compound COC1=CC=C(S(O)(=O)=O)C(N)=C1 BDCJBCKISOZMBR-UHFFFAOYSA-N 0.000 description 1
FJHGMUDVUAXUEK-UHFFFAOYSA-N 2-amino-4-methylbenzenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C(N)=C1 FJHGMUDVUAXUEK-UHFFFAOYSA-N 0.000 description 1
YMJXNYUOEJPKHH-UHFFFAOYSA-N 2-amino-4-nitrobenzenesulfonic acid Chemical compound NC1=CC([N+]([O-])=O)=CC=C1S(O)(=O)=O YMJXNYUOEJPKHH-UHFFFAOYSA-N 0.000 description 1
SKQMUKIJPUOECT-UHFFFAOYSA-N 2-amino-5-[(4-amino-9,10-dioxo-3,8-disulfoanthracen-1-yl)amino]benzoic acid Chemical compound C1=C(C(O)=O)C(N)=CC=C1NC1=CC(S(O)(=O)=O)=C(N)C2=C1C(=O)C1=C(S(O)(=O)=O)C=CC=C1C2=O SKQMUKIJPUOECT-UHFFFAOYSA-N 0.000 description 1
ZCGVPUAAMCMLTM-UHFFFAOYSA-N 2-amino-5-chlorobenzenesulfonic acid Chemical compound NC1=CC=C(Cl)C=C1S(O)(=O)=O ZCGVPUAAMCMLTM-UHFFFAOYSA-N 0.000 description 1
KZKGEEGADAWJFS-UHFFFAOYSA-N 2-amino-5-methoxybenzenesulfonic acid Chemical compound COC1=CC=C(N)C(S(O)(=O)=O)=C1 KZKGEEGADAWJFS-UHFFFAOYSA-N 0.000 description 1
LTPSRQRIPCVMKQ-UHFFFAOYSA-N 2-amino-5-methylbenzenesulfonic acid Chemical compound CC1=CC=C(N)C(S(O)(=O)=O)=C1 LTPSRQRIPCVMKQ-UHFFFAOYSA-N 0.000 description 1
LTASFWDWBYFZQQ-UHFFFAOYSA-N 2-amino-5-nitrobenzenesulfonic acid Chemical compound NC1=CC=C([N+]([O-])=O)C=C1S(O)(=O)=O LTASFWDWBYFZQQ-UHFFFAOYSA-N 0.000 description 1
ZMCHBSMFKQYNKA-UHFFFAOYSA-N 2-aminobenzenesulfonic acid Chemical compound NC1=CC=CC=C1S(O)(=O)=O ZMCHBSMFKQYNKA-UHFFFAOYSA-N 0.000 description 1
AKLDPNVZTZIVFA-UHFFFAOYSA-N 2-azaniumyl-4,5-dichlorobenzenesulfonate Chemical compound NC1=CC(Cl)=C(Cl)C=C1S(O)(=O)=O AKLDPNVZTZIVFA-UHFFFAOYSA-N 0.000 description 1
XXZDPVOWJBCNQC-UHFFFAOYSA-N 3-[(4-amino-2-methylphenyl)diazenyl]naphthalene-1,5-disulfonic acid Chemical compound CC1=CC(N)=CC=C1N=NC1=CC(S(O)(=O)=O)=C(C=CC=C2S(O)(=O)=O)C2=C1 XXZDPVOWJBCNQC-UHFFFAOYSA-N 0.000 description 1
RXXCIBALSKQCAE-UHFFFAOYSA-N 3-methylbutoxymethylbenzene Chemical compound CC(C)CCOCC1=CC=CC=C1 RXXCIBALSKQCAE-UHFFFAOYSA-N 0.000 description 1
XJCVRTZCHMZPBD-UHFFFAOYSA-N 3-nitroaniline Chemical compound NC1=CC=CC([N+]([O-])=O)=C1 XJCVRTZCHMZPBD-UHFFFAOYSA-N 0.000 description 1
TWMYIGNIDPMOSD-UHFFFAOYSA-N 4,6-diaminopyridine-3-carbonitrile Chemical compound NC1=CC(N)=C(C#N)C=N1 TWMYIGNIDPMOSD-UHFFFAOYSA-N 0.000 description 1
BEPFYFMEOJVCOC-UHFFFAOYSA-N 4-(naphthalen-1-yldiazenyl)-3-phenylnaphthalen-2-amine Chemical compound NC1=CC2=CC=CC=C2C(N=NC=2C3=CC=CC=C3C=CC=2)=C1C1=CC=CC=C1 BEPFYFMEOJVCOC-UHFFFAOYSA-N 0.000 description 1
RXNKCIBVUNMMAD-UHFFFAOYSA-N 4-[9-(4-amino-3-fluorophenyl)fluoren-9-yl]-2-fluoroaniline Chemical compound C1=C(F)C(N)=CC=C1C1(C=2C=C(F)C(N)=CC=2)C2=CC=CC=C2C2=CC=CC=C21 RXNKCIBVUNMMAD-UHFFFAOYSA-N 0.000 description 1
DRVYRUSLNIWBBL-UHFFFAOYSA-N 4-acetamido-2-amino-5-methylbenzenesulfonic acid Chemical compound CC(=O)NC1=CC(N)=C(S(O)(=O)=O)C=C1C DRVYRUSLNIWBBL-UHFFFAOYSA-N 0.000 description 1
SJCTXIKOXTUQHC-UHFFFAOYSA-N 4-amino-2,5-dichlorobenzenesulfonic acid Chemical compound NC1=CC(Cl)=C(S(O)(=O)=O)C=C1Cl SJCTXIKOXTUQHC-UHFFFAOYSA-N 0.000 description 1
NDYYJXGERWTRSD-UHFFFAOYSA-N 4-aminonaphthalene-2,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=C2C(N)=CC(S(O)(=O)=O)=CC2=C1 NDYYJXGERWTRSD-UHFFFAOYSA-N 0.000 description 1
TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 1
OVLITKPSPAIUJU-UHFFFAOYSA-N 5-methyl-7-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-2-amine Chemical compound N1=C(C)C=C(C(F)(F)F)N2N=C(N)N=C21 OVLITKPSPAIUJU-UHFFFAOYSA-N 0.000 description 1
APZQNXAMDJGBJZ-UHFFFAOYSA-N 6-[(2-acetamido-4-aminophenyl)diazenyl]naphthalene-1,3-disulfonic acid Chemical compound CC(=O)NC1=CC(N)=CC=C1N=NC1=CC=C(C(=CC(=C2)S(O)(=O)=O)S(O)(=O)=O)C2=C1 APZQNXAMDJGBJZ-UHFFFAOYSA-N 0.000 description 1
PJQUFZPSUQYROE-UHFFFAOYSA-N 7-[(2-acetamido-4-aminophenyl)diazenyl]naphthalene-1,3,6-trisulfonic acid Chemical compound CC(=O)NC1=CC(N)=CC=C1N=NC1=CC2=C(S(O)(=O)=O)C=C(S(O)(=O)=O)C=C2C=C1S(O)(=O)=O PJQUFZPSUQYROE-UHFFFAOYSA-N 0.000 description 1
XZDOEWBFAWRCLD-UHFFFAOYSA-N 7-[(4-aminophenyl)diazenyl]naphthalene-1,3,5-trisulfonic acid Chemical compound C1=CC(N)=CC=C1N=NC1=CC(S(O)(=O)=O)=C(C=C(C=C2S(O)(=O)=O)S(O)(=O)=O)C2=C1 XZDOEWBFAWRCLD-UHFFFAOYSA-N 0.000 description 1
GFPQSWFFPRQEHH-UHFFFAOYSA-N 7-aminonaphthalene-1,3,6-trisulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C=C(S(O)(=O)=O)C(N)=CC2=C1S(O)(=O)=O GFPQSWFFPRQEHH-UHFFFAOYSA-N 0.000 description 1
SROYVYGZVXMVOA-UHFFFAOYSA-N 9,10-dioxoanthracene-1,6-disulfonic acid Chemical compound O=C1C2=CC(S(=O)(=O)O)=CC=C2C(=O)C2=C1C=CC=C2S(O)(=O)=O SROYVYGZVXMVOA-UHFFFAOYSA-N 0.000 description 1
MMNWSHJJPDXKCH-UHFFFAOYSA-N 9,10-dioxoanthracene-2-sulfonic acid Chemical compound C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 MMNWSHJJPDXKCH-UHFFFAOYSA-N 0.000 description 1
WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Natural products CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
240000007817 Olea europaea Species 0.000 description 1
239000004952 Polyamide Substances 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 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
DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
MSSUFHMGCXOVBZ-UHFFFAOYSA-N anthraquinone-2,6-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 MSSUFHMGCXOVBZ-UHFFFAOYSA-N 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
238000009835 boiling Methods 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
125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000010941 cobalt Substances 0.000 description 1
229910017052 cobalt Inorganic materials 0.000 description 1
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
VMKJWLXVLHBJNK-UHFFFAOYSA-N cyanuric fluoride Chemical compound FC1=NC(F)=NC(F)=N1 VMKJWLXVLHBJNK-UHFFFAOYSA-N 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
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 1
238000009792 diffusion process Methods 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
QELUYTUMUWHWMC-UHFFFAOYSA-N edaravone Chemical compound O=C1CC(C)=NN1C1=CC=CC=C1 QELUYTUMUWHWMC-UHFFFAOYSA-N 0.000 description 1
125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
229910000039 hydrogen halide Inorganic materials 0.000 description 1
239000012433 hydrogen halide Substances 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000010985 leather Substances 0.000 description 1
NCBZRJODKRCREW-UHFFFAOYSA-N m-anisidine Chemical compound COC1=CC=CC(N)=C1 NCBZRJODKRCREW-UHFFFAOYSA-N 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
239000011707 mineral Substances 0.000 description 1
PEMGGJDINLGTON-UHFFFAOYSA-N n-(3-aminophenyl)acetamide Chemical compound CC(=O)NC1=CC=CC(N)=C1 PEMGGJDINLGTON-UHFFFAOYSA-N 0.000 description 1
CHMBIJAOCISYEW-UHFFFAOYSA-N n-(4-aminophenyl)acetamide Chemical compound CC(=O)NC1=CC=C(N)C=C1 CHMBIJAOCISYEW-UHFFFAOYSA-N 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
VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N p-toluenesulfonic acid Substances CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
238000009980 pad dyeing Methods 0.000 description 1
WXWCDTXEKCVRRO-UHFFFAOYSA-N para-Cresidine Chemical compound COC1=CC=C(C)C=C1N WXWCDTXEKCVRRO-UHFFFAOYSA-N 0.000 description 1
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical group 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
MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
239000004627 regenerated cellulose Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 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
238000010186 staining Methods 0.000 description 1
235000021286 stilbenes Nutrition 0.000 description 1
239000000126 substance Substances 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
150000003456 sulfonamides Chemical class 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000005406 washing Methods 0.000 description 1
230000004584 weight gain Effects 0.000 description 1
235000019786 weight gain 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
- C09B62/08—Azo dyes
- C09B62/082—Azo dyes dyes containing in the molecule at least one azo group and at least one other chromophore group
- 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
- D06P1/38—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 reactive dyes

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Textile Engineering (AREA)
Coloring (AREA)

CH1597575A 1975-12-09 1975-12-09 Process for the preparation of fibre-reactive dyestuffs CH619258A5 (en)

Priority Applications (11)

Application Number	Priority Date	Filing Date	Title
CH1597575A CH619258A5 (en)	1975-12-09	1975-12-09	Process for the preparation of fibre-reactive dyestuffs
CA267,271A CA1064915A (fr)	1975-12-09	1976-12-07	Teintures reagissant avec les fibres, procede pour leur fabrication et leur utilisation
DE19762655449 DE2655449A1 (de)	1975-12-09	1976-12-07	Faserreaktive farbstoffe, deren herstellung und verwendung
IT5249976A IT1066798B (it)	1975-12-09	1976-12-07	Coloranti reattivi per le fibre e procedimento per la loro produzione ed applicazione
ES454015A ES454015A1 (es)	1975-12-09	1976-12-07	Procedimiento para la preparacion de colorantes fibrorreac- tivos.
BR7608230A BR7608230A (pt)	1975-12-09	1976-12-08	Corantes reativos em relacao a fibra,sua preparacao e emprego
CS802476A CS194247B2 (en)	1975-12-09	1976-12-08	Method of preparing with fibres reactive dyes
FR7637036A FR2334724A1 (fr)	1975-12-09	1976-12-08	Colorants reactifs vis-a-vis de la fibre, leur procede de preparation et leur application
BE173042A BE849161A (fr)	1975-12-09	1976-12-08	Colorants reactifs vis-a-vis de la fibre, leur procede de preparation et leur application
JP14718476A JPS5269933A (en)	1975-12-09	1976-12-09	Fiber reactive dyes* process for producing same and application
GB5150976A GB1547659A (en)	1975-12-09	1976-12-09	Fibrereactive azo dyes process for their manufacture and use thereof

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH1597575A CH619258A5 (en)	1975-12-09	1975-12-09	Process for the preparation of fibre-reactive dyestuffs

Publications (1)

Publication Number	Publication Date
CH619258A5 true CH619258A5 (en)	1980-09-15

Family

ID=4413492

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1597575A CH619258A5 (en)	1975-12-09	1975-12-09	Process for the preparation of fibre-reactive dyestuffs

Country Status (3)

Country	Link
BE (1)	BE849161A (fr)
CA (1)	CA1064915A (fr)
CH (1)	CH619258A5 (fr)

1975
- 1975-12-09 CH CH1597575A patent/CH619258A5/de not_active IP Right Cessation
1976
- 1976-12-07 CA CA267,271A patent/CA1064915A/fr not_active Expired
- 1976-12-08 BE BE173042A patent/BE849161A/fr unknown

Also Published As

Publication number	Publication date
CA1064915A (fr)	1979-10-23
BE849161A (fr)	1977-06-08

Legal Events

Date	Code	Title	Description
1984-08-31	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
DE2614550C3 (de)	1981-06-25	Neue Reaktivfarbstoffe, ihre Herstellung und Verwendung zum Färben und Bedrucken von Cellulose sowie natürlichen und synthetischen Polyamidsubstraten
DE1644208C3 (de)	1978-06-01	Reaktivfarbstoffe
DE2560422C2 (de)	1986-01-30	Reaktivfarbstoffe, deren Herstellung und Verwendung
DE2611550C2 (de)	1987-03-26	Faserreaktive Farbstoffe, deren Herstellung und Verwendung
DE2927102A1 (de)	1980-01-17	Reaktivfarbstoffe, deren herstellung und verwendung
DE2650555A1 (de)	1977-05-18	Faserreaktive farbstoffe, deren herstellung und verwendung
DE2653199A1 (de)	1977-06-02	Faserreaktive farbstoffe, deren herstellung und verwendung
DE2814802A1 (de)	1978-10-19	Farbstoffe, deren herstellung und verwendung
DE1794315A1 (de)	1972-03-09	Reaktive Triazinfarbstoffe
CH638555A5 (de)	1983-09-30	Reaktivfarbstoffe und deren herstellung.
DE2331518A1 (de)	1974-01-10	Neue farbstoffe, deren herstellung und verwendung
DE2601043A1 (de)	1976-07-22	Tetrareaktive disazofarbstoffe, deren herstellung und verwendung
EP0584045A1 (fr)	1994-02-23	Colorants de fibres réactifs, leur préparation et leur utilisation
DE2839209C2 (de)	1986-07-24	Azofarbstoffe, deren Herstellung und Verwendung
CH621358A5 (en)	1981-01-30	Process for preparing fibre-reactive dyes
CH619258A5 (en)	1980-09-15	Process for the preparation of fibre-reactive dyestuffs
DE1419795C3 (de)	1974-03-21	Verfahren zur Herstellung von Disazoreaktivfarbstoffen
DE3151959A1 (de)	1983-07-07	Bisazoreaktivfarbstoffe, verfahren zu ihrer herstellung und ihre verwendung zum faerben und bedrucken von hydroxylgruppen- oder stickstoffhaltigem fasermaterial
DE1544447C3 (de)	1975-09-25	Stilbenazoreaktivfarbstoffe und Verfahren zur Herstellung dieser Farbstoffe
DE2751293A1 (de)	1978-05-24	Faserreaktive azofarbstoffe, deren herstellung und verwendung
DE2655449A1 (de)	1977-06-16	Faserreaktive farbstoffe, deren herstellung und verwendung
DE3510180A1 (de)	1986-09-25	Wasserloesliche azoverbindungen, verfahren zu deren herstellung und ihre verwendung als farbstoffe
DE1211733B (de)	1966-03-03	Verfahren zur Herstellung von Azofarbstoffen
DE2102217C3 (de)	1978-02-02	Reaktivfarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung
DE2203615A1 (de)	1973-05-30	Reaktivfarbstoffe, deren herstellung und verwendung