DE1644596A1 - Farbstoffe und Verfahren zu deren Herstellung - Google Patents
Farbstoffe und Verfahren zu deren HerstellungInfo
- Publication number
- DE1644596A1 DE1644596A1 DE19651644596 DE1644596A DE1644596A1 DE 1644596 A1 DE1644596 A1 DE 1644596A1 DE 19651644596 DE19651644596 DE 19651644596 DE 1644596 A DE1644596 A DE 1644596A DE 1644596 A1 DE1644596 A1 DE 1644596A1
- Authority
- DE
- Germany
- Prior art keywords
- dyes
- alkyl
- formula
- parts
- acyl
- 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
- 239000000975 dye Substances 0.000 title claims description 45
- 238000000034 method Methods 0.000 title claims description 6
- 239000004952 Polyamide Substances 0.000 claims description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 14
- 229920002647 polyamide Polymers 0.000 claims description 14
- 239000000835 fiber Substances 0.000 claims description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- -1 acyl radical Chemical class 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 238000004043 dyeing Methods 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 239000002657 fibrous material Substances 0.000 claims description 4
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 150000005840 aryl radicals Chemical class 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims 3
- 150000002790 naphthalenes Chemical class 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 230000004048 modification Effects 0.000 claims 1
- 238000012986 modification Methods 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 150000003460 sulfonic acids Chemical class 0.000 claims 1
- 239000000460 chlorine Substances 0.000 description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 11
- 230000007935 neutral effect Effects 0.000 description 8
- 238000001035 drying Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- ZYECOAILUNWEAL-NUDFZHEQSA-N (4z)-4-[[2-methoxy-5-(phenylcarbamoyl)phenyl]hydrazinylidene]-n-(3-nitrophenyl)-3-oxonaphthalene-2-carboxamide Chemical compound COC1=CC=C(C(=O)NC=2C=CC=CC=2)C=C1N\N=C(C1=CC=CC=C1C=1)/C(=O)C=1C(=O)NC1=CC=CC([N+]([O-])=O)=C1 ZYECOAILUNWEAL-NUDFZHEQSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 210000002268 wool Anatomy 0.000 description 4
- TXNSZCSYBXHETP-UHFFFAOYSA-N 2-chloro-n-(hydroxymethyl)acetamide Chemical compound OCNC(=O)CCl TXNSZCSYBXHETP-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- SQAINHDHICKHLX-UHFFFAOYSA-N 1-naphthaldehyde Chemical compound C1=CC=C2C(C=O)=CC=CC2=C1 SQAINHDHICKHLX-UHFFFAOYSA-N 0.000 description 2
- XBNVWXKPFORCRI-UHFFFAOYSA-N 2h-naphtho[2,3-f]quinolin-1-one Chemical compound C1=CC=CC2=CC3=C4C(=O)CC=NC4=CC=C3C=C21 XBNVWXKPFORCRI-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000001000 anthraquinone dye Substances 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 1
- IXMCSELMHRWGLL-UHFFFAOYSA-N 4-anilinonaphtho[2,3-f]quinolin-1-one Chemical compound N(C1=CC=CC=C1)N1C=CC(C2=C1C=CC1=CC3=CC=CC=C3C=C12)=O IXMCSELMHRWGLL-UHFFFAOYSA-N 0.000 description 1
- KNIUHBNRWZGIQQ-UHFFFAOYSA-N 7-diethoxyphosphinothioyloxy-4-methylchromen-2-one Chemical compound CC1=CC(=O)OC2=CC(OP(=S)(OCC)OCC)=CC=C21 KNIUHBNRWZGIQQ-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical group OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 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
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000000732 arylene group Chemical group 0.000 description 1
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004049 embossing Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- XMYQHJDBLRZMLW-UHFFFAOYSA-N methanolamine Chemical class NCO XMYQHJDBLRZMLW-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- HJYNGRZUBXMFGB-UHFFFAOYSA-N methoxymethylurea Chemical compound COCNC(N)=O HJYNGRZUBXMFGB-UHFFFAOYSA-N 0.000 description 1
- HWJHZLJIIWOTGZ-UHFFFAOYSA-N n-(hydroxymethyl)acetamide Chemical compound CC(=O)NCO HWJHZLJIIWOTGZ-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
- C09B5/02—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic ring being only condensed in peri position
- C09B5/16—Benz-diazabenzanthrones, e.g. anthrapyrimidones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEF0047688 | 1965-11-16 |
Publications (1)
Publication Number | Publication Date |
---|---|
DE1644596A1 true DE1644596A1 (de) | 1971-05-06 |
Family
ID=7101780
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE19651644596 Pending DE1644596A1 (de) | 1965-11-16 | 1965-11-16 | Farbstoffe und Verfahren zu deren Herstellung |
Country Status (7)
Families Citing this family (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0270306B1 (en) * | 1986-12-01 | 1991-03-27 | Sumitomo Chemical Company, Limited | Anthrapyridone compounds, their production process and their use |
US6635642B1 (en) | 1997-09-03 | 2003-10-21 | Guilford Pharmaceuticals Inc. | PARP inhibitors, pharmaceutical compositions comprising same, and methods of using same |
US6514983B1 (en) | 1997-09-03 | 2003-02-04 | Guilford Pharmaceuticals Inc. | Compounds, methods and pharmaceutical compositions for treating neural or cardiovascular tissue damage |
US6346536B1 (en) | 1997-09-03 | 2002-02-12 | Guilford Pharmaceuticals Inc. | Poly(ADP-ribose) polymerase inhibitors and method for treating neural or cardiovascular tissue damage using the same |
US6426415B1 (en) | 1997-09-03 | 2002-07-30 | Guilford Pharmaceuticals Inc. | Alkoxy-substituted compounds, methods and compositions for inhibiting parp activity |
US6291425B1 (en) | 1999-09-01 | 2001-09-18 | Guilford Pharmaceuticals Inc. | Compounds, methods and pharmaceutical compositions for treating cellular damage, such as neural or cardiovascular tissue damage |
US6197785B1 (en) | 1997-09-03 | 2001-03-06 | Guilford Pharmaceuticals Inc. | Alkoxy-substituted compounds, methods, and compositions for inhibiting PARP activity |
US6395749B1 (en) | 1998-05-15 | 2002-05-28 | Guilford Pharmaceuticals Inc. | Carboxamide compounds, methods, and compositions for inhibiting PARP activity |
US6387902B1 (en) | 1998-12-31 | 2002-05-14 | Guilford Pharmaceuticals, Inc. | Phenazine compounds, methods and pharmaceutical compositions for inhibiting PARP |
WO2001090077A1 (en) | 2000-05-19 | 2001-11-29 | Guilford Pharmaceuticals, Inc. | Sulfonamide and carbamide derivatives of 6(5h)phenanthridinones and their uses |
WO2001091796A2 (en) | 2000-06-01 | 2001-12-06 | Guilford Pharmaceuticals Inc. | Methods, compounds and compositions for treating gout |
WO2002006240A1 (en) | 2000-07-13 | 2002-01-24 | Guilford Pharmaceuticals Inc. | Substituted 4,9-dihydrocyclopenta[imn] phenanthridine-5-ones, derivatives thereof and their uses |
GB0509342D0 (en) * | 2005-05-06 | 2005-06-15 | Avecia Inkjet Ltd | Colorants and their use in ink jet printing |
CN101331120A (zh) | 2005-10-13 | 2008-12-24 | 史密丝克莱恩比彻姆公司 | 作为阿片样物质受体调节剂的酚醚化合物 |
CN112457684B (zh) * | 2020-12-24 | 2022-12-06 | 北京泛博化学股份有限公司 | 一种毛皮用酸性红染料及其制备方法和应用 |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2759939A (en) * | 1956-08-21 | Seriesand the preparation | ||
US2029007A (en) * | 1936-01-28 | xcoxch | ||
US2962497A (en) * | 1960-11-29 | Xsoih | ||
US2871240A (en) * | 1951-12-31 | 1959-01-27 | Gen Aniline & Film Corp | Dyestuffs derived from 2,5-dimethoxyterephthaloyl chloride and amino 1,9-anthrapyrimidine |
-
1965
- 1965-11-16 DE DE19651644596 patent/DE1644596A1/de active Pending
-
1966
- 1966-08-11 CH CH1159866A patent/CH470452A/de unknown
- 1966-09-27 GB GB43007/66A patent/GB1111037A/en not_active Expired
- 1966-11-04 US US591969A patent/US3534038A/en not_active Expired - Lifetime
- 1966-11-11 NL NL6615958A patent/NL6615958A/xx unknown
- 1966-11-16 FR FR83881A patent/FR1501294A/fr not_active Expired
- 1966-11-16 BE BE689775D patent/BE689775A/xx unknown
Also Published As
Publication number | Publication date |
---|---|
GB1111037A (en) | 1968-04-24 |
FR1501294A (fr) | 1967-11-10 |
NL6615958A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1967-05-17 |
US3534038A (en) | 1970-10-13 |
CH470452A (de) | 1969-03-31 |
BE689775A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1967-05-02 |
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