CH296545A - Process for preparing a vat dye. - Google Patents
Process for preparing a vat dye.Info
- Publication number
- CH296545A CH296545A CH296545DA CH296545A CH 296545 A CH296545 A CH 296545A CH 296545D A CH296545D A CH 296545DA CH 296545 A CH296545 A CH 296545A
- Authority
- CH
- Switzerland
- Prior art keywords
- sub
- process according
- chloride
- azodiphenyl
- anthraquinone
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 3
- 239000000984 vat dye Substances 0.000 title description 3
- 239000000975 dye Substances 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 6
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 claims description 6
- XOGPDSATLSAZEK-UHFFFAOYSA-N 2-Aminoanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(N)=CC=C3C(=O)C2=C1 XOGPDSATLSAZEK-UHFFFAOYSA-N 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 4
- 238000007363 ring formation reaction Methods 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 229910021591 Copper(I) chloride Inorganic materials 0.000 claims description 3
- 229920000742 Cotton Polymers 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims description 3
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 claims description 3
- 229940045803 cuprous chloride Drugs 0.000 claims description 3
- 235000011056 potassium acetate Nutrition 0.000 claims description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 239000012429 reaction media Substances 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims 2
- GCMIVLDLVDCTQI-UHFFFAOYSA-N C(=O)=NC1=C(C=2C(C3=CC=CC=C3C(C2C=C1)=O)=O)Cl Chemical compound C(=O)=NC1=C(C=2C(C3=CC=CC=C3C(C2C=C1)=O)=O)Cl GCMIVLDLVDCTQI-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 238000004043 dyeing Methods 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- -1 4,4'-azodiphenyl Chemical group 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 125000001475 halogen functional group Chemical group 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- 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
- C09B43/36—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 with amino-anthracene or amino-anthraquinone dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Coloring (AREA)
Description
Procédé de préparation d'un colorant pour cuve. Le présent brevet se rapporte à un pro cédé de préparation d'un colorant. pour cuve nouveau, c'est-à-dire du colorant répondant à la formule
EMI0001.0001
Ce procédé est caractérisé en ce qu'on fait réagir le chlorure d'un acide 4,4'-a.zodiphényl- 1-" - (1- halogéno - 2 - carbonylaminoanthraqui- none)
-4"'-earboxylique avec de la 2-amino- anthraquinone et qu'on fait agir sur l'amide dissymétrique ainsi obtenue une substance susceptible de fixer les acides et au moins un catalyseur pour former le noyau oxazolique.
La réaction entre le chlorure d'un acide 4,4'-azodiphényl -4" - (1-halogéno - 2 - carbonyl- aminoa.nthraquinone)-4"'-carboxylique et la 2-amino-anthraquinone est effectuée, de préfé- renee, dans un milieu ne prenant pas part à la réaction, c'est-à-dire chimiquement indiffé rent., par exemple le nitrobenzène ou le naph talène fondu, à une température élevée.
On utilise de préférence le chlorure de l'acide 4,4'-azodiphényl-4"- (1-chloro-2-carbonylamino- ant.hraqiûnone)-4"'-ca.rboxylique.
La réaction de cyclisation aboutissant à la formation du noyau oxazolique est effectuée, de préférence, à une température comprise entre 160 et 220 C. Comme substance suscep tible de fixer les acides, on peut utiliser le carbonate de sodium. Pour catalyser la réac tion de cyclisation, on peut utiliser, par exem ple, l'acétate de potassium, l'acétate de cuivre et le chlorure cuivreux. L'amide dissymétrique intermédiaire peut être soumise à la réaction de cyclisation soit dans le milieu réactionnel, soit après sa séparation.
Le chlorure d'acide 4,4'-azodiphényl-4"-(7-- chloro - 2 - carbonylaminoanthraquinone) - 4"'- carboxylique, utilisé comme l'une des matières de départ, peut être préparé en faisant réagir une 1-halogéno-S-aninoanthraquinone avec du chlorure d'acide 4,4'-azodiphényl-4",4"'-di- carboxylique en quantités pratiquement équi moléculaires dans un solvant inerte,
de préfé rence dans des conditions anhydres et à des températures comprises entre 120 et 200 C.
Le chlorure de l'acide 4,4'-azodiphényl- 4",4"'-dicarboxylique peut être obtenu par ré duction d'acide 4,4'-nitrophénylbenzoïque par du glucose et de la. soude caustique et action de chlorure de thionyle ou de pentachlorure de phosphore sur l'acide libre obtenu ou son sel sodique.
Le nouveau colorant. obtenu peut être con ditionné de la manière habituelle pour la tein ture, par exemple par malaxage ou empâ.tage acide, avec ou sans purification par blanchi ment à l'hypoehlorite de sodium. Il teint le coton en nuances jaunes brillantes à partir de cuves d'hydrosulfite alcalin de couleur brun rouge et présente une solidité particuliè rement bonne à. la lumière et une force tinc toriale excellente. Sa résistance à l'état. humide est. du même ordre de grandeur que celle qu'on rencontre chez la, plupart des colorants de cuve d'anthraquinone. On peut appliquer le nouveau colorant par les procédés de tein ture usuels.
Il teint rapidement et s'épuise bien en donnant des nuances brillantes in tenses même lorsqu'on opère à des tempéra tures élevées, par exemple de 801, <B>C,</B> qui ne sont pas de règle en teinturerie.
L'exemple suivant. montre comment on peut réaliser le présent procédé. Les parties utilisées sont en poids. <I>Exemple:</I> On met en suspension dans 500 parties de nitrobenzène, 35 parties de chlorure d'acide 4,4'-azodiphényl-4"-(1-ehloro-2-carbonvlamino- anthraquinone)-.1"'-earboxi-lique, on ajoute 0,3 partie de pyridine et. 8,7 parties de -aminoanthraquinone en remuant, on chauffe la masse à 310 C et. on maintient cette tem pérature pendant une demi-heure.
Après re froidissement à. 50 C, on. ajoute 15 parties de carbonate de sodium, 15 parties d'acétate de potassium, 0,5 partie d'acétate de cuivre et 0,5 partie de chlorure cuivreux, on chauffe la masse à. 31.0 C et. on maintient cette tempé rature pendant. î) heures. On refroidit alors le produit., on le filtre, on le lave tour à tour au nitrobenzène à. l'alcool et. à. l'eau chaude et on le sèche. Le produit forme une poudre jaune, soluble clans L'acide sulfurique concen tré en donnant une couleur brun orangé.
Il donne une cuve brun rouge au moyen de la quelle on peut. teindre le coton en nuances jaune brillant ayant de bonnes propriétés de solidité et une grande force tinctoriale.
Ce nouveau colorant. répond à, la, formule:
EMI0002.0020
Process for preparing a vat dye. The present patent relates to a process for preparing a dye. for new tank, that is to say dye corresponding to the formula
EMI0001.0001
This process is characterized in that the chloride of a 4,4'-a.zodiphenyl- 1- "- (1- halo - 2 - carbonylaminoanthraquinone) acid is reacted.
-4 "'- earboxylic with 2-amino-anthraquinone and that the unsymmetrical amide thus obtained is made to act on a substance capable of fixing acids and at least one catalyst to form the oxazolic ring.
The reaction between the chloride of a 4,4'-azodiphenyl -4 "- (1-halo - 2 - carbonyl- aminoa.nthraquinone) -4" '- carboxylic acid and 2-amino-anthraquinone is preferably carried out. - renee, in a medium not taking part in the reaction, that is to say chemically indifferent., for example molten nitrobenzene or naphthalene, at an elevated temperature.
4,4'-Azodiphenyl-4 "- (1-chloro-2-carbonylamino-ant.hraqiunone) -4" '- carboxylic acid chloride is preferably used.
The cyclization reaction resulting in the formation of the oxazolic nucleus is preferably carried out at a temperature between 160 and 220 ° C. As a substance capable of binding acids, sodium carbonate can be used. To catalyze the cyclization reaction, for example, potassium acetate, copper acetate and cuprous chloride can be used. The intermediate asymmetric amide can be subjected to the cyclization reaction either in the reaction medium or after its separation.
4,4'-Azodiphenyl-4 "- (7 - chloro - 2 - carbonylaminoanthraquinone) - 4" '- carboxylic acid chloride, used as one of the starting materials, can be prepared by reacting a 1 -halo-S-aninoanthraquinone with 4,4'-azodiphenyl-4 ", 4" '- dicarboxylic acid chloride in substantially equi molecular amounts in an inert solvent,
preferably under anhydrous conditions and at temperatures between 120 and 200 C.
4,4'-Azodiphenyl-4 ", 4" '- dicarboxylic acid chloride can be obtained by reduction of 4,4'-nitrophenylbenzoic acid with glucose and. caustic soda and the action of thionyl chloride or phosphorus pentachloride on the free acid obtained or its sodium salt.
The new dye. obtained can be packaged in the usual manner for dyeing, for example by kneading or acid impâ.tage, with or without purification by bleaching with sodium hypohlorite. It dyes cotton in brilliant yellow shades from vats of alkaline hydrosulfite of a reddish brown color and exhibits a particularly good fastness to. light and excellent torial strength. Its resistance to the state. humid is. of the same order of magnitude as that found in most anthraquinone vat dyes. The new dye can be applied by the usual dyeing methods.
It dyes quickly and wears off well giving intense shiny shades even when operating at high temperatures, for example 801, <B> C, </B> which are not the rule in dyeing.
The following example. shows how the present method can be carried out. The parts used are by weight. <I> Example: </I> Are suspended in 500 parts of nitrobenzene, 35 parts of 4,4'-azodiphenyl-4 "- (1-ehloro-2-carbonvlamino-anthraquinone) - acid chloride. "'-earboxi-lique, 0.3 part of pyridine and. 8.7 parts of -aminoanthraquinone while stirring, the mass is heated to 310 C and. this temperature is maintained for half an hour.
After cooling to. 50 C, on. add 15 parts of sodium carbonate, 15 parts of potassium acetate, 0.5 part of copper acetate and 0.5 part of cuprous chloride, the mass is heated to. 31.0 C and. this temperature is maintained for. î) hours. The product is then cooled, filtered and washed in turn with nitrobenzene. alcohol and. at. hot water and dry it. The product forms a yellow powder, soluble in concentrated sulfuric acid giving an orange-brown color.
It gives a red brown tank by means of which one can. dyeing cotton in brilliant yellow shades having good fastness properties and great tinctorial strength.
This new dye. answers, the, formula:
EMI0002.0020
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US296545XA | 1949-06-17 | 1949-06-17 | |
| CH292803T | 1950-06-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH296545A true CH296545A (en) | 1954-02-15 |
Family
ID=25733303
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH296545D CH296545A (en) | 1949-06-17 | 1950-06-14 | Process for preparing a vat dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH296545A (en) |
-
1950
- 1950-06-14 CH CH296545D patent/CH296545A/en unknown
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