DE32291C - Process for the preparation of orange-red and violet azo dyes by the action of diazo bodies on a-naphthol-disulfonic acid - Google Patents
Process for the preparation of orange-red and violet azo dyes by the action of diazo bodies on a-naphthol-disulfonic acidInfo
- Publication number
- DE32291C DE32291C DENDAT32291D DE32291DA DE32291C DE 32291 C DE32291 C DE 32291C DE NDAT32291 D DENDAT32291 D DE NDAT32291D DE 32291D A DE32291D A DE 32291DA DE 32291 C DE32291 C DE 32291C
- Authority
- DE
- Germany
- Prior art keywords
- naphthol
- disulfonic acid
- preparation
- orange
- red
- 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.)
- Expired - Lifetime
Links
- 239000002253 acid Substances 0.000 title claims description 6
- 239000000987 azo dye Substances 0.000 title claims 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title description 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-Naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 claims description 3
- 230000002378 acidificating Effects 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 150000008049 diazo compounds Chemical class 0.000 claims description 2
- 239000000835 fiber Substances 0.000 claims description 2
- 239000000975 dye Substances 0.000 description 7
- -1 monosulfodiazoazobenzene Chemical compound 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 235000002639 sodium chloride Nutrition 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- ZTAFEXGSSLGTTB-UHFFFAOYSA-N (5-sulfo-7-azoniabicyclo[4.1.0]hepta-1(6),2,4-trien-7-ylidene)azanide Chemical compound OS(=O)(=O)C1=CC=CC2=C1[N+]2=[N-] ZTAFEXGSSLGTTB-UHFFFAOYSA-N 0.000 description 1
- MBENGEYDAUUYCZ-UHFFFAOYSA-N 1-diazo-2H-naphthalene Chemical compound C1=CC=C2C(=[N+]=[N-])CC=CC2=C1 MBENGEYDAUUYCZ-UHFFFAOYSA-N 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L Calcium hydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- 235000015450 Tilia cordata Nutrition 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 210000002268 Wool Anatomy 0.000 description 1
- KVUMAMKEDVSBSO-UHFFFAOYSA-N [N+](=[N-])=C1C(C=CC=C1)N=NC1=CC=CC=C1 Chemical compound [N+](=[N-])=C1C(C=CC=C1)N=NC1=CC=CC=C1 KVUMAMKEDVSBSO-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- DMLAVOWQYNRWNQ-UHFFFAOYSA-N azobenzene Chemical compound C1=CC=CC=C1N=NC1=CC=CC=C1 DMLAVOWQYNRWNQ-UHFFFAOYSA-N 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 235000011116 calcium hydroxide Nutrition 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- FWFGVMYFCODZRD-UHFFFAOYSA-N oxidanium;hydrogen sulfate Chemical compound O.OS(O)(=O)=O FWFGVMYFCODZRD-UHFFFAOYSA-N 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 159000000000 sodium salts Chemical class 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
- C09B29/10—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group
- C09B29/16—Naphthol-sulfonic acids
Description
Cassella & 'Co. in granifurf a.m —
SSerfaljren }ur Stoffeluing »en orangeriti&en unb
unfc btofetten ^iaofarbftoffen burdj @mn>triune
»on ©tajoforpern auf a^ltl^iMM
SSotn 27, ffebsuar 1884 aß. Cassella & 'Co. in granifurf on -
SSerfaljren} ur Stoffeluing »en orangeriti & en unb
unfc btofetten ^ iaofarbftoffen burdj @mn> triune
»On © tajoforpern on a ^ ltl ^ iMM
SSotn 27, February 1884.
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
Die vorliegende Erfindung betrifft ein Verfahren zur Darstellung von orangen, rothen und violetten Farbstoffen, welches darin besteht, dafs man die Diazoverbindungen der Amine auf a-Naphtoldisulfosäure einwirken läfst. Die erhaltenen Farbstoffe besitzen die Eigenschaft, sich aus sauren Bädern langsam auf der thierischen Faser zu fixiren, und nähern sich somit den Pflanzenfarbstoffen.The present invention relates to a method for the representation of oranges, reds and violet dyes, which consists in using the diazo compounds of the Amines act on a-naphthol disulfonic acid running. The dyes obtained have the property of being slowly removed from acidic baths to fixate on the animal fiber, and thus approach the plant dyes.
So erhält man mit Diazobenzol Orange, mit Diazobenzolsulfosäure Röthlich-orange, mit deren höheren Homologen immer rothstichigeres Orange, mit Diazonaphtalin Roth-violett, mit diazotirter Naphtionsäure Violett, mit Diazoazobenzol Roth-violett, mit Monosulfodiazoazobenzol Violett, mit Disulfodiazoazobenzol Violett, mit deren Homologen Violett.So you get with diazobenzene orange, with diazobenzenesulfonic acid reddish orange with whose higher homologues are always reddish-tinged orange, with diazonaphthalene red-violet, with diazotized naphthoic acid violet, with diazoazobenzene red violet, with monosulfodiazoazobenzene Violet, with disulfodiazoazobenzene violet, with their homologues violet.
Mit den Diazoderivaten des Xylidins, Amidoazobenzols und ihrer SuIfο verbin düngen entstehen Farbstoffe von dunklerem Roth als die Farbstoffe, welche aus der Einwirkung dieser Körper auf die von der Naphtionsäure derivirenden α-Naphtolmonosulfosäure resultiren, und bilden dieselben auf Seide und Wolle einen guten Ersatz für Orseille.With the diazo derivatives of xylidine, amidoazobenzene and their suIfο compound fertilize arise Dyes of darker red than the dyes which result from the action of these Bodies resulting from the α-naphthol monosulfonic acid derived from naphthoic acid, and make a good substitute for Orseille on silk and wool.
Zur Darstellung der a-Naphtoldisulfosäure werden 30 kg a-Naphtol mit 90 kg Schwefelsäuremonohydrat ungefähr 8 bis 10 Stunden lang auf 100 bis 1100C. erhitzt, das Reactionsproduct wird dann in 600 kg kalten Wassers gegossen, durch Absättigung mit Kalkmilch die α-Naphtoldisulfosäure als Kalksalz gewonnen und dieses in das Natronsalz übergeführt. Letzteres dient zur Farbstoff bereitung.To prepare the a-naphthol disulfonic acid, 30 kg of a-naphthol are heated with 90 kg of sulfuric acid monohydrate for about 8 to 10 hours at 100 to 110 ° C., the reaction product is then poured into 600 kg of cold water, the α-naphthol disulfonic acid by saturation with milk of lime obtained as lime salt and this converted into the sodium salt. The latter is used to prepare the dye.
Beispiel: 10 kg Anilin und 30 kg Salzsäure werden in 100 kg Wasser gelöst, wobei man mit Eis bis auf o° C. abkühlt; man diazotirt sodann, indem man die Temperatur nicht über ο bis 2° C. steigen läfst, mit 7,40 kg Natrium=- nitrit in concentrirter wässeriger Lösung. Die erhaltene Lösung von Diazo benzolchlorhydrat wird in eine überschüssige Lösung des oben erhaltenen a-naphtoldisulfosauren Natrons gegossen, welche mit so viel Ammoniak versetzt ist, dafs die Flüssigkeit nach dem Zusatz der ganzen Menge des Diazobenzolchlorhydrates noch basisch ist. Der Farbstoff wird mit Kochsalz ausgefällt, abfiltrirt, geprefst, durch Umlösen in heifsem Wasser und Wiederaussalzen gereinigt, abfiltrirt, geprefst und getrocknet. Example: 10 kg of aniline and 30 kg of hydrochloric acid are dissolved in 100 kg of water, cooling with ice to 0 ° C .; one diazotized then, by not allowing the temperature to rise above ο to 2 ° C., with 7.40 kg of sodium = - nitrite in concentrated aqueous solution. The obtained solution of diazo benzene chlorohydrate is poured into an excess solution of the above obtained a-naphtoldisulfosauren sodium, which is mixed with so much ammonia that the liquid after the addition of the whole amount of the diazobenzene chlorohydrate is still basic. The dye comes with Table salt precipitated, filtered off, pressed, by dissolving in hot water and salting out again cleaned, filtered off, pressed and dried.
Claims (1)
'f aMpVrrÜüEnciL an9eeebene .„.„.^„M„B patents SRr 32 291 ti. XXII. lautet Berichtigt:' ;. ,,aSetjfaBren jur Safftellung »on orangerot^en ... itnb ütoletten .SlaofarBjioffen burcf ""'■'""; atetcp cathedral. 7. Suit he. under
'f a MpV rr Ü ü E nci L an 9ee level. ".". ^ " M " B patents SRr 32 291 ti. XXII. reads as corrected: ';. ,, aSetjfaBren jur Safftellung »on orangerot ^ en ... itnb ütoletten .SlaofarBjioffen burcf""'■'""
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE32291C true DE32291C (en) |
Family
ID=308320
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT32291D Expired - Lifetime DE32291C (en) | Process for the preparation of orange-red and violet azo dyes by the action of diazo bodies on a-naphthol-disulfonic acid |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE32291C (en) |
-
0
- DE DENDAT32291D patent/DE32291C/en not_active Expired - Lifetime
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