GB2027733A - Navy Blue Disperse Dyes, Dyeing Preparations and Compositions Containing Them, Process for Their Preparation and Their Use for the Dyeing or Printing of Synthetic Fibre Materials - Google Patents
Navy Blue Disperse Dyes, Dyeing Preparations and Compositions Containing Them, Process for Their Preparation and Their Use for the Dyeing or Printing of Synthetic Fibre Materials Download PDFInfo
- Publication number
- GB2027733A GB2027733A GB7926762A GB7926762A GB2027733A GB 2027733 A GB2027733 A GB 2027733A GB 7926762 A GB7926762 A GB 7926762A GB 7926762 A GB7926762 A GB 7926762A GB 2027733 A GB2027733 A GB 2027733A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dyeing
- preparation
- compound
- fibre materials
- polyester
- 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.)
- Granted
Links
- 238000004043 dyeing Methods 0.000 title claims abstract description 21
- 239000000463 material Substances 0.000 title claims abstract description 13
- 239000000203 mixture Substances 0.000 title claims abstract description 13
- 238000000034 method Methods 0.000 title claims abstract description 12
- 239000000986 disperse dye Substances 0.000 title claims abstract description 8
- 229920002994 synthetic fiber Polymers 0.000 title claims abstract description 8
- 238000002360 preparation method Methods 0.000 title claims description 18
- 239000000460 chlorine Substances 0.000 claims abstract description 9
- 229920000728 polyester Polymers 0.000 claims abstract description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 3
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 13
- 239000000975 dye Substances 0.000 claims description 12
- 230000008878 coupling Effects 0.000 claims description 4
- 238000010168 coupling process Methods 0.000 claims description 4
- 238000005859 coupling reaction Methods 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
- 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 description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000006185 dispersion Substances 0.000 claims description 2
- 238000001238 wet grinding Methods 0.000 claims description 2
- 238000012505 colouration Methods 0.000 abstract description 4
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 abstract description 3
- 239000000835 fiber Substances 0.000 abstract description 3
- 238000005299 abrasion Methods 0.000 abstract description 2
- 238000004040 coloring Methods 0.000 abstract description 2
- -1 propionylamino group Chemical group 0.000 abstract description 2
- 239000002912 waste gas Substances 0.000 abstract description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000006243 chemical reaction 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
- 238000001035 drying Methods 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- VQTGUFBGYOIUFS-UHFFFAOYSA-N nitrosylsulfuric acid Chemical compound OS(=O)(=O)ON=O VQTGUFBGYOIUFS-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 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)
Abstract
The invention provides a disperse dye of the general formula <IMAGE> wherein X represents a chlorine or bromine atom, R1 represents an alkyl radical having from 1 to 4 carbon atoms, and R2 represents a methyl or ethyl group. These dyestuffs may be used for dyeing and printing synthetic fibre materials, especially polyester fibre materials. They are superior to analogous dyestuffs having an acetylamino group in place of the propionylamino group in that they give colourations of distinctly lower abrasion and with no deposits when applied onto packages. They have a good fastness to light and to waste gases and they also have a good build up. They may be used for fast dyeing processes and for colouring the polyester portion in polyester-wool blends.
Description
SPECIFICATION
Navy Blue Disperse Dyes, Dyeing Preparations and Compositions Containing them. Process for their Preparation and their use for the Dyeing or Printing of Synthetic fibre Materials
The present invention provides navy blue disperse dyes, preparations and compositions containing them, process for their preparation and their use for the dyeing or printing of synthetic fibre materials.
The disperse dyes have the general formula
where
X represents a chlorine or bromine atom,
R1 represents an alkyl radical having from 1 to 4 carbon atoms, and
R2 represents a methyl or ethyl group.
The dyestuff is generally in free form.
A composition of the invention comprises a mixture of one or more compounds of the general formula 1 and one or more other disperse dyes.
The dyestuff(s) are usually used in the form of a dyestuff preparation containing, as well as the dyestuff or dyestuffs, a suitable carrier.
Dyestuffs of the general formula
wherein X, R, and R2 have the meanings given for formula 1 are disclosed in Belgian Patent 634,032.
The dyestuffs of the invention differ from the dyestuffs of formula 2 in that they contain the propionylamino group instead of the acetylamino group. It was not to be expected therefore that the dyestuffs of the formula 1 would differ advantageously from the corresponding dyestuffs of the formula 2 containing the acetylamino group.
We have surprisingly found, however, that the dyestuffs of the invention are superior to an analogous dyestuff of the formula 2 in that they give colourations of distinctly lower abrasion and with substantially no deposits, when applied onto packages.
Dyestuffs of the invention are suitable for dyeing and printing synthetic fibre materials, especially polyester fibrous materials. They have a good fastness to light and to waste gases, a good build up and a low sensitivity to reduction and to variations in temperature during dyeing. They may be used for fast dyeing process and for colouring the polyester portion in polyester-wool blends.
The dyestuffs of the invention are, moreover, suitable for dyeing the above fibre materials from organic solvents.
The dyestuffs according to the invention may be prepared by coupling diazotized 2,4-dinitro-6chloroaniline or diazotized 2,4-dinitro-6-bromoaniline with a coupling component of the general formula
wherein R1 and R2 are as defined above. The reaction is suitably carried out in acid, aqueous solution in known manner.
A dyeing preparation containing one or more of the dyestuffs of the invention and optionally one or more other disperse dyes may be prepared by wet grinding of the dyestuff(s) with one or more dispersion agents, for example lignin sulphonates.
The following Examples illustrate the invention:
Example 1
217.5 Parts by weight of 2,4-dinitro-6-chloroaniline were introduced into 1,000 parts by weight of 96% sulphuric acid and dissolved while stirring. Next, 320 parts by weight of 40% nitrosylsulphuric acid were added, while maintaining the temperature at 30 to 350C by exterior cooling. Stirring at 30 to 350C was continued for two hours. After this period diazotization was complete. The resulting diazonium salt solution was added within 60 minutes to a stirred solution of 4,000 parts by weight of water, 6,000 parts by weight of ice, 1,000 parts by weight of giacial acetic acid and 280 parts by weight of 2-ethylamino-4-propionylamino- 1 ,B-methoxyethoxybenzene.
Further quantities of ice were added during this addition to prevent a temperature rise above +50C. Stirring was continued for 3 hours, and the dyestuff formed was suction-filtered and washed with water until free from acid. Drying gave 410 parts by weight of the dyestuff which corresponds to a yield of 83% of the theoretical yield. The dyestuff had the formula
When applied onto polyester fibres dyeing compositions of this dyestuff provided deep navy blue colourations.
Examples 2 to 17
The dyestuffs listed in the following Table were prepared in analogous manner. They have the formula
wherein X, R1 and R2 are as defined above. When applied onto polyester fibre material these dyestuffs, too, provided deep, navy blue colourations.
Table
Example No. X R1 R2 2 Cl -CH3 CH3 3 Cl -CH2CH2CH3 - CH3 4 CI -CH(CH3)2 - CH3 5 Cl -CH2CH2CH2CH3 - CH3 6 Cl -CH2CH2CH3 -C2H 7 Cl -CH(CH3)2 - C2H 8 Cl -CH2CH2CH2CH3 - C2H 9 Br -CH3 - C2H 10 Br -QH5 - -C2H5 11 Br -CH2CH2CH3 -C2H 12 Br -CH(CH3)2 - C2H 13 Br -CH2CH2CH2CH3 - C2H -C2H5 14 Br -C2H5 - CH3 15 Br -CH2CH2CH3 - CH3 16 Br -CH2CH2CH2CH3 -CH3 yCH3 17 Br -CH -CH3 C2H6
Claims (16)
1. A compound of the general formula
wherein
X represents a chlorine or bromine atom,
R1 represents an alkyl radical having from 1 to 4 carbon atoms and
R2 represents a methyl or ethyl group.
2. The compound of the formula
3. A compound as claimed in claim 1 specified in any one of Examples 2 to 1 7 herein.
4. A process for the preparation of a compound claimed in claim 1, which comprises coupling diazotized 2,4-dinitro-6-chloroaniline or diazotized 2,4-dinitro-6-bromoaniline with a coupling component of the general formula
wherein R, and R2 have the meanings given in claim 1.
5. A process as claimed in claim 4, carried out substantially as described in any one of the
Examples 1 to 1 7 herein.
6. A compound as claimed in claim 1 whenever prepared by a process as claimed in claim 4 or claim 5.
7. A dyeing composition comprising at least one dyestuff as claimed in any one of claims 1 to 3 and 6, in admixture with one or more other disperse dyes.
8. A dyeing preparation which comprises a compound as claimed in any one of claims 1 to 3 and 6 or a composition as claimed in claim 7, and a suitable carrier.
9. A dyeing preparation as claimed in claim 8, which contains at least 20% by weight of a compound claimed in claim 1.
10. A dyeing preparation as claimed in claim 9, which contains from 20 to 80% by weight of a compound claimed in claim 1.
11. A process for the preparation of a dyeing preparation as claimed in claim 8, which comprises wet grinding the dyestuff or dyestuffs with one or more dispersion agents.
12. A dyeing preparation as claimed in claim 8, whenever prepared by a process as claimed in claim 11.
1 3. A compound claimed in any one of claims 1 to 3 and 6 for use for dyeing or printing synthetic fibre materials.
14. A process for dyeing or printing synthetic fibre materials, wherein there is used a compound as claimed in any one of claims 1 to 3 and 6 or a composition or preparation as claimed in any one of claims 7 to 10 and 12.
1 5. A process as claimed in claim 14, wherein the material is polyester.
16. Synthetic fibre material which has been dyed or printed with a compound as claimed in any one of claims 1 to 3 and 6 or with a composition or preparation as claimed in any one of claims 7 to 10 and 12.
1 7. Polyester-wool material in which the polyester has been dyed or printed with a compound as claimed n any one of claims 1 to 3 and 6 or with a composition or preparation as claimed in any one of claims 7 to 10 and 12. ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~
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 (2)
| Publication Number | Publication Date |
|---|---|
| GB2027733A true GB2027733A (en) | 1980-02-27 |
| GB2027733B GB2027733B (en) | 1982-11-03 |
Family
ID=6046016
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB7926762A Expired GB2027733B (en) | 1978-08-02 | 1979-08-01 | Navy blue disperse dyes dyeing preparations and compositions containing them process for their preparation and their use for the dyeing or printing of synthetic fibre materials |
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) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4494957A (en) * | 1982-05-17 | 1985-01-22 | Research Association Of Synethtic Dyestuffs | Dye compositions for polyester fibers |
| US4678476A (en) * | 1985-11-09 | 1987-07-07 | Cassella Aktiengesellschaft | Mixtures of blue mono-azo disperse dyestuffs and their use for dyeing polyester |
| US5037962A (en) * | 1988-10-11 | 1991-08-06 | Cassella Ag | β-modification of 1-(2,4-dinitro-6-chloro-phenylazo)-2-propionylamino-4-N-ethylamino-5-(2-methoxy-ethoxy)benzene, its preparation and its use |
| US5071443A (en) * | 1989-03-15 | 1991-12-10 | Cassella Aktiengesellschaft | Blue azo dyestuff mixture for strong blue color on hydrophobic fibers |
Families Citing this family (8)
| 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 |
| DE3222013A1 (en) * | 1982-06-11 | 1983-12-15 | Hoechst Ag, 6230 Frankfurt | METHOD FOR PRODUCING NUCLEAR-SUBSTITUTED N-ALKYLANILINES |
| JPH046649Y2 (en) * | 1987-07-24 | 1992-02-24 | ||
| 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 GB GB7926762A patent/GB2027733B/en not_active Expired
- 1979-08-01 BR BR7904927A patent/BR7904927A/en not_active IP Right Cessation
- 1979-08-01 MX MX178744A patent/MX150602A/en unknown
- 1979-08-02 BE BE0/196572A patent/BE878039A/en not_active IP Right Cessation
- 1979-08-02 FR FR7919842A patent/FR2432537B1/en not_active Expired
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4494957A (en) * | 1982-05-17 | 1985-01-22 | Research Association Of Synethtic Dyestuffs | Dye compositions for polyester fibers |
| US4678476A (en) * | 1985-11-09 | 1987-07-07 | Cassella Aktiengesellschaft | Mixtures of blue mono-azo disperse dyestuffs and their use for dyeing polyester |
| USRE33908E (en) * | 1985-11-09 | 1992-05-05 | Cassella Aktiengesellschaft | Mixtures of blue mono-azo disperse dyestuffs and their use for dyeing polyester |
| US5037962A (en) * | 1988-10-11 | 1991-08-06 | Cassella Ag | β-modification of 1-(2,4-dinitro-6-chloro-phenylazo)-2-propionylamino-4-N-ethylamino-5-(2-methoxy-ethoxy)benzene, its preparation and its use |
| US5071443A (en) * | 1989-03-15 | 1991-12-10 | Cassella Aktiengesellschaft | Blue azo dyestuff mixture for strong blue color on hydrophobic fibers |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2432537B1 (en) | 1986-07-04 |
| BE878039A (en) | 1980-02-04 |
| DE2833854C2 (en) | 1980-09-04 |
| CH642988A5 (en) | 1984-05-15 |
| DE2833854B1 (en) | 1980-01-03 |
| FR2432537A1 (en) | 1980-02-29 |
| BR7904927A (en) | 1980-05-06 |
| GB2027733B (en) | 1982-11-03 |
| IT7924818A0 (en) | 1979-07-31 |
| IT1165279B (en) | 1987-04-22 |
| JPS5523190A (en) | 1980-02-19 |
| MX150602A (en) | 1984-06-06 |
| JPS6261617B2 (en) | 1987-12-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19950801 |