DE2101223C3 - SuIfonsäuregruppenfreie basische Styrylfarbstoffe, ihre Herstellung und Verwendung - Google Patents
SuIfonsäuregruppenfreie basische Styrylfarbstoffe, ihre Herstellung und VerwendungInfo
- Publication number
- DE2101223C3 DE2101223C3 DE19712101223 DE2101223A DE2101223C3 DE 2101223 C3 DE2101223 C3 DE 2101223C3 DE 19712101223 DE19712101223 DE 19712101223 DE 2101223 A DE2101223 A DE 2101223A DE 2101223 C3 DE2101223 C3 DE 2101223C3
- Authority
- DE
- Germany
- Prior art keywords
- formula
- dyes
- styryl dyes
- compound
- ethyl
- 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
Links
- 239000000975 dye Substances 0.000 title claims description 32
- 125000005504 styryl group Chemical group 0.000 title claims description 10
- 125000000542 sulfonic acid group Chemical group 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 11
- 238000004043 dyeing Methods 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- -1 alkyl radical Chemical class 0.000 claims description 7
- 150000001450 anions Chemical class 0.000 claims description 7
- 229920002239 polyacrylonitrile Polymers 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 239000000835 fiber Substances 0.000 claims description 6
- 239000004952 Polyamide Substances 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 229920002647 polyamide Polymers 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 239000004753 textile Substances 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 229920000728 polyester Polymers 0.000 claims description 3
- WPWHSFAFEBZWBB-UHFFFAOYSA-N 1-butyl radical Chemical compound [CH2]CCC WPWHSFAFEBZWBB-UHFFFAOYSA-N 0.000 claims description 2
- 229920001577 copolymer Polymers 0.000 claims description 2
- 239000010985 leather Substances 0.000 claims description 2
- 239000000123 paper Substances 0.000 claims description 2
- 229920003023 plastic Polymers 0.000 claims description 2
- 239000004033 plastic Substances 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- VDMXGJJMPKAYQP-UHFFFAOYSA-N 5-chloro-1,3,3-trimethyl-2-methylideneindole Chemical compound ClC1=CC=C2N(C)C(=C)C(C)(C)C2=C1 VDMXGJJMPKAYQP-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical group OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- ZXYNGLRGFYLTQZ-UHFFFAOYSA-M [Zn]Cl Chemical compound [Zn]Cl ZXYNGLRGFYLTQZ-UHFFFAOYSA-M 0.000 description 1
- DQPBABKTKYNPMH-UHFFFAOYSA-M amino sulfate Chemical compound NOS([O-])(=O)=O DQPBABKTKYNPMH-UHFFFAOYSA-M 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 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
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-M chloroacetate Chemical compound [O-]C(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-M 0.000 description 1
- 229940089960 chloroacetate Drugs 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- 229940008406 diethyl sulfate Drugs 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- VFNGKCDDZUSWLR-UHFFFAOYSA-L disulfate(2-) Chemical compound [O-]S(=O)(=O)OS([O-])(=O)=O VFNGKCDDZUSWLR-UHFFFAOYSA-L 0.000 description 1
- 238000005108 dry cleaning Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 229910001410 inorganic ion Inorganic materials 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000010409 ironing Methods 0.000 description 1
- 229940001447 lactate Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000004994 m-toluidines Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 230000007935 neutral effect Effects 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
- 239000013535 sea water Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229940086735 succinate Drugs 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000003466 welding Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
-
- 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
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/14—Styryl dyes
-
- 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
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/14—Styryl dyes
- C09B23/145—Styryl dyes the ethylene chain carrying an heterocyclic residue, e.g. heterocycle-CH=CH-C6H5
-
- 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
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/70—Material containing nitrile groups
- D06P3/76—Material containing nitrile groups using basic dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH51470A CH520179A (de) | 1970-01-15 | 1970-01-15 | Verfahren zur Herstellung sulfonsäuregruppenfreier basischer Styrylverbindungen |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2101223A1 DE2101223A1 (de) | 1971-07-29 |
| DE2101223B2 DE2101223B2 (de) | 1974-01-17 |
| DE2101223C3 true DE2101223C3 (de) | 1974-08-22 |
Family
ID=4188741
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712101223 Expired DE2101223C3 (de) | 1970-01-15 | 1971-01-12 | SuIfonsäuregruppenfreie basische Styrylfarbstoffe, ihre Herstellung und Verwendung |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS5250202B1 (enExample) |
| BE (1) | BE761326A (enExample) |
| BR (1) | BR7100153D0 (enExample) |
| CA (1) | CA946389A (enExample) |
| CH (1) | CH520179A (enExample) |
| DE (1) | DE2101223C3 (enExample) |
| ES (1) | ES387222A1 (enExample) |
| FR (1) | FR2075435A5 (enExample) |
| GB (1) | GB1335575A (enExample) |
| NL (1) | NL142718B (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4702730B2 (ja) | 1999-12-02 | 2011-06-15 | 株式会社林原生物化学研究所 | スチリル色素 |
-
1970
- 1970-01-15 CH CH51470A patent/CH520179A/de not_active IP Right Cessation
- 1970-12-22 JP JP45116562A patent/JPS5250202B1/ja active Pending
- 1970-12-29 CA CA101,574A patent/CA946389A/en not_active Expired
- 1970-12-29 GB GB6149370A patent/GB1335575A/en not_active Expired
-
1971
- 1971-01-07 BE BE761326A patent/BE761326A/xx unknown
- 1971-01-11 BR BR15371A patent/BR7100153D0/pt unknown
- 1971-01-12 DE DE19712101223 patent/DE2101223C3/de not_active Expired
- 1971-01-12 FR FR7100763A patent/FR2075435A5/fr not_active Expired
- 1971-01-13 ES ES387222A patent/ES387222A1/es not_active Expired
- 1971-01-14 NL NL7100502A patent/NL142718B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BE761326A (fr) | 1971-06-16 |
| JPS5250202B1 (enExample) | 1977-12-22 |
| NL7100502A (enExample) | 1971-07-19 |
| ES387222A1 (es) | 1973-12-16 |
| GB1335575A (en) | 1973-10-31 |
| DE2101223B2 (de) | 1974-01-17 |
| DE2101223A1 (de) | 1971-07-29 |
| BR7100153D0 (pt) | 1973-05-03 |
| CH520179A (de) | 1972-03-15 |
| NL142718B (nl) | 1974-07-15 |
| CA946389A (en) | 1974-04-30 |
| FR2075435A5 (enExample) | 1971-10-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2413299C3 (de) | Verfahren zum Spinnfärben von Polymeren oder Mischpolymeren des Acrylnitrils | |
| DE1619633A1 (de) | Verfahren zum Faerben oder Bedrucken | |
| EP0029136B1 (de) | Quartäre und basische Azamethinverbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung als Farbmittel | |
| DE2759888C2 (de) | Neue kationische Farbstoffe, deren Herstellung und Verwendung zum Färben, Bedrucken und Spinnfärben von Materialien aus Homo- oder Mischpolymerisaten des Acrylnitrils | |
| DE1906709C3 (de) | Verfahren zur Herstellung basischer Azofarbstoffe und ihre Verwendung | |
| CH460981A (de) | Verfahren zur Herstellung von Hydrazinderivaten | |
| DE1965993C3 (de) | Sulfogruppenfreie Azofarbstoffe, Verfahren zu deren Herstellung und ihre Verwendung zum Färben und Bedrucken von Papier | |
| DE2929285C2 (de) | Kationische Oxazinfarbstoffe | |
| DE2101223C3 (de) | SuIfonsäuregruppenfreie basische Styrylfarbstoffe, ihre Herstellung und Verwendung | |
| DE2200027A1 (de) | Sulfonsaeuregruppenfreie basische Styrylfarbstoffe,ihre Herstellung und Verwendung | |
| DE1929397C3 (de) | Verfahren zur Herstellung von carboxylgruppenhaltigen Cycloimmoniumfarbstoffen der Styrylreihe und die Verwendung der Farbstoffe zum Färben, Klotzen oder Bedrucken von Textilmaterial aus Acrylnitrilpolymerisaten oder -mischpolymerisaten | |
| DE2917996A1 (de) | Organische verbindungen, deren herstellung und verwendung | |
| EP0050263B1 (de) | Kationische Farbstoffe, ihre Herstellung und Verwendung zum Färben kationisch färbbarer Fasern und Papier | |
| DE3029746A1 (de) | Organische verbindungen, deren herstellung und verwendung | |
| EP0055221A2 (de) | Monokationische Farbsalze | |
| DE2527792A1 (de) | Organische verbindungen, ihre herstellung und verwendung | |
| DE2023632C3 (de) | Basische Anthrachinonfarbstoffe, ihre Herstellung und Verwendung | |
| DE2055919A1 (de) | Sulfonsauregruppenfreie basische Chino phthalonfarbstoffe, ihre Herstellung und Verwendung | |
| DE1644320C3 (de) | Basische Monoazofarbstoffe und Verfahren zu ihrer Herstellung | |
| DE1937885A1 (de) | Basische Monoazofarbstoffe,ihre Herstellung und Verwendung | |
| DE2509095A1 (de) | Azoverbindungen | |
| CH532112A (de) | Verfahren zur Herstellung von basischen Azoverbindungen | |
| CH512558A (de) | Verfahren zur Herstellung von sulfonsäuregruppenfreien Anthrachinonverbindungen | |
| CH517149A (de) | Verfahren zur Herstellung von basischen Azoverbindungen | |
| EP0037374A2 (de) | Methinverbindungen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8339 | Ceased/non-payment of the annual fee |