AT403925B - Verfahren zur herstellung von wasserlöslichen, trockenen leukoschwefelfarbstoffen - Google Patents

Verfahren zur herstellung von wasserlöslichen, trockenen leukoschwefelfarbstoffen Download PDF

Info

Publication number: AT403925B
Authority: AT; Austria
Prior art keywords: dye; dyes; leucosulfur; dry; water
Prior art date: 1991-05-23

Application number

AT0105992A

Other languages

German (de)

English (en)

Other versions

ATA105992A (de

Original Assignee

Clariant Finance Bvi Ltd

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.)

1991-05-23

Filing date

1992-05-22

Publication date

1998-06-25

1991-05-23 Priority claimed from GB919111194A external-priority patent/GB9111194D0/en

1991-05-23 Priority claimed from GB919111211A external-priority patent/GB9111211D0/en

1991-11-25 Priority claimed from GB919124998A external-priority patent/GB9124998D0/en

1991-11-25 Priority claimed from GB919124959A external-priority patent/GB9124959D0/en

1992-05-22 Application filed by Clariant Finance Bvi Ltd filed Critical Clariant Finance Bvi Ltd

1997-11-15 Publication of ATA105992A publication Critical patent/ATA105992A/de

1998-06-25 Application granted granted Critical

1998-06-25 Publication of AT403925B publication Critical patent/AT403925B/de

Links

239000000975 dye Substances 0.000 title claims description 77
238000004519 manufacturing process Methods 0.000 title claims description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 76
238000000034 method Methods 0.000 claims description 56
239000000203 mixture Substances 0.000 claims description 42
238000004043 dyeing Methods 0.000 claims description 32
239000000988 sulfur dye Substances 0.000 claims description 32
238000001035 drying Methods 0.000 claims description 29
230000003647 oxidation Effects 0.000 claims description 27
238000007254 oxidation reaction Methods 0.000 claims description 27
238000006722 reduction reaction Methods 0.000 claims description 21
238000002360 preparation method Methods 0.000 claims description 20
239000012065 filter cake Substances 0.000 claims description 18
239000000843 powder Substances 0.000 claims description 18
229910052945 inorganic sulfide Inorganic materials 0.000 claims description 16
150000008044 alkali metal hydroxides Chemical class 0.000 claims description 14
238000006243 chemical reaction Methods 0.000 claims description 13
239000003638 chemical reducing agent Substances 0.000 claims description 12
-1 alkali metal sulfite Chemical class 0.000 claims description 10
239000003795 chemical substances by application Substances 0.000 claims description 10
239000000758 substrate Substances 0.000 claims description 10
150000001728 carbonyl compounds Chemical class 0.000 claims description 8
235000000346 sugar Nutrition 0.000 claims description 8
239000004753 textile Substances 0.000 claims description 8
239000012736 aqueous medium Substances 0.000 claims description 7
229910052783 alkali metal Inorganic materials 0.000 claims description 6
229920002678 cellulose Polymers 0.000 claims description 6
239000001913 cellulose Substances 0.000 claims description 6
239000000463 material Substances 0.000 claims description 6
230000007717 exclusion Effects 0.000 claims description 5
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 claims description 4
239000012669 liquid formulation Substances 0.000 claims description 4
239000002244 precipitate Substances 0.000 claims description 4
238000004513 sizing Methods 0.000 claims description 4
229910052708 sodium Inorganic materials 0.000 claims description 4
239000011734 sodium Substances 0.000 claims description 4
239000000725 suspension Substances 0.000 claims description 4
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 3
230000014759 maintenance of location Effects 0.000 claims description 3
229930194542 Keto Natural products 0.000 claims description 2
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 claims description 2
239000003945 anionic surfactant Substances 0.000 claims description 2
LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 claims description 2
125000000468 ketone group Chemical group 0.000 claims description 2
239000002904 solvent Substances 0.000 claims description 2
239000003381 stabilizer Substances 0.000 claims description 2
238000003756 stirring Methods 0.000 claims description 2
239000003086 colorant Substances 0.000 claims 1
239000002609 medium Substances 0.000 claims 1
239000011347 resin Substances 0.000 claims 1
229920005989 resin Polymers 0.000 claims 1
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 81
239000000047 product Substances 0.000 description 51
229910052717 sulfur Inorganic materials 0.000 description 36
239000011593 sulfur Substances 0.000 description 36
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 33
239000000243 solution Substances 0.000 description 32
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 27
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 26
239000008103 glucose Substances 0.000 description 25
239000011541 reaction mixture Substances 0.000 description 14
229920000742 Cotton Polymers 0.000 description 13
238000001704 evaporation Methods 0.000 description 12
230000008020 evaporation Effects 0.000 description 12
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
229910052979 sodium sulfide Inorganic materials 0.000 description 9
GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 9
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 8
230000015572 biosynthetic process Effects 0.000 description 8
239000007795 chemical reaction product Substances 0.000 description 8
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 7
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 7
229910000037 hydrogen sulfide Inorganic materials 0.000 description 7
239000007788 liquid Substances 0.000 description 7
239000011550 stock solution Substances 0.000 description 7
SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 6
VYZAHLCBVHPDDF-UHFFFAOYSA-N Dinitrochlorobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 VYZAHLCBVHPDDF-UHFFFAOYSA-N 0.000 description 6
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
239000007864 aqueous solution Substances 0.000 description 6
238000001914 filtration Methods 0.000 description 6
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 6
150000003568 thioethers Chemical class 0.000 description 6
238000007280 thionation reaction Methods 0.000 description 6
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 5
239000002253 acid Substances 0.000 description 5
238000005470 impregnation Methods 0.000 description 5
235000002639 sodium chloride Nutrition 0.000 description 5
PGYZAKRTYUHXRA-UHFFFAOYSA-N 2,10-dinitro-12h-[1,4]benzothiazino[3,2-b]phenothiazin-3-one Chemical compound S1C2=CC(=O)C([N+]([O-])=O)=CC2=NC2=C1C=C1SC3=CC=C([N+](=O)[O-])C=C3NC1=C2 PGYZAKRTYUHXRA-UHFFFAOYSA-N 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 4
238000004040 coloring Methods 0.000 description 4
150000001875 compounds Chemical class 0.000 description 4
239000004744 fabric Substances 0.000 description 4
229910052739 hydrogen Inorganic materials 0.000 description 4
239000001257 hydrogen Substances 0.000 description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
XLSMFKSTNGKWQX-UHFFFAOYSA-N hydroxyacetone Chemical compound CC(=O)CO XLSMFKSTNGKWQX-UHFFFAOYSA-N 0.000 description 4
QTWZICCBKBYHDM-UHFFFAOYSA-N leucomethylene blue Chemical compound C1=C(N(C)C)C=C2SC3=CC(N(C)C)=CC=C3NC2=C1 QTWZICCBKBYHDM-UHFFFAOYSA-N 0.000 description 4
229910052760 oxygen Inorganic materials 0.000 description 4
239000001301 oxygen Substances 0.000 description 4
150000008163 sugars Chemical class 0.000 description 4
RYYXDZDBXNUPOG-UHFFFAOYSA-N 4,5,6,7-tetrahydro-1,3-benzothiazole-2,6-diamine;dihydrochloride Chemical compound Cl.Cl.C1C(N)CCC2=C1SC(N)=N2 RYYXDZDBXNUPOG-UHFFFAOYSA-N 0.000 description 3
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 3
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
239000004952 Polyamide Substances 0.000 description 3
239000013543 active substance Substances 0.000 description 3
150000001340 alkali metals Chemical class 0.000 description 3
238000009835 boiling Methods 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
239000001046 green dye Substances 0.000 description 3
239000008101 lactose Substances 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
150000002978 peroxides Chemical class 0.000 description 3
229920002647 polyamide Polymers 0.000 description 3
238000001556 precipitation Methods 0.000 description 3
238000010992 reflux Methods 0.000 description 3
239000007787 solid Substances 0.000 description 3
238000003860 storage Methods 0.000 description 3
239000000080 wetting agent Substances 0.000 description 3
AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 2
OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 2
VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 2
FMKXFJQAVQXMPX-UHFFFAOYSA-N 4-(9h-carbazol-3-ylimino)cyclohexa-2,5-dien-1-one Chemical compound C1=CC(=O)C=CC1=NC1=CC=C(NC=2C3=CC=CC=2)C3=C1 FMKXFJQAVQXMPX-UHFFFAOYSA-N 0.000 description 2
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
239000004202 carbamide Substances 0.000 description 2
150000001768 cations Chemical group 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
239000008121 dextrose Substances 0.000 description 2
239000000835 fiber Substances 0.000 description 2
238000009472 formulation Methods 0.000 description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
239000000155 melt Substances 0.000 description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
150000002772 monosaccharides Chemical class 0.000 description 2
239000012299 nitrogen atmosphere Substances 0.000 description 2
239000004745 nonwoven fabric Substances 0.000 description 2
229920001542 oligosaccharide Polymers 0.000 description 2
150000002482 oligosaccharides Chemical class 0.000 description 2
OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 2
239000005077 polysulfide Substances 0.000 description 2
229920001021 polysulfide Polymers 0.000 description 2
150000008117 polysulfides Polymers 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
235000010265 sodium sulphite Nutrition 0.000 description 2
229940048842 sodium xylenesulfonate Drugs 0.000 description 2
QUCDWLYKDRVKMI-UHFFFAOYSA-M sodium;3,4-dimethylbenzenesulfonate Chemical compound [Na+].CC1=CC=C(S([O-])(=O)=O)C=C1C QUCDWLYKDRVKMI-UHFFFAOYSA-M 0.000 description 2
239000012265 solid product Substances 0.000 description 2
238000001694 spray drying Methods 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
239000004094 surface-active agent Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
235000020357 syrup Nutrition 0.000 description 2
239000006188 syrup Substances 0.000 description 2
238000012360 testing method Methods 0.000 description 2
239000002562 thickening agent Substances 0.000 description 2
239000000984 vat dye Substances 0.000 description 2
239000002351 wastewater Substances 0.000 description 2
HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 1
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 1
JHCVSMXLFULOSU-UHFFFAOYSA-N 3-ethylphenol;methylcarbamic acid Chemical compound CNC(O)=O.CCC1=CC=CC(O)=C1 JHCVSMXLFULOSU-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical class [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 description 1
GUBGYTABKSRVRQ-CUHNMECISA-N D-Cellobiose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-CUHNMECISA-N 0.000 description 1
WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 description 1
QWIZNVHXZXRPDR-UHFFFAOYSA-N D-melezitose Natural products O1C(CO)C(O)C(O)C(O)C1OC1C(O)C(CO)OC1(CO)OC1OC(CO)C(O)C(O)C1O QWIZNVHXZXRPDR-UHFFFAOYSA-N 0.000 description 1
HMFHBZSHGGEWLO-SOOFDHNKSA-N D-ribofuranose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H]1O HMFHBZSHGGEWLO-SOOFDHNKSA-N 0.000 description 1
241000196324 Embryophyta Species 0.000 description 1
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RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
239000005715 Fructose Substances 0.000 description 1
229920001732 Lignosulfonate Polymers 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
MUPFEKGTMRGPLJ-RMMQSMQOSA-N Raffinose Natural products O(C[C@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O[C@@]2(CO)[C@H](O)[C@@H](O)[C@@H](CO)O2)O1)[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 MUPFEKGTMRGPLJ-RMMQSMQOSA-N 0.000 description 1
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240000008042 Zea mays Species 0.000 description 1
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125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
239000000654 additive Substances 0.000 description 1
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150000001320 aldopentoses Chemical class 0.000 description 1
150000007824 aliphatic compounds Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
HMFHBZSHGGEWLO-UHFFFAOYSA-N alpha-D-Furanose-Ribose Natural products OCC1OC(O)C(O)C1O HMFHBZSHGGEWLO-UHFFFAOYSA-N 0.000 description 1
WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 description 1
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
PYMYPHUHKUWMLA-WDCZJNDASA-N arabinose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-WDCZJNDASA-N 0.000 description 1
239000012752 auxiliary agent Substances 0.000 description 1
DLRVVLDZNNYCBX-ZZFZYMBESA-N beta-melibiose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@H](O)O1 DLRVVLDZNNYCBX-ZZFZYMBESA-N 0.000 description 1
239000011575 calcium Substances 0.000 description 1
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150000001720 carbohydrates Chemical class 0.000 description 1
235000014633 carbohydrates Nutrition 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
QBWCMBCROVPCKQ-UHFFFAOYSA-N chlorous acid Chemical class OCl=O QBWCMBCROVPCKQ-UHFFFAOYSA-N 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000006477 desulfuration reaction Methods 0.000 description 1
230000023556 desulfurization Effects 0.000 description 1
238000011161 development Methods 0.000 description 1
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
LVTYICIALWPMFW-UHFFFAOYSA-N diisopropanolamine Chemical compound CC(O)CNCC(C)O LVTYICIALWPMFW-UHFFFAOYSA-N 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
238000007598 dipping method Methods 0.000 description 1
150000002016 disaccharides Chemical class 0.000 description 1
238000007323 disproportionation reaction Methods 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000002657 fibrous material Substances 0.000 description 1
239000006260 foam Substances 0.000 description 1
229940017705 formaldehyde sulfoxylate Drugs 0.000 description 1
229930182830 galactose Natural products 0.000 description 1
125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 1
239000008187 granular material Substances 0.000 description 1
150000002366 halogen compounds Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical class [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 1
125000005842 heteroatom Chemical group 0.000 description 1
150000002402 hexoses Chemical class 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
SBGKURINHGJRFN-UHFFFAOYSA-N hydroxymethanesulfinic acid Chemical compound OCS(O)=O SBGKURINHGJRFN-UHFFFAOYSA-N 0.000 description 1
ICIWUVCWSCSTAQ-UHFFFAOYSA-N iodic acid Chemical class OI(=O)=O ICIWUVCWSCSTAQ-UHFFFAOYSA-N 0.000 description 1
150000002596 lactones Chemical group 0.000 description 1
239000010985 leather Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
230000007774 longterm Effects 0.000 description 1
235000020429 malt syrup Nutrition 0.000 description 1
QWIZNVHXZXRPDR-WSCXOGSTSA-N melezitose Chemical compound O([C@@]1(O[C@@H]([C@H]([C@@H]1O[C@@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)O)CO)CO)[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O QWIZNVHXZXRPDR-WSCXOGSTSA-N 0.000 description 1
229910000000 metal hydroxide Inorganic materials 0.000 description 1
229910044991 metal oxide Inorganic materials 0.000 description 1
150000004706 metal oxides Chemical class 0.000 description 1
235000013379 molasses Nutrition 0.000 description 1
239000000178 monomer Substances 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
239000002245 particle Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
HEZHYQDYRPUXNJ-UHFFFAOYSA-L potassium dithionite Chemical compound [K+].[K+].[O-]S(=O)S([O-])=O HEZHYQDYRPUXNJ-UHFFFAOYSA-L 0.000 description 1
BHZRJJOHZFYXTO-UHFFFAOYSA-L potassium sulfite Chemical compound [K+].[K+].[O-]S([O-])=O BHZRJJOHZFYXTO-UHFFFAOYSA-L 0.000 description 1
235000019252 potassium sulphite Nutrition 0.000 description 1
239000002243 precursor Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
238000007639 printing Methods 0.000 description 1
RYVMUASDIZQXAA-UHFFFAOYSA-N pyranoside Natural products O1C2(OCC(C)C(OC3C(C(O)C(O)C(CO)O3)O)C2)C(C)C(C2(CCC3C4(C)CC5O)C)C1CC2C3CC=C4CC5OC(C(C1O)O)OC(CO)C1OC(C1OC2C(C(OC3C(C(O)C(O)C(CO)O3)O)C(O)C(CO)O2)O)OC(CO)C(O)C1OC1OCC(O)C(O)C1O RYVMUASDIZQXAA-UHFFFAOYSA-N 0.000 description 1
230000005855 radiation Effects 0.000 description 1
MUPFEKGTMRGPLJ-ZQSKZDJDSA-N raffinose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO[C@@H]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO)O2)O)O1 MUPFEKGTMRGPLJ-ZQSKZDJDSA-N 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
238000001226 reprecipitation Methods 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
239000003352 sequestering agent Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000017550 sodium carbonate Nutrition 0.000 description 1
UKLNMMHNWFDKNT-UHFFFAOYSA-M sodium chlorite Chemical compound [Na+].[O-]Cl=O UKLNMMHNWFDKNT-UHFFFAOYSA-M 0.000 description 1
229960002218 sodium chlorite Drugs 0.000 description 1
SRRKNRDXURUMPP-UHFFFAOYSA-N sodium disulfide Chemical compound [Na+].[Na+].[S-][S-] SRRKNRDXURUMPP-UHFFFAOYSA-N 0.000 description 1
HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
HYHCSLBZRBJJCH-UHFFFAOYSA-N sodium polysulfide Chemical compound [Na+].S HYHCSLBZRBJJCH-UHFFFAOYSA-N 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
HLWRUJAIJJEZDL-UHFFFAOYSA-M sodium;2-[2-[bis(carboxymethyl)amino]ethyl-(carboxymethyl)amino]acetate Chemical compound [Na+].OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC([O-])=O HLWRUJAIJJEZDL-UHFFFAOYSA-M 0.000 description 1
238000005507 spraying Methods 0.000 description 1
238000010025 steaming Methods 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
238000005987 sulfurization reaction Methods 0.000 description 1
238000001308 synthesis method Methods 0.000 description 1
239000000979 synthetic dye Substances 0.000 description 1
238000010189 synthetic method Methods 0.000 description 1
239000008399 tap water Substances 0.000 description 1
235000020679 tap water Nutrition 0.000 description 1
125000003396 thiol group Chemical group [H]S* 0.000 description 1
150000007944 thiolates Chemical group 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
238000012549 training Methods 0.000 description 1
ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
239000006200 vaporizer Substances 0.000 description 1
230000004584 weight gain Effects 0.000 description 1
235000019786 weight gain Nutrition 0.000 description 1
210000002268 wool Anatomy 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
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0077—Preparations with possibly reduced vat, sulfur or indigo dyes
- 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
- C09B49/00—Sulfur dyes

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Coloring (AREA)
Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
Removal Of Specific Substances (AREA)

AT0105992A 1991-05-23 1992-05-22 Verfahren zur herstellung von wasserlöslichen, trockenen leukoschwefelfarbstoffen AT403925B (de)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
GB919111194A GB9111194D0 (en)	1991-05-23	1991-05-23	Improvements in or relating to organic compounds
GB919111211A GB9111211D0 (en)	1991-05-23	1991-05-23	Improvements in or relating to organic compounds
GB919124998A GB9124998D0 (en)	1991-11-25	1991-11-25	Improvements in or relating to organic compounds
GB919124959A GB9124959D0 (en)	1991-11-25	1991-11-25	Improvements in or relating to organic compounds

Publications (2)

Publication Number	Publication Date
ATA105992A ATA105992A (de)	1997-11-15
AT403925B true AT403925B (de)	1998-06-25

Family

ID=27450684

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
AT0105992A AT403925B (de)	1991-05-23	1992-05-22	Verfahren zur herstellung von wasserlöslichen, trockenen leukoschwefelfarbstoffen

Country Status (10)

Country	Link
JP (1)	JPH05140469A (it)
AT (1)	AT403925B (it)
BR (1)	BR9202015A (it)
CH (1)	CH683775A5 (it)
DE (1)	DE4215678A1 (it)
ES (1)	ES2047448B1 (it)
FR (1)	FR2676742B1 (it)
GB (1)	GB2255981B (it)
IT (1)	IT1254369B (it)
TR (1)	TR26911A (it)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB9224368D0 (en) *	1992-11-20	1993-01-13	Sandoz Ltd	Improvements in or relating to organic compounds
US5302441A (en) *	1991-11-15	1994-04-12	The Mead Corporation	Postformable decorative laminating paper
US5632782A (en) *	1994-09-01	1997-05-27	Clariant Finance (Bvi) Ltd.	Exhaust dyeing process for sulphur dyes
GB9504870D0 (en) *	1995-03-10	1995-04-26	Sandoz Ltd	Improvements in or relating to organic compounds
GB9504888D0 (en) *	1995-03-10	1995-04-26	Sandoz Ltd	Improvements in or relating to oraganic compounds
TR199600348A2 (tr) *	1995-05-03	1996-11-21	Clariant Int Ltd	Kükürtlü boyalar,bunlarin imali ve kullanimi.
US20070012412A1 (en) *	2005-07-15	2007-01-18	Schweitzer-Mauduit International, Inc.	Laminate paper having increased pH stability and method of making same
JP5308259B2 (ja) *	2009-07-14	2013-10-09	大王製紙株式会社	板紙及びその製造方法

Citations (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB2201165A (en) *	1987-02-16	1988-08-24	Sandoz Ltd	Leuco sulphur dye compositions with reduced content of inorganic sulphide

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DE200391C (it) *
BE459281A (it) *
DE251101C (it) *
FR301419A (it) *
DE198691C (it) *
FR698491A (fr) *	1929-04-15	1931-01-31	Ici Ltd	Perfectionnements apportés à la production et à la fabrication de préparations stables d'indigo-leucoïque
FR908875A (fr) *	1943-12-24	1946-04-22	Ste Ind Chim Bale	Procédé de teinture des fibres artificielles en colorants au soufre
CA1081936A (en) *	1975-11-19	1980-07-22	Richard L. Doerr	Oxidation of vat and sulfur dyes with vanadate activated bromate or iodate in combination with a nitrate
DE3532341A1 (de) *	1985-09-11	1987-03-19	Hoechst Ag	Verfahren und mittel zum einbadigen reoxidieren und seifen von faerbungen mit kuepen- oder schwefelkuepenfarbstoffen
US4917706B2 (en) *	1988-02-01	1996-02-20	Sandoz Ltd	Liquid compositions of prereduced sulfur dyes and production thereof
ES2005094A6 (es) *	1987-02-16	1989-03-01	Cardoner Sa	Procedimiento de obtencion y aplicacion de colorantes sulfurosos liqu idos reducidos en forma de leuco de bajo contenido en sulfuro sodico.

1992
- 1992-05-13 DE DE4215678A patent/DE4215678A1/de not_active Withdrawn
- 1992-05-21 FR FR9206352A patent/FR2676742B1/fr not_active Expired - Lifetime
- 1992-05-21 CH CH1640/92A patent/CH683775A5/de not_active IP Right Cessation
- 1992-05-22 GB GB9210931A patent/GB2255981B/en not_active Expired - Fee Related
- 1992-05-22 ES ES09201058A patent/ES2047448B1/es not_active Expired - Fee Related
- 1992-05-22 IT ITRM920384A patent/IT1254369B/it active
- 1992-05-22 AT AT0105992A patent/AT403925B/de not_active IP Right Cessation
- 1992-05-22 JP JP4130766A patent/JPH05140469A/ja active Pending
- 1992-05-22 TR TR00449/92A patent/TR26911A/xx unknown
- 1992-05-27 BR BR929202015A patent/BR9202015A/pt not_active IP Right Cessation

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB2201165A (en) *	1987-02-16	1988-08-24	Sandoz Ltd	Leuco sulphur dye compositions with reduced content of inorganic sulphide

Also Published As

Publication number	Publication date
GB9210931D0 (en)	1992-07-08
BR9202015A (pt)	1993-11-30
ES2047448A1 (es)	1994-02-16
ITRM920384A0 (it)	1992-05-22
FR2676742B1 (fr)	2000-09-15
ITRM920384A1 (it)	1993-11-22
ATA105992A (de)	1997-11-15
CH683775A5 (de)	1994-05-13
JPH05140469A (ja)	1993-06-08
GB2255981A (en)	1992-11-25
IT1254369B (it)	1995-09-14
FR2676742A1 (fr)	1992-11-27
ES2047448B1 (es)	1994-11-01
DE4215678A1 (de)	1992-11-26
TR26911A (tr)	1994-08-22
GB2255981B (en)	1995-02-01

Legal Events

Date	Code	Title	Description
1994-11-15	RER	Ceased as to paragraph 5 lit. 3 law introducing patent treaties
2001-07-15	ELJ	Ceased due to non-payment of the annual fee

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EP0113856B1 (de)	1986-09-24	Verfahren zur Verbesserung der Lichtechtheit von Polyamidfärbungen
EP0699797A2 (de)	1996-03-06	Ausziehfärbeverfahren für Schwefelfarbstoffe
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DE3804700C2 (de)	2003-05-08	Flüssige Farbstoff-Zubereitung
CH683775A5 (de)	1994-05-13	Trockene Leukoschwefelfarbstoffe.
DE2857698C2 (de)	1983-03-31	Farbstofflösungen, die Gemische von Anthrachinonverbindungen enthalten sowie Herstellung und Verwendung der Farbstofflösungen
DE3781893T2 (de)	1993-02-04	Wasserloesliche formazanfarbstoffe und faerbeverfahren damit.
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DE2324809C3 (it)	1977-06-08
EP0016933B1 (de)	1982-05-12	Verfahren zum Färben und Bedrucken mit Schwefelfarbstoffen und Verfahren zur Herstellung färbefertiger Schwefelfarbstoffzubereitungen, sowie nach dem Herstellungsverfahren erhaltene Schwefelfarbstoffzubereitung
DE2743066C3 (de)	1981-02-19	Farbstoffpräparationen
DE2719719B1 (de)	1978-01-05	Farbstoffl\sungen, verfahren zu deren herstellung und ihre verwendung
DE2301638C3 (de)	1975-07-31	Verfahren zur Herstellung von sulfongruppenhaltigen Phenol-Formaldehyd-Kondensationsprodukten
DE2748744C3 (de)	1981-10-01	Kondensationsprodukt aus Phenothiazin und p-Nitrosophenol, Verfahren zu seiner Herstellung und seine Verwendung zur Herstellung grüner Schwefelfarbstoffe
EP0087703A1 (de)	1983-09-07	Verfahren zur Herstellung von Reaktivfarbstoffpräparationen
EP0426617B1 (de)	1996-05-22	Faserreaktive Formazanfarbstoffe, Verfahren zu deren Herstellung und deren Verwendung
DE2601470C2 (de)	1977-04-28	Verfahren zur Herstellung von Kondensationsfarbstoffen
DE3114033A1 (de)	1982-10-21	Schwefelfarbstoffe, verfahren zu ihrer herstellung und ihre verwendung
DE2816983A1 (de)	1978-11-02	Stabile, fluessige, hochkonzentrierte farbstoffzubereitungen, ihre herstellung und verwendung
DE1769856A1 (de)	1973-03-01	Bedruckte textilfasern und verfahren zu deren herstellung
DE125589C (it)
DE2417253C2 (de)	1976-02-19	Flüssige Farbstoffzubereitungen eines Reaktivfarbstoffes