GB2174406A - Disazo pyridone dyes - Google Patents
Disazo pyridone dyes Download PDFInfo
- Publication number
- GB2174406A GB2174406A GB08610005A GB8610005A GB2174406A GB 2174406 A GB2174406 A GB 2174406A GB 08610005 A GB08610005 A GB 08610005A GB 8610005 A GB8610005 A GB 8610005A GB 2174406 A GB2174406 A GB 2174406A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- compound
- mixture
- compounds
- parts
- 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
- 239000000975 dye Substances 0.000 title description 11
- -1 Disazo pyridone Chemical compound 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 39
- 229920000728 polyester Polymers 0.000 claims abstract description 4
- 239000000203 mixture Substances 0.000 claims description 22
- 238000004043 dyeing Methods 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 6
- QPQKUYVSJWQSDY-CCEZHUSRSA-N 4-(phenylazo)aniline Chemical compound C1=CC(N)=CC=C1\N=N\C1=CC=CC=C1 QPQKUYVSJWQSDY-CCEZHUSRSA-N 0.000 claims description 3
- 239000002270 dispersing agent Substances 0.000 claims description 3
- QPQKUYVSJWQSDY-UHFFFAOYSA-N 4-phenyldiazenylaniline Chemical compound C1=CC(N)=CC=C1N=NC1=CC=CC=C1 QPQKUYVSJWQSDY-UHFFFAOYSA-N 0.000 claims description 2
- 230000008878 coupling Effects 0.000 claims description 2
- 238000010168 coupling process Methods 0.000 claims description 2
- 238000005859 coupling reaction Methods 0.000 claims description 2
- 239000004744 fabric Substances 0.000 claims description 2
- 239000000945 filler Substances 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- 239000000758 substrate Substances 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000004753 textile Substances 0.000 abstract description 3
- 239000000986 disperse dye Substances 0.000 abstract description 2
- 229920002301 cellulose acetate Polymers 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 6
- 238000001816 cooling Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- 239000012954 diazonium Substances 0.000 description 2
- 150000001989 diazonium salts Chemical class 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- QEORVDCGZONWCJ-UHFFFAOYSA-N 2-[[4-[2-cyanoethyl(ethyl)amino]phenyl]diazenyl]-5-nitrobenzonitrile Chemical compound C1=CC(N(CCC#N)CC)=CC=C1N=NC1=CC=C([N+]([O-])=O)C=C1C#N QEORVDCGZONWCJ-UHFFFAOYSA-N 0.000 description 1
- 229920002284 Cellulose triacetate Polymers 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 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
- VJMAITQRABEEKP-UHFFFAOYSA-N [6-(phenylmethoxymethyl)-1,4-dioxan-2-yl]methyl acetate Chemical compound O1C(COC(=O)C)COCC1COCC1=CC=CC=C1 VJMAITQRABEEKP-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000003118 aryl group Chemical group 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
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010016 exhaust dyeing Methods 0.000 description 1
- 238000009998 heat setting Methods 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Substances [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 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
- 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
- C09B31/12—Disazo dyes from other coupling components "C"
- C09B31/14—Heterocyclic components
- C09B31/153—Heterocyclic components containing a six-membered ring with one nitrogen atom as the only ring hetero-atom
-
- 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
- C09B67/0055—Mixtures of two or more disazo dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A compound of formula I <IMAGE> in which n is an integer from 2 to 9 inclusive. These compounds are useful as disperse dyes for polyester and cellulose acetate textiles. They may be used alone or in combination with compounds of formula (I) in which n is 0 or 1.
Description
SPECIFICATION
Improvements in or relating to organic compounds
The invention relates to new disazo compounds suitable as disperse dyes.
According to the invention, there is provided a compound of formula I
in which n is an integer from 2 to 9 inclusive.
Prefereably n is an integer from 3 to 5 inclusive, more preferably n is 3.
Compounds of formula I can usefully be combined with other compounds of formula I in which n is zero or 1 inclusive, preferably where n is 1.
Preferred mixtures of compounds of formula I comprise 50 to 80% by weight of compounds of formula I in which n is 2 to 9, (of which preferably at least 20% is a compound where n=3) and 20-50% of a compound of formula I where n is 0 or 1.
Preferred mixtures according to the invention are those containing i) 30 to 80% of the compound of formula I where n is 3, ii) 0 to 50% of a compound of formula I where n is 2,4 or 5 and iii) 20 to 50% of the compound of formula I where n is 1, provided components i) and ii) form at least 50%.
More preferred mixtures according to the invention are those containing 50 to 80% of the compound of formula I where n is 3 and 20 to 50% of the compound of formula I where n is 1.
Formula I is shown in one tautomeric form of the compounds of formula I and for the avoidance of doubt it is stated that formula I in this specification refers to all tautomeric forms.
Compounds of formula I can be prepared from known compounds by known methods, for example by diazotising p-aminoazobenzene and coupling the diazotised aminoazobenzene with a compound of formula II
where the symbols are as defined above.
The incorporation of dyes according to the invention into dyeing preparation may be carried out by known methods for example by milling in the presence of dispersing agent and/or filler.
The preparations may be atomised or vacuum dried. These dyeing preparations can, with the addition of little or a lot of water, be used for so called long or short dyebaths.
The dyes according to the invention can be used for exhaust dyeing, padding or printing.
The dyes according to the invention exhaust well on textile material made of fully synthetic or semi-synthetic hydrophobic high molecular weight material. The dyes according to the invention can be used for exhaustion dyeing, padding or printing of textile material made out of linear aromatic polyester, cellulose 21/2 acetate or cellulose triacetate.
Dyeing, padding or printing can be carried out according to known methods, as described for example in French Patent 1,445,371.
Dyeings made with dyes according to the invention have good fastness properties, particularly good light fastness, good thermofixation, good sublimation fastness and good fastness to pleating. The dyes of the invention have good build-up, a rapid exhaust and a fast fixing rate and exhaust well from the dyeing bath.
The invention will now be illustrated by the following Examples in which all parts and percentages are by weight and all temperatures are in "C unless indicated to the contrary. 1 part by volume is equivalent to the volume of 1 part by weight of water.
Example 1
The compound of formula la
can be prepared as follows.
32 Parts of 4-aminoazobenzene are stirred overnight in 150 parts of 15% HCI and the mixture is added to 350 parts of an ice/water mixture. The mixture (which is in part crystallised out) is then diazotised with 34 parts by volume of an aqueous 5-n- sodium nitrite solution over about 30 minutes at 5 to 100. The crystalline material goes into solution.
After 2 hours the small excess of nitrous acid generated is destroyed with a little amidosulphonic acid and the dark red-brown diazonium salt solution is clear filtered.
106 Parts of a solution (38.6%) of 40.9 parts of 1-y-n-butoxy-n-propyl-3-cyano-6-hydroxy-4methyl-pyridone-2 (in the form of the monoethanolamine salt) in 300 parts of water are reacted with the diazonium salt solution over about 1 hour whilst cooling (keeping the temperature below 10").
The pH is held at 3 to 6 by the addition of sodium acetate. The mixture is stirred for several hours, without cooling, the undissolved dyestuff is filtered off and washed salt free with water.
A max for the resulting dyestuff of formula 1 a is 458 ,um.
Example 2
A 60:40% mixture of the compound of formula la (defined in Example 1
and the compound of formula 2a
can be prepared as follows.
Instead of using 105 parts of the solution of 40.9 parts of 1-y n-butoxy-n-propyl-3-cyano-6hydroxy-4-methyl pyridone-2 in 300 parts of water in Example 1, 63.6 parts of a mixture of a 38.6% aqueous solution of 1-y-n-butoxy-n-propyl-3-cyano-6-hydroxy-4-methylpyridone-2 and 28.2 parts of a 51.9% aqueous solution of 1-y-ethoxy-n-propyl-3-cyano-6-hydroxy-4-methyl- pyridone-2 mixed together in 300 parts of water are used in the procedure of Example 1.
Examples 3 to 19
Compounds of formula I
(where n is given in the Table below) and mixtures thereof, can be prepared by a method analogous to that of Examples 1 or 2 respectively from appropriate starting materials.
TABLE
EX. n % max nm
No.
3 2 100 461
4 5 100 461
5 7 100 460
3 75 6 # 460 3 50 7 # 460 3 67 8 # 460 5 33 2 50 9 # 459 3 50 10 # 50 1 461 50 3 70 11 # 460 3 50 12 # 0 20 461 1 30 1 33 1/3 13 # 3 33 1/3 461 5 33 1/3 1 30 14 # 2 30 460 3 40 2 40 15 # 5 35 460 7 25 0 40 16 # 2 30 461 4 30 Table continued NEoX: n max
30 17 ss 50 459 9 20 18 25 1 { 25 460 32 25 25 19 1 47.5 Colour 3 3 47.5 Yellow-brown ) C.I. 5 Disperse Red 73 Application Example
250 Parts of a 16% aqueous paste of the dyestuff mixture of Example 2 are milled together with 60 parts of a commercially available lignin sulphonate dispersing agent in a glass bead mill until the average diameter of the particles is 1 ,am. The glass beads are filtered off and the pH is brought to 7 to 8. The preparation is then dried in a hot air atomiser. The resulting fine powder contains 45% of the pure dyestuff mixture.
1 Part of the preparation as above is stirred into 4000 parts of water, buffered at 5 pH and having a temperature of 60 to form a dyeing bath.
100 Parts of a polyester fabric are immersed in the dyeing bath and, are dyed in a closed vessel for 1 hour at 130 . After cooling, washing, saponifying, washing a second time and drying, a level dyeing with good fastness properties is obtained.
Claims (1)
1. A compound of formula I
in which n is an integer from 2 to 9.
2. A compound of formula I according to Claim 1, in which n is 3 to 5 inclusive.
3. A compound of formula I according to Claim 1 or Claim 2, in which n is 3.
4. A mixture of compounds of formula I, defined in Claim 1, comprising
a) a compound of formula I, in which n is as defined in Claim 1; and
b) a compound of formula I, in which n is 0 or 1.
5. A mixture according to Claim 4, in which 50 to 80% (based on the total weight of the mixture) of component a) and 20 to 50% based on the total weight of the mixture of component b) are present.
6. A mixture according to Claim 4, comprising
i) 30-80% of the compound of formula I defined in Claim 1 in which n is 3;
ii) 0-50% of a compound of formula I defined in Claim 1, in which n is 2, 4 or 5; and
iii) 20-50% of a compound of formula I defined in Claim 1, in which n is 1, provided components i) and ii) together form at least 50%.
7. A process for preparing a compound of formula I according to any one of Claims 1 to 3, comprising diazotising p-aminoazobenzene and coupling the diazotised aminoazobenzene with a compound of formula II
where n is as defined in Claim 1.
8. A dyeing preparation comprising a compound of formula I according to any one of Claims 1 to 3 or a mixture of compounds of formula I according to any one of Claims 4 to 6, and a dispersing agent or a filler.
9. A process for dyeing a substrate comprising applying to the substrate a compound of formula I according to any one of Claims 1 to 3 or a mixture to any one of Claims 4 to 6.
10. A substrate to which a compound of formula I according to any one of Claims 1 to 3 or a mixture according to any one of Claims 4 to 6 has been applied.
11. A compound of formula I defined in Claim 1, substantially as herein defined with reference to any one of Examples 1 to 19.
13. A process according to Claim 7 substantially as herein described with reference to any one of Examples 1 to 9.
14. A process for applying a compound according to Claim 1 or a mixture according to Claim 4, substantially as herein described with reference to the Application Example.
15. Polyester fabric to which a compound according to Claim 1 or a mixture according to
Claim 3 has been applied.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3515370 | 1985-04-27 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| GB8610005D0 GB8610005D0 (en) | 1986-05-29 |
| GB2174406A true GB2174406A (en) | 1986-11-05 |
| GB2174406B GB2174406B (en) | 1989-07-12 |
Family
ID=6269368
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8610005A Expired GB2174406B (en) | 1985-04-27 | 1986-04-24 | Disazo pyridone dyes |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPS61250061A (en) |
| FR (1) | FR2581073A1 (en) |
| GB (1) | GB2174406B (en) |
| IT (1) | IT1203776B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4772292A (en) * | 1985-02-21 | 1988-09-20 | Cassella Aktiengesellschaft | Mixture of yellow disperse dyestuffs containing pyridone disazo dye |
| US5623060A (en) * | 1993-09-04 | 1997-04-22 | Basf Aktiengesellschaft | Dye mixture containing at least four diazo dyes having the same color with a diaminopyridine coupling component |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1295893A (en) * | 1969-04-03 | 1972-11-08 | ||
| GB1296857A (en) * | 1968-11-12 | 1972-11-22 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2801951A1 (en) * | 1978-01-18 | 1979-07-19 | Basf Ag | AZO DYES |
| DE3505899A1 (en) * | 1985-02-21 | 1986-08-21 | Cassella Ag, 6000 Frankfurt | MIX OF YELLOW DISPERSION DYES |
-
1986
- 1986-04-18 FR FR8605753A patent/FR2581073A1/en active Pending
- 1986-04-24 GB GB8610005A patent/GB2174406B/en not_active Expired
- 1986-04-25 JP JP61094995A patent/JPS61250061A/en active Pending
- 1986-04-28 IT IT47941/86A patent/IT1203776B/en active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1296857A (en) * | 1968-11-12 | 1972-11-22 | ||
| GB1295893A (en) * | 1969-04-03 | 1972-11-08 |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4772292A (en) * | 1985-02-21 | 1988-09-20 | Cassella Aktiengesellschaft | Mixture of yellow disperse dyestuffs containing pyridone disazo dye |
| US5623060A (en) * | 1993-09-04 | 1997-04-22 | Basf Aktiengesellschaft | Dye mixture containing at least four diazo dyes having the same color with a diaminopyridine coupling component |
Also Published As
| Publication number | Publication date |
|---|---|
| IT8647941A0 (en) | 1986-04-28 |
| GB8610005D0 (en) | 1986-05-29 |
| IT1203776B (en) | 1989-02-23 |
| GB2174406B (en) | 1989-07-12 |
| FR2581073A1 (en) | 1986-10-31 |
| JPS61250061A (en) | 1986-11-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |