DE1644190A1 - Verfahren zur Herstellung von reaktiven Azofarbstoffen und deren Metallkomplexverbindungen - Google Patents
Verfahren zur Herstellung von reaktiven Azofarbstoffen und deren MetallkomplexverbindungenInfo
- Publication number
- DE1644190A1 DE1644190A1 DE19671644190 DE1644190A DE1644190A1 DE 1644190 A1 DE1644190 A1 DE 1644190A1 DE 19671644190 DE19671644190 DE 19671644190 DE 1644190 A DE1644190 A DE 1644190A DE 1644190 A1 DE1644190 A1 DE 1644190A1
- Authority
- DE
- Germany
- Prior art keywords
- groups
- radical
- substituted
- coupling
- benzene series
- 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.)
- Pending
Links
- -1 metal complex compounds Chemical class 0.000 title claims description 12
- 238000000034 method Methods 0.000 title claims description 10
- 239000000987 azo dye Substances 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title description 3
- 239000000975 dye Substances 0.000 claims description 35
- 238000005859 coupling reaction Methods 0.000 claims description 25
- 239000002253 acid Substances 0.000 claims description 21
- 230000008878 coupling Effects 0.000 claims description 21
- 238000010168 coupling process Methods 0.000 claims description 21
- 150000001989 diazonium salts Chemical class 0.000 claims description 8
- 150000001555 benzenes Chemical class 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 150000004982 aromatic amines Chemical class 0.000 claims description 5
- 230000007935 neutral effect Effects 0.000 claims description 5
- 230000002378 acidificating effect Effects 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 3
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- UMWMJMJPVRELFU-UHFFFAOYSA-N nitrosulfamic acid Chemical compound OS(=O)(=O)N[N+]([O-])=O UMWMJMJPVRELFU-UHFFFAOYSA-N 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- HJEINPVZRDJRBY-UHFFFAOYSA-N Disul Chemical compound OS(=O)(=O)OCCOC1=CC=C(Cl)C=C1Cl HJEINPVZRDJRBY-UHFFFAOYSA-N 0.000 claims 1
- 238000004090 dissolution Methods 0.000 claims 1
- 229940124530 sulfonamide Drugs 0.000 claims 1
- 150000003456 sulfonamides Chemical class 0.000 claims 1
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 14
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 229920003043 Cellulose fiber Polymers 0.000 description 8
- 238000004043 dyeing Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 235000017557 sodium bicarbonate Nutrition 0.000 description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 239000000835 fiber Substances 0.000 description 5
- 239000001103 potassium chloride Substances 0.000 description 5
- 235000011164 potassium chloride Nutrition 0.000 description 5
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 4
- 235000019219 chocolate Nutrition 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- 239000004952 Polyamide Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 229910000365 copper sulfate Inorganic materials 0.000 description 3
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229920002647 polyamide Polymers 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000000985 reactive dye Substances 0.000 description 3
- 239000004753 textile Substances 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
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000004699 copper complex Chemical class 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 238000001465 metallisation Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000020477 pH reduction Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 125000000542 sulfonic acid group Chemical group 0.000 description 2
- 235000013311 vegetables Nutrition 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 239000002169 Metam Chemical class 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 206010065954 Stubbornness Diseases 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- 238000009954 braiding Methods 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 241001233037 catfish Species 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 235000019646 color tone Nutrition 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000009918 complex formation Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical compound C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- HYVVJDQGXFXBRZ-UHFFFAOYSA-N metam Chemical class CNC(S)=S HYVVJDQGXFXBRZ-UHFFFAOYSA-N 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 150000003839 salts Chemical class 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
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- WVAKABMNNSMCDK-UHFFFAOYSA-N sulfacarbamide Chemical compound NC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 WVAKABMNNSMCDK-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing 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
-
- 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
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
- C09B45/04—Azo compounds in general
-
- 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
- C09B62/515—Metal complex azo dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Polyamides (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US51996966A | 1966-01-11 | 1966-01-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1644190A1 true DE1644190A1 (de) | 1971-07-15 |
Family
ID=24070634
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19671644190 Pending DE1644190A1 (de) | 1966-01-11 | 1967-01-07 | Verfahren zur Herstellung von reaktiven Azofarbstoffen und deren Metallkomplexverbindungen |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3445451A (en, 2012) |
| AT (1) | AT261769B (en, 2012) |
| BE (1) | BE692436A (en, 2012) |
| CH (1) | CH477532A (en, 2012) |
| DE (1) | DE1644190A1 (en, 2012) |
| FR (1) | FR1509302A (en, 2012) |
| GB (1) | GB1141751A (en, 2012) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3755201A (en) * | 1971-07-26 | 1973-08-28 | Colgate Palmolive Co | Laundry product containing mixed dye bluing agents |
| AU2003274104A1 (en) * | 2002-06-10 | 2003-12-22 | Ciba Speciality Chemicals Holding Inc. | Method of dyeing or printing synthetic polyamide fibre materials using reactive dyes |
| MY139010A (en) * | 2005-01-21 | 2009-08-28 | Ciba Holding Inc | 6-azo-5, 5'-dihydroxy -7,7'-disulfo-2-2'-dinaphthylamine derivatives |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2670265A (en) * | 1954-02-23 | Process |
-
1966
- 1966-01-11 US US519969A patent/US3445451A/en not_active Expired - Lifetime
-
1967
- 1967-01-06 CH CH18367A patent/CH477532A/de not_active IP Right Cessation
- 1967-01-07 DE DE19671644190 patent/DE1644190A1/de active Pending
- 1967-01-09 AT AT20467A patent/AT261769B/de active
- 1967-01-11 FR FR90659A patent/FR1509302A/fr not_active Expired
- 1967-01-11 GB GB1585/67A patent/GB1141751A/en not_active Expired
- 1967-01-11 BE BE692436D patent/BE692436A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US3445451A (en) | 1969-05-20 |
| GB1141751A (en) | 1969-01-29 |
| FR1509302A (fr) | 1968-01-12 |
| AT261769B (de) | 1968-05-10 |
| BE692436A (en, 2012) | 1967-07-11 |
| CH477532A (de) | 1969-08-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2142412C3 (de) | Disazoverbindungen, deren Herstellung und Verwendung zum Färben und Bedrucken von Polyamid oder Polyurethanfasermaterialien | |
| DE1544539A1 (de) | Verfahren zur Herstellung von Disazofarbstoffen und deren Metallkomplexverbindungen | |
| DE1644155B2 (de) | Verfahren zur herstellung von disazofarbstoffen und deren metallkomplexverbindungen | |
| DE1046220B (de) | Verfahren zur Herstellung von Monoazofarbstoffen und deren Metallkomplexverbindungen | |
| DE1644190A1 (de) | Verfahren zur Herstellung von reaktiven Azofarbstoffen und deren Metallkomplexverbindungen | |
| DE2355279C2 (de) | Auf der Faser diazotierbare Direktfarbstoffe ihre Herstellung und Verwendung | |
| EP0514330B1 (de) | Azofarbstoffe | |
| DE2154942A1 (de) | Neue monoazo-reaktivfarbstoffe, ihre verwendung und verfahren zu ihrer herstellung | |
| DE1644162C3 (de) | Ein wasserlöslicher Pyrazolon-monoazofarbstoff und Verfahren zu dessen Herstellung | |
| DE1769398B2 (de) | Wasserlösliche Phthalocyanin-Azofarbstoffe sowie Verfahren zu deren Herstellung und deren Verwendung | |
| DE2604799A1 (de) | Wasserloesliche, braune 1 zu 2- chrom-mischkomplexfarbstoffe, verfahren zu ihrer herstellung und ihre verwendung zum faerben von natuerlichen und synthetischen polyamidfasern | |
| DE1544518C3 (de) | Verfahren zur Herstellung wasserlöslicher 1 zu i-Kupfer-,1 zu 2-Kobalt- oder 1 zu 2-Chromkomplex-Disazofarbstoffe und deren Verwendung | |
| DE1544541C3 (en, 2012) | ||
| DE889488C (de) | Verfahren zur Herstellung von Azofarbstoffen | |
| DE1544500B2 (de) | Metallhaltige disazoreaktivfarbstoffe und verfahren zu deren herstellung | |
| DE2408907C3 (de) | Wasserlösliche Tetrakisazofarbstoffe, Verfahren zu deren Herstellung und ihre Verwendung zum Färben von Leder | |
| AT281220B (de) | Verfahren zur Herstellung von neuen, wasserlöslichen, faserreaktiven Phenylazo-phthalocyaninfarbstoffen | |
| DE2047025C3 (de) | Wasserlösliche 1 zu 1-Kupferkomplex-Disazofarbstoffe, Verfahren zu deren Herstellung und ihre Verwendung zum Färben oder Bedrucken von nativen oder regenerierten Cellulosefaser«, Leder, Wolle, Seide, Polyamid- oder Polyurethanfasern | |
| DE909451C (de) | Verfahren zum kontinuierlichen Faerben und Drucken von Cellulosefaserstoffen | |
| DE1802466C3 (de) | Wasserlösliche, faserreaktive Phthalocyaninfarbstoffe und Verfahren zu ihrer Herstellung | |
| DE2126143A1 (de) | Wasserlösliche Monoazofarbstoffe und Verfahren zu ihrer Herstellung | |
| DE699144C (de) | Verfahren zur Herstellung von wasserunloeslichen Monoazofarbstoffen | |
| DE2533250B2 (de) | Verfahren zur Herstellung von wasserlöslichen Kupferkomplex-Azofarbstoffen und ihre Verwendung zum Färben von Cellulosefasermaterialien | |
| DE637089C (de) | Verfahren zur Herstellung von wasserunloeslichen Azofarbstoffen | |
| DE1544564C3 (en, 2012) |