CA1066460A - Mixture of water-insoluble monoazo dyestuffs for colouring textile materials consisting at least partly of linear, aromatic polyesters - Google Patents
Mixture of water-insoluble monoazo dyestuffs for colouring textile materials consisting at least partly of linear, aromatic polyestersInfo
- Publication number
- CA1066460A CA1066460A CA248,817A CA248817A CA1066460A CA 1066460 A CA1066460 A CA 1066460A CA 248817 A CA248817 A CA 248817A CA 1066460 A CA1066460 A CA 1066460A
- Authority
- CA
- Canada
- Prior art keywords
- mixture
- composition
- linear
- partly
- dyestuffs
- 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
- 239000000203 mixture Substances 0.000 title claims abstract description 96
- 229920000728 polyester Polymers 0.000 title claims abstract description 19
- 239000004753 textile Substances 0.000 title claims abstract description 17
- 125000003118 aryl group Chemical group 0.000 title claims abstract description 16
- 239000000463 material Substances 0.000 title claims abstract description 16
- 238000004040 coloring Methods 0.000 title claims abstract description 9
- 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 abstract description 7
- 238000002844 melting Methods 0.000 claims abstract description 15
- 230000008018 melting Effects 0.000 claims abstract description 14
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 11
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 10
- 150000002367 halogens Chemical group 0.000 claims abstract description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 6
- 125000004423 acyloxy group Chemical group 0.000 claims abstract description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 5
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
- 239000001257 hydrogen Substances 0.000 claims abstract description 4
- 239000002270 dispersing agent Substances 0.000 claims abstract description 3
- 239000002245 particle Substances 0.000 claims abstract description 3
- 150000002431 hydrogen Chemical group 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims description 11
- 238000005859 coupling reaction Methods 0.000 claims description 8
- 150000001989 diazonium salts Chemical class 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 230000008878 coupling Effects 0.000 claims description 6
- 238000010168 coupling process Methods 0.000 claims description 6
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 239000000975 dye Substances 0.000 abstract description 27
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 abstract description 7
- 150000001555 benzenes Chemical class 0.000 abstract description 4
- 238000012505 colouration Methods 0.000 abstract description 3
- 125000005843 halogen group Chemical group 0.000 abstract description 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 abstract description 2
- 125000005415 substituted alkoxy group Chemical group 0.000 abstract description 2
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 2
- 238000004043 dyeing Methods 0.000 description 20
- 239000006185 dispersion Substances 0.000 description 12
- -1 polyethylene terephthalate Polymers 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000004744 fabric Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 229920000139 polyethylene terephthalate Polymers 0.000 description 5
- 239000005020 polyethylene terephthalate Substances 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 238000009835 boiling Methods 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229940051881 anilide analgesics and antipyretics Drugs 0.000 description 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 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 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 239000012954 diazonium Substances 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- RNVCVTLRINQCPJ-UHFFFAOYSA-N ortho-methyl aniline Natural products CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 2
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- SWGJCIMEBVHMTA-UHFFFAOYSA-K trisodium;6-oxido-4-sulfo-5-[(4-sulfonatonaphthalen-1-yl)diazenyl]naphthalene-2-sulfonate Chemical compound [Na+].[Na+].[Na+].C1=CC=C2C(N=NC3=C4C(=CC(=CC4=CC=C3O)S([O-])(=O)=O)S([O-])(=O)=O)=CC=C(S([O-])(=O)=O)C2=C1 SWGJCIMEBVHMTA-UHFFFAOYSA-K 0.000 description 2
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- HEQOJEGTZCTHCF-UHFFFAOYSA-N 2-amino-1-phenylethanone Chemical class NCC(=O)C1=CC=CC=C1 HEQOJEGTZCTHCF-UHFFFAOYSA-N 0.000 description 1
- AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 1
- UOBYKYZJUGYBDK-UHFFFAOYSA-N 2-naphthoic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CC=C21 UOBYKYZJUGYBDK-UHFFFAOYSA-N 0.000 description 1
- UDAQUPSJOGVPIX-UHFFFAOYSA-N 3-hydroxy-7-methoxynaphthalene-2-carboxylic acid Chemical compound C1=C(O)C(C(O)=O)=CC2=CC(OC)=CC=C21 UDAQUPSJOGVPIX-UHFFFAOYSA-N 0.000 description 1
- XWPDPFLBSAPRCO-UHFFFAOYSA-N 4-(chloromethoxy)aniline Chemical class NC1=CC=C(OCCl)C=C1 XWPDPFLBSAPRCO-UHFFFAOYSA-N 0.000 description 1
- XZWXQSGFZHRDNB-UHFFFAOYSA-N 7-bromo-3-hydroxynaphthalene-2-carboxylic acid Chemical compound BrC1=CC=C2C=C(O)C(C(=O)O)=CC2=C1 XZWXQSGFZHRDNB-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 240000008886 Ceratonia siliqua Species 0.000 description 1
- 235000013912 Ceratonia siliqua Nutrition 0.000 description 1
- 244000303965 Cyamopsis psoralioides Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical class CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 1
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000003931 anilides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 1
- POJOORKDYOPQLS-UHFFFAOYSA-L barium(2+) 5-chloro-2-[(2-hydroxynaphthalen-1-yl)diazenyl]-4-methylbenzenesulfonate Chemical compound [Ba+2].C1=C(Cl)C(C)=CC(N=NC=2C3=CC=CC=C3C=CC=2O)=C1S([O-])(=O)=O.C1=C(Cl)C(C)=CC(N=NC=2C3=CC=CC=C3C=CC=2O)=C1S([O-])(=O)=O POJOORKDYOPQLS-UHFFFAOYSA-L 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical compound C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004966 cyanoalkyl group Chemical group 0.000 description 1
- 239000011928 denatured alcohol Substances 0.000 description 1
- PHHWLDOIMGFHOZ-UHFFFAOYSA-L disodium;dinaphthalen-1-ylmethanedisulfonate Chemical compound [Na+].[Na+].C1=CC=C2C(C(C=3C4=CC=CC=C4C=CC=3)(S(=O)(=O)[O-])S([O-])(=O)=O)=CC=CC2=C1 PHHWLDOIMGFHOZ-UHFFFAOYSA-L 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229940052295 esters of aminobenzoic acid for local anesthesia Drugs 0.000 description 1
- BMOAQMNPJSPXIU-UHFFFAOYSA-N ethyl 2-(3-fluoro-4-nitrophenyl)propanoate Chemical compound CCOC(=O)C(C)C1=CC=C([N+]([O-])=O)C(F)=C1 BMOAQMNPJSPXIU-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- KUDPGZONDFORKU-UHFFFAOYSA-N n-chloroaniline Chemical class ClNC1=CC=CC=C1 KUDPGZONDFORKU-UHFFFAOYSA-N 0.000 description 1
- 235000010292 orthophenyl phenol Nutrition 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
- C09B67/0046—Mixtures of two or more azo dyes
- C09B67/0051—Mixtures of two or more azo dyes mixture of two or more monoazo 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/10—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group
- C09B29/18—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group ortho-Hydroxy carbonamides
- C09B29/20—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group ortho-Hydroxy carbonamides of the naphthalene series
-
- 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
- C09B43/32—Preparation of azo dyes from other azo compounds by reacting carboxylic or sulfonic groups, or derivatives thereof, with amines; by reacting keto-groups with amines
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/16—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using dispersed, e.g. acetate, dyestuffs
- D06P1/18—Azo dyes
-
- 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
- Y10S8/922—Polyester fiber
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Dispersion Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Coloring (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH390175A CH619584GA3 (en, 2012) | 1975-03-26 | 1975-03-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1066460A true CA1066460A (en) | 1979-11-20 |
Family
ID=4265934
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA248,817A Expired CA1066460A (en) | 1975-03-26 | 1976-03-25 | Mixture of water-insoluble monoazo dyestuffs for colouring textile materials consisting at least partly of linear, aromatic polyesters |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4115055A (en, 2012) |
| JP (1) | JPS51119719A (en, 2012) |
| BR (1) | BR7601812A (en, 2012) |
| CA (1) | CA1066460A (en, 2012) |
| CH (2) | CH619584GA3 (en, 2012) |
| DE (1) | DE2612964A1 (en, 2012) |
| ES (1) | ES446368A1 (en, 2012) |
| FR (1) | FR2305475A1 (en, 2012) |
| GB (1) | GB1537335A (en, 2012) |
| IT (1) | IT1058585B (en, 2012) |
| MX (1) | MX4350E (en, 2012) |
| ZA (1) | ZA761862B (en, 2012) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4226596A (en) * | 1977-11-11 | 1980-10-07 | Rohner Ag Pratteln | Process for printing unions |
| SU908062A1 (ru) * | 1978-09-18 | 1983-06-07 | Центральный научно-исследовательский институт шерстяной промышленности | Кислотные бромбензолазокрасители дл крашени и одновременно огнезашитной отделки материалов из натуральных полиамидных волокон |
| CH653048A5 (de) * | 1981-08-28 | 1985-12-13 | Sandoz Ag | Azo-pigmentfarbstoffe. |
| DE3445930A1 (de) * | 1984-12-17 | 1986-06-26 | Cassella Ag, 6000 Frankfurt | Farbstoffmischungen, verfahren zu ihrer herstellung und verfahren zum faerben und bedrucken von hydrophoben fasermaterialien |
| DE3930393A1 (de) * | 1989-09-12 | 1991-03-21 | Hoechst Ag | Mehrkomponenten-mischungen hochroter dispersions-azofarbstoffe |
| US5286287A (en) * | 1990-10-11 | 1994-02-15 | Toyo Ink Manufacturing Co., Ltd. | Monoazo lake pigment suitable for use in printing ink and process for the production thereof |
| US5428137A (en) * | 1992-01-31 | 1995-06-27 | Orient Chemical Industries, Ltd. | Monoazo liquid dye and solutions thereof |
| JP2986609B2 (ja) * | 1992-05-14 | 1999-12-06 | オリヱント化学工業株式会社 | アゾ液体染料およびそれを含むインキ組成物 |
| US6084101A (en) * | 1996-10-11 | 2000-07-04 | Kabushiki Kaisha Ueno Seiyaku Oyo Kenkyujo | Naphtol derivative and process for producing the same |
| DE69931753D1 (de) * | 1998-10-16 | 2006-07-20 | Ueno Seiyaku Oyo Kenkyujo Kk | Azoverbindungen sowie verfahren zur herstellung derselben |
| CN103210044A (zh) * | 2010-10-25 | 2013-07-17 | 株式会社目立康 | 偶氮色素、眼用镜片材料、眼用镜片材料的制造方法和眼用镜片 |
| TW202346485A (zh) | 2022-03-28 | 2023-12-01 | 瑞士商杭斯曼高級材料公司 | 基於2-羥基萘-3-羧酸的分散偶氮染料 |
| WO2024170676A1 (en) * | 2023-02-17 | 2024-08-22 | Archroma (Switzerland) Gmbh | New class of disperse azo dyes, a process for the preparation thereof and the use thereof |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1122868A (fr) * | 1954-05-21 | 1956-09-13 | Basf Ag | Procédé pour la teinture d'objets en polyamides et en polyuréthanes |
| DE1199732B (de) | 1957-01-05 | 1965-09-02 | Kuhlmann Ets | Verfahren zum Faerben bzw. Bedrucken von Polyesterfasern |
| US3043647A (en) * | 1957-01-05 | 1962-07-10 | Cie Francaise Des Matiers Colo | Colouring of polyester fiberes |
| DE1110609B (de) | 1959-12-08 | 1961-07-13 | Hoechst Ag | Verfahren zum Faerben und Bedrucken von geformten Gebilden aus linearen aromatischen Polyestern, insbesondere Polyaethylenterephthalaten |
| CH377314A (de) | 1959-12-08 | 1964-06-30 | Hoechst Ag | Verfahren zum Färben und Bedrucken von textilen Gebilden aus linearen aromatischen Polyestern, insbesondere Polyäthylenterephthalaten |
| DE1131639B (de) | 1959-12-08 | 1962-06-20 | Hoechst Ag | Verfahren zum Faerben und Bedrucken von geformten Gebilden aus linearen aromatischen Polyestern, insbesondere Polyaethylenterephthalaten, oder aus Polyamiden |
| DE1110608B (de) | 1959-12-08 | 1961-07-13 | Hoechst Ag | Verfahren zum Faerben und Bedrucken von geformten Gebilden aus linearen aromatischen Polyestern, insbesondere Polyaethylenterephthalaten |
| DE1225138B (de) | 1961-04-28 | 1966-09-22 | Hoechst Ag | Verfahren zum Faerben und Bedrucken von geformten Gebilden aus linearen aromatischenPolyestern, insbesondere Polyaethylen-terephtalaten |
| US3383160A (en) * | 1964-03-31 | 1968-05-14 | Gen Aniline & Film Corp | Method for dyeing polyester fibers with monoazo dyestuffs |
| DE1285443B (de) | 1965-02-11 | 1968-12-19 | Cassella Farbwerke Mainkur Ag | Verfahren zum Faerben und Bedrucken von Fasergut aus hochmolekularen Polyestern |
-
1975
- 1975-03-26 CH CH390175A patent/CH619584GA3/xx not_active IP Right Cessation
-
1976
- 1976-03-16 CH CH326676A patent/CH629840A5/de not_active IP Right Cessation
- 1976-03-25 US US05/670,548 patent/US4115055A/en not_active Expired - Lifetime
- 1976-03-25 BR BR7601812A patent/BR7601812A/pt unknown
- 1976-03-25 CA CA248,817A patent/CA1066460A/en not_active Expired
- 1976-03-25 ES ES446368A patent/ES446368A1/es not_active Expired
- 1976-03-26 DE DE19762612964 patent/DE2612964A1/de not_active Withdrawn
- 1976-03-26 FR FR7608941A patent/FR2305475A1/fr active Granted
- 1976-03-26 MX MX76100306U patent/MX4350E/es unknown
- 1976-03-26 IT IT21637/76A patent/IT1058585B/it active
- 1976-03-26 ZA ZA761862A patent/ZA761862B/xx unknown
- 1976-03-26 JP JP51033448A patent/JPS51119719A/ja active Pending
- 1976-03-26 GB GB12327/76A patent/GB1537335A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CH629840A5 (de) | 1982-05-14 |
| GB1537335A (en) | 1978-12-29 |
| CH619584B (en, 2012) | |
| BR7601812A (pt) | 1976-09-28 |
| FR2305475A1 (fr) | 1976-10-22 |
| ZA761862B (en) | 1977-04-27 |
| MX4350E (es) | 1982-04-05 |
| CH619584GA3 (en, 2012) | 1980-10-15 |
| DE2612964A1 (de) | 1976-10-07 |
| FR2305475B1 (en, 2012) | 1979-07-13 |
| JPS51119719A (en) | 1976-10-20 |
| US4115055A (en) | 1978-09-19 |
| IT1058585B (it) | 1982-05-10 |
| ES446368A1 (es) | 1977-06-16 |
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