CH642988A5 - NAVY BLUE DISPERSION DYES AND COLOR PREPARATIONS CONTAINING THEM AND A METHOD FOR THE PRODUCTION THEREOF. - Google Patents
NAVY BLUE DISPERSION DYES AND COLOR PREPARATIONS CONTAINING THEM AND A METHOD FOR THE PRODUCTION THEREOF. Download PDFInfo
- Publication number
- CH642988A5 CH642988A5 CH702379A CH702379A CH642988A5 CH 642988 A5 CH642988 A5 CH 642988A5 CH 702379 A CH702379 A CH 702379A CH 702379 A CH702379 A CH 702379A CH 642988 A5 CH642988 A5 CH 642988A5
- Authority
- CH
- Switzerland
- Prior art keywords
- dyes
- formula
- dyeing
- group
- dinitro
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 8
- 238000000034 method Methods 0.000 title claims description 4
- 239000006185 dispersion Substances 0.000 title description 2
- 238000004519 manufacturing process Methods 0.000 title 1
- 239000000975 dye Substances 0.000 claims description 23
- 239000000460 chlorine Substances 0.000 claims description 11
- 238000004043 dyeing Methods 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 229920000728 polyester Polymers 0.000 claims description 4
- LHRIICYSGQGXSX-UHFFFAOYSA-N 2-chloro-4,6-dinitroaniline Chemical compound NC1=C(Cl)C=C([N+]([O-])=O)C=C1[N+]([O-])=O LHRIICYSGQGXSX-UHFFFAOYSA-N 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 239000000986 disperse dye Substances 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 239000000835 fiber Substances 0.000 claims description 2
- 239000002657 fibrous material Substances 0.000 claims description 2
- 230000008878 coupling Effects 0.000 claims 3
- 238000010168 coupling process Methods 0.000 claims 3
- 238000005859 coupling reaction Methods 0.000 claims 3
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims 2
- 230000035945 sensitivity Effects 0.000 claims 2
- KWMDHCLJYMVBNS-UHFFFAOYSA-N 2-bromo-4,6-dinitroaniline Chemical compound NC1=C(Br)C=C([N+]([O-])=O)C=C1[N+]([O-])=O KWMDHCLJYMVBNS-UHFFFAOYSA-N 0.000 claims 1
- 238000005299 abrasion Methods 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 239000012209 synthetic fiber Substances 0.000 claims 1
- 229920002994 synthetic fiber Polymers 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- OMONCKYJLBVWOQ-UHFFFAOYSA-N 1-ethoxy-2-methoxybenzene Chemical compound CCOC1=CC=CC=C1OC OMONCKYJLBVWOQ-UHFFFAOYSA-N 0.000 description 1
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- -1 lithium sulfonates Chemical class 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000001238 wet grinding 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
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
- C09B29/0833—Amino benzenes characterised by the substituent on the benzene ring excepted the substituents: CH3, C2H5, O-alkyl, NHCO-alkyl, NHCOO-alkyl, NHCO- C6H5, NHCOO-C6H5
- C09B29/0834—Amino benzenes characterised by the substituent on the benzene ring excepted the substituents: CH3, C2H5, O-alkyl, NHCO-alkyl, NHCOO-alkyl, NHCO- C6H5, NHCOO-C6H5 linked through -O-
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Gegenstand der vorliegenden Erfindung sind neue marineblaue Dispersionsfarbstoffe und diese enthaltende Färbepräparationen sowie Verfahren zu deren Herstellung, wobei die neuen Dispersionsfarbstoffe der Formel 1 The present invention relates to new navy blue disperse dyes and dyeing preparations containing them, and to processes for their preparation, the new disperse dyes of the formula 1
y=r \H y = r \ H
NHCOCnHc £ t> NHCOCnHc £ t>
45 45
°2N \ \_/~ ° 2N \ \ _ / ~
X X
R1 R1
H H
(1) (1)
NH-CO-C2H5 NH-CO-C2H5
entsprechen, in welcher X ein Chlor- oder Bromatom, Rt eine Alkylgruppe mit 1 bis 4 Kohlenstoffatomen und R2 eine Methyl* oder Äthylgruppe bedeuten. correspond in which X is a chlorine or bromine atom, Rt is an alkyl group having 1 to 4 carbon atoms and R2 is a methyl * or ethyl group.
In der belgischen Patentschrift Nr. 634 032 sind Farbstoffe der Formel 2 Belgian Patent No. 634 032 contains dyes of the formula 2
o2h in welcher R] und R2 die weiter oben genannten Bedeutungen haben, vorzugsweise in saurer, wässriger Lösung. o2h in which R] and R2 have the meanings given above, preferably in acidic, aqueous solution.
Die Herstellung von Färbepräparationen aus den erfindungsgemässen Farbstoffen und gegebenenfalls weiteren Dis-sopersionsfarbstoffen erfolgt z.B. durch Nassmahlung der neuen Farbstoffe mit Dispergiermitteln, beispielsweise mit Li-gninsulfonaten. The preparation of coloring preparations from the dyes according to the invention and, if appropriate, further dispersion dyes is carried out e.g. by wet grinding the new dyes with dispersants, for example with lithium sulfonates.
Beispiel 1 example 1
55 217,5 Gewichtsteile 2,4-Dinitro-6-chloranilin werden in 1000 Gewichtsteilen 96%ige Schwefelsäure eingetragen und unter Rühren gelöst. Anschliessend lässt man 320 Gewichtsteile 40%ige Nitrosylschwefelsäure zulaufen, wobei man mittels Aussenkühlung die Temperatur bei 30-35 °C hält. Dann so rührt man zwei Stunden bei 30-35 °C. Nach Ablauf dieser Zeit ist die Diazotierung beendet. Die so erhaltene Diazoni-umsalzlösung lässt man innerhalb von 60 Minuten zu einer gerührten Mischung aus 4000 Gewichtsteilen Wasser, 6000 (2), Gewichtsteilen Eis, 1000 Gewichtsteilen Eisessig und 280 Ge-' 65wichtsteilen 2-Äthylamino-4-propionylamino-l-ß-methoxy-äthoxybenzol laufen. Die Temperatur soll dabei + 5 °C nicht übersteigen, was durch Zugabe von weiterem Eis erreicht wird. Man rührt 3 Stunden nach, filtriert den gebildeten 55 217.5 parts by weight of 2,4-dinitro-6-chloroaniline are introduced into 1000 parts by weight of 96% sulfuric acid and dissolved with stirring. Then 320 parts by weight of 40% nitrosylsulfuric acid are run in, the temperature being kept at 30-35 ° C. by means of external cooling. Then stir for two hours at 30-35 ° C. After this time, the diazotization is complete. The diazonium salt solution thus obtained is left over 60 minutes to a stirred mixture of 4000 parts by weight of water, 6000 (2) parts by weight of ice, 1000 parts by weight of glacial acetic acid and 280 parts by weight of 2-ethylamino-4-propionylamino-1-ß- run methoxy-ethoxybenzene. The temperature should not exceed + 5 ° C, which is achieved by adding more ice. The mixture is stirred for 3 hours, the formed
3 3rd
642 988 642 988
Farbstoff ab und wäscht ihn mit Wasser säurefrei. Nach dem in welcher X, R] und R2 die vorhergenannten Bedeutungen Dye and washes it acid-free with water. After which X, R] and R2 have the meanings mentioned above
Trocknen erhält man 410 Gewichtsteile Farbstoff, was einer Ausbeute von 83% der Theorie entspricht. Der so erhaltene Farbstoff entspricht der Formel Drying gives 410 parts by weight of dye, which corresponds to a yield of 83% of theory. The dye thus obtained corresponds to the formula
NO, NO,
OC~H-OCH-j 2 4 3 OC ~ H-OCH-j 2 4 3
°2NH\ZVN=N -^-»Ch2 5 ° 2NH \ ZVN = N - ^ - »Ch2 5
Cl Cl
NHCOC2H5 NHCOC2H5
Mit Färbepräparationen des Farbstoffs können Polyesterfasern tief marineblau gefärbt werden. With dye preparations of the dye, polyester fibers can be dyed deep navy blue.
In analoger Weise werden die in der Tabelle angegeben neuen Farbstoffe der allgemeinen Formel o2n haben, hergestellt. Sie ergeben ebenfalls auf Polyesterfasermaterialien tiefe, marineblaue Färbungen. The new dyes of the general formula o2n given in the table are prepared in an analogous manner. They also produce deep, navy-blue colors on polyester fiber materials.
10 10th
Tabelle table
Beispiel Nr. Example No.
x r. x r.
r2 r2
2 2nd
Cl Cl
-ch3 -ch3
-ch3 -ch3
3 3rd
Cl Cl
-ch2ch2ch3 -ch2ch2ch3
-ch3 -ch3
4 4th
Cl Cl
-ch(ch3)2 -ch (ch3) 2
-ch3 -ch3
5 5
Cl Cl
-ch2ch2ch2ch3 -ch2ch2ch2ch3
-ch3 -ch3
6 6
Cl Cl
-ch2ch2ch3 -ch2ch2ch3
-c2h5 -c2h5
7 7
Cl Cl
-ch(ch3)2 -ch (ch3) 2
-c2h5 -c2h5
8 8th
Cl Cl
-ch2ch2ch2ch3 -ch2ch2ch2ch3
-c2h5 -c2h5
9 9
Br Br
-ch3 -ch3
-c2h5 -c2h5
10 . 10th
Br Br
-c2h5 -c2h5
-c2h5 -c2h5
11 11
Br Br
-ch2ch2ch3 -ch2ch2ch3
-c2h5 -c2h5
12 12
Br Br
-ch(ch3)2 -ch (ch3) 2
-c2h5 -c2h5
13 13
Br Br
-ch2ch2ch2ch3 -ch2ch2ch2ch3
-c2h5 -c2h5
14 14
Br Br
-c2h5 -c2h5
-ch3 -ch3
15 15
Br Br
-ch2ch2ch3 -ch2ch2ch3
-ch3 -ch3
16 16
Br Br
-ch2ch2ch2ch3 -ch2ch2ch2ch3
-ch3 -ch3
17 17th
X X
NHCOC2H5 NHCOC2H5
Br Br
-ch -ch
-c2h5 -c2h5
-ch, -ch,
C C.
Claims (4)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2833854A DE2833854C2 (en) | 1978-08-02 | 1978-08-02 | New navy blue disperse dyes, processes for their production and their use for dyeing or printing synthetic fiber materials |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH642988A5 true CH642988A5 (en) | 1984-05-15 |
Family
ID=6046016
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH702379A CH642988A5 (en) | 1978-08-02 | 1979-07-30 | NAVY BLUE DISPERSION DYES AND COLOR PREPARATIONS CONTAINING THEM AND A METHOD FOR THE PRODUCTION THEREOF. |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS5523190A (en) |
| BE (1) | BE878039A (en) |
| BR (1) | BR7904927A (en) |
| CH (1) | CH642988A5 (en) |
| DE (1) | DE2833854C2 (en) |
| FR (1) | FR2432537B1 (en) |
| GB (1) | GB2027733B (en) |
| IT (1) | IT1165279B (en) |
| MX (1) | MX150602A (en) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3121320A1 (en) * | 1981-05-29 | 1982-12-16 | Hoechst Ag, 6000 Frankfurt | NEW COLOR PRESENTATIONS, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE FOR COLORING AND PRINTING SYNTHETIC FIBER MATERIALS |
| DE3133355A1 (en) * | 1981-08-22 | 1983-03-10 | Hoechst Ag, 6000 Frankfurt | NEW NAVY BLUE DISPERSION DYES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE FOR COLORING OR PRINTING SYNTHETIC FIBER MATERIALS |
| US4494957A (en) * | 1982-05-17 | 1985-01-22 | Research Association Of Synethtic Dyestuffs | Dye compositions for polyester fibers |
| DE3222013A1 (en) * | 1982-06-11 | 1983-12-15 | Hoechst Ag, 6230 Frankfurt | METHOD FOR PRODUCING NUCLEAR-SUBSTITUTED N-ALKYLANILINES |
| DE3539771A1 (en) * | 1985-11-09 | 1987-05-14 | Cassella Ag | MIXTURES OF BLUE DISPERSION DYES AND THEIR USE FOR DYING POLYESTER |
| JPH046649Y2 (en) * | 1987-07-24 | 1992-02-24 | ||
| DE3834530A1 (en) * | 1988-10-11 | 1990-04-12 | Cassella Ag | COLOR-RESISTANT MONOAZO DYE, THEIR PRODUCTION AND USE |
| DE3908445A1 (en) * | 1989-03-15 | 1990-09-20 | Cassella Ag | DYE MIXTURE |
| JPH04286577A (en) * | 1991-03-13 | 1992-10-12 | Kanebo Ltd | Package transfer device |
| JPH04115859U (en) * | 1991-03-26 | 1992-10-15 | 株式会社豊田自動織機製作所 | Pezgu tray separation device |
| JPH0623967U (en) * | 1992-08-05 | 1994-03-29 | 村田機械株式会社 | Tray with sideways pegs |
| JP3048093B2 (en) * | 1992-09-11 | 2000-06-05 | 鐘紡株式会社 | Package transfer device |
-
1978
- 1978-08-02 DE DE2833854A patent/DE2833854C2/en not_active Expired
-
1979
- 1979-07-30 CH CH702379A patent/CH642988A5/en not_active IP Right Cessation
- 1979-07-31 IT IT24818/79A patent/IT1165279B/en active
- 1979-07-31 JP JP9686379A patent/JPS5523190A/en active Granted
- 1979-08-01 MX MX178744A patent/MX150602A/en unknown
- 1979-08-01 GB GB7926762A patent/GB2027733B/en not_active Expired
- 1979-08-01 BR BR7904927A patent/BR7904927A/en not_active IP Right Cessation
- 1979-08-02 FR FR7919842A patent/FR2432537B1/en not_active Expired
- 1979-08-02 BE BE0/196572A patent/BE878039A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5523190A (en) | 1980-02-19 |
| DE2833854C2 (en) | 1980-09-04 |
| FR2432537A1 (en) | 1980-02-29 |
| JPS6261617B2 (en) | 1987-12-22 |
| MX150602A (en) | 1984-06-06 |
| GB2027733B (en) | 1982-11-03 |
| FR2432537B1 (en) | 1986-07-04 |
| BR7904927A (en) | 1980-05-06 |
| IT7924818A0 (en) | 1979-07-31 |
| GB2027733A (en) | 1980-02-27 |
| BE878039A (en) | 1980-02-04 |
| IT1165279B (en) | 1987-04-22 |
| DE2833854B1 (en) | 1980-01-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |