CH569762A5 - Azo dyes contg thiophene ring - as disperse dyes for synthetic fibres with good resistance to light - Google Patents
Azo dyes contg thiophene ring - as disperse dyes for synthetic fibres with good resistance to lightInfo
- Publication number
- CH569762A5 CH569762A5 CH998672A CH998672A CH569762A5 CH 569762 A5 CH569762 A5 CH 569762A5 CH 998672 A CH998672 A CH 998672A CH 998672 A CH998672 A CH 998672A CH 569762 A5 CH569762 A5 CH 569762A5
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- alkyl
- hydrogen
- formula
- chlorine
- Prior art date
Links
- 239000000986 disperse dye Substances 0.000 title abstract description 4
- 239000000987 azo dye Substances 0.000 title abstract 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 title 1
- 229920002994 synthetic fiber Polymers 0.000 title 1
- 239000000460 chlorine Substances 0.000 claims abstract description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 17
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 14
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- 230000008878 coupling Effects 0.000 claims abstract description 12
- 238000010168 coupling process Methods 0.000 claims abstract description 12
- 238000005859 coupling reaction Methods 0.000 claims abstract description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 12
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 8
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract description 7
- 125000003118 aryl group Chemical group 0.000 claims abstract description 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 5
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims abstract description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000006678 phenoxycarbonyl group Chemical group 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
- 125000001424 substituent group Chemical group 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 8
- 125000002252 acyl group Chemical group 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- VHPMGVXTLGJECO-UHFFFAOYSA-N [Rh]C#N Chemical compound [Rh]C#N VHPMGVXTLGJECO-UHFFFAOYSA-N 0.000 claims description 4
- 125000004442 acylamino group Chemical group 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000004423 acyloxy group Chemical group 0.000 claims description 3
- 150000001989 diazonium salts Chemical class 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 229920000728 polyester Polymers 0.000 abstract description 8
- 238000004043 dyeing Methods 0.000 abstract description 7
- 239000000126 substance Substances 0.000 abstract description 4
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 abstract description 2
- 239000004952 Polyamide Substances 0.000 abstract description 2
- 229920002647 polyamide Polymers 0.000 abstract description 2
- 239000002689 soil Substances 0.000 abstract description 2
- 238000000859 sublimation Methods 0.000 abstract description 2
- 230000008022 sublimation Effects 0.000 abstract description 2
- 239000002904 solvent Substances 0.000 abstract 1
- -1 phenoxycarbonyl radical Chemical class 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 239000000975 dye Substances 0.000 description 8
- 239000002657 fibrous material Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 4
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- CFBYBPOBHYGXNZ-UHFFFAOYSA-N 2-amino-4-methyl-5-nitrothiophene-3-carbonitrile Chemical compound CC1=C([N+]([O-])=O)SC(N)=C1C#N CFBYBPOBHYGXNZ-UHFFFAOYSA-N 0.000 description 1
- DKKVIKAIZCKPOQ-UHFFFAOYSA-N CCN(CC)N(C1=CC=CC=C1)S(C)(=O)=O Chemical compound CCN(CC)N(C1=CC=CC=C1)S(C)(=O)=O DKKVIKAIZCKPOQ-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 229920002284 Cellulose triacetate Polymers 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- FHNINJWBTRXEBC-UHFFFAOYSA-N Sudan III Chemical compound OC1=CC=C2C=CC=CC2=C1N=NC(C=C1)=CC=C1N=NC1=CC=CC=C1 FHNINJWBTRXEBC-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 238000000889 atomisation Methods 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Substances ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- WBLIXGSTEMXDSM-UHFFFAOYSA-N chloromethane Chemical compound Cl[CH2] WBLIXGSTEMXDSM-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Chemical class 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 238000009998 heat setting Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000013535 sea water Substances 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
-
- 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
- C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
- C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
- C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
- C09B29/3617—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom
- C09B29/3621—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring
- C09B29/3626—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring from a pyridine ring containing one or more hydroxyl groups (or = O)
- C09B29/3634—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring from a pyridine ring containing one or more hydroxyl groups (or = O) from diazotized heterocyclic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Priority Applications (16)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH998672A CH569762A5 (en) | 1972-07-04 | 1972-07-04 | Azo dyes contg thiophene ring - as disperse dyes for synthetic fibres with good resistance to light |
| NL7309098A NL7309098A (cs) | 1972-07-04 | 1973-06-29 | |
| DE19732333447 DE2333447A1 (de) | 1972-07-04 | 1973-06-30 | In wasser schwer loesliche azoverbindungen, ihre herstellung und verwendung |
| DD17199273A DD105821A5 (cs) | 1972-07-04 | 1973-07-02 | |
| BE133029A BE801805A (fr) | 1972-07-04 | 1973-07-02 | Nouveaux colorants azoiques peu solubles dans l'eau et leur preparation |
| GB3136173A GB1434654A (en) | 1972-07-04 | 1973-07-02 | Thiophene azo dyestuffs |
| ES416503A ES416503A1 (es) | 1972-07-04 | 1973-07-02 | Procedimiento para la produccion de compuestos azoicos de poca solubilidad en agua. |
| JP7445873A JPS4944031A (cs) | 1972-07-04 | 1973-07-03 | |
| BR4938/73A BR7304938D0 (pt) | 1972-07-04 | 1973-07-03 | Processo para a preparacao de compostos azoicos dificilmente soluveis em agua |
| PL1973163801A PL90271B1 (cs) | 1972-07-04 | 1973-07-03 | |
| ZA00734547A ZA734547B (en) | 1972-07-04 | 1973-07-04 | Azo compounds of low water-solubility |
| AU57728/73A AU5772873A (en) | 1972-07-04 | 1973-07-04 | Azo compounds |
| CS4845A CS166674B2 (cs) | 1972-07-04 | 1973-07-04 | |
| AR24891673A AR198849A1 (es) | 1972-07-04 | 1973-07-04 | Colorantes azoicos poco solubles en agua y procedimiento para prepararlos |
| FR7324597A FR2190883B1 (cs) | 1972-07-04 | 1973-07-04 | |
| IT5122573A IT989734B (it) | 1972-07-04 | 1973-07-04 | Composti azoici difficilmente solu bili in acqua procedimento di prepa razione e loro impiego per la tintura di composti organici |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH998672A CH569762A5 (en) | 1972-07-04 | 1972-07-04 | Azo dyes contg thiophene ring - as disperse dyes for synthetic fibres with good resistance to light |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH569762A5 true CH569762A5 (en) | 1975-11-28 |
Family
ID=4357861
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH998672A CH569762A5 (en) | 1972-07-04 | 1972-07-04 | Azo dyes contg thiophene ring - as disperse dyes for synthetic fibres with good resistance to light |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE801805A (cs) |
| BR (1) | BR7304938D0 (cs) |
| CH (1) | CH569762A5 (cs) |
| CS (1) | CS166674B2 (cs) |
| PL (1) | PL90271B1 (cs) |
| ZA (1) | ZA734547B (cs) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH584257A5 (cs) * | 1973-09-06 | 1977-01-31 | Sandoz Ag |
-
1972
- 1972-07-04 CH CH998672A patent/CH569762A5/de not_active IP Right Cessation
-
1973
- 1973-07-02 BE BE133029A patent/BE801805A/xx unknown
- 1973-07-03 BR BR4938/73A patent/BR7304938D0/pt unknown
- 1973-07-03 PL PL1973163801A patent/PL90271B1/pl unknown
- 1973-07-04 ZA ZA00734547A patent/ZA734547B/xx unknown
- 1973-07-04 CS CS4845A patent/CS166674B2/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL90271B1 (cs) | 1977-01-31 |
| ZA734547B (en) | 1975-02-26 |
| CS166674B2 (cs) | 1976-03-29 |
| BR7304938D0 (pt) | 1974-08-29 |
| BE801805A (fr) | 1974-01-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |