CA1097621A - Obtention industrielle et emploi de colorants azoiques reagissant avec les fibres - Google Patents

Obtention industrielle et emploi de colorants azoiques reagissant avec les fibres

Info

Publication number: CA1097621A
Authority: CA; Canada
Prior art keywords: formula; fibre; carboxyl; methyl; chlorine
Prior art date: 1976-07-12
Legal status (The legal status 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 status listed.): Expired

Application number

CA282,331A

Other languages

English (en)

Inventor

Herbert Seiler

Gert Hegar

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

BASF Schweiz AG

Original Assignee

Individual

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.)

1976-07-12

Filing date

1977-07-08

Publication date

1981-03-17

1976-07-12 Priority claimed from LU75367A external-priority patent/LU75367A1/xx

1977-06-06 Priority claimed from LU77492A external-priority patent/LU77492A1/xx

1977-07-08 Application filed by Individual filed Critical Individual

1981-03-17 Application granted granted Critical

1981-03-17 Publication of CA1097621A publication Critical patent/CA1097621A/fr

Status Expired legal-status Critical Current

Links

238000004519 manufacturing process Methods 0.000 title claims description 4
239000000975 dye Substances 0.000 claims abstract description 45
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 31
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 15
125000003545 alkoxy group Chemical group 0.000 claims abstract description 9
125000000217 alkyl group Chemical group 0.000 claims abstract description 9
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 8
229910052736 halogen Inorganic materials 0.000 claims abstract description 7
150000002367 halogens Chemical class 0.000 claims abstract description 7
UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims abstract description 7
-1 ureido, nitro, methylsulfonyl Chemical group 0.000 claims description 93
125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 53
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 46
239000000460 chlorine Chemical group 0.000 claims description 38
238000000034 method Methods 0.000 claims description 32
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 31
229910052801 chlorine Chemical group 0.000 claims description 31
238000005859 coupling reaction Methods 0.000 claims description 30
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 30
230000008878 coupling Effects 0.000 claims description 28
238000010168 coupling process Methods 0.000 claims description 28
238000006482 condensation reaction Methods 0.000 claims description 22
239000007858 starting material Substances 0.000 claims description 16
229910052802 copper Inorganic materials 0.000 claims description 14
239000010949 copper Substances 0.000 claims description 14
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 13
238000004043 dyeing Methods 0.000 claims description 13
239000003795 chemical substances by application Substances 0.000 claims description 10
239000007859 condensation product Substances 0.000 claims description 10
VMKJWLXVLHBJNK-UHFFFAOYSA-N cyanuric fluoride Chemical compound FC1=NC(F)=NC(F)=N1 VMKJWLXVLHBJNK-UHFFFAOYSA-N 0.000 claims description 10
238000007639 printing Methods 0.000 claims description 10
239000000203 mixture Substances 0.000 claims description 9
238000009833 condensation Methods 0.000 claims description 6
230000005494 condensation Effects 0.000 claims description 6
239000002184 metal Substances 0.000 claims description 6
229910052751 metal Inorganic materials 0.000 claims description 6
125000003277 amino group Chemical group 0.000 claims description 5
239000000463 material Substances 0.000 claims description 4
YAIKCRUPEVOINQ-UHFFFAOYSA-N 2-aminonaphthalene-1,5-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC2=C(S(O)(=O)=O)C(N)=CC=C21 YAIKCRUPEVOINQ-UHFFFAOYSA-N 0.000 claims description 3
WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 3
125000004442 acylamino group Chemical group 0.000 claims description 3
229920003043 Cellulose fiber Polymers 0.000 claims description 2
230000010933 acylation Effects 0.000 claims description 2
238000005917 acylation reaction Methods 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
235000013350 formula milk Nutrition 0.000 claims 66
238000009472 formulation Methods 0.000 claims 6
RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 claims 6
ZDFCTUISEBJBEQ-UHFFFAOYSA-N 3-amino-4-hydroxynaphthalene-1,5-disulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=C(O)C(N)=CC(S(O)(=O)=O)=C21 ZDFCTUISEBJBEQ-UHFFFAOYSA-N 0.000 claims 1
APRRQJCCBSJQOQ-UHFFFAOYSA-N 4-amino-5-hydroxynaphthalene-2,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(O)=C2C(N)=CC(S(O)(=O)=O)=CC2=C1 APRRQJCCBSJQOQ-UHFFFAOYSA-N 0.000 claims 1
HIMMCCJEMMCUJS-UHFFFAOYSA-N 4-fluorotriazine Chemical compound FC1=CC=NN=N1 HIMMCCJEMMCUJS-UHFFFAOYSA-N 0.000 claims 1
LXBDMUVQELXOKG-UHFFFAOYSA-N 4-hydroxy-5-[(4-nitrobenzoyl)amino]naphthalene-2,7-disulfonic acid Chemical compound C=12C(O)=CC(S(O)(=O)=O)=CC2=CC(S(O)(=O)=O)=CC=1NC(=O)C1=CC=C([N+]([O-])=O)C=C1 LXBDMUVQELXOKG-UHFFFAOYSA-N 0.000 claims 1
KKAMNIDZQVXDJV-UHFFFAOYSA-N 7-acetamido-4-hydroxynaphthalene-2-sulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(NC(=O)C)=CC=C21 KKAMNIDZQVXDJV-UHFFFAOYSA-N 0.000 claims 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
150000004699 copper complex Chemical class 0.000 claims 1
238000007127 saponification reaction Methods 0.000 claims 1
239000004753 textile Substances 0.000 claims 1
125000001424 substituent group Chemical group 0.000 abstract 1
239000002253 acid Substances 0.000 description 24
239000000243 solution Substances 0.000 description 15
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 11
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
229940108928 copper Drugs 0.000 description 8
241000219146 Gossypium Species 0.000 description 5
150000001875 compounds Chemical class 0.000 description 5
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 5
239000004744 fabric Substances 0.000 description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
239000011780 sodium chloride Substances 0.000 description 5
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 5
229920000742 Cotton Polymers 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
239000003513 alkali Substances 0.000 description 4
150000001448 anilines Chemical class 0.000 description 4
229920002678 cellulose Polymers 0.000 description 4
239000001913 cellulose Substances 0.000 description 4
229940075566 naphthalene Drugs 0.000 description 4
150000003254 radicals Chemical class 0.000 description 4
230000036647 reaction Effects 0.000 description 4
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 3
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Substances ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 3
229910000040 hydrogen fluoride Inorganic materials 0.000 description 3
150000002500 ions Chemical class 0.000 description 3
230000007935 neutral effect Effects 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
239000011734 sodium Substances 0.000 description 3
210000002268 wool Anatomy 0.000 description 3
FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
239000005749 Copper compound Substances 0.000 description 2
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 2
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-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
239000004952 Polyamide Substances 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
238000009835 boiling Methods 0.000 description 2
150000001880 copper compounds Chemical class 0.000 description 2
ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
150000002790 naphthalenes Chemical class 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
229920002647 polyamide Polymers 0.000 description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
238000010792 warming Methods 0.000 description 2
238000005406 washing Methods 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
ULHFFAFDSSHFDA-UHFFFAOYSA-N 1-amino-2-ethoxybenzene Chemical compound CCOC1=CC=CC=C1N ULHFFAFDSSHFDA-UHFFFAOYSA-N 0.000 description 1
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
HIVUAOXLSJITPA-UHFFFAOYSA-N 2-amino-5-hydroxynaphthalene-1,7-disulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=C(S(O)(=O)=O)C(N)=CC=C21 HIVUAOXLSJITPA-UHFFFAOYSA-N 0.000 description 1
MJNYPLCGWXFYPD-UHFFFAOYSA-N 2-amino-5-sulfobenzoic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1C(O)=O MJNYPLCGWXFYPD-UHFFFAOYSA-N 0.000 description 1
QPKNFEVLZVJGBM-UHFFFAOYSA-N 2-aminonaphthalen-1-ol Chemical compound C1=CC=CC2=C(O)C(N)=CC=C21 QPKNFEVLZVJGBM-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
AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 1
FTZQXOJYPFINKJ-UHFFFAOYSA-N 2-fluoroaniline Chemical compound NC1=CC=CC=C1F FTZQXOJYPFINKJ-UHFFFAOYSA-N 0.000 description 1
DHXPRBHRJQAXHK-UHFFFAOYSA-N 4-amino-3-hydroxy-7-nitronaphthalene-1-sulfonic acid Chemical compound [O-][N+](=O)C1=CC=C2C(N)=C(O)C=C(S(O)(=O)=O)C2=C1 DHXPRBHRJQAXHK-UHFFFAOYSA-N 0.000 description 1
HTYRTGGIOAMLRR-UHFFFAOYSA-N 5-amino-4-hydroxybenzene-1,3-disulfonic acid Chemical compound NC1=CC(S(O)(=O)=O)=CC(S(O)(=O)=O)=C1O HTYRTGGIOAMLRR-UHFFFAOYSA-N 0.000 description 1
YKVBYISUDGOVDM-UHFFFAOYSA-N 6-acetamido-4-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(O)C2=CC(NC(=O)C)=CC=C21 YKVBYISUDGOVDM-UHFFFAOYSA-N 0.000 description 1
HBZVNWNSRNTWPS-UHFFFAOYSA-N 6-amino-4-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(O)C2=CC(N)=CC=C21 HBZVNWNSRNTWPS-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
SBEZNUQJZHDWEU-UHFFFAOYSA-L C(=O)([O-])C(O)C(O)C(=O)[O-].[Cu+2].[Na+] Chemical compound C(=O)([O-])C(O)C(O)C(=O)[O-].[Cu+2].[Na+] SBEZNUQJZHDWEU-UHFFFAOYSA-L 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
239000004471 Glycine Substances 0.000 description 1
IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
241001237728 Precis Species 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
DPDMMXDBJGCCQC-UHFFFAOYSA-N [Na].[Cl] Chemical compound [Na].[Cl] DPDMMXDBJGCCQC-UHFFFAOYSA-N 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
230000009918 complex formation Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
150000001879 copper Chemical class 0.000 description 1
235000014987 copper Nutrition 0.000 description 1
230000020335 dealkylation Effects 0.000 description 1
238000006900 dealkylation reaction Methods 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 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
238000001465 metallisation Methods 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
239000011707 mineral Substances 0.000 description 1
VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
238000009980 pad dyeing Methods 0.000 description 1
DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 description 1
HCTVWSOKIJULET-LQDWTQKMSA-M phenoxymethylpenicillin potassium Chemical compound [K+].N([C@H]1[C@H]2SC([C@@H](N2C1=O)C([O-])=O)(C)C)C(=O)COC1=CC=CC=C1 HCTVWSOKIJULET-LQDWTQKMSA-M 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
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000004627 regenerated cellulose Substances 0.000 description 1
RBWSWDPRDBEWCR-RKJRWTFHSA-N sodium;(2r)-2-[(2r)-3,4-dihydroxy-5-oxo-2h-furan-2-yl]-2-hydroxyethanolate Chemical compound [Na+].[O-]C[C@@H](O)[C@H]1OC(=O)C(O)=C1O RBWSWDPRDBEWCR-RKJRWTFHSA-N 0.000 description 1
238000001694 spray drying Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
239000011975 tartaric acid 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
- C09B62/02—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

Landscapes

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

CA282,331A 1976-07-12 1977-07-08 Obtention industrielle et emploi de colorants azoiques reagissant avec les fibres Expired CA1097621A (fr)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date
LU75367A LU75367A1 (fr)	1976-07-12	1976-07-12
LU75367		1976-07-12
LU77492		1977-06-06
LU77492A LU77492A1 (fr)	1977-06-06	1977-06-06

Publications (1)

Publication Number	Publication Date
CA1097621A true CA1097621A (fr)	1981-03-17

Family

ID=26640206

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA282,331A Expired CA1097621A (fr)	1976-07-12	1977-07-08	Obtention industrielle et emploi de colorants azoiques reagissant avec les fibres

Country Status (8)

Country	Link
JP (1)	JPS6011066B2 (fr)
CA (1)	CA1097621A (fr)
CH (1)	CH629839A5 (fr)
CS (1)	CS191197B2 (fr)
DE (1)	DE2731258A1 (fr)
FR (1)	FR2358450A1 (fr)
GB (1)	GB1566814A (fr)
IT (1)	IT1116356B (fr)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH627206A5 (fr) *	1978-07-06	1981-12-31	Ciba Geigy Ag
DE2838608A1 (de) *	1978-09-05	1980-03-20	Bayer Ag	Azo-reaktivfarbstoffe
DE2839562A1 (de) *	1978-09-12	1980-03-27	Bayer Ag	Faserreaktive azofarbstoffe
DE2847916C2 (de) *	1978-11-04	1984-04-26	Basf Ag, 6700 Ludwigshafen	Reaktivfarbstoffe und deren Verwendung
JPS55149753A (en) *	1979-05-11	1980-11-21	Kawasaki Steel Corp	Continuous casting method of bloom
DE3135949A1 (de) *	1981-09-10	1983-03-24	Bayer Ag, 5090 Leverkusen	Azo-reaktivfarbstoffe
CH655735A5 (de) *	1982-09-17	1986-05-15	Sandoz Ag	Reaktive monoazoverbindungen.
JPS6033145B2 (ja) *	1982-10-27	1985-08-01	三菱化学株式会社	記録液
DE3881767D1 (de) *	1987-07-16	1993-07-22	Bayer Ag	Reaktivfarbstoffe.

1977
- 1977-07-08 CH CH848277A patent/CH629839A5/de not_active IP Right Cessation
- 1977-07-08 CA CA282,331A patent/CA1097621A/fr not_active Expired
- 1977-07-08 IT IT5020077A patent/IT1116356B/it active
- 1977-07-11 DE DE19772731258 patent/DE2731258A1/de active Pending
- 1977-07-11 FR FR7721340A patent/FR2358450A1/fr active Granted
- 1977-07-12 JP JP52082624A patent/JPS6011066B2/ja not_active Expired
- 1977-07-12 GB GB2930577A patent/GB1566814A/en not_active Expired
- 1977-07-12 CS CS464377A patent/CS191197B2/cs unknown

Also Published As

Publication number	Publication date
JPS6011066B2 (ja)	1985-03-22
CH629839A5 (en)	1982-05-14
GB1566814A (en)	1980-05-08
JPS5322526A (en)	1978-03-02
DE2731258A1 (de)	1978-01-19
IT1116356B (it)	1986-02-10
CS191197B2 (en)	1979-06-29
FR2358450A1 (fr)	1978-02-10
FR2358450B1 (fr)	1980-01-04

Legal Events

Date	Code	Title	Description
1998-03-17	MKEX	Expiry

Publication	Publication Date	Title
CA1087172A (fr)	1980-10-07	Modes de preparation et d'emploi de matieres colorantes
CA1077469A (fr)	1980-05-13	Colorants reactifs, leur fabrication et leur utilisation
US3758470A (en)	1973-09-11	Triazinyl anthraquinones
US2945021A (en)	1960-07-12	Monoazo and disazo triazine dyes
JPS6048546B2 (ja)	1985-10-28	繊維反応性染料およびその製法
US3627749A (en)	1971-12-14	Mono-and disazo dyestuffs containing triazinylureylene groups
US2914531A (en)	1959-11-24	New dyestufes of the peri-dicarboxylic acid imide series
US3068219A (en)	1962-12-11	Formazane dyes containing a halogen-pyrimidyl substituent
US3558621A (en)	1971-01-26	Anthraquinone reactive dyestuffs
CA1097621A (fr)	1981-03-17	Obtention industrielle et emploi de colorants azoiques reagissant avec les fibres
US3459729A (en)	1969-08-05	Monoazo triazine containing dyestuffs
US4507236A (en)	1985-03-26	Fibre-reactive dyes, containing both chloro and fluoro triazine radicals
US2950165A (en)	1960-08-23	New dyeing process
US3226176A (en)	1965-12-28	Cellulose, wool, silk and leather fibers fast-dyed with chlorotriazine containing reactive dyestuffs
CA1099704A (fr)	1981-04-21	Procede d'obtention et emploi de colorants
US4906739A (en)	1990-03-06	Fibre-reactive azo dyes containing a monofluororotriazine group
US3261826A (en)	1966-07-19	Monoazo triazine containing dyestuffs
US2892828A (en)	1959-06-30	Triazine monoazo dyestuffs
CA1052777A (fr)	1979-04-17	Colorants diazoiques tetrareactifs
US2817659A (en)	1957-12-24	Polyazo dyestuffs
US4082739A (en)	1978-04-04	Fibre-reactive dyestuff containing a bis-triazinylamino
US3340247A (en)	1967-09-05	Disazo triazine dyestuffs
US3658782A (en)	1972-04-25	Reactive disazo triazine dyestuffs made from a diamino diphenylure disulphonic acid
US2860129A (en)	1958-11-11	Dichlorotriazine monoazodyestuffs
US3415825A (en)	1968-12-10	Anthraquinone dyestuffs