DE2142412C3 - Disazoverbindungen, deren Herstellung und Verwendung zum Färben und Bedrucken von Polyamid oder Polyurethanfasermaterialien - Google Patents
Disazoverbindungen, deren Herstellung und Verwendung zum Färben und Bedrucken von Polyamid oder PolyurethanfasermaterialienInfo
- Publication number
- DE2142412C3 DE2142412C3 DE2142412A DE2142412A DE2142412C3 DE 2142412 C3 DE2142412 C3 DE 2142412C3 DE 2142412 A DE2142412 A DE 2142412A DE 2142412 A DE2142412 A DE 2142412A DE 2142412 C3 DE2142412 C3 DE 2142412C3
- Authority
- DE
- Germany
- Prior art keywords
- radical
- dyeing
- dye
- parts
- amino
- 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
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title claims description 14
- 239000004952 Polyamide Substances 0.000 title description 10
- 229920002647 polyamide Polymers 0.000 title description 10
- 238000004043 dyeing Methods 0.000 title description 5
- 239000002657 fibrous material Substances 0.000 title description 2
- 229920006306 polyurethane fiber Polymers 0.000 title description 2
- 238000004519 manufacturing process Methods 0.000 title 1
- -1 alkoxy radical Chemical class 0.000 description 25
- 239000000975 dye Substances 0.000 description 24
- 125000000217 alkyl group Chemical group 0.000 description 13
- 150000003254 radicals Chemical group 0.000 description 13
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
- 125000004432 carbon atom Chemical group C* 0.000 description 12
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
- 230000008878 coupling Effects 0.000 description 8
- 238000010168 coupling process Methods 0.000 description 8
- 238000005859 coupling reaction Methods 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- 239000001257 hydrogen Substances 0.000 description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- 239000002253 acid Substances 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000000835 fiber Substances 0.000 description 6
- 229910000029 sodium carbonate Inorganic materials 0.000 description 6
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N methanesulfonic acid Substances CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 3
- VOWZNBNDMFLQGM-UHFFFAOYSA-N 2,5-dimethylaniline Chemical compound CC1=CC=C(C)C(N)=C1 VOWZNBNDMFLQGM-UHFFFAOYSA-N 0.000 description 2
- HXDOZKJGKXYMEW-UHFFFAOYSA-N 4-ethylphenol Chemical compound CCC1=CC=C(O)C=C1 HXDOZKJGKXYMEW-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- OHBQPCCCRFSCAX-UHFFFAOYSA-N Hydroquinone dimethyl ether Natural products COC1=CC=C(OC)C=C1 OHBQPCCCRFSCAX-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- VQFAIAKCILWQPZ-UHFFFAOYSA-N bromoacetone Chemical compound CC(=O)CBr VQFAIAKCILWQPZ-UHFFFAOYSA-N 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 229940098779 methanesulfonic acid Drugs 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 125000000547 substituted alkyl group Chemical group 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- UKDOTCFNLHHKOF-FGRDZWBJSA-N (z)-1-chloroprop-1-ene;(z)-1,2-dichloroethene Chemical group C\C=C/Cl.Cl\C=C/Cl UKDOTCFNLHHKOF-FGRDZWBJSA-N 0.000 description 1
- YHRUOJUYPBUZOS-UHFFFAOYSA-N 1,3-dichloropropane Chemical compound ClCCCCl YHRUOJUYPBUZOS-UHFFFAOYSA-N 0.000 description 1
- ULHFFAFDSSHFDA-UHFFFAOYSA-N 1-amino-2-ethoxybenzene Chemical compound CCOC1=CC=CC=C1N ULHFFAFDSSHFDA-UHFFFAOYSA-N 0.000 description 1
- XPKFTIYOZUJAGA-UHFFFAOYSA-N 2,5-diethoxyaniline Chemical compound CCOC1=CC=C(OCC)C(N)=C1 XPKFTIYOZUJAGA-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
- REXUYBKPWIPONM-UHFFFAOYSA-N 2-bromoacetonitrile Chemical compound BrCC#N REXUYBKPWIPONM-UHFFFAOYSA-N 0.000 description 1
- LDLCZOVUSADOIV-UHFFFAOYSA-N 2-bromoethanol Chemical compound OCCBr LDLCZOVUSADOIV-UHFFFAOYSA-N 0.000 description 1
- VZIQXGLTRZLBEX-UHFFFAOYSA-N 2-chloro-1-propanol Chemical compound CC(Cl)CO VZIQXGLTRZLBEX-UHFFFAOYSA-N 0.000 description 1
- VIRWKAJWTKAIMA-UHFFFAOYSA-N 2-chloroethyl acetate Chemical compound CC(=O)OCCCl VIRWKAJWTKAIMA-UHFFFAOYSA-N 0.000 description 1
- JNAYPRPPXRWGQO-UHFFFAOYSA-N 2-chloropropanenitrile Chemical compound CC(Cl)C#N JNAYPRPPXRWGQO-UHFFFAOYSA-N 0.000 description 1
- 125000004810 2-methylpropylene group Chemical group [H]C([H])([H])C([H])(C([H])([H])[*:2])C([H])([H])[*:1] 0.000 description 1
- ZLCSFXXPPANWQY-UHFFFAOYSA-N 3-ethyltoluene Chemical compound CCC1=CC=CC(C)=C1 ZLCSFXXPPANWQY-UHFFFAOYSA-N 0.000 description 1
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N Acetylene Chemical compound C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- XJUZRXYOEPSWMB-UHFFFAOYSA-N Chloromethyl methyl ether Chemical compound COCCl XJUZRXYOEPSWMB-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- BULLHNJGPPOUOX-UHFFFAOYSA-N chloroacetone Chemical compound CC(=O)CCl BULLHNJGPPOUOX-UHFFFAOYSA-N 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Substances ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- XBYOCRCRHQJSIG-UHFFFAOYSA-N chloromethoxybenzene Chemical compound ClCOC1=CC=CC=C1 XBYOCRCRHQJSIG-UHFFFAOYSA-N 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 1
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N ortho-diethylbenzene Natural products CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 1
- IMACFCSSMIZSPP-UHFFFAOYSA-N phenacyl chloride Chemical compound ClCC(=O)C1=CC=CC=C1 IMACFCSSMIZSPP-UHFFFAOYSA-N 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 239000004753 textile Substances 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
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/28—Preparation of azo dyes from other azo compounds by etherification of hydroxyl groups
-
- 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
- C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
- C09B31/02—Disazo dyes
- C09B31/06—Disazo dyes from a coupling component "C" containing a directive hydroxyl group
- C09B31/062—Phenols
- C09B31/065—Phenols containing acid groups, e.g. —CO2H, —SO3H, —PO3H2, —OSO3H, —OPO2H2; Salts thereof
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/916—Natural fiber dyeing
- Y10S8/917—Wool or silk
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/92—Synthetic fiber dyeing
- Y10S8/924—Polyamide fiber
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1264770A CH536347A (de) | 1970-08-25 | 1970-08-25 | Verfahren zur Herstellung von Disazoverbindungen und deren Verwendung |
| CH1179871 | 1971-08-11 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2142412A1 DE2142412A1 (de) | 1972-03-02 |
| DE2142412B2 DE2142412B2 (de) | 1980-02-14 |
| DE2142412C3 true DE2142412C3 (de) | 1980-10-09 |
Family
ID=25708922
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2142412A Expired DE2142412C3 (de) | 1970-08-25 | 1971-08-24 | Disazoverbindungen, deren Herstellung und Verwendung zum Färben und Bedrucken von Polyamid oder Polyurethanfasermaterialien |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3932378A (enExample) |
| JP (1) | JPS577181B1 (enExample) |
| AT (1) | AT308926B (enExample) |
| BE (1) | BE771692A (enExample) |
| CA (1) | CA926386A (enExample) |
| CS (1) | CS167943B2 (enExample) |
| DE (1) | DE2142412C3 (enExample) |
| ES (1) | ES394466A1 (enExample) |
| FR (1) | FR2103494B1 (enExample) |
| GB (1) | GB1330383A (enExample) |
| NL (1) | NL171170C (enExample) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4199318A (en) * | 1971-03-11 | 1980-04-22 | Toms River Chemical Corporation | Washfast disazo dyestuffs |
| CA996930A (en) * | 1972-06-08 | 1976-09-14 | E.I. Du Pont De Nemours And Company | Yellow to orange disazo acid dyes for nylon |
| US4055560A (en) * | 1972-06-08 | 1977-10-25 | E. I. Du Pont De Nemours And Company | Sulfophenyl-azo-phenyl-azo-(4-hydroxyalkoxyphenyl) compounds |
| CA999854A (en) * | 1972-07-21 | 1976-11-16 | James F. Feeman | Yellow, orange and scarlet disazo dyes |
| DE2718620C2 (de) * | 1977-04-27 | 1982-10-21 | Basf Ag, 6700 Ludwigshafen | Sulfonsäuregruppenhaltige Disazofarbstoffe und deren Verwendung |
| DE2849086A1 (de) * | 1978-11-11 | 1980-05-22 | Bayer Ag | Disazoverbindung |
| US4384870A (en) * | 1980-08-08 | 1983-05-24 | Sandoz Ltd. | Disazo compounds having a sulfo group-containing diazo component radical, a 1,4-phenylene middle component radical having a substituted amino group and a coupling component radical having a free, acylated or etherified hydroxy group |
| US4340385A (en) * | 1981-02-23 | 1982-07-20 | Sandoz, Inc. | Stable, concentrated, aqueous compositions containing para-sulfophenyl-azo-substituted 1,4-phenylene-azo-para-2-hydroxypropoxyphenyl dyes |
| EP0083299B2 (de) * | 1981-12-29 | 1990-06-13 | Ciba-Geigy Ag | Verfahren zum Trichromie-Färben oder -Bedrucken |
| ATE19533T1 (de) * | 1982-04-08 | 1986-05-15 | Ciba Geigy Ag | Verfahren zum trichromie-faerben oder -bedrucken. |
| DE3222909A1 (de) * | 1982-06-18 | 1983-12-22 | Bayer Ag, 5090 Leverkusen | Diazofarbstoffe |
| DE3237369A1 (de) * | 1982-10-08 | 1984-04-12 | Bayer Ag, 5090 Leverkusen | Disazofarbstoffe |
| DE3340272A1 (de) * | 1983-11-08 | 1985-05-15 | Bayer Ag, 5090 Leverkusen | Farbstoffmischung |
| US4749784A (en) * | 1985-03-11 | 1988-06-07 | Crompton & Knowles Corporation | Alkanol substituted disazo orange dye for nylon |
| EP0194377A3 (en) * | 1985-03-11 | 1988-06-08 | CROMPTON & KNOWLES CORPORATION | Disazo orange dyes for nylon |
| GB2236542B (en) * | 1989-10-06 | 1992-04-15 | Sandoz Ltd | Dye mixtures and their use in trichromatic dyeing processes |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1711390A (en) * | 1925-01-06 | 1929-04-30 | Chemical Works Formerly Sandoz | Manufacture of azodyestuffs for dyeing cellulose esters |
| DE617666C (de) * | 1933-07-18 | 1935-08-23 | Ici Ltd | Verfahren zur Herstellung von sekundaeren Disazofarbstoffen |
| FR1201549A (fr) * | 1958-04-21 | 1959-12-30 | Cfmc | Nouveaux colorants disazoïques métallisables et leurs complexes métallifères |
| GB882533A (en) * | 1958-06-06 | 1961-11-15 | Ciba Ltd | Water-insoluble disazo-dyestuffs and process for their manufacture |
| US3060168A (en) * | 1959-07-17 | 1962-10-23 | Ciba Ltd | Water-insoluble disazo-dyestuffs |
| US3274172A (en) * | 1962-09-24 | 1966-09-20 | Sumitomo Chemical Co | Disazo disperse dyestuffs |
| US3485814A (en) * | 1965-08-12 | 1969-12-23 | Du Pont | Disazo sulfonic acid dyes |
| CH532640A (de) * | 1969-04-17 | 1973-01-15 | Ciba Geigy Ag | Verwendung bestimmter Disazoverbindungen als Farbstoffe |
| DE1963674A1 (de) * | 1969-12-19 | 1971-06-24 | Hoechst Ag | Neue Disazofarbstoffe und Verfahren zu deren Herstellung |
-
1971
- 1971-08-17 CA CA120716A patent/CA926386A/en not_active Expired
- 1971-08-18 US US05/172,877 patent/US3932378A/en not_active Expired - Lifetime
- 1971-08-24 GB GB3967371A patent/GB1330383A/en not_active Expired
- 1971-08-24 BE BE771692A patent/BE771692A/xx unknown
- 1971-08-24 DE DE2142412A patent/DE2142412C3/de not_active Expired
- 1971-08-24 NL NLAANVRAGE7111635,A patent/NL171170C/xx not_active IP Right Cessation
- 1971-08-24 AT AT739071A patent/AT308926B/de not_active IP Right Cessation
- 1971-08-24 FR FR717130728A patent/FR2103494B1/fr not_active Expired
- 1971-08-24 ES ES394466A patent/ES394466A1/es not_active Expired
- 1971-08-25 CS CS6088A patent/CS167943B2/cs unknown
- 1971-08-25 JP JP6448971A patent/JPS577181B1/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| NL171170C (nl) | 1983-02-16 |
| AU3255871A (en) | 1973-02-22 |
| FR2103494A1 (enExample) | 1972-04-14 |
| CA926386A (en) | 1973-05-15 |
| NL171170B (nl) | 1982-09-16 |
| AT308926B (de) | 1973-07-25 |
| CS167943B2 (enExample) | 1976-05-28 |
| FR2103494B1 (enExample) | 1973-06-29 |
| BE771692A (fr) | 1972-02-24 |
| DE2142412A1 (de) | 1972-03-02 |
| DE2142412B2 (de) | 1980-02-14 |
| GB1330383A (en) | 1973-09-19 |
| NL7111635A (enExample) | 1972-02-29 |
| ES394466A1 (es) | 1974-09-16 |
| US3932378A (en) | 1976-01-13 |
| JPS577181B1 (enExample) | 1982-02-09 |
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