DE2161761C2 - Wasserlösliche, reaktive Azofarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung zum Färben und Bedrucken von Leder, Wolle, Seide, Polyamid- und Polyurethanfasern sowie nativen oder regenerierten Cellulosefasern - Google Patents
Wasserlösliche, reaktive Azofarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung zum Färben und Bedrucken von Leder, Wolle, Seide, Polyamid- und Polyurethanfasern sowie nativen oder regenerierten CellulosefasernInfo
- Publication number
- DE2161761C2 DE2161761C2 DE19712161761 DE2161761A DE2161761C2 DE 2161761 C2 DE2161761 C2 DE 2161761C2 DE 19712161761 DE19712161761 DE 19712161761 DE 2161761 A DE2161761 A DE 2161761A DE 2161761 C2 DE2161761 C2 DE 2161761C2
- Authority
- DE
- Germany
- Prior art keywords
- acid
- sulfonic acid
- yellow
- same
- dye
- 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 9
- 229920003043 Cellulose fiber Polymers 0.000 title description 15
- 238000004043 dyeing Methods 0.000 title description 15
- 238000000034 method Methods 0.000 title description 15
- 210000002268 wool Anatomy 0.000 title description 14
- 239000004627 regenerated cellulose Substances 0.000 title description 4
- 239000004952 Polyamide Substances 0.000 title description 3
- 239000010985 leather Substances 0.000 title description 3
- 229920002647 polyamide Polymers 0.000 title description 3
- 229920006306 polyurethane fiber Polymers 0.000 title description 3
- 238000004519 manufacturing process Methods 0.000 title description 2
- 239000000975 dye Substances 0.000 description 47
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 28
- 239000002253 acid Substances 0.000 description 28
- -1 naphthylene radical Chemical class 0.000 description 17
- 239000000243 solution Substances 0.000 description 17
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 16
- 239000001103 potassium chloride Substances 0.000 description 14
- 235000011164 potassium chloride Nutrition 0.000 description 14
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
- 230000008878 coupling Effects 0.000 description 12
- 238000010168 coupling process Methods 0.000 description 12
- 238000005859 coupling reaction Methods 0.000 description 12
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 11
- ZCGVPUAAMCMLTM-UHFFFAOYSA-N 2-amino-5-chlorobenzenesulfonic acid Chemical compound NC1=CC=C(Cl)C=C1S(O)(=O)=O ZCGVPUAAMCMLTM-UHFFFAOYSA-N 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 239000012954 diazonium Substances 0.000 description 9
- 150000001989 diazonium salts Chemical class 0.000 description 9
- 239000002657 fibrous material Substances 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 125000003545 alkoxy group Chemical group 0.000 description 7
- 125000000217 alkyl group Chemical group 0.000 description 7
- 125000005843 halogen group Chemical group 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Inorganic materials [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- JJRKPZFHGCNWIV-UHFFFAOYSA-N 5-amino-2,3-dichlorobenzenesulfonic acid Chemical compound NC1=CC(Cl)=C(Cl)C(S(O)(=O)=O)=C1 JJRKPZFHGCNWIV-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 230000007935 neutral effect Effects 0.000 description 6
- 235000017557 sodium bicarbonate Nutrition 0.000 description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
- YAIKCRUPEVOINQ-UHFFFAOYSA-N 2-aminonaphthalene-1,5-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC2=C(S(O)(=O)=O)C(N)=CC=C21 YAIKCRUPEVOINQ-UHFFFAOYSA-N 0.000 description 5
- CMOLPZZVECHXKN-UHFFFAOYSA-N 7-aminonaphthalene-1,3-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(S(O)(=O)=O)C2=CC(N)=CC=C21 CMOLPZZVECHXKN-UHFFFAOYSA-N 0.000 description 5
- 229920000742 Cotton Polymers 0.000 description 5
- 125000004390 alkyl sulfonyl group Chemical group 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
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 5
- DCYBHNIOTZBCFS-UHFFFAOYSA-N 2-amino-5-[(4-sulfophenyl)diazenyl]benzenesulfonic acid Chemical compound C1=C(S(O)(=O)=O)C(N)=CC=C1N=NC1=CC=C(S(O)(=O)=O)C=C1 DCYBHNIOTZBCFS-UHFFFAOYSA-N 0.000 description 4
- LTPSRQRIPCVMKQ-UHFFFAOYSA-N 2-amino-5-methylbenzenesulfonic acid Chemical compound CC1=CC=C(N)C(S(O)(=O)=O)=C1 LTPSRQRIPCVMKQ-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- SJCTXIKOXTUQHC-UHFFFAOYSA-N 4-amino-2,5-dichlorobenzenesulfonic acid Chemical compound NC1=CC(Cl)=C(S(O)(=O)=O)C=C1Cl SJCTXIKOXTUQHC-UHFFFAOYSA-N 0.000 description 3
- KZCSUEYBKAPKNH-UHFFFAOYSA-N 6-aminonaphthalene-1,3-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KZCSUEYBKAPKNH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 125000003282 alkyl amino group Chemical group 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical class O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 150000003857 carboxamides Chemical class 0.000 description 2
- 125000002843 carboxylic acid group Chemical group 0.000 description 2
- FPVGTPBMTFTMRT-NSKUCRDLSA-L fast yellow Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C(N)=CC=C1\N=N\C1=CC=C(S([O-])(=O)=O)C=C1 FPVGTPBMTFTMRT-NSKUCRDLSA-L 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- IQZPDFORWZTSKT-UHFFFAOYSA-N nitrosulphonic acid Chemical compound OS(=O)(=O)[N+]([O-])=O IQZPDFORWZTSKT-UHFFFAOYSA-N 0.000 description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 2
- 230000000865 phosphorylative effect Effects 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000000985 reactive dye Substances 0.000 description 2
- 238000005185 salting out Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000010025 steaming Methods 0.000 description 2
- 229950000244 sulfanilic acid Drugs 0.000 description 2
- 230000001180 sulfating effect Effects 0.000 description 2
- 150000003470 sulfuric acid monoesters Chemical class 0.000 description 2
- JVVRJMXHNUAPHW-UHFFFAOYSA-N 1h-pyrazol-5-amine Chemical compound NC=1C=CNN=1 JVVRJMXHNUAPHW-UHFFFAOYSA-N 0.000 description 1
- YMAYPJGBQFEYAV-UHFFFAOYSA-N 2-(dichloroamino)benzenesulfonic acid Chemical compound ClN(C1=CC=CC=C1S(=O)(=O)O)Cl YMAYPJGBQFEYAV-UHFFFAOYSA-N 0.000 description 1
- BDHNZWFPUYTGGS-UHFFFAOYSA-N 2-(methylamino)benzenesulfonic acid Chemical compound CNC1=CC=CC=C1S(O)(=O)=O BDHNZWFPUYTGGS-UHFFFAOYSA-N 0.000 description 1
- YBAQDUMZKYHASY-UHFFFAOYSA-N 2-amino-5-[(3-nitrobenzoyl)amino]benzenesulfonic acid Chemical compound C1=C(S(O)(=O)=O)C(N)=CC=C1NC(=O)C1=CC=CC([N+]([O-])=O)=C1 YBAQDUMZKYHASY-UHFFFAOYSA-N 0.000 description 1
- ZMCHBSMFKQYNKA-UHFFFAOYSA-N 2-aminobenzenesulfonic acid Chemical compound NC1=CC=CC=C1S(O)(=O)=O ZMCHBSMFKQYNKA-UHFFFAOYSA-N 0.000 description 1
- FYTLHYRDGXRYEY-UHFFFAOYSA-N 5-Methyl-3-pyrazolamine Chemical compound CC=1C=C(N)NN=1 FYTLHYRDGXRYEY-UHFFFAOYSA-N 0.000 description 1
- YUNBHHWDQDGWHC-UHFFFAOYSA-N 6-aminonaphthalene-1-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC2=CC(N)=CC=C21 YUNBHHWDQDGWHC-UHFFFAOYSA-N 0.000 description 1
- SEMRCUIXRUXGJX-UHFFFAOYSA-N 6-aminonaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=CC2=CC(N)=CC=C21 SEMRCUIXRUXGJX-UHFFFAOYSA-N 0.000 description 1
- HKTWHHAJDJCUPC-UHFFFAOYSA-N 7-aminonaphthalene-1,3,5-trisulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(S(O)(=O)=O)C2=CC(N)=CC(S(O)(=O)=O)=C21 HKTWHHAJDJCUPC-UHFFFAOYSA-N 0.000 description 1
- GFPQSWFFPRQEHH-UHFFFAOYSA-N 7-aminonaphthalene-1,3,6-trisulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C=C(S(O)(=O)=O)C(N)=CC2=C1S(O)(=O)=O GFPQSWFFPRQEHH-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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical group NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000005599 alkyl carboxylate group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- DMVOXQPQNTYEKQ-UHFFFAOYSA-N biphenyl-4-amine Chemical group C1=CC(N)=CC=C1C1=CC=CC=C1 DMVOXQPQNTYEKQ-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000002270 phosphoric acid ester group Chemical group 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 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
- 239000012266 salt solution Substances 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE792586D BE792586A (fr) | 1971-12-13 | Colorants azoiques reactifs hydrosolubles et leur preparation | |
| DE19712161761 DE2161761C2 (de) | 1971-12-13 | 1971-12-13 | Wasserlösliche, reaktive Azofarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung zum Färben und Bedrucken von Leder, Wolle, Seide, Polyamid- und Polyurethanfasern sowie nativen oder regenerierten Cellulosefasern |
| CH1790172A CH568364A5 (enExample) | 1971-12-13 | 1972-12-08 | |
| FR7243978A FR2163502B1 (enExample) | 1971-12-13 | 1972-12-11 | |
| JP12353272A JPS5222003B2 (enExample) | 1971-12-13 | 1972-12-11 | |
| GB5714172A GB1413315A (en) | 1971-12-13 | 1972-12-11 | Watersoluble reactive azo dyestuffs |
| IT3272772A IT971721B (it) | 1971-12-13 | 1972-12-11 | Azocoloranti reattivi idrosolubi li e procedimento per la loro preparazione |
| IN2130/72A IN138883B (enExample) | 1971-12-13 | 1972-12-12 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712161761 DE2161761C2 (de) | 1971-12-13 | 1971-12-13 | Wasserlösliche, reaktive Azofarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung zum Färben und Bedrucken von Leder, Wolle, Seide, Polyamid- und Polyurethanfasern sowie nativen oder regenerierten Cellulosefasern |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2161761A1 DE2161761A1 (de) | 1973-06-14 |
| DE2161761C2 true DE2161761C2 (de) | 1983-03-24 |
Family
ID=5827827
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712161761 Expired DE2161761C2 (de) | 1971-12-13 | 1971-12-13 | Wasserlösliche, reaktive Azofarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung zum Färben und Bedrucken von Leder, Wolle, Seide, Polyamid- und Polyurethanfasern sowie nativen oder regenerierten Cellulosefasern |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS5222003B2 (enExample) |
| BE (1) | BE792586A (enExample) |
| CH (1) | CH568364A5 (enExample) |
| DE (1) | DE2161761C2 (enExample) |
| FR (1) | FR2163502B1 (enExample) |
| GB (1) | GB1413315A (enExample) |
| IN (1) | IN138883B (enExample) |
| IT (1) | IT971721B (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6509354B1 (en) | 1998-04-27 | 2003-01-21 | Kumiai Chemical Industry Co., Ltd. | 3-arylphenyl sulfide derivative and insecticide and miticide |
| EP1424368A1 (en) * | 2002-11-29 | 2004-06-02 | Clariant International Ltd. | Mono azo dyes |
| JP2006506482A (ja) * | 2002-11-13 | 2006-02-23 | クラリアント インターナショナル リミティド | モノアゾ染料 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1073691A (fr) * | 1952-02-19 | 1954-09-28 | Hoechst Ag | Colorants azoïques appartenant aux séries de la pyrazolone et du pyrazol et procédé de préparation de ces colorants |
| GB1220422A (en) * | 1968-02-28 | 1971-01-27 | Sumitomo Chemical Co | Reactive yellow monoazo dyes of the phenylazo-pyrazole series and process for the preparation thereof |
-
0
- BE BE792586D patent/BE792586A/xx not_active IP Right Cessation
-
1971
- 1971-12-13 DE DE19712161761 patent/DE2161761C2/de not_active Expired
-
1972
- 1972-12-08 CH CH1790172A patent/CH568364A5/xx not_active IP Right Cessation
- 1972-12-11 FR FR7243978A patent/FR2163502B1/fr not_active Expired
- 1972-12-11 IT IT3272772A patent/IT971721B/it active
- 1972-12-11 JP JP12353272A patent/JPS5222003B2/ja not_active Expired
- 1972-12-11 GB GB5714172A patent/GB1413315A/en not_active Expired
- 1972-12-12 IN IN2130/72A patent/IN138883B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IT971721B (it) | 1974-05-10 |
| FR2163502A1 (enExample) | 1973-07-27 |
| GB1413315A (en) | 1975-11-12 |
| JPS4866621A (enExample) | 1973-09-12 |
| BE792586A (fr) | 1973-06-12 |
| CH568364A5 (enExample) | 1975-10-31 |
| IN138883B (enExample) | 1976-04-10 |
| JPS5222003B2 (enExample) | 1977-06-14 |
| DE2161761A1 (de) | 1973-06-14 |
| FR2163502B1 (enExample) | 1976-08-20 |
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