DE79972C - - Google Patents
Info
- Publication number
- DE79972C DE79972C DENDAT79972D DE79972DA DE79972C DE 79972 C DE79972 C DE 79972C DE NDAT79972 D DENDAT79972 D DE NDAT79972D DE 79972D A DE79972D A DE 79972DA DE 79972 C DE79972 C DE 79972C
- Authority
- DE
- Germany
- Prior art keywords
- monoethyl
- phenylenediamine
- homologues
- monomethyl
- toluenediamine
- 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
- 238000000034 method Methods 0.000 claims description 8
- 230000000875 corresponding Effects 0.000 claims description 6
- FRPAGJPHUNNVLJ-UHFFFAOYSA-N 2-N-ethylbenzene-1,2-diamine Chemical compound CCNC1=CC=CC=C1N FRPAGJPHUNNVLJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- HJSUAIIUCAMPJQ-UHFFFAOYSA-N 1-propylcyclohexa-3,5-diene-1,2-diamine Chemical compound CCCC1(N)C=CC=CC1N HJSUAIIUCAMPJQ-UHFFFAOYSA-N 0.000 claims description 2
- 150000004987 o-phenylenediamines Chemical class 0.000 claims description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000000975 dye Substances 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- XKBQWBOFFVJBHI-UHFFFAOYSA-N 1-ethylcyclohexa-3,5-diene-1,2-diamine Chemical compound CCC1(N)C=CC=CC1N XKBQWBOFFVJBHI-UHFFFAOYSA-N 0.000 description 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N O-Phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 150000003460 sulfonic acids Chemical class 0.000 description 2
- ZMBQZWCDYKGVLW-UHFFFAOYSA-N 1-methylcyclohexa-3,5-diene-1,2-diamine Chemical class CC1(N)C=CC=CC1N ZMBQZWCDYKGVLW-UHFFFAOYSA-N 0.000 description 1
- RPKCLSMBVQLWIN-UHFFFAOYSA-N 2-N-methylbenzene-1,2-diamine Chemical compound CNC1=CC=CC=C1N RPKCLSMBVQLWIN-UHFFFAOYSA-N 0.000 description 1
- AZLFTFIVWFCCLK-UHFFFAOYSA-N CC1(C(C=CC=C1)NC)N Chemical compound CC1(C(C=CC=C1)NC)N AZLFTFIVWFCCLK-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- -1 monoethyl-o-tolylenediamine Chemical compound 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 239000002966 varnish Substances 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
- C09B17/00—Azine dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
KLASSE 22: Farbstoffe, Firnisse, Lacke.CLASS 22: dyes, varnishes, lacquers.
derselben.the same.
Zehnter Zusatz zum Patente JU 66361 vom 12. März 1892.Tenth addition to patent JU 66361 of March 12, 1892.
Patentirt im Deutschen Reiche vom 7. Juni 1894 ab. Längste Dauer: 11. März 1907. Patented in the German Empire on June 7, 1894. Longest duration: March 11, 1907.
Ersetzt man in dem in Anspruch 1. der Patentschrift Nr. 71665 beschriebenen Verfahren, bestehend in der Condensation von Oxynaphtochinonanil mit Monomethyl-o-toluylendiamin, das letztere durch andere monoalkylirte o-Diamine wie das Monoäthyl-o-toluylendiamin oder die entsprechenden Alkylderivate des o-Phenylendiamins, so erhält man die entsprechenden Homologen des Indulins C.2iH19NB. Das so aus Monoäthyl-o-toluylendiamin entstehende a -Phenyl -ß-äthyleurhodin ist von dem Indulin C2iHlgN3, dem a-Phenylß-methyleurhodin der Patentschrift Nr. 66361, durch eine etwas blauere Nuance unterschieden, in gleichem Sinne unterscheidet sich das aus Monoäthyl-o-phenylendiamin entstehende niedere Homologe des α,-Phenyl-ß-äthyleurhodins von dem a-Phenyl-3-methyleurhodin, dem Indulin C.2SHl7N3 der Patentschrift Nr. 71666. If in the process described in claim 1 of patent specification no. 71665, consisting in the condensation of oxynaphthoquinonanil with monomethyl-o-tolylenediamine, the latter is replaced by other monoalkylated o-diamines such as monoethyl-o-tolylenediamine or the corresponding alkyl derivatives of the o Phenylenediamine, the corresponding homologues of indulin C. 2i H 19 N B are obtained . The thus of monoethyl-o-toluene diamine produced a phenyl -beta-äthyleurhodin of which is Indulin C 2i H lg N 3, the a-Phenylß-methyleurhodin patent specification no. 66361, distinguished by a somewhat bluer shade is different in the same sense the lower homologue of α, -phenyl-ß-äthyleurhodin of the a-phenyl-3-methyleurhodin, the indulin C. 2S H 17 N 3 of the patent specification No. 71666, which arises from monoethyl-o-phenylenediamine.
Ebenso erhält man Monosulfosäuren dieser Farbstoffe, wenn man in dem in Anspruch 2. der genannten Patentschrift beschriebenen Verfahren, bestehend in der Condensation von Oxynaphtochinonanilsulfosäure mit Monomethylo-toluylendiamin, das letztere durch die oben angeführten monoalkylirten o-Diamine ersetzt; diese Sulfosäuren sind wie die Sulfosäure der Patentschrift Nr. 71665 in Wasser schwer löslich, sie finden zur Darstellung wasserlöslicher Sulfosäuren Verwendung.Monosulfonic acids of these dyes are also obtained if one in the claim 2. the aforementioned patent process described, consisting in the condensation of Oxynaphthoquinonanilsulfonic acid with monomethylo-toluenediamine, the latter is replaced by the monoalkylated o-diamines given above; these sulfonic acids are like the sulfonic acid of the Patent No. 71665 is sparingly soluble in water, you will find more water-soluble for the preparation Sulfonic acids use.
Ersetzt man ferner in dem Verfahren der Patentschrift Nr. 79540, bestehend in der Condensation von Oxynaphtochinonimid mit Monomethyl-o-toluylendiamin, das letztere durch das Monoäthyl-o-toluylendiamin oder durch die entsprechenden monoalkylirten ο - Phenylendiamine, so erhält man die entsprechenden am Azinstickstoff alkylirten Eurhodine, nämlich das ß-Aethyleurhodin bezw. die niederen Homologen des ß-Methyl- und ß-Aethyleurhodins, deren Zusammensetzung durch die folgenden Formeln ausgedrückt wird:Replaced also in the process of patent specification No. 79540, consisting in condensation of oxynaphtoquinonimide with monomethyl-o-toluenediamine, the latter by the monoethyl-o-toluenediamine or by the corresponding monoalkylated ο-phenylenediamines, one obtains the corresponding am Azine nitrogen alkylated Eurhodine, namely the ß-Ethyleurhodin respectively. the lower homologues of ß-methyl- and ß-ethylleurhodine, their composition by the following Expressed formulas:
HNHN
AlkylAlkyl
/S-Alkyleurhodin aus Oxynaphtochinonimid
und Monoalkyl-o-toluylendiamin./ S-Alkyleurhodine from Oxynaphthoquinonimide
and monoalkyl-o-toluenediamine.
HNJHNJ
AlkylAlkyl
/3-Alkyleurhodin (niederes Homolog) aus/ 3-alkyleurhodine (lower homolog)
Oxynaphtochinonimid und Monoalkyl-o-Oxynaphtoquinonimide and monoalkyl-o-
phenylendiamin.phenylenediamine.
Das so aus Monoäthyl-o-toluylendiamin entstehende ß-Aethyleurhodin ist identisch mit dem in der Patentschrift Nr. 79960 beschriebenen Farbstoff, welcher von dem ß-Methyleurhodin (Patentschriften Nr. 77226 und Nr. 79540) sich durch etwas blauere Nuance unterscheidet.The resulting from monoethyl-o-toluylenediamine ß-Ethyleurhodin is identical to that dye described in Patent No. 79960, which is derived from β-methyleurhodine (Patent specifications No. 77226 and No. 79540) differs by a slightly bluer shade.
Von den aus monoalkylirten o-Phenylendiaminen entstehenden Farbstoffen ist der aus Monomethyl-o-phenylendiamin gebildete — das niedere Homologe des ß-Methyleurhodins der Patentschrift Nr. 77226 — von letzterem nicht wesentlich unterschieden, und ebenso stimmt der aus Monoäthyl-o-phenylendiamin entstehende Farbstoff mit dem aus dem entsprechenden monoalkylirten o-Toluylendiamin hergestellten in seinen wesentlichen Eigenschaften überein.Of the dyes formed from monoalkylated o-phenylenediamines, the one is off Monomethyl-o-phenylenediamine formed - the lower homologue of ß-methyleurhodins of Patent Specification No. 77226 - not significantly different from the latter, and it is also true the dye resulting from monoethyl-o-phenylenediamine with that from the corresponding monoalkylated o-toluenediamine produced in its essential properties.
Claims (3)
Publications (1)
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DE79972C true DE79972C (en) |
Family
ID=352570
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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Country Status (1)
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DE (1) | DE79972C (en) |
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- DE DENDAT79972D patent/DE79972C/de active Active
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