DE2126143C3 - Wasserlösliche Monoazofarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung zum Färben oder Bedrucken - Google Patents
Wasserlösliche Monoazofarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung zum Färben oder BedruckenInfo
- Publication number
- DE2126143C3 DE2126143C3 DE19712126143 DE2126143A DE2126143C3 DE 2126143 C3 DE2126143 C3 DE 2126143C3 DE 19712126143 DE19712126143 DE 19712126143 DE 2126143 A DE2126143 A DE 2126143A DE 2126143 C3 DE2126143 C3 DE 2126143C3
- Authority
- DE
- Germany
- Prior art keywords
- weight
- parts
- dye
- acid ester
- water
- 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 44
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 title claims description 7
- 238000004043 dyeing Methods 0.000 title description 11
- 238000000034 method Methods 0.000 title description 5
- 238000002360 preparation method Methods 0.000 title description 2
- 239000002253 acid Substances 0.000 claims description 8
- 150000007513 acids Chemical class 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 21
- -1 methoxy, methyl Chemical group 0.000 description 21
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 20
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Inorganic materials [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 17
- 239000000243 solution Substances 0.000 description 13
- 230000008878 coupling Effects 0.000 description 12
- 238000010168 coupling process Methods 0.000 description 12
- 238000005859 coupling reaction Methods 0.000 description 12
- 239000000843 powder Substances 0.000 description 10
- 229910000029 sodium carbonate Inorganic materials 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 229920003043 Cellulose fiber Polymers 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 239000011780 sodium chloride Substances 0.000 description 9
- HUYJTJXLNBOVFO-UHFFFAOYSA-N 7-hydroxynaphthalene-1-sulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=CC(O)=CC=C21 HUYJTJXLNBOVFO-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000004627 regenerated cellulose Substances 0.000 description 8
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 7
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000012954 diazonium Substances 0.000 description 6
- 150000001989 diazonium salts Chemical class 0.000 description 6
- 230000002378 acidificating effect Effects 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- 238000005185 salting out Methods 0.000 description 4
- 235000010288 sodium nitrite Nutrition 0.000 description 4
- MBDUIEKYVPVZJH-UHFFFAOYSA-N 1-ethylsulfonylethane Chemical compound CCS(=O)(=O)CC MBDUIEKYVPVZJH-UHFFFAOYSA-N 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 150000003014 phosphoric acid esters Chemical class 0.000 description 3
- 239000001103 potassium chloride Substances 0.000 description 3
- 235000011164 potassium chloride Nutrition 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- JBCUKQQIWSWEOK-UHFFFAOYSA-N 2-(benzenesulfonyl)aniline Chemical compound NC1=CC=CC=C1S(=O)(=O)C1=CC=CC=C1 JBCUKQQIWSWEOK-UHFFFAOYSA-N 0.000 description 2
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000010985 leather Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 229920006306 polyurethane fiber Polymers 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 230000001180 sulfating effect Effects 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- PWJNDVAKQLOWRZ-UHFFFAOYSA-N 1-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=CC=C2C(O)=C(S(O)(=O)=O)C=CC2=C1 PWJNDVAKQLOWRZ-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
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- YOCIQNIEQYCORH-UHFFFAOYSA-M chembl2028361 Chemical compound [Na+].OC1=CC=C2C=C(S([O-])(=O)=O)C=CC2=C1N=NC1=CC=CC=C1 YOCIQNIEQYCORH-UHFFFAOYSA-M 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000434 metal complex dye Substances 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- 239000001048 orange dye Substances 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 125000002270 phosphoric acid ester group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000985 reactive dye Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000002130 sulfonic acid ester group Chemical group 0.000 description 1
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003899 tartaric acid esters Chemical class 0.000 description 1
- 238000001291 vacuum drying 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
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
- C09B62/503—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring the reactive group being an esterified or non-esterified hydroxyalkyl sulfonyl or mercaptoalkyl sulfonyl group, a quaternised or non-quaternised aminoalkyl sulfonyl group, a heterylmercapto alkyl sulfonyl group, a vinyl sulfonyl or a substituted vinyl sulfonyl group, or a thiophene-dioxide group
- C09B62/507—Azo dyes
- C09B62/51—Monoazo dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Paper (AREA)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712126143 DE2126143C3 (de) | 1971-05-26 | 1971-05-26 | Wasserlösliche Monoazofarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung zum Färben oder Bedrucken |
| AR24215872A AR193868A1 (es) | 1971-05-26 | 1972-05-24 | Colorantes monoazoicos insolubles en agua,procedimiento para su preparacion,y composiciones y productos que los contienen |
| IT2481272A IT955818B (it) | 1971-05-26 | 1972-05-24 | Monoazocoloranti idrosolubili e procedimento per la loro prepara zione |
| GB2449572A GB1386165A (en) | 1971-05-26 | 1972-05-24 | Water-soluble monoazo dyestuffs and process for preparing them |
| AU42652/72A AU4265272A (en) | 1971-05-26 | 1972-05-24 | Water-soluble monoazo dyestuffs and process for preparing them |
| JP5085272A JPS5427371B1 (enExample) | 1971-05-26 | 1972-05-24 | |
| CA142,966A CA984385A (en) | 1971-05-26 | 1972-05-25 | Water-soluble monoazo dyestuffs and process for preparing them |
| BR332072A BR7203320D0 (pt) | 1971-05-26 | 1972-05-25 | Processo para a preparacao de monoazo-corantes hidrossoluveis |
| CS364772A CS155990B2 (enExample) | 1971-05-26 | 1972-05-26 | |
| BE784046A BE784046A (fr) | 1971-05-26 | 1972-05-26 | Colorants azoiques solubles dans l'eau |
| FR7218873A FR2139127B1 (enExample) | 1971-05-26 | 1972-05-26 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712126143 DE2126143C3 (de) | 1971-05-26 | 1971-05-26 | Wasserlösliche Monoazofarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung zum Färben oder Bedrucken |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2126143A1 DE2126143A1 (de) | 1972-12-14 |
| DE2126143B2 DE2126143B2 (de) | 1975-05-15 |
| DE2126143C3 true DE2126143C3 (de) | 1976-01-08 |
Family
ID=5808991
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712126143 Expired DE2126143C3 (de) | 1971-05-26 | 1971-05-26 | Wasserlösliche Monoazofarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung zum Färben oder Bedrucken |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JPS5427371B1 (enExample) |
| AR (1) | AR193868A1 (enExample) |
| AU (1) | AU4265272A (enExample) |
| BE (1) | BE784046A (enExample) |
| BR (1) | BR7203320D0 (enExample) |
| CA (1) | CA984385A (enExample) |
| CS (1) | CS155990B2 (enExample) |
| DE (1) | DE2126143C3 (enExample) |
| FR (1) | FR2139127B1 (enExample) |
| GB (1) | GB1386165A (enExample) |
| IT (1) | IT955818B (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3903224A1 (de) * | 1989-02-03 | 1990-08-09 | Hoechst Ag | Wasserloesliche azoverbindungen, verfahren zu ihrer herstellung und ihre verwendung als farbstoffe |
| DE3905074A1 (de) * | 1989-02-18 | 1990-08-23 | Hoechst Ag | Wasserloesliche azoverbindungen, verfahren zu ihrer herstellung und ihre verwendung als farbstoffe |
| DE3916712A1 (de) * | 1989-05-23 | 1990-12-06 | Hoechst Ag | Wasserloesliche azoverbindungen, verfahren zu ihrer herstellung und ihre verwendung als farbstoffe |
-
1971
- 1971-05-26 DE DE19712126143 patent/DE2126143C3/de not_active Expired
-
1972
- 1972-05-24 GB GB2449572A patent/GB1386165A/en not_active Expired
- 1972-05-24 IT IT2481272A patent/IT955818B/it active
- 1972-05-24 JP JP5085272A patent/JPS5427371B1/ja active Pending
- 1972-05-24 AU AU42652/72A patent/AU4265272A/en not_active Expired
- 1972-05-24 AR AR24215872A patent/AR193868A1/es active
- 1972-05-25 BR BR332072A patent/BR7203320D0/pt unknown
- 1972-05-25 CA CA142,966A patent/CA984385A/en not_active Expired
- 1972-05-26 BE BE784046A patent/BE784046A/xx not_active IP Right Cessation
- 1972-05-26 FR FR7218873A patent/FR2139127B1/fr not_active Expired
- 1972-05-26 CS CS364772A patent/CS155990B2/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5427371B1 (enExample) | 1979-09-10 |
| CA984385A (en) | 1976-02-24 |
| DE2126143B2 (de) | 1975-05-15 |
| FR2139127B1 (enExample) | 1977-12-23 |
| IT955818B (it) | 1973-09-29 |
| GB1386165A (en) | 1975-03-05 |
| DE2126143A1 (de) | 1972-12-14 |
| FR2139127A1 (enExample) | 1973-01-05 |
| CS155990B2 (enExample) | 1974-06-24 |
| BE784046A (fr) | 1972-11-27 |
| AU4265272A (en) | 1973-11-29 |
| BR7203320D0 (pt) | 1973-06-12 |
| AR193868A1 (es) | 1973-05-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 |