GB2034731A - Anthraquinone reactive dyestuffs - Google Patents
Anthraquinone reactive dyestuffs Download PDFInfo
- Publication number
- GB2034731A GB2034731A GB7913438A GB7913438A GB2034731A GB 2034731 A GB2034731 A GB 2034731A GB 7913438 A GB7913438 A GB 7913438A GB 7913438 A GB7913438 A GB 7913438A GB 2034731 A GB2034731 A GB 2034731A
- Authority
- GB
- United Kingdom
- Prior art keywords
- denotes
- reactive dyestuff
- group
- amino
- solution
- Prior art date
- 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.)
- Withdrawn
Links
- 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 title claims description 21
- 150000004056 anthraquinones Chemical class 0.000 title description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 29
- 239000000463 material Substances 0.000 claims abstract description 15
- 238000004043 dyeing Methods 0.000 claims abstract description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000000547 substituted alkyl group Chemical group 0.000 claims abstract description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 5
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 4
- 125000001424 substituent group Chemical group 0.000 claims abstract description 4
- 229910052731 fluorine Inorganic materials 0.000 claims abstract 2
- 150000002790 naphthalenes Chemical class 0.000 claims abstract 2
- -1 sulphophenyl Chemical group 0.000 claims description 63
- 239000000975 dye Substances 0.000 claims description 44
- 238000000034 method Methods 0.000 claims description 22
- 238000006482 condensation reaction Methods 0.000 claims description 20
- 150000001875 compounds Chemical class 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 7
- 229910006069 SO3H Inorganic materials 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 241000080590 Niso Species 0.000 claims 1
- 239000000835 fiber Substances 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000004753 textile Substances 0.000 abstract description 5
- 229910052794 bromium Inorganic materials 0.000 abstract description 4
- 239000004952 Polyamide Substances 0.000 abstract description 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract description 2
- 229920002647 polyamide Polymers 0.000 abstract description 2
- 229920002635 polyurethane Polymers 0.000 abstract description 2
- 239000004814 polyurethane Substances 0.000 abstract description 2
- 239000004627 regenerated cellulose Substances 0.000 abstract description 2
- 210000002268 wool Anatomy 0.000 abstract description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 75
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 39
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 28
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical class [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 21
- 239000000203 mixture Substances 0.000 description 20
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 17
- 229910000029 sodium carbonate Inorganic materials 0.000 description 14
- SGHZXLIDFTYFHQ-UHFFFAOYSA-L Brilliant Blue 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=CC=2)S([O-])(=O)=O)C=CC=1N(CC)CC1=CC=CC(S([O-])(=O)=O)=C1 SGHZXLIDFTYFHQ-UHFFFAOYSA-L 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 239000004744 fabric Substances 0.000 description 10
- 229920000742 Cotton Polymers 0.000 description 9
- 241000219146 Gossypium Species 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000001103 potassium chloride Substances 0.000 description 9
- 235000011164 potassium chloride Nutrition 0.000 description 9
- 239000011780 sodium chloride Substances 0.000 description 8
- 229920002678 cellulose Polymers 0.000 description 7
- 239000001913 cellulose Substances 0.000 description 7
- 150000004985 diamines Chemical class 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 6
- QZZSAWGVHXXMID-UHFFFAOYSA-N 1-amino-4-bromo-9,10-dioxoanthracene-2-sulfonic acid Chemical compound C1=CC=C2C(=O)C3=C(Br)C=C(S(O)(=O)=O)C(N)=C3C(=O)C2=C1 QZZSAWGVHXXMID-UHFFFAOYSA-N 0.000 description 5
- 239000013067 intermediate product Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 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 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- VMKJWLXVLHBJNK-UHFFFAOYSA-N cyanuric fluoride Chemical compound FC1=NC(F)=NC(F)=N1 VMKJWLXVLHBJNK-UHFFFAOYSA-N 0.000 description 4
- YSZURGRPNNAJIP-UHFFFAOYSA-N 1-amino-4-[3-(methylamino)propylamino]-9,10-dioxoanthracene-2-sulfonic acid Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(N)=C(S(O)(=O)=O)C=C2NCCCNC YSZURGRPNNAJIP-UHFFFAOYSA-N 0.000 description 3
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 241001024304 Mino Species 0.000 description 2
- SUZRRICLUFMAQD-UHFFFAOYSA-N N-Methyltaurine Chemical compound CNCCS(O)(=O)=O SUZRRICLUFMAQD-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 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
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 2
- 150000008041 alkali metal carbonates Chemical class 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 229910000318 alkali metal phosphate Inorganic materials 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- XTUZGQLUQGRWKK-UHFFFAOYSA-N 1-amino-4-(2-aminoethylamino)-9,10-dioxoanthracene-2-sulfonic acid Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(N)=C(S(O)(=O)=O)C=C2NCCN XTUZGQLUQGRWKK-UHFFFAOYSA-N 0.000 description 1
- CAENSGQUBQOCPW-UHFFFAOYSA-N 1-amino-4-(3-aminopropylamino)-9,10-dioxoanthracene-2-sulfonic acid Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(N)=C(S(O)(=O)=O)C=C2NCCCN CAENSGQUBQOCPW-UHFFFAOYSA-N 0.000 description 1
- LHVHXDQBDWDYLC-UHFFFAOYSA-N 1-amino-4-[2-(methylamino)ethylamino]-9,10-dioxoanthracene-2-sulfonic acid Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(N)=C(S(O)(=O)=O)C=C2NCCNC LHVHXDQBDWDYLC-UHFFFAOYSA-N 0.000 description 1
- WMDKSPBXMXOUNA-UHFFFAOYSA-N 1-amino-4-bromo-9,10-dioxoanthracene-2,6-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C(=O)C3=C(Br)C=C(S(O)(=O)=O)C(N)=C3C(=O)C2=C1 WMDKSPBXMXOUNA-UHFFFAOYSA-N 0.000 description 1
- HZLNPTRTHJTESP-UHFFFAOYSA-N 2-(3-aminopropyl)cyclohexan-1-amine Chemical compound NCCCC1CCCCC1N HZLNPTRTHJTESP-UHFFFAOYSA-N 0.000 description 1
- QKQDEUFSMBOPKY-UHFFFAOYSA-N 2-[2-(aminomethyl)cyclohexyl]ethanamine Chemical compound NCC1C(CCCC1)CCN QKQDEUFSMBOPKY-UHFFFAOYSA-N 0.000 description 1
- STMZGJLCKJFMLQ-UHFFFAOYSA-N 2-[3-(2-aminoethyl)cyclohexyl]ethanamine Chemical compound NCCC1CCCC(CCN)C1 STMZGJLCKJFMLQ-UHFFFAOYSA-N 0.000 description 1
- XUXZELZSNNYLRE-UHFFFAOYSA-N 2-[4-(2-aminoethyl)cyclohexyl]ethanamine Chemical compound NCCC1CCC(CCN)CC1 XUXZELZSNNYLRE-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
- SODXNTSWWHSDCE-UHFFFAOYSA-N 3-(2-aminoethyl)cyclohexan-1-amine Chemical compound NCCC1CCCC(N)C1 SODXNTSWWHSDCE-UHFFFAOYSA-N 0.000 description 1
- MKIHMLQZXBIQTH-UHFFFAOYSA-N 3-(3-aminopropyl)cyclohexan-1-amine Chemical compound NCCCC1CCCC(N)C1 MKIHMLQZXBIQTH-UHFFFAOYSA-N 0.000 description 1
- OEFAIWKFALHMEY-UHFFFAOYSA-N 3-(aminomethyl)cyclohexan-1-amine Chemical compound NCC1CCCC(N)C1 OEFAIWKFALHMEY-UHFFFAOYSA-N 0.000 description 1
- ZAJAQTYSTDTMCU-UHFFFAOYSA-N 3-aminobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1 ZAJAQTYSTDTMCU-UHFFFAOYSA-N 0.000 description 1
- VFGQLNVWQRKCAU-UHFFFAOYSA-N 4-(2-aminoethyl)cyclohexan-1-amine Chemical compound NCCC1CCC(N)CC1 VFGQLNVWQRKCAU-UHFFFAOYSA-N 0.000 description 1
- IMUUNYPYNWXUBO-UHFFFAOYSA-N 4-aminobenzene-1,3-disulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1S(O)(=O)=O IMUUNYPYNWXUBO-UHFFFAOYSA-N 0.000 description 1
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 1
- 102100031499 Anomalous homeobox protein Human genes 0.000 description 1
- LPYYEHAKVRDCGN-UHFFFAOYSA-N C=1C=CC(S(O)(=O)=O)=CC=1N(CC(=O)O)C1=CC(F)=NN(F)N1 Chemical compound C=1C=CC(S(O)(=O)=O)=CC=1N(CC(=O)O)C1=CC(F)=NN(F)N1 LPYYEHAKVRDCGN-UHFFFAOYSA-N 0.000 description 1
- UGWXECUKSRMRMQ-UHFFFAOYSA-N FN1NC(=CC(=N1)F)N(C)C1=C(C=CC(=C1)S(=O)(=O)O)C(=O)O Chemical compound FN1NC(=CC(=N1)F)N(C)C1=C(C=CC(=C1)S(=O)(=O)O)C(=O)O UGWXECUKSRMRMQ-UHFFFAOYSA-N 0.000 description 1
- LIJJJYIJOQLUKU-UHFFFAOYSA-N FN1NC(=CC(=N1)F)N(CCS(=O)(=O)O)C Chemical compound FN1NC(=CC(=N1)F)N(CCS(=O)(=O)O)C LIJJJYIJOQLUKU-UHFFFAOYSA-N 0.000 description 1
- VXCVYVKTWMCGHO-UHFFFAOYSA-N FN1NC(=CC(=N1)F)N(CS(=O)(=O)O)C Chemical compound FN1NC(=CC(=N1)F)N(CS(=O)(=O)O)C VXCVYVKTWMCGHO-UHFFFAOYSA-N 0.000 description 1
- RHDVUDBGYQBCHS-UHFFFAOYSA-N FN1NC(=CC(=N1)F)NC1=C(C=C(C(=C1)S(=O)(=O)O)S(=O)(=O)O)C Chemical compound FN1NC(=CC(=N1)F)NC1=C(C=C(C(=C1)S(=O)(=O)O)S(=O)(=O)O)C RHDVUDBGYQBCHS-UHFFFAOYSA-N 0.000 description 1
- PHIGOBPDMXRQNR-UHFFFAOYSA-N FN1NC(=CC(=N1)F)NC1=CC(=CC(=C1)S(=O)(=O)O)C(=O)O Chemical compound FN1NC(=CC(=N1)F)NC1=CC(=CC(=C1)S(=O)(=O)O)C(=O)O PHIGOBPDMXRQNR-UHFFFAOYSA-N 0.000 description 1
- GCTNZAAJROBYBD-UHFFFAOYSA-N FN1NC(=CC(=N1)F)NCCS(=O)(=O)O Chemical compound FN1NC(=CC(=N1)F)NCCS(=O)(=O)O GCTNZAAJROBYBD-UHFFFAOYSA-N 0.000 description 1
- 101000796261 Homo sapiens Anomalous homeobox protein Proteins 0.000 description 1
- GVBROBTVYCUONK-UHFFFAOYSA-N O=C1C2=CC=CC=C2C(=O)C2=C1C(N)=C(S(O)(=O)=O)C=C2NCCCCN Chemical class O=C1C2=CC=CC=C2C(=O)C2=C1C(N)=C(S(O)(=O)=O)C=C2NCCCCN GVBROBTVYCUONK-UHFFFAOYSA-N 0.000 description 1
- 101100120433 Schizosaccharomyces pombe (strain 972 / ATCC 24843) fnx1 gene Proteins 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- ZBLACDIKXKCJGF-UHFFFAOYSA-N [2-(aminomethyl)cyclobutyl]methanamine Chemical compound NCC1CCC1CN ZBLACDIKXKCJGF-UHFFFAOYSA-N 0.000 description 1
- QLBRROYTTDFLDX-UHFFFAOYSA-N [3-(aminomethyl)cyclohexyl]methanamine Chemical compound NCC1CCCC(CN)C1 QLBRROYTTDFLDX-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
- 150000007513 acids Chemical class 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 229940072056 alginate Drugs 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- RVPUETSFKVWTTO-UHFFFAOYSA-N methylaminomethanesulfonic acid Chemical compound CNCS(O)(=O)=O RVPUETSFKVWTTO-UHFFFAOYSA-N 0.000 description 1
- QHJABUZHRJTCAR-UHFFFAOYSA-N n'-methylpropane-1,3-diamine Chemical compound CNCCCN QHJABUZHRJTCAR-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000005270 trialkylamine group Chemical group 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
- C09B62/06—Anthracene dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19782817781 DE2817781A1 (de) | 1978-04-22 | 1978-04-22 | Anthrachinon-reaktivfarbstoffe |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB2034731A true GB2034731A (en) | 1980-06-11 |
Family
ID=6037796
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB7913438A Withdrawn GB2034731A (en) | 1978-04-22 | 1979-04-18 | Anthraquinone reactive dyestuffs |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS54139936A (fr) |
| BE (1) | BE875727A (fr) |
| BR (1) | BR7902390A (fr) |
| DE (1) | DE2817781A1 (fr) |
| ES (1) | ES479768A1 (fr) |
| FR (1) | FR2423517A1 (fr) |
| GB (1) | GB2034731A (fr) |
| IT (1) | IT7922021A0 (fr) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5601622A (en) * | 1994-10-14 | 1997-02-11 | Ciba-Geigy Corporation | Fibre-reactive anthraquinone dyes, process for their preparation, and their use |
| USD377875S (en) | 1994-10-20 | 1997-02-11 | President Office Furniture Ltd. | Leg support |
| US7507263B2 (en) * | 1994-10-14 | 2009-03-24 | Huntsman International Llc | Fibre-reactive anthraquinone dyes, process for their preparation and the use thereof |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6092357A (ja) * | 1983-10-26 | 1985-05-23 | Sumitomo Chem Co Ltd | アントラキノン化合物およびそれを用いる染色または捺染法 |
-
1978
- 1978-04-22 DE DE19782817781 patent/DE2817781A1/de not_active Withdrawn
-
1979
- 1979-04-18 GB GB7913438A patent/GB2034731A/en not_active Withdrawn
- 1979-04-19 IT IT7922021A patent/IT7922021A0/it unknown
- 1979-04-19 BR BR7902390A patent/BR7902390A/pt unknown
- 1979-04-20 ES ES479768A patent/ES479768A1/es not_active Expired
- 1979-04-20 BE BE0/194729A patent/BE875727A/fr not_active IP Right Cessation
- 1979-04-20 FR FR7910004A patent/FR2423517A1/fr active Pending
- 1979-04-20 JP JP4808479A patent/JPS54139936A/ja active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5601622A (en) * | 1994-10-14 | 1997-02-11 | Ciba-Geigy Corporation | Fibre-reactive anthraquinone dyes, process for their preparation, and their use |
| US5718730A (en) * | 1994-10-14 | 1998-02-17 | Ciba Specialty Chemicals Corporation | Fibre-reactive anthraquinone dyes, process for their preparation, and their use |
| US7507263B2 (en) * | 1994-10-14 | 2009-03-24 | Huntsman International Llc | Fibre-reactive anthraquinone dyes, process for their preparation and the use thereof |
| USD377875S (en) | 1994-10-20 | 1997-02-11 | President Office Furniture Ltd. | Leg support |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2423517A1 (fr) | 1979-11-16 |
| BR7902390A (pt) | 1979-11-20 |
| IT7922021A0 (it) | 1979-04-19 |
| DE2817781A1 (de) | 1979-10-31 |
| ES479768A1 (es) | 1979-11-16 |
| JPS54139936A (en) | 1979-10-30 |
| BE875727A (fr) | 1979-10-22 |
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