DE2502154A1 - Verfahren zum faerben von hydrophoben fasern - Google Patents
Verfahren zum faerben von hydrophoben fasernInfo
- Publication number
- DE2502154A1 DE2502154A1 DE19752502154 DE2502154A DE2502154A1 DE 2502154 A1 DE2502154 A1 DE 2502154A1 DE 19752502154 DE19752502154 DE 19752502154 DE 2502154 A DE2502154 A DE 2502154A DE 2502154 A1 DE2502154 A1 DE 2502154A1
- Authority
- DE
- Germany
- Prior art keywords
- carbon atoms
- parts
- group
- formula
- adduct
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 80
- 239000000835 fiber Substances 0.000 title claims description 24
- 230000002209 hydrophobic effect Effects 0.000 title claims description 10
- -1 alkyl radical Chemical class 0.000 claims description 70
- 125000004432 carbon atom Chemical group C* 0.000 claims description 61
- 125000000217 alkyl group Chemical group 0.000 claims description 31
- 238000004043 dyeing Methods 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 239000000975 dye Substances 0.000 claims description 21
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 239000000460 chlorine Substances 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 13
- 229910052801 chlorine Inorganic materials 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 239000003995 emulsifying agent Substances 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 10
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 9
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 239000000986 disperse dye Substances 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 150000002989 phenols Chemical class 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 2
- 150000001555 benzenes Chemical class 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 238000010016 exhaust dyeing Methods 0.000 claims description 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 2
- 150000003254 radicals Chemical class 0.000 claims 4
- LLLVZDVNHNWSDS-UHFFFAOYSA-N 4-methylidene-3,5-dioxabicyclo[5.2.2]undeca-1(9),7,10-triene-2,6-dione Chemical compound C1(C2=CC=C(C(=O)OC(=C)O1)C=C2)=O LLLVZDVNHNWSDS-UHFFFAOYSA-N 0.000 claims 1
- 150000005840 aryl radicals Chemical class 0.000 claims 1
- 230000005494 condensation Effects 0.000 claims 1
- 238000009833 condensation Methods 0.000 claims 1
- 235000021323 fish oil Nutrition 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 110
- 239000003921 oil Substances 0.000 description 73
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 58
- 235000019441 ethanol Nutrition 0.000 description 55
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
- 238000002156 mixing Methods 0.000 description 38
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 34
- 229910052938 sodium sulfate Inorganic materials 0.000 description 34
- 235000011152 sodium sulphate Nutrition 0.000 description 34
- DYBIGIADVHIODH-UHFFFAOYSA-N 2-nonylphenol;oxirane Chemical compound C1CO1.CCCCCCCCCC1=CC=CC=C1O DYBIGIADVHIODH-UHFFFAOYSA-N 0.000 description 28
- 238000004040 coloring Methods 0.000 description 18
- 229910052757 nitrogen Inorganic materials 0.000 description 17
- 239000000203 mixture Substances 0.000 description 14
- 239000000047 product Substances 0.000 description 11
- 239000007789 gas Substances 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 7
- 229920000728 polyester Polymers 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 5
- VIUIFWLCOJRYQF-UHFFFAOYSA-N 1-(2-benzyl-4-chlorophenoxy)propan-2-ol Chemical compound CC(O)COC1=CC=C(Cl)C=C1CC1=CC=CC=C1 VIUIFWLCOJRYQF-UHFFFAOYSA-N 0.000 description 4
- YQUQWHNMBPIWGK-UHFFFAOYSA-N 4-isopropylphenol Chemical compound CC(C)C1=CC=C(O)C=C1 YQUQWHNMBPIWGK-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 239000004744 fabric Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- ZQBAKBUEJOMQEX-UHFFFAOYSA-N phenyl salicylate Chemical compound OC1=CC=CC=C1C(=O)OC1=CC=CC=C1 ZQBAKBUEJOMQEX-UHFFFAOYSA-N 0.000 description 4
- JAXQBGLSXVAFMO-UHFFFAOYSA-N 2-[2-(4-cyclohexylphenoxy)ethoxy]ethanol Chemical compound C1=CC(OCCOCCO)=CC=C1C1CCCCC1 JAXQBGLSXVAFMO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000007046 ethoxylation reaction Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000012258 stirred mixture Substances 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 2
- YPBXFEZZIARTHS-UHFFFAOYSA-N 1-(2,4-dichlorophenoxy)propan-1-ol Chemical compound CCC(O)OC1=CC=C(Cl)C=C1Cl YPBXFEZZIARTHS-UHFFFAOYSA-N 0.000 description 2
- VVFYQBFGXTYSMW-UHFFFAOYSA-N 1-chloro-1-phenoxyethanol Chemical class CC(O)(Cl)OC1=CC=CC=C1 VVFYQBFGXTYSMW-UHFFFAOYSA-N 0.000 description 2
- GNGDSXKYHXETLB-UHFFFAOYSA-N 2-(2-benzylphenoxy)ethanol Chemical compound OCCOC1=CC=CC=C1CC1=CC=CC=C1 GNGDSXKYHXETLB-UHFFFAOYSA-N 0.000 description 2
- HGYJADMDWCVAIY-UHFFFAOYSA-N 2-(2-propan-2-ylphenoxy)ethanol Chemical compound CC(C)C1=CC=CC=C1OCCO HGYJADMDWCVAIY-UHFFFAOYSA-N 0.000 description 2
- XXYAWUVYASYUDE-UHFFFAOYSA-N 2-(4-chloro-2-propan-2-ylphenoxy)ethanol Chemical compound CC(C)C1=CC(Cl)=CC=C1OCCO XXYAWUVYASYUDE-UHFFFAOYSA-N 0.000 description 2
- FPKROJQUJYKRPV-UHFFFAOYSA-N 2-(4-ethylphenoxy)ethanol Chemical compound CCC1=CC=C(OCCO)C=C1 FPKROJQUJYKRPV-UHFFFAOYSA-N 0.000 description 2
- ZMWWUPALOIERNV-UHFFFAOYSA-N 2-(4-propan-2-ylphenoxy)ethanol Chemical compound CC(C)C1=CC=C(OCCO)C=C1 ZMWWUPALOIERNV-UHFFFAOYSA-N 0.000 description 2
- CPWZXPYBVCANNT-UHFFFAOYSA-N 2-(p-Cyclohexyl-phenoxy)ethanol Natural products C1=CC(OCCO)=CC=C1C1CCCCC1 CPWZXPYBVCANNT-UHFFFAOYSA-N 0.000 description 2
- VLOXWQVQELFSOB-UHFFFAOYSA-N 2-[2,6-di(butan-2-yl)phenoxy]ethanol Chemical compound CCC(C)C1=CC=CC(C(C)CC)=C1OCCO VLOXWQVQELFSOB-UHFFFAOYSA-N 0.000 description 2
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 2
- CRBJBYGJVIBWIY-UHFFFAOYSA-N 2-isopropylphenol Chemical compound CC(C)C1=CC=CC=C1O CRBJBYGJVIBWIY-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- CFKMVGJGLGKFKI-UHFFFAOYSA-N 4-chloro-m-cresol Chemical compound CC1=CC(O)=CC=C1Cl CFKMVGJGLGKFKI-UHFFFAOYSA-N 0.000 description 2
- 229920002284 Cellulose triacetate Polymers 0.000 description 2
- 229920000812 Crimplene Polymers 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 2
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 235000019445 benzyl alcohol Nutrition 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000001804 emulsifying effect Effects 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- VLJSLTNSFSOYQR-UHFFFAOYSA-N meta-isopropyl phenol Natural products CC(C)C1=CC=CC(O)=C1 VLJSLTNSFSOYQR-UHFFFAOYSA-N 0.000 description 2
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 2
- 229960000969 phenyl salicylate Drugs 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- QPVRKFOKCKORDP-UHFFFAOYSA-N 1,3-dimethylcyclohexa-2,4-dien-1-ol Chemical compound CC1=CC(C)(O)CC=C1 QPVRKFOKCKORDP-UHFFFAOYSA-N 0.000 description 1
- TUXPWIFOXNLDNJ-UHFFFAOYSA-N 1-(2-benzylphenoxy)ethanol Chemical compound CC(O)OC1=CC=CC=C1CC1=CC=CC=C1 TUXPWIFOXNLDNJ-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- MMALDENJQINSHY-UHFFFAOYSA-N 2,4,5-tri(propan-2-yl)phenol Chemical compound CC(C)C1=CC(C(C)C)=C(C(C)C)C=C1O MMALDENJQINSHY-UHFFFAOYSA-N 0.000 description 1
- HVFKKINZIWVNQG-UHFFFAOYSA-N 2,4,6-tri(propan-2-yl)phenol Chemical compound CC(C)C1=CC(C(C)C)=C(O)C(C(C)C)=C1 HVFKKINZIWVNQG-UHFFFAOYSA-N 0.000 description 1
- KEUMBYCOWGLRBQ-UHFFFAOYSA-N 2,4-di(propan-2-yl)phenol Chemical compound CC(C)C1=CC=C(O)C(C(C)C)=C1 KEUMBYCOWGLRBQ-UHFFFAOYSA-N 0.000 description 1
- FHTGJZOULSYEOB-UHFFFAOYSA-N 2,6-di(butan-2-yl)phenol Chemical compound CCC(C)C1=CC=CC(C(C)CC)=C1O FHTGJZOULSYEOB-UHFFFAOYSA-N 0.000 description 1
- MBBSUPCYATWRHO-UHFFFAOYSA-N 2-(2,3,5-trimethylphenoxy)ethanol Chemical compound CC1=CC(C)=C(C)C(OCCO)=C1 MBBSUPCYATWRHO-UHFFFAOYSA-N 0.000 description 1
- VGUYXVJASZMATM-UHFFFAOYSA-N 2-(2,4-dichloro-3,5-dimethylphenoxy)ethanol Chemical compound CC1=CC(OCCO)=C(Cl)C(C)=C1Cl VGUYXVJASZMATM-UHFFFAOYSA-N 0.000 description 1
- FCZXMAPGISKNAG-UHFFFAOYSA-N 2-(2-chloro-6-methylphenoxy)ethanol Chemical compound CC1=CC=CC(Cl)=C1OCCO FCZXMAPGISKNAG-UHFFFAOYSA-N 0.000 description 1
- NKNSHHXMFCVKFL-UHFFFAOYSA-N 2-(2-cyclooctylphenoxy)ethanol Chemical class OCCOC1=CC=CC=C1C1CCCCCCC1 NKNSHHXMFCVKFL-UHFFFAOYSA-N 0.000 description 1
- RTSGUXCRCGQWJD-UHFFFAOYSA-N 2-(2-cyclopentylphenoxy)ethanol Chemical compound OCCOC1=CC=CC=C1C1CCCC1 RTSGUXCRCGQWJD-UHFFFAOYSA-N 0.000 description 1
- PFIMUSALHVWGLC-UHFFFAOYSA-N 2-(2-ethylphenoxy)ethanol Chemical compound CCC1=CC=CC=C1OCCO PFIMUSALHVWGLC-UHFFFAOYSA-N 0.000 description 1
- KIAQEENWWYGTQH-UHFFFAOYSA-N 2-(2-heptylphenoxy)ethanol Chemical compound CCCCCCCC1=CC=CC=C1OCCO KIAQEENWWYGTQH-UHFFFAOYSA-N 0.000 description 1
- TZPGMPHLPCOZFD-UHFFFAOYSA-N 2-(2-tert-butyl-6-methylphenoxy)ethanol Chemical compound CC1=CC=CC(C(C)(C)C)=C1OCCO TZPGMPHLPCOZFD-UHFFFAOYSA-N 0.000 description 1
- UZXFXOSXXYLVMI-UHFFFAOYSA-N 2-(4-chloro-3,5-dimethylphenoxy)ethanol Chemical compound CC1=CC(OCCO)=CC(C)=C1Cl UZXFXOSXXYLVMI-UHFFFAOYSA-N 0.000 description 1
- BHNQPLPANNDEGL-UHFFFAOYSA-N 2-(4-octylphenoxy)ethanol Chemical compound CCCCCCCCC1=CC=C(OCCO)C=C1 BHNQPLPANNDEGL-UHFFFAOYSA-N 0.000 description 1
- KGPFHDDLZCYWAO-UHFFFAOYSA-N 2-(4-tert-butylphenoxy)ethanol Chemical compound CC(C)(C)C1=CC=C(OCCO)C=C1 KGPFHDDLZCYWAO-UHFFFAOYSA-N 0.000 description 1
- MJONFJRVFQBOPE-UHFFFAOYSA-N 2-[2,6-di(propan-2-yl)phenoxy]ethanol Chemical compound CC(C)C1=CC=CC(C(C)C)=C1OCCO MJONFJRVFQBOPE-UHFFFAOYSA-N 0.000 description 1
- MFRYURSIASLONB-UHFFFAOYSA-N 2-[2-(1-phenylethyl)phenoxy]ethanol Chemical compound C=1C=CC=C(OCCO)C=1C(C)C1=CC=CC=C1 MFRYURSIASLONB-UHFFFAOYSA-N 0.000 description 1
- QQTZEXKAMSUNBN-UHFFFAOYSA-N 2-[2-(2-phenylethenyl)phenoxy]ethanol Chemical class OCCOC1=CC=CC=C1C=CC1=CC=CC=C1 QQTZEXKAMSUNBN-UHFFFAOYSA-N 0.000 description 1
- LXRRLTDIQDKLSG-UHFFFAOYSA-N 2-[4-(1-methylcyclohexyl)phenoxy]ethanol Chemical compound C=1C=C(OCCO)C=CC=1C1(C)CCCCC1 LXRRLTDIQDKLSG-UHFFFAOYSA-N 0.000 description 1
- CDMGNVWZXRKJNS-UHFFFAOYSA-N 2-benzylphenol Chemical compound OC1=CC=CC=C1CC1=CC=CC=C1 CDMGNVWZXRKJNS-UHFFFAOYSA-N 0.000 description 1
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 1
- WZHMADCMYLSOMO-UHFFFAOYSA-N 2-cyclooctylphenol Chemical class OC1=CC=CC=C1C1CCCCCCC1 WZHMADCMYLSOMO-UHFFFAOYSA-N 0.000 description 1
- RYEOKUZOKVMDHY-UHFFFAOYSA-N 2-hydroxyethyl benzenecarboperoxoate Chemical compound OCCOOC(=O)C1=CC=CC=C1 RYEOKUZOKVMDHY-UHFFFAOYSA-N 0.000 description 1
- GSBICRJXEDSPTE-UHFFFAOYSA-N 2-phenoxy-1-phenylethanol Chemical compound C=1C=CC=CC=1C(O)COC1=CC=CC=C1 GSBICRJXEDSPTE-UHFFFAOYSA-N 0.000 description 1
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 1
- YYOQJBLGFMMRLJ-UHFFFAOYSA-N 3,5-di(propan-2-yl)phenol Chemical compound CC(C)C1=CC(O)=CC(C(C)C)=C1 YYOQJBLGFMMRLJ-UHFFFAOYSA-N 0.000 description 1
- GOLORTLGFDVFDW-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one Chemical compound C1=CC=C2NC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 GOLORTLGFDVFDW-UHFFFAOYSA-N 0.000 description 1
- OAHMVZYHIJQTQC-UHFFFAOYSA-N 4-cyclohexylphenol Chemical compound C1=CC(O)=CC=C1C1CCCCC1 OAHMVZYHIJQTQC-UHFFFAOYSA-N 0.000 description 1
- FBWSRAOCSJQZJA-UHFFFAOYSA-N 4-iminonaphthalen-1-one Chemical compound C1=CC=C2C(=N)C=CC(=O)C2=C1 FBWSRAOCSJQZJA-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 101100260565 Dictyostelium discoideum thyA gene Proteins 0.000 description 1
- 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 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000012932 acetate dye Substances 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 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
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 125000000522 cyclooctenyl group Chemical group C1(=CCCCCCC1)* 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000006182 dimethyl benzyl group Chemical group 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- FQMCMHQTSGVJIP-UHFFFAOYSA-N ethanol;2-(2-hydroxyethoxy)ethanol Chemical compound CCO.OCCOCCO FQMCMHQTSGVJIP-UHFFFAOYSA-N 0.000 description 1
- PZLGBVIKYPHZTH-UHFFFAOYSA-N ethene;2-nonylphenol Chemical group C=C.CCCCCCCCCC1=CC=CC=C1O PZLGBVIKYPHZTH-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229940013317 fish oils Drugs 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- DBNYMXPUYZOHQN-UHFFFAOYSA-N n'-[2-(octadecylamino)ethyl]ethane-1,2-diamine Chemical compound CCCCCCCCCCCCCCCCCCNCCNCCN DBNYMXPUYZOHQN-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 229960005323 phenoxyethanol Drugs 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- OLBCVFGFOZPWHH-UHFFFAOYSA-N propofol Chemical compound CC(C)C1=CC=CC(C(C)C)=C1O OLBCVFGFOZPWHH-UHFFFAOYSA-N 0.000 description 1
- 150000003902 salicylic acid esters Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 101150068774 thyX gene Proteins 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 150000003739 xylenols Chemical class 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
- D06P1/62—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds with sulfate, sulfonate, sulfenic or sulfinic groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2603—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen
- C08G65/2606—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups
- C08G65/2612—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups containing aromatic or arylaliphatic hydroxyl groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
- C08L71/02—Polyalkylene oxides
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
- D06P1/60—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing polyethers
- D06P1/613—Polyethers without nitrogen
- D06P1/6131—Addition products of hydroxyl groups-containing compounds with oxiranes
- D06P1/6135—Addition products of hydroxyl groups-containing compounds with oxiranes from aromatic alcohols or from phenols, naphthols
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
- D06P1/64—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
- D06P1/651—Compounds without nitrogen
- D06P1/65106—Oxygen-containing compounds
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/34—Material containing ester groups
- D06P3/36—Material containing ester groups using dispersed dyestuffs
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/34—Material containing ester groups
- D06P3/52—Polyesters
- D06P3/54—Polyesters using dispersed dyestuffs
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Dispersion Chemistry (AREA)
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB304274A GB1481862A (en) | 1974-01-23 | 1974-01-23 | Dyeing of hydrophobic fibres |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2502154A1 true DE2502154A1 (de) | 1975-07-24 |
Family
ID=9750859
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752502154 Pending DE2502154A1 (de) | 1974-01-23 | 1975-01-21 | Verfahren zum faerben von hydrophoben fasern |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS50111376A (en, 2012) |
| BE (2) | BE824646A (en, 2012) |
| CH (2) | CH65675A4 (en, 2012) |
| DE (1) | DE2502154A1 (en, 2012) |
| FR (1) | FR2258483B1 (en, 2012) |
| GB (1) | GB1481862A (en, 2012) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1979000116A1 (en) * | 1977-08-29 | 1979-03-08 | Siegfried Ag | New glycol compounds for lowering the lipid content |
| EP0002408A1 (fr) * | 1977-11-26 | 1979-06-13 | SOCIETE DE RECHERCHES INDUSTRIELLES S.O.R.I. Société anonyme dite: | Nouveaux composés phénoxy-alcanols substitués, leur procédé de préparation et leur application en thérapeutique |
| US4233026A (en) * | 1976-12-21 | 1980-11-11 | Hoechst Aktiengesellschaft | Reducing grinding time and compositions therefor |
| US4275068A (en) * | 1977-08-29 | 1981-06-23 | Siegfried Ag | Lipid lowering alkylene glycols and ester derivatives thereof |
| EP0035678A3 (de) * | 1980-03-05 | 1981-09-30 | BASF Aktiengesellschaft | Verfahren zum Färben von carrierfrei färbbaren Polyesterfasern |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3066352D1 (en) | 1979-05-04 | 1984-03-08 | Ciba Geigy Ag | Dyeing composition and processes for dyeing fabrics made of polyester or a polyester blend with cotton or wool |
| DE3734159A1 (de) * | 1987-10-09 | 1989-04-20 | Bayer Ag | Egalisiermittel |
-
1974
- 1974-01-23 GB GB304274A patent/GB1481862A/en not_active Expired
-
1975
- 1975-01-20 CH CH65675D patent/CH65675A4/xx unknown
- 1975-01-20 CH CH65675A patent/CH585813B5/xx not_active IP Right Cessation
- 1975-01-21 DE DE19752502154 patent/DE2502154A1/de active Pending
- 1975-01-22 FR FR7501956A patent/FR2258483B1/fr not_active Expired
- 1975-01-22 BE BE152598A patent/BE824646A/xx unknown
- 1975-01-22 BE BE152597A patent/BE824645A/xx unknown
- 1975-01-23 JP JP50009360A patent/JPS50111376A/ja active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4233026A (en) * | 1976-12-21 | 1980-11-11 | Hoechst Aktiengesellschaft | Reducing grinding time and compositions therefor |
| WO1979000116A1 (en) * | 1977-08-29 | 1979-03-08 | Siegfried Ag | New glycol compounds for lowering the lipid content |
| US4275068A (en) * | 1977-08-29 | 1981-06-23 | Siegfried Ag | Lipid lowering alkylene glycols and ester derivatives thereof |
| EP0002408A1 (fr) * | 1977-11-26 | 1979-06-13 | SOCIETE DE RECHERCHES INDUSTRIELLES S.O.R.I. Société anonyme dite: | Nouveaux composés phénoxy-alcanols substitués, leur procédé de préparation et leur application en thérapeutique |
| EP0035678A3 (de) * | 1980-03-05 | 1981-09-30 | BASF Aktiengesellschaft | Verfahren zum Färben von carrierfrei färbbaren Polyesterfasern |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2258483B1 (en, 2012) | 1978-03-10 |
| BE824646A (fr) | 1975-07-22 |
| AU7747275A (en) | 1976-07-22 |
| CH585813B5 (en, 2012) | 1977-03-15 |
| BE824645A (fr) | 1975-07-22 |
| GB1481862A (en) | 1977-08-03 |
| CH65675A4 (en, 2012) | 1976-03-15 |
| FR2258483A1 (en, 2012) | 1975-08-18 |
| JPS50111376A (en, 2012) | 1975-09-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0055401A1 (de) | Insektizide und akarizide Mittel und ihre Verwendung | |
| EP0491764A1 (de) | Benzophenonether-ester, verfahren zu ihrer herstellung, sowie ihre verwendung zur verbesserung der lichtstabilität von polyesterfärbungen. | |
| EP0382138B1 (de) | Hilfsmittelgemisch und seine Verwendung beim Färben von synthetischen Fasermaterialien | |
| DE2502154A1 (de) | Verfahren zum faerben von hydrophoben fasern | |
| EP0207002A2 (de) | Entschäumungsmittel für wässrige Systeme und ihre Verwendung | |
| DE3112427A1 (de) | Marineblaue farbstoffmischungen | |
| EP0032188A1 (de) | Oberflächenaktive Verbindungen auf Basis arylierter Fettkörper und deren Verwendung | |
| US4255152A (en) | Process for the dyeing of hydrophobic fibres | |
| EP0403718A2 (de) | Styroloxid-Produkte | |
| EP0009126B1 (de) | 1,3-Bisarylglycerinäther und deren Verwendung | |
| DE2630988C2 (de) | Azofarbstoffe | |
| EP0378048A1 (de) | Styroloxid-Anlagerungsprodukte | |
| EP0064029B1 (de) | Hilfsmittelgemisch und seine Verwendung als Faltenfreimittel beim Färben oder optischen Aufhellen von Polyesterfasern enthaltenden Textilmaterialien | |
| EP0323401B1 (de) | Wässrige Dispersion eines metallisierbaren Farbstoffes | |
| EP0064030B1 (de) | Färbereihilfsmittelgemisch und seine Verwendung beim Färben von synthetischen Fasermaterialien | |
| EP0414631A1 (de) | Hilfsmittelgemisch und seine Verwendung beim Färben von Polyesterfasermaterialien | |
| DE2830154C2 (de) | Azofarbstoffe | |
| DE1569664C3 (de) | Phthaloperinonfarbstoffe und Verfahren zu ihrer Herstellung | |
| CH635856A5 (de) | Neue disazofarbstoffe und deren herstellung. | |
| DE3247400C2 (en, 2012) | ||
| DE1288066B (en, 2012) | ||
| EP0420807A1 (de) | Anlagerungsprodukte von Alkylenoxid und Styroloxid an Arylalkanole | |
| DE3246383C2 (en, 2012) | ||
| DE4026255A1 (de) | Sulfogruppenhaltige aromatische verbindungen, deren herstellung und verwendung | |
| DE1802210C3 (de) | Emulgiermittel fur wasserunlos liehe Carrier fur das Farben und Be drucken von synthetischen Fasern |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHN | Withdrawal |