DE4238231A1 - - Google Patents
Info
- Publication number
- DE4238231A1 DE4238231A1 DE4238231A DE4238231A DE4238231A1 DE 4238231 A1 DE4238231 A1 DE 4238231A1 DE 4238231 A DE4238231 A DE 4238231A DE 4238231 A DE4238231 A DE 4238231A DE 4238231 A1 DE4238231 A1 DE 4238231A1
- Authority
- DE
- Germany
- Prior art keywords
- alkyl
- formula
- dye
- weight
- percent
- 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.)
- Withdrawn
Links
- 239000000975 dye Substances 0.000 claims description 69
- 239000000203 mixture Substances 0.000 claims description 36
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 239000000986 disperse dye Substances 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 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 239000000835 fiber Substances 0.000 claims description 6
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 5
- 238000004043 dyeing Methods 0.000 claims description 5
- 125000005359 phenoxyalkyl group Chemical group 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- -1 phenylaminocarbonyl Chemical group 0.000 claims description 4
- 230000002209 hydrophobic effect Effects 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 238000007639 printing Methods 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- 230000008878 coupling Effects 0.000 description 8
- 238000010168 coupling process Methods 0.000 description 8
- 238000005859 coupling reaction Methods 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 5
- 239000012362 glacial acetic acid Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 238000000227 grinding Methods 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 239000003086 colorant Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 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 2
- 229920001732 Lignosulfonate Polymers 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 2
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 2
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 2
- 235000011130 ammonium sulphate Nutrition 0.000 description 2
- ZHZPDMZPDWXVMJ-UHFFFAOYSA-N benzyl 2-aminobenzoate Chemical compound NC1=CC=CC=C1C(=O)OCC1=CC=CC=C1 ZHZPDMZPDWXVMJ-UHFFFAOYSA-N 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 2
- 239000012954 diazonium Substances 0.000 description 2
- 150000001989 diazonium salts Chemical class 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- RLXXBBHXOBWALJ-UHFFFAOYSA-N 2-phenoxyethyl 2-aminobenzoate Chemical compound NC1=CC=CC=C1C(=O)OCCOC1=CC=CC=C1 RLXXBBHXOBWALJ-UHFFFAOYSA-N 0.000 description 1
- 229920002284 Cellulose triacetate Polymers 0.000 description 1
- 229920001410 Microfiber Polymers 0.000 description 1
- 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 1
- VJMAITQRABEEKP-UHFFFAOYSA-N [6-(phenylmethoxymethyl)-1,4-dioxan-2-yl]methyl acetate Chemical compound O1C(COC(=O)C)COCC1COCC1=CC=CC=C1 VJMAITQRABEEKP-UHFFFAOYSA-N 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 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
- 239000007900 aqueous suspension Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000001045 blue dye Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229960000956 coumarin Drugs 0.000 description 1
- 235000001671 coumarin Nutrition 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000009998 heat setting Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000003658 microfiber Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- RWZYAGGXGHYGMB-UHFFFAOYSA-N o-aminobenzenecarboxylic acid Natural products NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical class OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 239000004576 sand Substances 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
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010023 transfer printing Methods 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
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
- C09B67/0041—Blends of pigments; Mixtured crystals; Solid solutions mixtures containing one azo dye
-
- 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
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/02—Coumarine dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Coloring (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Polymerisation Methods In General (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4137822 | 1991-11-16 | ||
| DE4201539 | 1992-01-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE4238231A1 true DE4238231A1 (id) | 1993-05-19 |
Family
ID=25909235
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE4238231A Withdrawn DE4238231A1 (id) | 1991-11-16 | 1992-11-12 |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPH06100793A (id) |
| CH (1) | CH684597A5 (id) |
| DE (1) | DE4238231A1 (id) |
| ES (1) | ES2065237B1 (id) |
| FR (1) | FR2683822B1 (id) |
| GB (1) | GB2261439B (id) |
| IT (1) | IT1263025B (id) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19512424A1 (de) * | 1995-04-03 | 1996-10-10 | Bayer Ag | Grüne Dispersionsfarbstoffmischungen |
| CN103073918B (zh) * | 2013-01-21 | 2014-10-15 | 江苏亚邦染料股份有限公司 | 一组中温型三原色分散染料 |
| CN105541852B (zh) * | 2016-01-29 | 2017-09-15 | 扬州大学 | 2‑（香豆素‑3‑基）‑6‑甲基吡啶并[5,4‑c]香豆素的合成方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1594324A (id) * | 1968-07-08 | 1970-06-01 | ||
| DE1917278B2 (de) * | 1969-04-03 | 1974-06-27 | Basf Ag, 6700 Ludwigshafen | Monoazofarbstoffe, Verfahren zu deren Herstellung und Farbstoffzubereitungen |
| US3704302A (en) * | 1969-04-18 | 1972-11-28 | Sumitomo Chemical Co | Certain cumarin quinazolinones |
| BE795380A (fr) * | 1972-02-15 | 1973-08-13 | Sandoz Sa | Nouveaux composes heterocycliques peu solubles dans l'eau, leur preparation et leur utilisation comme colorants |
| GB1543933A (en) * | 1975-07-02 | 1979-04-11 | Basf Ag | Dyes of the coumarin series |
| DE2739841C2 (de) * | 1977-09-03 | 1979-10-25 | Bayer Ag, 5090 Leverkusen | Transferdruckverfahren |
| DE3012863A1 (de) * | 1980-04-02 | 1981-10-08 | Cassella Ag, 6000 Frankfurt | Farbstoffmischung, verfahren zu ihrer herstellung, sie enthaltende farbstoffe und verfahren zum faerben und bedrucken von synthetischem, hydrophobem fasermaterial |
| US4548613A (en) * | 1984-05-18 | 1985-10-22 | American Hoechst Corporation | Yellow disperse dyestuff mixtures and dyeing process |
| DE3736817A1 (de) * | 1987-10-30 | 1989-05-11 | Basf Ag | Pyridonazofarbstoffe und ihre verwendung |
| US5038415A (en) * | 1989-01-10 | 1991-08-13 | Sumitomo Chemical Company, Limited | Disperse dye composition useful for dyeing of printing hydrophobic fiber materials: mixture of pyridone mono-azo dyes and optionally a quino-phthalone |
-
1992
- 1992-11-10 FR FR9213650A patent/FR2683822B1/fr not_active Expired - Fee Related
- 1992-11-12 DE DE4238231A patent/DE4238231A1/de not_active Withdrawn
- 1992-11-12 IT ITRM920823A patent/IT1263025B/it active IP Right Grant
- 1992-11-12 GB GB9223700A patent/GB2261439B/en not_active Expired - Fee Related
- 1992-11-13 ES ES09202300A patent/ES2065237B1/es not_active Expired - Lifetime
- 1992-11-13 CH CH3507/92A patent/CH684597A5/de not_active IP Right Cessation
- 1992-11-13 JP JP4303442A patent/JPH06100793A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| IT1263025B (it) | 1996-07-23 |
| ITRM920823A1 (it) | 1994-05-12 |
| ES2065237B1 (es) | 1995-10-01 |
| GB2261439A (en) | 1993-05-19 |
| CH684597A5 (de) | 1994-10-31 |
| ITRM920823A0 (it) | 1992-11-12 |
| FR2683822A1 (fr) | 1993-05-21 |
| ES2065237A1 (es) | 1995-02-01 |
| FR2683822B1 (fr) | 1994-12-23 |
| GB9223700D0 (en) | 1992-12-23 |
| GB2261439B (en) | 1995-02-08 |
| JPH06100793A (ja) | 1994-04-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |