DE2250865A1 - Anthrachinonverbindungen - Google Patents
AnthrachinonverbindungenInfo
- Publication number
- DE2250865A1 DE2250865A1 DE2250865A DE2250865A DE2250865A1 DE 2250865 A1 DE2250865 A1 DE 2250865A1 DE 2250865 A DE2250865 A DE 2250865A DE 2250865 A DE2250865 A DE 2250865A DE 2250865 A1 DE2250865 A1 DE 2250865A1
- Authority
- DE
- Germany
- Prior art keywords
- nylon
- acid
- ing
- parts
- dyes
- 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
- 150000001875 compounds Chemical class 0.000 title description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- -1 Anthraquinone compounds Chemical class 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 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 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
- 229910052744 lithium Inorganic materials 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 3
- 239000011591 potassium Substances 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 150000002641 lithium Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 239000000975 dye Substances 0.000 description 25
- 229920001778 nylon Polymers 0.000 description 17
- 239000004677 Nylon Substances 0.000 description 13
- 239000002253 acid Substances 0.000 description 8
- 238000004043 dyeing Methods 0.000 description 7
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 6
- 239000000835 fiber Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000004952 Polyamide Substances 0.000 description 5
- 238000004040 coloring Methods 0.000 description 5
- 229920002647 polyamide Polymers 0.000 description 5
- 239000004753 textile Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 3
- 238000010186 staining Methods 0.000 description 3
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 2
- ZRWICZHXYMHBDP-UHFFFAOYSA-N 2-chlorosulfonylbenzoic acid Chemical class OC(=O)C1=CC=CC=C1S(Cl)(=O)=O ZRWICZHXYMHBDP-UHFFFAOYSA-N 0.000 description 2
- LMRKXSDOAFUINK-UHFFFAOYSA-N 3-chlorosulfonylbenzoic acid Chemical compound OC(=O)C1=CC=CC(S(Cl)(=O)=O)=C1 LMRKXSDOAFUINK-UHFFFAOYSA-N 0.000 description 2
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 2
- 229920002302 Nylon 6,6 Polymers 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- QZZSAWGVHXXMID-UHFFFAOYSA-N 1-amino-4-bromo-9,10-dioxoanthracene-2-sulfonic acid Chemical compound C1=CC=C2C(=O)C3=C(Br)C=C(S(O)(=O)=O)C(N)=C3C(=O)C2=C1 QZZSAWGVHXXMID-UHFFFAOYSA-N 0.000 description 1
- XYJQBDLJABAHGK-UHFFFAOYSA-N 2-chloro-4-chlorosulfonylbenzoic acid Chemical compound OC(=O)C1=CC=C(S(Cl)(=O)=O)C=C1Cl XYJQBDLJABAHGK-UHFFFAOYSA-N 0.000 description 1
- XHFNLMKGUSRXQF-UHFFFAOYSA-N 3-chloro-4-chlorosulfonylbenzoic acid Chemical compound OC(=O)C1=CC=C(S(Cl)(=O)=O)C(Cl)=C1 XHFNLMKGUSRXQF-UHFFFAOYSA-N 0.000 description 1
- WAEWUWLDBSNLMD-UHFFFAOYSA-N 3-chlorosulfonyl-5-nitrobenzoic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=CC(S(Cl)(=O)=O)=C1 WAEWUWLDBSNLMD-UHFFFAOYSA-N 0.000 description 1
- JSWVCUXQICMATE-UHFFFAOYSA-N 4-amino-2,5-dimethylphenol Chemical compound CC1=CC(O)=C(C)C=C1N JSWVCUXQICMATE-UHFFFAOYSA-N 0.000 description 1
- ZWKXEALJTBALGD-UHFFFAOYSA-N 4-amino-2-ethylphenol Chemical compound CCC1=CC(N)=CC=C1O ZWKXEALJTBALGD-UHFFFAOYSA-N 0.000 description 1
- HDGMAACKJSBLMW-UHFFFAOYSA-N 4-amino-2-methylphenol Chemical class CC1=CC(N)=CC=C1O HDGMAACKJSBLMW-UHFFFAOYSA-N 0.000 description 1
- PTCSSXYPZOFISK-UHFFFAOYSA-N 4-chlorosulfonylbenzoic acid Chemical compound OC(=O)C1=CC=C(S(Cl)(=O)=O)C=C1 PTCSSXYPZOFISK-UHFFFAOYSA-N 0.000 description 1
- QGNGOGOOPUYKMC-UHFFFAOYSA-N 4-hydroxy-6-methylaniline Chemical compound CC1=CC(O)=CC=C1N QGNGOGOOPUYKMC-UHFFFAOYSA-N 0.000 description 1
- CISMZCVQNVNWJW-UHFFFAOYSA-N 5-chlorosulfonyl-2-fluorobenzoic acid Chemical compound OC(=O)C1=CC(S(Cl)(=O)=O)=CC=C1F CISMZCVQNVNWJW-UHFFFAOYSA-N 0.000 description 1
- FMWIOAWRARBKDQ-UHFFFAOYSA-N 5-chlorosulfonyl-2-methylbenzoic acid Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1C(O)=O FMWIOAWRARBKDQ-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 241000974482 Aricia saepiolus Species 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000001045 blue dye Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- SMBQBQBNOXIFSF-UHFFFAOYSA-N dilithium Chemical class [Li][Li] SMBQBQBNOXIFSF-UHFFFAOYSA-N 0.000 description 1
- KCIDZIIHRGYJAE-YGFYJFDDSA-L dipotassium;[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] phosphate Chemical class [K+].[K+].OC[C@H]1O[C@H](OP([O-])([O-])=O)[C@H](O)[C@@H](O)[C@H]1O KCIDZIIHRGYJAE-YGFYJFDDSA-L 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 150000002085 enols Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052736 halogen Chemical class 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- 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
- C09B1/32—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups
- C09B1/34—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups sulfonated
- C09B1/343—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups sulfonated only sulfonated in the anthracene nucleus
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Coloring (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US00190816A US3813402A (en) | 1971-10-20 | 1971-10-20 | Blue anthraquinone acid dyes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2250865A1 true DE2250865A1 (de) | 1973-05-03 |
Family
ID=22702915
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2250865A Pending DE2250865A1 (de) | 1971-10-20 | 1972-10-17 | Anthrachinonverbindungen |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3813402A (enExample) |
| JP (1) | JPS4849821A (enExample) |
| BE (1) | BE789281A (enExample) |
| CA (1) | CA966122A (enExample) |
| CH (1) | CH572077A5 (enExample) |
| DE (1) | DE2250865A1 (enExample) |
| ES (1) | ES407245A1 (enExample) |
| FR (1) | FR2156721B1 (enExample) |
| GB (1) | GB1389706A (enExample) |
| IT (1) | IT969656B (enExample) |
| NL (1) | NL7214161A (enExample) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE748554C (de) * | 1937-11-16 | 1945-01-10 | Verfahren zur Herstellung von sauren Farbstoffen der Anthrachinonreihe |
-
0
- BE BE789281D patent/BE789281A/xx not_active IP Right Cessation
-
1971
- 1971-10-20 US US00190816A patent/US3813402A/en not_active Expired - Lifetime
-
1972
- 1972-09-11 CA CA151,422A patent/CA966122A/en not_active Expired
- 1972-10-03 ES ES407245A patent/ES407245A1/es not_active Expired
- 1972-10-09 CH CH1474872A patent/CH572077A5/xx not_active IP Right Cessation
- 1972-10-12 FR FR7236214A patent/FR2156721B1/fr not_active Expired
- 1972-10-17 DE DE2250865A patent/DE2250865A1/de active Pending
- 1972-10-18 GB GB4806172A patent/GB1389706A/en not_active Expired
- 1972-10-18 IT IT30618/72A patent/IT969656B/it active
- 1972-10-18 JP JP47103718A patent/JPS4849821A/ja active Pending
- 1972-10-19 NL NL7214161A patent/NL7214161A/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| ES407245A1 (es) | 1976-02-16 |
| IT969656B (it) | 1974-04-10 |
| FR2156721A1 (enExample) | 1973-06-01 |
| CA966122A (en) | 1975-04-15 |
| US3813402A (en) | 1974-05-28 |
| FR2156721B1 (enExample) | 1976-03-26 |
| BE789281A (fr) | 1973-03-26 |
| CH572077A5 (enExample) | 1976-01-30 |
| JPS4849821A (enExample) | 1973-07-13 |
| GB1389706A (en) | 1975-04-09 |
| NL7214161A (enExample) | 1973-04-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHA | Expiration of time for request for examination |