DE2222032C2 - Wasserlösliche, faserreaktive Azofarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung - Google Patents
Wasserlösliche, faserreaktive Azofarbstoffe, Verfahren zu ihrer Herstellung und ihre VerwendungInfo
- Publication number
- DE2222032C2 DE2222032C2 DE19722222032 DE2222032A DE2222032C2 DE 2222032 C2 DE2222032 C2 DE 2222032C2 DE 19722222032 DE19722222032 DE 19722222032 DE 2222032 A DE2222032 A DE 2222032A DE 2222032 C2 DE2222032 C2 DE 2222032C2
- Authority
- DE
- Germany
- Prior art keywords
- alkyl
- yellow
- sulfonamide
- aniline
- formula
- 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
- 239000000987 azo dye Substances 0.000 title claims description 8
- 238000000034 method Methods 0.000 title description 24
- 238000002360 preparation method Methods 0.000 title description 3
- -1 cyano, hydroxy Chemical group 0.000 claims description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 5
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000005521 carbonamide group Chemical group 0.000 claims description 4
- 150000001735 carboxylic acids Chemical class 0.000 claims description 4
- 150000002790 naphthalenes Chemical class 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 229940124530 sulfonamide Drugs 0.000 claims description 4
- 150000003456 sulfonamides Chemical class 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical class O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 claims 1
- 150000003460 sulfonic acids Chemical group 0.000 claims 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 42
- 239000000975 dye Substances 0.000 description 29
- 238000004043 dyeing Methods 0.000 description 14
- 239000002253 acid Substances 0.000 description 13
- 210000002268 wool Anatomy 0.000 description 13
- 239000000463 material Substances 0.000 description 12
- 230000008878 coupling Effects 0.000 description 11
- 238000010168 coupling process Methods 0.000 description 11
- 238000005859 coupling reaction Methods 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 229920002678 cellulose Polymers 0.000 description 7
- 239000001913 cellulose Substances 0.000 description 7
- 238000007639 printing Methods 0.000 description 7
- 238000001694 spray drying Methods 0.000 description 7
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 7
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- 230000002378 acidificating effect Effects 0.000 description 6
- 239000012954 diazonium Substances 0.000 description 6
- 150000001989 diazonium salts Chemical class 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
- 239000001103 potassium chloride Substances 0.000 description 4
- 235000011164 potassium chloride Nutrition 0.000 description 4
- 239000000985 reactive dye Substances 0.000 description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- CSIFGMFVGDBOQC-UHFFFAOYSA-N 3-iminobutanenitrile Chemical compound CC(=N)CC#N CSIFGMFVGDBOQC-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-N Metaphosphoric acid Chemical compound OP(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000003931 anilides Chemical class 0.000 description 1
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-N diphosphoric acid Chemical compound OP(O)(=O)OP(O)(O)=O XPPKVPWEQAFLFU-UHFFFAOYSA-N 0.000 description 1
- 125000006125 ethylsulfonyl group Chemical group 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000010985 leather Substances 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
- 239000011976 maleic acid Substances 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- XBCIOBSQHJYVBQ-UHFFFAOYSA-N naphthalen-1-ylhydrazine Chemical compound C1=CC=C2C(NN)=CC=CC2=C1 XBCIOBSQHJYVBQ-UHFFFAOYSA-N 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 238000007649 pad printing Methods 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 125000002270 phosphoric acid ester group Chemical group 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 229940005657 pyrophosphoric acid Drugs 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Inorganic materials [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 230000001180 sulfating effect Effects 0.000 description 1
- 239000004753 textile Substances 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
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
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/002—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the linkage of the reactive group being alternatively specified
- C09B62/006—Azodyes
- C09B62/008—Monoazo dyes
- C09B62/0088—Monoazo dyes with heterocyclic compound as coupling component
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19722222032 DE2222032C2 (de) | 1972-05-05 | 1972-05-05 | Wasserlösliche, faserreaktive Azofarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung |
| IN1019/CAL/73A IN138889B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-05-05 | 1973-05-01 | |
| CH625073A CH599315A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-05-05 | 1973-05-02 | |
| IT2369873A IT987123B (it) | 1972-05-05 | 1973-05-03 | Azocomposti idrosolubili e pro cedimento per la loro prepara zione |
| FR7316156A FR2184644B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-05-05 | 1973-05-04 | |
| JP4922873A JPS4961229A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-05-05 | 1973-05-04 | |
| BE130828A BE799194A (fr) | 1972-05-05 | 1973-05-07 | Colorants azoiques solubles dans l'eau et leur preparation, |
| GB2166873A GB1413250A (en) | 1972-05-05 | 1973-05-07 | Water-soluble azo compounds having fibre-reactive dyeing properties |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19722222032 DE2222032C2 (de) | 1972-05-05 | 1972-05-05 | Wasserlösliche, faserreaktive Azofarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2222032A1 DE2222032A1 (de) | 1973-11-22 |
| DE2222032C2 true DE2222032C2 (de) | 1982-07-01 |
Family
ID=5844132
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722222032 Expired DE2222032C2 (de) | 1972-05-05 | 1972-05-05 | Wasserlösliche, faserreaktive Azofarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung |
Country Status (8)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010034832A1 (de) * | 2008-09-29 | 2010-04-01 | Basf Se | Monoazofarbstoffe für die lederfärbung |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1172097A (fr) * | 1956-01-27 | 1959-02-05 | Ciba Geigy | Nouveaux colorants, leur préparation et leurs emplois |
| FR1178011A (fr) * | 1956-06-29 | 1959-05-04 | Ciba Geigy | Nouveaux colorants monoazoïques, leur préparation et leurs emplois |
| FR1182529A (fr) * | 1956-09-14 | 1959-06-25 | Ciba Geigy | Nouveaux colorants azoïques, leur procédé de préparation et leur utilisation |
| BE565650A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1957-03-12 | |||
| FR1246743A (fr) * | 1957-11-20 | 1960-11-25 | Sandoz Ag | Colorants cyanuriques hydrosolubles, leur procédé de fabrication et leurs applications |
| FR1293764A (fr) * | 1961-05-31 | 1962-05-18 | Ciba Geigy | Colorants nouveaux et leur procédé de préparation et d'emploi |
| FR1327016A (fr) * | 1961-08-18 | 1963-05-17 | Ciba Geigy | Colorants nouveaux, leur procédé de préparation et leurs emplois |
| FR1344653A (fr) * | 1962-12-28 | 1963-11-29 | Geigy Ag J R | Nouveaux colorants azoïques réactifs contenant un noyau triazinylique et leur préparation |
| FR1406198A (fr) * | 1963-08-27 | 1965-07-16 | Ciba Geigy | Colorants monoazoïques nouveaux, leur procédé d'obtention et leur emploi |
-
1972
- 1972-05-05 DE DE19722222032 patent/DE2222032C2/de not_active Expired
-
1973
- 1973-05-01 IN IN1019/CAL/73A patent/IN138889B/en unknown
- 1973-05-02 CH CH625073A patent/CH599315A5/xx not_active IP Right Cessation
- 1973-05-03 IT IT2369873A patent/IT987123B/it active
- 1973-05-04 JP JP4922873A patent/JPS4961229A/ja active Pending
- 1973-05-04 FR FR7316156A patent/FR2184644B1/fr not_active Expired
- 1973-05-07 BE BE130828A patent/BE799194A/xx not_active IP Right Cessation
- 1973-05-07 GB GB2166873A patent/GB1413250A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2184644A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1973-12-28 |
| IN138889B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-04-10 |
| DE2222032A1 (de) | 1973-11-22 |
| JPS4961229A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-06-13 |
| BE799194A (fr) | 1973-11-07 |
| FR2184644B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-02-11 |
| CH599315A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1978-05-31 |
| IT987123B (it) | 1975-02-20 |
| GB1413250A (en) | 1975-11-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| D2 | Grant after examination | ||
| 8339 | Ceased/non-payment of the annual fee |