JPH0423031B2 - - Google Patents
Info
- Publication number
- JPH0423031B2 JPH0423031B2 JP2207964A JP20796490A JPH0423031B2 JP H0423031 B2 JPH0423031 B2 JP H0423031B2 JP 2207964 A JP2207964 A JP 2207964A JP 20796490 A JP20796490 A JP 20796490A JP H0423031 B2 JPH0423031 B2 JP H0423031B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- hydrogen atom
- alkyl group
- unsubstituted
- 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 - Lifetime
Links
- 239000000975 dye Substances 0.000 claims description 50
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 45
- 150000001875 compounds Chemical class 0.000 claims description 41
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 38
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 32
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 32
- 238000000034 method Methods 0.000 claims description 28
- 238000004043 dyeing Methods 0.000 claims description 26
- 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 23
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 20
- 239000004744 fabric Substances 0.000 claims description 15
- 239000000984 vat dye Substances 0.000 claims description 14
- -1 β-naphthyl group Chemical group 0.000 claims description 14
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 12
- 239000000988 sulfur dye Substances 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 239000000463 material Substances 0.000 claims description 8
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 7
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 7
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 150000001768 cations Chemical class 0.000 claims description 4
- 229920002678 cellulose Polymers 0.000 claims description 4
- 239000001913 cellulose Substances 0.000 claims description 4
- 229920000728 polyester Polymers 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 229910006069 SO3H Inorganic materials 0.000 claims 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims 3
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims 3
- 238000001238 wet grinding Methods 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 239000000203 mixture Substances 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 229920000742 Cotton Polymers 0.000 description 11
- 239000006185 dispersion Substances 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- 238000010186 staining Methods 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- TXFPEBPIARQUIG-UHFFFAOYSA-N 4'-hydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1 TXFPEBPIARQUIG-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 6
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 6
- NCKMMSIFQUPKCK-UHFFFAOYSA-N 2-benzyl-4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1CC1=CC=CC=C1 NCKMMSIFQUPKCK-UHFFFAOYSA-N 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- NVBMUOYFLVUZJU-UHFFFAOYSA-N propane-1,2-diol;sulfurous acid Chemical compound OS(O)=O.CC(O)CO NVBMUOYFLVUZJU-UHFFFAOYSA-N 0.000 description 5
- 159000000000 sodium salts Chemical class 0.000 description 5
- CFKMVGJGLGKFKI-UHFFFAOYSA-N 4-chloro-m-cresol Chemical compound CC1=CC(O)=CC=C1Cl CFKMVGJGLGKFKI-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 238000004048 vat dyeing Methods 0.000 description 4
- KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 description 3
- JZODKRWQWUWGCD-UHFFFAOYSA-N 2,5-di-tert-butylbenzene-1,4-diol Chemical compound CC(C)(C)C1=CC(O)=C(C(C)(C)C)C=C1O JZODKRWQWUWGCD-UHFFFAOYSA-N 0.000 description 3
- 229940073735 4-hydroxy acetophenone Drugs 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000004056 anthraquinones Chemical class 0.000 description 3
- 229940116901 diethyldithiocarbamate Drugs 0.000 description 3
- LMBWSYZSUOEYSN-UHFFFAOYSA-N diethyldithiocarbamic acid Chemical compound CCN(CC)C(S)=S LMBWSYZSUOEYSN-UHFFFAOYSA-N 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 238000010025 steaming Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- ULUIMLJNTCECJU-UHFFFAOYSA-N 3-amino-4-hydroxybenzenesulfonate;hydron Chemical compound NC1=CC(S(O)(=O)=O)=CC=C1O ULUIMLJNTCECJU-UHFFFAOYSA-N 0.000 description 2
- MDWVSAYEQPLWMX-UHFFFAOYSA-N 4,4'-Methylenebis(2,6-di-tert-butylphenol) Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 MDWVSAYEQPLWMX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 150000001336 alkenes Chemical group 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- VDEUYMSGMPQMIK-UHFFFAOYSA-N benzhydroxamic acid Chemical compound ONC(=O)C1=CC=CC=C1 VDEUYMSGMPQMIK-UHFFFAOYSA-N 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 229910001385 heavy metal Inorganic materials 0.000 description 2
- 239000003906 humectant Substances 0.000 description 2
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 150000002736 metal compounds Chemical class 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 238000003801 milling Methods 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- OIPPWFOQEKKFEE-UHFFFAOYSA-N orcinol Chemical compound CC1=CC(O)=CC(O)=C1 OIPPWFOQEKKFEE-UHFFFAOYSA-N 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 229920000768 polyamine Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000009958 sewing Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- YUKQRDCYNOVPGJ-UHFFFAOYSA-N thioacetamide Chemical compound CC(N)=S YUKQRDCYNOVPGJ-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 1
- YHOMKYYXCBXANK-UHFFFAOYSA-N 2,3-di(pentan-2-yl)phenol Chemical compound CCCC(C)C1=CC=CC(O)=C1C(C)CCC YHOMKYYXCBXANK-UHFFFAOYSA-N 0.000 description 1
- CZNRFEXEPBITDS-UHFFFAOYSA-N 2,5-bis(2-methylbutan-2-yl)benzene-1,4-diol Chemical compound CCC(C)(C)C1=CC(O)=C(C(C)(C)CC)C=C1O CZNRFEXEPBITDS-UHFFFAOYSA-N 0.000 description 1
- HNURKXXMYARGAY-UHFFFAOYSA-N 2,6-Di-tert-butyl-4-hydroxymethylphenol Chemical class CC(C)(C)C1=CC(CO)=CC(C(C)(C)C)=C1O HNURKXXMYARGAY-UHFFFAOYSA-N 0.000 description 1
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- MQWCQFCZUNBTCM-UHFFFAOYSA-N 2-tert-butyl-6-(3-tert-butyl-2-hydroxy-5-methylphenyl)sulfanyl-4-methylphenol Chemical compound CC(C)(C)C1=CC(C)=CC(SC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O MQWCQFCZUNBTCM-UHFFFAOYSA-N 0.000 description 1
- 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 1
- LSEHCENPUMUIKC-UHFFFAOYSA-N 4-cyclohexylbenzene-1,3-diol Chemical compound OC1=CC(O)=CC=C1C1CCCCC1 LSEHCENPUMUIKC-UHFFFAOYSA-N 0.000 description 1
- QNTARNCGFNQQRP-UHFFFAOYSA-N 5-carbamothioylsulfanylpentyl carbamodithioate Chemical compound NC(=S)SCCCCCSC(N)=S QNTARNCGFNQQRP-UHFFFAOYSA-N 0.000 description 1
- HUKPVYBUJRAUAG-UHFFFAOYSA-N 7-benzo[a]phenalenone Chemical group C1=CC(C(=O)C=2C3=CC=CC=2)=C2C3=CC=CC2=C1 HUKPVYBUJRAUAG-UHFFFAOYSA-N 0.000 description 1
- MDNWOSOZYLHTCG-UHFFFAOYSA-N Dichlorophen Chemical compound OC1=CC=C(Cl)C=C1CC1=CC(Cl)=CC=C1O MDNWOSOZYLHTCG-UHFFFAOYSA-N 0.000 description 1
- VLCDUOXHFNUCKK-UHFFFAOYSA-N N,N'-Dimethylthiourea Chemical compound CNC(=S)NC VLCDUOXHFNUCKK-UHFFFAOYSA-N 0.000 description 1
- UTGQNNCQYDRXCH-UHFFFAOYSA-N N,N'-diphenyl-1,4-phenylenediamine Chemical compound C=1C=C(NC=2C=CC=CC=2)C=CC=1NC1=CC=CC=C1 UTGQNNCQYDRXCH-UHFFFAOYSA-N 0.000 description 1
- 229930192627 Naphthoquinone Natural products 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- 235000002597 Solanum melongena Nutrition 0.000 description 1
- 244000061458 Solanum melongena Species 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- BGNXCDMCOKJUMV-UHFFFAOYSA-N Tert-Butylhydroquinone Chemical compound CC(C)(C)C1=CC(O)=CC=C1O BGNXCDMCOKJUMV-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- FZEYVTFCMJSGMP-UHFFFAOYSA-N acridone Chemical class C1=CC=C2C(=O)C3=CC=CC=C3NC2=C1 FZEYVTFCMJSGMP-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 description 1
- BSXBWLBCNVXEQB-UHFFFAOYSA-N anthracene-9,10-dione;1,3-oxazole Chemical class C1=COC=N1.C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 BSXBWLBCNVXEQB-UHFFFAOYSA-N 0.000 description 1
- BEQBQOAWTXSRIB-UHFFFAOYSA-N anthracene-9,10-dione;1,3-thiazole Chemical class C1=CSC=N1.C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 BEQBQOAWTXSRIB-UHFFFAOYSA-N 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000004054 benzoquinones Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 229910052593 corundum Inorganic materials 0.000 description 1
- 239000010431 corundum Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 1
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- SZRLKIKBPASKQH-UHFFFAOYSA-M dibutyldithiocarbamate Chemical class CCCCN(C([S-])=S)CCCC SZRLKIKBPASKQH-UHFFFAOYSA-M 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- MZGNSEAPZQGJRB-UHFFFAOYSA-N dimethyldithiocarbamic acid Chemical class CN(C)C(S)=S MZGNSEAPZQGJRB-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- AWYFNIZYMPNGAI-UHFFFAOYSA-L ethylenebis(dithiocarbamate) Chemical compound [S-]C(=S)NCCNC([S-])=S AWYFNIZYMPNGAI-UHFFFAOYSA-L 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 150000003949 imides Chemical group 0.000 description 1
- 235000019239 indanthrene blue RS Nutrition 0.000 description 1
- UHOKSCJSTAHBSO-UHFFFAOYSA-N indanthrone blue Chemical compound C1=CC=C2C(=O)C3=CC=C4NC5=C6C(=O)C7=CC=CC=C7C(=O)C6=CC=C5NC4=C3C(=O)C2=C1 UHOKSCJSTAHBSO-UHFFFAOYSA-N 0.000 description 1
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- BSIHWSXXPBAGTC-UHFFFAOYSA-N isoviolanthrone Chemical group C12=CC=CC=C2C(=O)C2=CC=C3C(C4=C56)=CC=C5C5=CC=CC=C5C(=O)C6=CC=C4C4=C3C2=C1C=C4 BSIHWSXXPBAGTC-UHFFFAOYSA-N 0.000 description 1
- 238000009981 jet dyeing Methods 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- VYQNWZOUAUKGHI-UHFFFAOYSA-N monobenzone Chemical compound C1=CC(O)=CC=C1OCC1=CC=CC=C1 VYQNWZOUAUKGHI-UHFFFAOYSA-N 0.000 description 1
- 229960000990 monobenzone Drugs 0.000 description 1
- NOUUUQMKVOUUNR-UHFFFAOYSA-N n,n'-diphenylethane-1,2-diamine Chemical compound C=1C=CC=CC=1NCCNC1=CC=CC=C1 NOUUUQMKVOUUNR-UHFFFAOYSA-N 0.000 description 1
- 125000006606 n-butoxy group Chemical group 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 150000002791 naphthoquinones Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- UKODFQOELJFMII-UHFFFAOYSA-N pentamethyldiethylenetriamine Chemical compound CN(C)CCN(C)CCN(C)C UKODFQOELJFMII-UHFFFAOYSA-N 0.000 description 1
- WSRHMJYUEZHUCM-UHFFFAOYSA-N perylene-1,2,3,4-tetracarboxylic acid Chemical class C=12C3=CC=CC2=CC=CC=1C1=C(C(O)=O)C(C(O)=O)=C(C(O)=O)C2=C1C3=CC=C2C(=O)O WSRHMJYUEZHUCM-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- XWGJFPHUCFXLBL-UHFFFAOYSA-M rongalite Chemical compound [Na+].OCS([O-])=O XWGJFPHUCFXLBL-UHFFFAOYSA-M 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- UOULCEYHQNCFFH-UHFFFAOYSA-M sodium;hydroxymethanesulfonate Chemical compound [Na+].OCS([O-])(=O)=O UOULCEYHQNCFFH-UHFFFAOYSA-M 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000007447 staining method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000004250 tert-Butylhydroquinone Substances 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- 235000019281 tert-butylhydroquinone Nutrition 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 150000003556 thioamides Chemical class 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- LUUMBHMWFNNZPH-UHFFFAOYSA-N tris(3,5-ditert-butyl-4-hydroxyphenyl) phosphite Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(OP(OC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)OC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 LUUMBHMWFNNZPH-UHFFFAOYSA-N 0.000 description 1
- UGCDBQWJXSAYIL-UHFFFAOYSA-N vat blue 6 Chemical compound O=C1C2=CC=CC=C2C(=O)C(C=C2Cl)=C1C1=C2NC2=C(C(=O)C=3C(=CC=CC=3)C3=O)C3=CC(Cl)=C2N1 UGCDBQWJXSAYIL-UHFFFAOYSA-N 0.000 description 1
- YKSGNOMLAIJTLT-UHFFFAOYSA-N violanthrone Chemical group C12=C3C4=CC=C2C2=CC=CC=C2C(=O)C1=CC=C3C1=CC=C2C(=O)C3=CC=CC=C3C3=CC=C4C1=C32 YKSGNOMLAIJTLT-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 150000003751 zinc 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
- D06P1/22—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 vat dyestuffs including indigo
- D06P1/221—Reducing systems; Reducing catalysts
-
- 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
- D06P1/30—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 sulfur dyes
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Coloring (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH964480 | 1980-12-30 | ||
| CH9644/80-6 | 1980-12-30 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP56216091A Division JPS57133281A (en) | 1980-12-30 | 1981-12-29 | Vat dye or sulfur dye preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0376876A JPH0376876A (ja) | 1991-04-02 |
| JPH0423031B2 true JPH0423031B2 (enExample) | 1992-04-21 |
Family
ID=4354139
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP56216091A Granted JPS57133281A (en) | 1980-12-30 | 1981-12-29 | Vat dye or sulfur dye preparation |
| JP2207964A Granted JPH0376876A (ja) | 1980-12-30 | 1990-08-06 | バツト染料または硫化染料用染浴または捺染ペースト |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP56216091A Granted JPS57133281A (en) | 1980-12-30 | 1981-12-29 | Vat dye or sulfur dye preparation |
Country Status (5)
| Country | Link |
|---|---|
| US (2) | US4519805A (enExample) |
| EP (1) | EP0055694B1 (enExample) |
| JP (2) | JPS57133281A (enExample) |
| DE (1) | DE3174788D1 (enExample) |
| ZA (1) | ZA818967B (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3704125A1 (de) * | 1987-02-11 | 1988-08-25 | Basf Ag | Verwendung von cyclischen estern der schwefligen saeure beim faerben von textilmaterialien aus polyamid und verfahren zum faerben |
| JPS63271963A (ja) * | 1987-04-28 | 1988-11-09 | Nec Corp | 半導体装置の製造方法 |
| US4886518A (en) * | 1987-10-01 | 1989-12-12 | Ciba-Geigy Corporation | Dyeing cellulose fibres without incurring ending with colorless pyrimidine, triazine, aromatic, furfuryl or quinolinyl compound |
| JPH07103056B2 (ja) * | 1989-02-08 | 1995-11-08 | 大塚製薬株式会社 | 神経細胞変性修復又は保護剤 |
| US5108505A (en) * | 1990-05-16 | 1992-04-28 | Hewlett-Packard Company | Waterfast inks via cyclodextrin inclusion complex |
| IT1271814B (it) * | 1994-12-28 | 1997-06-09 | Alpi Spa | Tintura di fogli di legno mediante coloranti appartenenti alla classe "al tino". |
| US5961670A (en) * | 1995-05-03 | 1999-10-05 | Clariant Finance (Bvi) Limited | Sulfur dyes |
| ID27444A (id) | 1998-06-23 | 2001-04-12 | Henkel Ommanditgesellschaft Au | Zat pewarna |
| CN104372685A (zh) * | 2014-12-05 | 2015-02-25 | 江苏太子鳄服饰有限公司 | 布料的耐洗印染方法 |
Family Cites Families (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1130908A (enExample) * | ||||
| US1803219A (en) * | 1931-04-28 | Formerly saostooz | ||
| GB354777A (en) * | 1930-03-10 | 1931-08-10 | James Morton | Improvements in and relating to dyeing with vat dyestuffs |
| US2074150A (en) * | 1934-05-01 | 1937-03-16 | Nat Aniline & Chem Co Inc | Vat dye assistants and method of using |
| US2069215A (en) * | 1934-08-18 | 1937-02-02 | Du Pont | Printing process and composition therefor |
| CH192294A (de) * | 1936-01-15 | 1937-07-31 | Chem Ind Basel | Präparat zum Drucken von Textilstoffen. |
| US2087866A (en) * | 1937-03-17 | 1937-07-20 | Du Pont | Vat dyestuff preparations |
| FR835854A (fr) * | 1937-03-30 | 1939-01-05 | Durand & Huguenin Sa | Procédé pour la teinture et l'impression de la soie naturelle avec les éthersels de dérivés leuconiques de colorants à cuve |
| US2256806A (en) * | 1938-11-28 | 1941-09-23 | Nat Aniline & Chem Co Inc | Vat dye composition |
| US2256809A (en) * | 1938-11-28 | 1941-09-23 | Nat Aniline & Chem Co Inc | Production of resist effects |
| GB616440A (en) * | 1946-11-02 | 1949-01-21 | Alan Stanley Pern | Process for dyeing |
| DE912450C (de) * | 1951-12-18 | 1954-05-31 | Bayer Ag | Verfahren zum Faerben oder Bedrucken von Acrylnitrilpolymerisaten mit Kuepenfabstoffen |
| DE896335C (de) * | 1951-12-29 | 1953-11-12 | Basf Ag | Verfahren zum Verkuepen von Kuepenfarbstoffen |
| FR1068097A (fr) * | 1952-10-03 | 1954-06-22 | Southern Dyestuff Corp | Colorants de cuve liquides concentrés |
| US2852331A (en) * | 1955-06-01 | 1958-09-16 | Gen Aniline & Film Corp | Low viscosity stabilized vat dye pastes |
| US2893813A (en) * | 1956-07-31 | 1959-07-07 | Gen Aniline & Film Corp | Indo-carbon black dyestuff compositions |
| US2921830A (en) * | 1956-07-31 | 1960-01-19 | Gen Aniline & Film Corp | Hydron blue dyestuff compositions |
| BE571349A (enExample) * | 1957-09-19 | |||
| DE1086209B (de) * | 1959-04-18 | 1960-08-04 | Basf Ag | Druckpasten für das Direkt- oder Ätzdruckverfahren |
| NL254607A (enExample) * | 1959-08-08 | |||
| DE1163284B (de) * | 1960-10-15 | 1964-02-20 | Hoechst Ag | Verwendung von Methylendiarylverbindungen als Dispergiermittel fuer in Wasser unloesliche oder schwer loesliche Farbstoffe |
| DE1286499B (de) * | 1962-01-25 | 1969-01-09 | Bayer Ag | Egalisiermittel fuer das Faerben von Polyestergebilden |
| US3201190A (en) * | 1962-05-28 | 1965-08-17 | Eastman Kodak Co | Dyed cellulose ester textile materials resistant to chlorine fading |
| GB982500A (en) * | 1963-07-12 | 1965-02-03 | Metal Hydrides Inc | Improvements in dyeing with acid leuco vat dyes |
| FR1393050A (fr) * | 1964-05-11 | 1965-03-19 | Hoechst Ag | Procédé de teinture et d'impression de matières textiles en fibres de cellulose naturelle ou régénérée |
| US3532455A (en) * | 1967-09-19 | 1970-10-06 | American Cyanamid Co | Method for producing sulfurized vat dyes by thionation and products thereof |
| DE2229130A1 (de) * | 1972-06-15 | 1974-01-10 | Basf Ag | Schnellfixierverfahren zum kontinuierlichen faerben von stoffbahnen aus cellulose enthaltendem fasermaterial mit kuepenfarbstoffen |
| DE2350961A1 (de) * | 1973-10-11 | 1975-04-24 | Basf Ag | Reduktionsmittelkombination zum einbadigen faerben von cellulose enthaltendem textilmaterial mit kuepen- und/oder schwefelfarbstoffen |
| DE2356548A1 (de) * | 1973-11-13 | 1975-06-26 | Cassella Farbwerke Mainkur Ag | Verfahren zum faerben von polyamidfasern mit schwefelfarbstoffen |
| DE2416300A1 (de) * | 1974-04-04 | 1975-10-16 | Cassella Farbwerke Mainkur Ag | Verfahren zum faerben von zellulosehaltigen textilmaterialien mit schwefelfarbstoffen |
| CH598404B5 (enExample) * | 1975-04-04 | 1978-04-28 | Ciba Geigy Ag | |
| DE2525021A1 (de) * | 1975-06-05 | 1976-12-23 | Hoechst Ag | Verfahren und mittel zur herstellung von direktdrucken und buntaetzen mit kuepen- oder schwefelfarbstoffen |
| DE2628903A1 (de) * | 1976-06-28 | 1978-01-05 | Boc Ltd | Dithionit-stabilisator-zubereitung, verfahren zu ihrer herstellung und verwendung des stabilisators in der zubereitung |
| DE2657774C2 (de) * | 1976-12-21 | 1982-06-16 | Hoechst Ag, 6000 Frankfurt | Verwendung eines wasserlöslichen nicht-ionogenen Polyglykoläthers als Mahlhilfsmittel und wäßrige Zubereitungen von in Wasser schwer- bis unlöslichen Farbstoffen |
| DE2901461A1 (de) * | 1979-01-16 | 1980-07-24 | Hoechst Ag | Verwendung oxalkylierter novolakharze als praeparationsmittel fuer dispersionsfarbstoffe und damit hergestellte zubereitungen |
| GB2114166B (en) * | 1982-02-03 | 1985-08-14 | Sandoz Ltd | Level dyeing of polyester materials |
-
1981
- 1981-12-22 DE DE8181810513T patent/DE3174788D1/de not_active Expired
- 1981-12-22 EP EP81810513A patent/EP0055694B1/de not_active Expired
- 1981-12-29 US US06/335,428 patent/US4519805A/en not_active Expired - Fee Related
- 1981-12-29 JP JP56216091A patent/JPS57133281A/ja active Granted
- 1981-12-29 ZA ZA818967A patent/ZA818967B/xx unknown
-
1988
- 1988-03-08 US US07/169,093 patent/US4886549A/en not_active Expired - Fee Related
-
1990
- 1990-08-06 JP JP2207964A patent/JPH0376876A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0329827B2 (enExample) | 1991-04-25 |
| ZA818967B (en) | 1982-11-24 |
| DE3174788D1 (en) | 1986-07-10 |
| JPS57133281A (en) | 1982-08-17 |
| EP0055694A3 (en) | 1983-01-19 |
| EP0055694A2 (de) | 1982-07-07 |
| EP0055694B1 (de) | 1986-06-04 |
| US4886549A (en) | 1989-12-12 |
| JPH0376876A (ja) | 1991-04-02 |
| US4519805A (en) | 1985-05-28 |
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