DE1644498A1 - Verfahren zur Herstellung wasserunloeslicher Anthrachinonfarbstoffe - Google Patents
Verfahren zur Herstellung wasserunloeslicher AnthrachinonfarbstoffeInfo
- Publication number
- DE1644498A1 DE1644498A1 DE19651644498 DE1644498A DE1644498A1 DE 1644498 A1 DE1644498 A1 DE 1644498A1 DE 19651644498 DE19651644498 DE 19651644498 DE 1644498 A DE1644498 A DE 1644498A DE 1644498 A1 DE1644498 A1 DE 1644498A1
- Authority
- DE
- Germany
- Prior art keywords
- parts
- acid
- dihydroxy
- diamino
- dye
- 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 14
- 238000002360 preparation method Methods 0.000 title claims description 7
- 239000001000 anthraquinone dye Substances 0.000 title claims description 4
- -1 anthraquinone radical Chemical class 0.000 claims description 21
- IYHIKYZDSVTAPF-UHFFFAOYSA-N 1,2-diamino-3,4-dihydroxyanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(N)=C(N)C(O)=C2O IYHIKYZDSVTAPF-UHFFFAOYSA-N 0.000 claims description 11
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 9
- 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 claims description 5
- 125000005041 acyloxyalkyl group Chemical group 0.000 claims description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 150000008064 anhydrides Chemical class 0.000 claims description 3
- 150000005840 aryl radicals Chemical class 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 claims description 2
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical compound OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 2
- 229960004365 benzoic acid Drugs 0.000 claims 1
- 235000010233 benzoic acid Nutrition 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 239000000975 dye Substances 0.000 description 47
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 34
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
- 239000000835 fiber Substances 0.000 description 14
- 239000000047 product Substances 0.000 description 13
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 229920000728 polyester Polymers 0.000 description 12
- 238000000859 sublimation Methods 0.000 description 11
- 230000008022 sublimation Effects 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 238000004043 dyeing Methods 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 229920000742 Cotton Polymers 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 239000003513 alkali Substances 0.000 description 6
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- ORFSSYGWXNGVFB-UHFFFAOYSA-N sodium 4-amino-6-[[4-[4-[(8-amino-1-hydroxy-5,7-disulfonaphthalen-2-yl)diazenyl]-3-methoxyphenyl]-2-methoxyphenyl]diazenyl]-5-hydroxynaphthalene-1,3-disulfonic acid Chemical compound COC1=C(C=CC(=C1)C2=CC(=C(C=C2)N=NC3=C(C4=C(C=C3)C(=CC(=C4N)S(=O)(=O)O)S(=O)(=O)O)O)OC)N=NC5=C(C6=C(C=C5)C(=CC(=C6N)S(=O)(=O)O)S(=O)(=O)O)O.[Na+] ORFSSYGWXNGVFB-UHFFFAOYSA-N 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- SVDDJQGVOFZBNX-UHFFFAOYSA-N 2-chloroethyl carbonochloridate Chemical compound ClCCOC(Cl)=O SVDDJQGVOFZBNX-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 235000011054 acetic acid Nutrition 0.000 description 4
- 150000004056 anthraquinones Chemical class 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 239000004744 fabric Substances 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 229920000139 polyethylene terephthalate Polymers 0.000 description 3
- 239000005020 polyethylene terephthalate Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 3
- 239000002699 waste material Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- 229920003043 Cellulose fiber Polymers 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical compound OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 description 2
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 238000003801 milling Methods 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000001256 steam distillation Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000000542 sulfonic acid group Chemical group 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- 239000000984 vat dye Substances 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- YYTSGNJTASLUOY-UHFFFAOYSA-N 1-chloropropan-2-ol Chemical compound CC(O)CCl YYTSGNJTASLUOY-UHFFFAOYSA-N 0.000 description 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- WAXMTENYNOYEBU-UHFFFAOYSA-N 1-phenylanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C1=CC=CC=C1 WAXMTENYNOYEBU-UHFFFAOYSA-N 0.000 description 1
- NOGFHTGYPKWWRX-UHFFFAOYSA-N 2,2,6,6-tetramethyloxan-4-one Chemical compound CC1(C)CC(=O)CC(C)(C)O1 NOGFHTGYPKWWRX-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- VZIQXGLTRZLBEX-UHFFFAOYSA-N 2-chloro-1-propanol Chemical compound CC(Cl)CO VZIQXGLTRZLBEX-UHFFFAOYSA-N 0.000 description 1
- FTOKYBLHOYVORA-UHFFFAOYSA-N 2-chlorobutan-1-ol Chemical compound CCC(Cl)CO FTOKYBLHOYVORA-UHFFFAOYSA-N 0.000 description 1
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 1
- LAMUXTNQCICZQX-UHFFFAOYSA-N 3-chloropropan-1-ol Chemical compound OCCCCl LAMUXTNQCICZQX-UHFFFAOYSA-N 0.000 description 1
- MTXMEFUEBCFWCY-UHFFFAOYSA-N 3-chloropropyl carbonochloridate Chemical compound ClCCCOC(Cl)=O MTXMEFUEBCFWCY-UHFFFAOYSA-N 0.000 description 1
- MOLVDYADKVCUCB-UHFFFAOYSA-N 4,8-diamino-1,5-dihydroxy-2-(4-hydroxyphenyl)anthracene-9,10-dione Chemical compound OC1=C2C(=O)C=3C(N)=CC=C(O)C=3C(=O)C2=C(N)C=C1C1=CC=C(O)C=C1 MOLVDYADKVCUCB-UHFFFAOYSA-N 0.000 description 1
- DXPPIPWXPIZBTD-UHFFFAOYSA-N 4,8-diamino-2-(5-cyclohexyl-2-hydroxyphenyl)-1,5-dihydroxyanthracene-9,10-dione Chemical compound OC1=C(C=C(C=2C(C3=C(C=CC(=C3C(C12)=O)N)O)=O)N)C1=C(C=CC(=C1)C1CCCCC1)O DXPPIPWXPIZBTD-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- RZVHIXYEVGDQDX-UHFFFAOYSA-N 9,10-anthraquinone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 RZVHIXYEVGDQDX-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- PLFAADCTFJTHOV-UHFFFAOYSA-N NC1=CC(=C(O)C2=C1C(=O)C1=C(O)C=CC(N)=C1C2=O)C1=C(O)C=CC(=C1)C1=CC=CC=C1 Chemical compound NC1=CC(=C(O)C2=C1C(=O)C1=C(O)C=CC(N)=C1C2=O)C1=C(O)C=CC(=C1)C1=CC=CC=C1 PLFAADCTFJTHOV-UHFFFAOYSA-N 0.000 description 1
- YZZUGWPXUAIYBR-UHFFFAOYSA-N OC1=C(C=C(C=2C(C3=C(C=CC(=C3C(C12)=O)N)O)=O)N)C1=CC(=C(C=C1)O)C1=CC=CC=C1 Chemical compound OC1=C(C=C(C=2C(C3=C(C=CC(=C3C(C12)=O)N)O)=O)N)C1=CC(=C(C=C1)O)C1=CC=CC=C1 YZZUGWPXUAIYBR-UHFFFAOYSA-N 0.000 description 1
- YRLXZPWCPITLLH-UHFFFAOYSA-N OC1=C(C=C(C=2C(C3=C(C=CC(=C3C(C12)=O)N)O)=O)N)C1=CC(=C(C=C1)O)Cl Chemical compound OC1=C(C=C(C=2C(C3=C(C=CC(=C3C(C12)=O)N)O)=O)N)C1=CC(=C(C=C1)O)Cl YRLXZPWCPITLLH-UHFFFAOYSA-N 0.000 description 1
- KJSMWTXEIOQAIE-UHFFFAOYSA-N OC1=C(C=C(C=2C(C3=C(C=CC(=C3C(C12)=O)N)O)=O)N)C1=CC(=C(C=C1)O)O Chemical compound OC1=C(C=C(C=2C(C3=C(C=CC(=C3C(C12)=O)N)O)=O)N)C1=CC(=C(C=C1)O)O KJSMWTXEIOQAIE-UHFFFAOYSA-N 0.000 description 1
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- 229910019142 PO4 Inorganic materials 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- UCEYQFLQQSRUIE-UHFFFAOYSA-N [ClH]1NN=CC=C1 Chemical group [ClH]1NN=CC=C1 UCEYQFLQQSRUIE-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000005224 alkoxybenzenes Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 1
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- 125000004432 carbon atom Chemical group C* 0.000 description 1
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- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 229940106681 chloroacetic acid Drugs 0.000 description 1
- 229930016911 cinnamic acid Natural products 0.000 description 1
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- 239000003086 colorant Substances 0.000 description 1
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- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
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- 238000001035 drying Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
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- 239000012065 filter cake Substances 0.000 description 1
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- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
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- 238000009998 heat setting Methods 0.000 description 1
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- 239000012433 hydrogen halide Substances 0.000 description 1
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- 150000005204 hydroxybenzenes Chemical class 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- RMIODHQZRUFFFF-UHFFFAOYSA-N methoxyacetic acid Chemical compound COCC(O)=O RMIODHQZRUFFFF-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical class O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- 229960003424 phenylacetic acid Drugs 0.000 description 1
- 239000003279 phenylacetic acid Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000000985 reactive dye Substances 0.000 description 1
- 238000006894 reductive elimination reaction Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
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- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
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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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
- C09B1/28—Dyes with amino groups substituted by hydrocarbon radicals substituted by alkyl, aralkyl or cyclo alkyl groups
-
- 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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
- C09B1/51—N-substituted amino-hydroxy anthraquinone
- C09B1/515—N-alkyl, N-aralkyl or N-cycloalkyl derivatives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1229364 | 1964-09-22 | ||
| CH1135865A CH477506A (de) | 1964-09-22 | 1965-08-12 | Verfahren zur Herstellung neuer wasserunlöslicher Anthrachinonfarbstoffe |
| CH185866A CH449137A (de) | 1965-03-18 | 1966-02-10 | Einrichtung zum Überwachen bzw. Steuern des Erwärmungsvorganges eines Werkstückes, abhängig von der am Werkstück liegenden Spannung und dem das Werkstück durchfliessenden Strom |
| CH186866A CH492755A (de) | 1964-09-22 | 1966-02-10 | Verfahren zur Herstellung wasserunlöslicher Anthrachinonfarbstoffe |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1644498A1 true DE1644498A1 (de) | 1971-05-06 |
Family
ID=39146905
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19651644498 Pending DE1644498A1 (de) | 1964-09-22 | 1965-09-17 | Verfahren zur Herstellung wasserunloeslicher Anthrachinonfarbstoffe |
| DE19671644517 Pending DE1644517A1 (de) | 1964-09-22 | 1967-02-01 | Verfahren zur Herstellung wasserunloeslicher Anthrachinonfarbstoffe |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19671644517 Pending DE1644517A1 (de) | 1964-09-22 | 1967-02-01 | Verfahren zur Herstellung wasserunloeslicher Anthrachinonfarbstoffe |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3484460A (enExample) |
| BE (2) | BE693748A (enExample) |
| CH (2) | CH477506A (enExample) |
| DE (2) | DE1644498A1 (enExample) |
| ES (1) | ES336613A2 (enExample) |
| FR (2) | FR1468810A (enExample) |
| GB (2) | GB1063976A (enExample) |
| NL (2) | NL6512278A (enExample) |
| SE (1) | SE313384B (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2108364C3 (de) * | 1971-02-22 | 1974-01-03 | Farbwerke Hoechst Ag, Vormals Meister Lucius & Bruening, 6000 Frankfurt | FarbstofTgemische mit neutralem Verhalten bei künstlicher Beleuchtung zum einbadigen Färben von Mischungen aus Polyesterfasern und Wolle |
| DE3040102A1 (de) * | 1980-10-24 | 1982-06-03 | Merck Patent Gmbh, 6100 Darmstadt | Dichroitische anthrachinonfarbstoffe, diese enthaltende fluessigkristalline dielektrika und elektrooptisches anzeigeelement |
| CN104530759A (zh) * | 2014-12-18 | 2015-04-22 | 太湖亚太精化有限公司 | 一种稳定性好的分散型染料及其制备方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1336690A (en) * | 1920-04-13 | John flammangr | ||
| US1352732A (en) * | 1918-10-15 | 1920-09-14 | Henry C Egerton | Weather-strip |
| US2338908A (en) * | 1939-11-25 | 1944-01-11 | Eastman Kodak Co | Anthraquinone compounds and material colored therewith |
| US2319043A (en) * | 1940-02-28 | 1943-05-11 | Eastman Kodak Co | Anthraquinone compounds and cellulose derivatives colored therewith |
| US3265460A (en) * | 1960-03-22 | 1966-08-09 | Allied Chem | Dyeing of synthetic fibers |
-
0
- BE BE669879D patent/BE669879A/xx unknown
-
1965
- 1965-08-12 CH CH1135865A patent/CH477506A/de not_active IP Right Cessation
- 1965-09-14 US US487322A patent/US3484460A/en not_active Expired - Lifetime
- 1965-09-16 GB GB39605/65A patent/GB1063976A/en not_active Expired
- 1965-09-17 DE DE19651644498 patent/DE1644498A1/de active Pending
- 1965-09-21 NL NL6512278A patent/NL6512278A/xx unknown
- 1965-09-21 FR FR32078A patent/FR1468810A/fr not_active Expired
-
1966
- 1966-02-10 CH CH186866A patent/CH492755A/de not_active IP Right Cessation
-
1967
- 1967-01-27 GB GB4250/67A patent/GB1121745A/en not_active Expired
- 1967-02-01 DE DE19671644517 patent/DE1644517A1/de active Pending
- 1967-02-07 BE BE693748D patent/BE693748A/xx unknown
- 1967-02-08 FR FR94213A patent/FR91837E/fr not_active Expired
- 1967-02-09 NL NL6701993A patent/NL6701993A/xx unknown
- 1967-02-09 SE SE1817/67A patent/SE313384B/xx unknown
- 1967-02-09 ES ES336613A patent/ES336613A2/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB1121745A (en) | 1968-07-31 |
| CH492755A (de) | 1970-06-30 |
| US3484460A (en) | 1969-12-16 |
| BE669879A (enExample) | 1966-03-21 |
| FR1468810A (fr) | 1967-02-10 |
| NL6701993A (enExample) | 1967-08-11 |
| BE693748A (enExample) | 1967-08-07 |
| ES336613A2 (es) | 1968-04-01 |
| CH477506A (de) | 1969-08-31 |
| NL6512278A (enExample) | 1966-03-23 |
| DE1644517A1 (de) | 1971-10-21 |
| GB1063976A (en) | 1967-04-05 |
| SE313384B (enExample) | 1969-08-11 |
| FR91837E (fr) | 1968-08-16 |
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