DE229525C - - Google Patents
Info
- Publication number
- DE229525C DE229525C DENDAT229525D DE229525DA DE229525C DE 229525 C DE229525 C DE 229525C DE NDAT229525 D DENDAT229525 D DE NDAT229525D DE 229525D A DE229525D A DE 229525DA DE 229525 C DE229525 C DE 229525C
- Authority
- DE
- Germany
- Prior art keywords
- parts
- sulfonic acid
- dye
- dyes
- methylbenzene
- 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.)
- Active
Links
- 239000000975 dye Substances 0.000 claims description 10
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 4
- DTQVHBIQMCFTSZ-UHFFFAOYSA-N 4-amino-3-chloro-5-methylbenzenesulfonic acid Chemical compound CC1=CC(S(O)(=O)=O)=CC(Cl)=C1N DTQVHBIQMCFTSZ-UHFFFAOYSA-N 0.000 claims description 2
- 230000000875 corresponding Effects 0.000 claims description 2
- 150000008049 diazo compounds Chemical class 0.000 claims description 2
- 229960000943 Tartrazine Drugs 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- UJMBCXLDXJUMFB-GLCFPVLVSA-K tartrazine Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)C1=NN(C=2C=CC(=CC=2)S([O-])(=O)=O)C(=O)C1\N=N\C1=CC=C(S([O-])(=O)=O)C=C1 UJMBCXLDXJUMFB-GLCFPVLVSA-K 0.000 claims 1
- 235000012756 tartrazine Nutrition 0.000 claims 1
- 239000004149 tartrazine Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
- 230000020477 pH reduction Effects 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 235000002639 sodium chloride Nutrition 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XHWHHMNORMIBBB-UHFFFAOYSA-N 2,2,3,3-tetrahydroxybutanedioic acid Chemical compound OC(=O)C(O)(O)C(O)(O)C(O)=O XHWHHMNORMIBBB-UHFFFAOYSA-N 0.000 description 1
- -1 3-chloro-2-amino-i-methylbenzene-5-sulfonic acid Diazo compound Chemical class 0.000 description 1
- 241000947840 Alteromonadales Species 0.000 description 1
- QFFVPLLCYGOFPU-UHFFFAOYSA-N Barium chromate Chemical compound [Ba+2].[O-][Cr]([O-])(=O)=O QFFVPLLCYGOFPU-UHFFFAOYSA-N 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N Sulfamic acid Chemical class NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- 210000002268 Wool Anatomy 0.000 description 1
- 239000002253 acid Substances 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
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- IPDZRJWASWZYQD-UHFFFAOYSA-N chloro-(2-methylphenyl)sulfamic acid Chemical compound CC1=CC=CC=C1N(Cl)S(O)(=O)=O IPDZRJWASWZYQD-UHFFFAOYSA-N 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000001808 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000725 suspension Substances 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
- C09B27/00—Preparations in which the azo group is formed in any way other than by diazotising and coupling, e.g. oxidation
- C09B27/06—Tartrazines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
- M 229525 KLASSE 22 a. GRUPPE- M 229525 CLASS 22 a. GROUP
BADISCHE ANILIN- & SODA-FABRIK in LUDWIGSHAFEN a. Rh.BADISCHE ANILINE & SODA FACTORY in LUDWIGSHAFEN a. Rh.
Behandelt man die 2-Acidylamino-i-methylbenzol-5-sulfosäure in wäßriger Lösung mit Chlor und spaltet man in dem erhaltenen Reaktionsprodukt die Acidylgruppe ab, so erhält man eine bisher unbekannte Chlortoluidinsulfosäure von nachstehender Konstitution:If the 2-acidylamino-i-methylbenzene-5-sulfonic acid is treated in aqueous solution with chlorine and cleavage of the acidyl group in the resulting reaction product is obtained a previously unknown chlorotoluidine sulfonic acid of the following constitution:
NHNH
SO3H.SO 3 H.
Es hat sich nun gezeigt, daß diese Aminosulfosäure von großer Bedeutung für die Darstellung von Farbstoffen der Pyrazolonreihe ist, da die damit hergestellten Produkte eine außergewöhnlich grünstichige Nuance aufweisen und sich durch eine besonders gute Lichtechtheit auszeichnen. Die grünende Wirkung des RestesIt has now been shown that this aminosulfonic acid is of great importance for the representation of dyes of the pyrazolone series, since the products made with them are a exhibit exceptionally greenish nuances and are characterized by particularly good lightfastness distinguish. The greening effect of the rest
CH,CH,
tritt schon hervor, wenn er einmal in das Farbstoffmolekül eingeführt wird, und zwar gleichgültig, ob er zum Aufbau des Pyrazolonmoleküls (Tartrazinogens) gedient hat, oder ob eine diesem Rest entsprechende Diazoverbindung zur Endkuppelung verwendet wurde. Eine besonders große Verschiebung der Nuance nach Grün hin findet statt, wenn man den genannten Rest zweimal in das Farbstoffmolekül einführt.already emerges once it is introduced into the dye molecule, namely It does not matter whether it was used to build up the pyrazolone molecule (tartrazinogen), or whether a diazo compound corresponding to this residue was used for the end coupling. A particularly large shift in the shade towards green takes place when you use the introduces said residue twice into the dye molecule.
11 Teile eines 100 prozentigen Natriumsalzes der Dioxyweinsäure werden mit etwa 50 Teilen Wasser angerührt und mit einer Suspension von 24 Teilen des Hydrazins der 3-Chlor-2-amino -1 - methylbenzol - 5 - sulf osäure in etwa 50 Teilen Wasser versetzt. Man erwärmt hierauf zunächst auf 50 °, später auf 70 bis 80 °, wobei allmählich vollständige Lösung eintritt. Der gebildete Farbstoff wird, wenn nötig, nach vorherigem Ansäuern mit Kochsalz oder Chlorkalium gefällt. Er wird abgesaugt, gepreßt und getrocknet.11 parts of a 100 percent sodium salt the dioxy tartaric acid are mixed with about 50 parts of water and mixed with a suspension of 24 parts of the hydrazine of 3-chloro-2-amino -1-methylbenzene-5-sulfonic acid in about 50 parts of water are added. It is then heated first to 50 °, later to 70 to 80 °, gradually complete dissolution occurs. The dye formed is, if necessary, precipitated after previous acidification with table salt or potassium chloride. He is sucked off, pressed and dried.
Die aus diesem Farbstoff hergestellten Lacke und die damit erzeugten Färbungen zeichnen sich durch eine hervorragend reine, zitronengelbe Nuance aus, wie sie bis jetzt mit Farbstoffen dieser Klasse auch nicht annäherndThe paints made from this dye and the colorations produced with them draw is characterized by an exceptionally pure, lemon-yellow shade, as it has been with colorings up to now not even close to this class
erreicht werden konnte; auch die Lichtechtheit der damit hergestellten Färbungen und der daraus hergestellten Lacke entspricht den höchsten Anforderungen.could be achieved; also the lightfastness of the dyeings produced therewith and the paints made from it meet the highest requirements.
Die aus 22,2 Teilen 3-Chlor-2-amino-i-methylbenzol-5-sulfosäure in der üblichen Weise dargestellte Diazoverbindung läßt man unter Rühren einlaufen in eine mit der nötigen Menge Soda versetzte konzentrierte Lösung von 30 Teilen i-p-Sulfophenyl-s-pyrazolon-scarbonsäure. Nach etwa halbstündigem Rühren erwärmt man auf 50 °, worauf man den Farbstoff, wenn nötig, nach vorherigem Ansäuern mit Kochsalz aussalzt. Man saugt ab, preßt und trocknet.The from 22.2 parts of 3-chloro-2-amino-i-methylbenzene-5-sulfonic acid Diazo compound prepared in the usual way is allowed to run into one of the necessary compounds with stirring Amount of soda added concentrated solution of 30 parts of i-p-sulfophenyl-s-pyrazolonecarboxylic acid. After about half an hour of stirring, the mixture is heated to 50 °, whereupon the dye, if necessary, after previous acidification salted out with table salt. One sucks off, presses and dries.
Der Farbstoff löst sich leicht mit gelber Farbe in Wasser und färbt Wolle in reinen gelben Tönen an.The dye easily dissolves in water with yellow color and dyes wool in pure yellow tones.
Claims (1)
Publications (1)
Publication Number | Publication Date |
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DE229525C true DE229525C (en) |
Family
ID=489822
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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DENDAT229525D Active DE229525C (en) |
Country Status (1)
Country | Link |
---|---|
DE (1) | DE229525C (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9738341B2 (en) | 2013-05-10 | 2017-08-22 | Balanced Bicycle Seats Llc | Bicycle seat |
-
0
- DE DENDAT229525D patent/DE229525C/de active Active
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9738341B2 (en) | 2013-05-10 | 2017-08-22 | Balanced Bicycle Seats Llc | Bicycle seat |
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