CA2327679C - Triphendioxazine dyestuffs for dyeing organic substrates - Google Patents
Triphendioxazine dyestuffs for dyeing organic substrates Download PDFInfo
- Publication number
- CA2327679C CA2327679C CA002327679A CA2327679A CA2327679C CA 2327679 C CA2327679 C CA 2327679C CA 002327679 A CA002327679 A CA 002327679A CA 2327679 A CA2327679 A CA 2327679A CA 2327679 C CA2327679 C CA 2327679C
- Authority
- CA
- Canada
- Prior art keywords
- parts
- formula
- dyeing
- compounds
- dyes
- 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.)
- Expired - Fee Related
Links
- 238000004043 dyeing Methods 0.000 title claims abstract description 47
- 239000000758 substrate Substances 0.000 title claims abstract description 15
- 238000000034 method Methods 0.000 claims abstract description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000001257 hydrogen Substances 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims description 18
- 239000004952 Polyamide Substances 0.000 claims description 17
- 229920002647 polyamide Polymers 0.000 claims description 17
- 210000002268 wool Anatomy 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 13
- -1 naphthyl radical Chemical group 0.000 claims description 12
- 238000007639 printing Methods 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 150000005840 aryl radicals Chemical class 0.000 claims description 5
- 239000007800 oxidant agent Substances 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 5
- 150000003455 sulfinic acids Chemical class 0.000 claims description 5
- 229920002678 cellulose Polymers 0.000 claims description 4
- 239000001913 cellulose Substances 0.000 claims description 4
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical class [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 239000000976 ink Substances 0.000 claims description 3
- 125000005385 peroxodisulfate group Chemical group 0.000 claims description 3
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 5
- 239000000975 dye Substances 0.000 description 58
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- 150000003254 radicals Chemical class 0.000 description 16
- 239000002253 acid Substances 0.000 description 10
- 229910006069 SO3H Inorganic materials 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 8
- 239000000463 material Substances 0.000 description 7
- 239000000985 reactive dye Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- 239000004744 fabric Substances 0.000 description 6
- 239000010985 leather Substances 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
- 159000000000 sodium salts Chemical class 0.000 description 5
- 229920000742 Cotton Polymers 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- SJEYSFABYSGQBG-UHFFFAOYSA-M Patent blue Chemical compound [Na+].C1=CC(N(CC)CC)=CC=C1C(C=1C(=CC(=CC=1)S([O-])(=O)=O)S([O-])(=O)=O)=C1C=CC(=[N+](CC)CC)C=C1 SJEYSFABYSGQBG-UHFFFAOYSA-M 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000000980 acid dye Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 125000001624 naphthyl group Chemical group 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- 239000004753 textile Substances 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229920002292 Nylon 6 Polymers 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000002657 fibrous material Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- 235000013912 Ceratonia siliqua Nutrition 0.000 description 2
- 240000008886 Ceratonia siliqua Species 0.000 description 2
- 239000004677 Nylon Substances 0.000 description 2
- 229920002302 Nylon 6,6 Polymers 0.000 description 2
- 229920000297 Rayon Polymers 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- JEHKKBHWRAXMCH-UHFFFAOYSA-N benzenesulfinic acid Chemical compound O[S@@](=O)C1=CC=CC=C1 JEHKKBHWRAXMCH-UHFFFAOYSA-N 0.000 description 2
- 239000007844 bleaching agent Substances 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 235000013312 flour Nutrition 0.000 description 2
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 229920001778 nylon Polymers 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 2
- 125000001174 sulfone group Chemical group 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- GIAFURWZWWWBQT-UHFFFAOYSA-N 2-(2-aminoethoxy)ethanol Chemical compound NCCOCCO GIAFURWZWWWBQT-UHFFFAOYSA-N 0.000 description 1
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 1
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 1
- UHBDEGXSISTGPG-UHFFFAOYSA-N 3-aminobenzenesulfinic acid Chemical compound NC1=CC=CC(S(O)=O)=C1 UHBDEGXSISTGPG-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- FXJVNINSOKCNJP-UHFFFAOYSA-N 4-methylbenzenesulfinic acid Chemical compound CC1=CC=C(S(O)=O)C=C1 FXJVNINSOKCNJP-UHFFFAOYSA-N 0.000 description 1
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 0 CC(C1=Nc2c3)=C4Oc(c(*)c(cc5)NN)c5N=C4C(*)=C1Oc2c(C=*)c(NN)c3S(*)(=O)=O Chemical compound CC(C1=Nc2c3)=C4Oc(c(*)c(cc5)NN)c5N=C4C(*)=C1Oc2c(C=*)c(NN)c3S(*)(=O)=O 0.000 description 1
- XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical class [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 235000019687 Lamb Nutrition 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 238000006887 Ullmann reaction Methods 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 241001416177 Vicugna pacos Species 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910001413 alkali metal ion Inorganic materials 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- DIZPMCHEQGEION-UHFFFAOYSA-H aluminium sulfate (anhydrous) Chemical compound [Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O DIZPMCHEQGEION-UHFFFAOYSA-H 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 1
- 239000012935 ammoniumperoxodisulfate Substances 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 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 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- SXDBWCPKPHAZSM-UHFFFAOYSA-M bromate Chemical class [O-]Br(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-M 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 210000000085 cashmere Anatomy 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- ZBNARPCCDMHDDV-UHFFFAOYSA-N chembl1206040 Chemical compound C1=C(S(O)(=O)=O)C=C2C=C(S(O)(=O)=O)C(N=NC3=CC=C(C=C3C)C=3C=C(C(=CC=3)N=NC=3C(=CC4=CC(=CC(N)=C4C=3O)S(O)(=O)=O)S(O)(=O)=O)C)=C(O)C2=C1N ZBNARPCCDMHDDV-UHFFFAOYSA-N 0.000 description 1
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- SOCTUWSJJQCPFX-UHFFFAOYSA-N dichromate(2-) Chemical compound [O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O SOCTUWSJJQCPFX-UHFFFAOYSA-N 0.000 description 1
- SWYAODARJIJAKL-UHFFFAOYSA-L disodium 3-[[4-[1-[4-[(1,7-dihydroxy-3-sulfonatonaphthalen-2-yl)diazenyl]-3-methylphenyl]cyclohexyl]-2-methylphenyl]diazenyl]-4,6-dihydroxynaphthalene-2-sulfonate Chemical compound [Na+].[Na+].Cc1cc(ccc1N=Nc1c(O)c2cc(O)ccc2cc1S([O-])(=O)=O)C1(CCCCC1)c1ccc(N=Nc2c(O)c3cc(O)ccc3cc2S([O-])(=O)=O)c(C)c1 SWYAODARJIJAKL-UHFFFAOYSA-L 0.000 description 1
- FPVGTPBMTFTMRT-UHFFFAOYSA-L disodium;2-amino-5-[(4-sulfonatophenyl)diazenyl]benzenesulfonate Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C(N)=CC=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 FPVGTPBMTFTMRT-UHFFFAOYSA-L 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 235000019233 fast yellow AB Nutrition 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 235000021323 fish oil Nutrition 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- ICIWUVCWSCSTAQ-UHFFFAOYSA-N iodic acid Chemical class OI(=O)=O ICIWUVCWSCSTAQ-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229910000464 lead oxide Inorganic materials 0.000 description 1
- ACKFDYCQCBEDNU-UHFFFAOYSA-J lead(2+);tetraacetate Chemical compound [Pb+2].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O ACKFDYCQCBEDNU-UHFFFAOYSA-J 0.000 description 1
- XNEFVTBPCXGIRX-UHFFFAOYSA-N methanesulfinic acid Chemical compound CS(O)=O XNEFVTBPCXGIRX-UHFFFAOYSA-N 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 239000010446 mirabilite Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 210000000050 mohair Anatomy 0.000 description 1
- LTSBKUWFXANFCU-UHFFFAOYSA-N naphthalene-2-sulfinic acid Chemical compound C1=CC=CC2=CC(S(=O)O)=CC=C21 LTSBKUWFXANFCU-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- YEXPOXQUZXUXJW-UHFFFAOYSA-N oxolead Chemical compound [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 239000013535 sea water Substances 0.000 description 1
- 229910001923 silver oxide Inorganic materials 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- KIEOKOFEPABQKJ-UHFFFAOYSA-N sodium dichromate Chemical compound [Na+].[Na+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O KIEOKOFEPABQKJ-UHFFFAOYSA-N 0.000 description 1
- 229910001415 sodium ion Inorganic materials 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
- CHLCPTJLUJHDBO-UHFFFAOYSA-M sodium;benzenesulfinate Chemical compound [Na+].[O-]S(=O)C1=CC=CC=C1 CHLCPTJLUJHDBO-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002759 woven fabric 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
- C09B62/046—Specific dyes not provided for in group C09B62/06 - C09B62/10
-
- 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
- C09B19/00—Oxazine dyes
- C09B19/02—Bisoxazines prepared from aminoquinones
-
- 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
- C09B56/00—Azo dyes containing other chromophoric systems
- C09B56/10—Formazane-azo dyes
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/916—Natural fiber dyeing
- Y10S8/917—Wool or silk
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/916—Natural fiber dyeing
- Y10S8/918—Cellulose textile
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/92—Synthetic fiber dyeing
- Y10S8/924—Polyamide fiber
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH805/98 | 1998-04-03 | ||
| CH80598 | 1998-04-03 | ||
| PCT/IB1999/000338 WO1999051681A1 (en) | 1998-04-03 | 1999-03-01 | Triphendioxazine dyestuffs for dyeing organic substrates |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2327679A1 CA2327679A1 (en) | 1999-10-14 |
| CA2327679C true CA2327679C (en) | 2007-10-30 |
Family
ID=4195606
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002327679A Expired - Fee Related CA2327679C (en) | 1998-04-03 | 1999-03-01 | Triphendioxazine dyestuffs for dyeing organic substrates |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US6319289B1 (enExample) |
| EP (1) | EP1066340B1 (enExample) |
| JP (1) | JP4624554B2 (enExample) |
| KR (1) | KR100619113B1 (enExample) |
| CN (1) | CN1118520C (enExample) |
| CA (1) | CA2327679C (enExample) |
| DE (1) | DE69902243T2 (enExample) |
| ES (1) | ES2180271T3 (enExample) |
| TR (1) | TR200002865T2 (enExample) |
| WO (1) | WO1999051681A1 (enExample) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0002966D0 (en) | 2000-02-10 | 2000-03-29 | Clariant Int Ltd | New triphendioxazine pigments |
| JP2001348499A (ja) | 2000-03-06 | 2001-12-18 | Clariant Internatl Ltd | 顔料の調製 |
| AU2001290185B8 (en) * | 2000-12-05 | 2007-01-25 | Clariant Finance (Bvi) Limited | Trichromatic dyeing process |
| CN1942528B (zh) * | 2004-04-06 | 2011-02-23 | 克莱里安特财务(Bvi)有限公司 | 染色方法 |
| ES2294711T3 (es) | 2004-05-19 | 2008-04-01 | Clariant Finance (Bvi) Limited | Colorantes monoazoicos. |
| JP5090905B2 (ja) | 2004-05-19 | 2012-12-05 | クラリアント ファイナンス （ビーブイアイ） リミティド | 橋架けモノアゾ染料 |
| DE102004063724A1 (de) | 2004-12-31 | 2006-07-13 | Dystar Textilfarben Gmbh & Co. Deutschland Kg | Reaktive Triphendioxazin-Farbstoffe,Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE602007001604D1 (de) | 2006-04-07 | 2009-08-27 | Clariant Finance Bvi Ltd | Säurefarbstoffe |
| MX2008014473A (es) | 2006-05-16 | 2008-11-27 | Clariant Finance Bvi Ltd | Tintes de acido disazo. |
| EP2258684A1 (en) | 2009-05-14 | 2010-12-08 | Clariant International Ltd | Monoazo compounds |
| EP2251386A1 (en) | 2009-05-14 | 2010-11-17 | Clariant International Ltd. | Pyrazolone bisazo dyes |
| ES2383577T3 (es) | 2009-05-14 | 2012-06-22 | Clariant International Ltd. | Compuestos orgánicos |
| EP2258686A1 (en) | 2009-05-14 | 2010-12-08 | Clariant International Ltd | Monoazo compounds |
| EP2251382A1 (en) | 2009-05-14 | 2010-11-17 | Clariant International Ltd. | Monoazo compounds |
| EP2251383A1 (en) | 2009-05-14 | 2010-11-17 | Clariant International Ltd. | Organic compounds |
| EP2251381A1 (en) | 2009-05-14 | 2010-11-17 | Clariant International Ltd. | Monoazo compounds |
| EP2258683A1 (en) | 2009-05-14 | 2010-12-08 | Clariant International Ltd. | Bisazo compounds |
| PT2258685E (pt) | 2009-05-14 | 2013-12-10 | Clariant Finance Bv Ltd | Compostos bisazo |
| EP2251385A1 (en) | 2009-05-14 | 2010-11-17 | Clariant International Ltd. | Pyrazolone bisazo dyes |
| EP2251384A1 (en) | 2009-05-14 | 2010-11-17 | Clariant International Ltd. | Pyrazolone monoazo dyes |
| ES2403068T3 (es) | 2010-07-29 | 2013-05-13 | Clariant Finance (Bvi) Limited | Tintes ácidos |
| ES2497191T3 (es) | 2011-10-22 | 2014-09-22 | Clariant International Ltd. | Colorantes ácidos trisazoicos basados en piridonas |
| PT2584008E (pt) | 2011-10-22 | 2014-08-28 | Clariant Int Ltd | Corantes de ácidos trisazo à base de naftóis |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2673809B2 (ja) * | 1988-02-15 | 1997-11-05 | コニカ株式会社 | 新規な写真用カプラー |
| ES2070937T3 (es) * | 1989-02-01 | 1995-06-16 | Sumitomo Chemical Co | Compuestos de dioxazina asimetricos reactivos con las fibras y su uso como tintes reactivos con las fibras. |
| JP3074796B2 (ja) * | 1990-08-21 | 2000-08-07 | 住友化学工業株式会社 | 非対称ジオキサジン化合物及びそれを用いて繊維材料を染色又は捺染する方法 |
| JPH05209134A (ja) * | 1991-11-05 | 1993-08-20 | Sumitomo Chem Co Ltd | 非対称ジオキサジン化合物及びそれを用いて繊維材料を染色又は捺染する方法 |
| AU653266B2 (en) * | 1991-11-05 | 1994-09-22 | Sumitomo Chemical Company, Limited | Asymmetric dioxazine compounds and method for dyeing or printing fiber materials using the same |
| JPH0673670A (ja) * | 1992-06-22 | 1994-03-15 | Sumitomo Chem Co Ltd | 非対称ジオキサジン化合物及びそれを用いて繊維材料を染色又は捺染する方法 |
| AU662996B2 (en) * | 1992-09-11 | 1995-09-21 | Sumitomo Chemical Company, Limited | Reactive dye composition and method for dyeing or printing fiber materials using the same |
| JPH06107961A (ja) * | 1992-09-28 | 1994-04-19 | Sumitomo Chem Co Ltd | 非対称ジオキサジン化合物およびそれを用いて繊維材料を染色または捺染する方法 |
| JPH06299474A (ja) * | 1993-04-14 | 1994-10-25 | Sumitomo Chem Co Ltd | 反応染料を用いる繊維材料の染色または捺染方法 |
| EP0639624A1 (de) * | 1993-08-19 | 1995-02-22 | Bayer Ag | Phthaloperinonfarbstoffe |
| DE4415780A1 (de) | 1994-05-05 | 1995-11-09 | Bayer Ag | Triphendioxazin-Reaktivfarbstoffe |
| DE19541985A1 (de) * | 1995-11-10 | 1997-05-15 | Dystar Textilfarben Gmbh & Co | Verfahren zur Herstellung von beidseitig amidierten Triphendioxazinfarbstoffen und neue Triphendioxazinfarbstoffe |
-
1999
- 1999-03-01 TR TR2000/02865T patent/TR200002865T2/xx unknown
- 1999-03-01 ES ES99903853T patent/ES2180271T3/es not_active Expired - Lifetime
- 1999-03-01 CN CN99804579A patent/CN1118520C/zh not_active Expired - Lifetime
- 1999-03-01 DE DE69902243T patent/DE69902243T2/de not_active Expired - Lifetime
- 1999-03-01 WO PCT/IB1999/000338 patent/WO1999051681A1/en not_active Ceased
- 1999-03-01 KR KR1020007010990A patent/KR100619113B1/ko not_active Expired - Lifetime
- 1999-03-01 JP JP2000542397A patent/JP4624554B2/ja not_active Expired - Lifetime
- 1999-03-01 EP EP99903853A patent/EP1066340B1/en not_active Expired - Lifetime
- 1999-03-01 CA CA002327679A patent/CA2327679C/en not_active Expired - Fee Related
- 1999-03-31 US US09/283,079 patent/US6319289B1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| WO1999051681A1 (en) | 1999-10-14 |
| CN1118520C (zh) | 2003-08-20 |
| CN1295601A (zh) | 2001-05-16 |
| US6319289B1 (en) | 2001-11-20 |
| CA2327679A1 (en) | 1999-10-14 |
| ES2180271T3 (es) | 2003-02-01 |
| EP1066340B1 (en) | 2002-07-24 |
| TR200002865T2 (tr) | 2001-04-20 |
| EP1066340A1 (en) | 2001-01-10 |
| JP4624554B2 (ja) | 2011-02-02 |
| KR20010042413A (ko) | 2001-05-25 |
| KR100619113B1 (ko) | 2006-09-04 |
| DE69902243T2 (de) | 2003-03-06 |
| JP2002510735A (ja) | 2002-04-09 |
| DE69902243D1 (de) | 2002-08-29 |
| HK1036818A1 (zh) | 2002-01-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20180301 |