DE292569C - - Google Patents
Info
- Publication number
- DE292569C DE292569C DENDAT292569D DE292569DA DE292569C DE 292569 C DE292569 C DE 292569C DE NDAT292569 D DENDAT292569 D DE NDAT292569D DE 292569D A DE292569D A DE 292569DA DE 292569 C DE292569 C DE 292569C
- Authority
- DE
- Germany
- Prior art keywords
- blue
- isatin
- black
- derivatives
- homologues
- 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 8
- 238000006467 substitution reaction Methods 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 3
- 230000007717 exclusion Effects 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 150000003672 ureas Chemical class 0.000 claims description 2
- JXDYKVIHCLTXOP-UHFFFAOYSA-N Pseudoisatin Natural products C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 description 6
- -1 isatin anilide Chemical class 0.000 description 5
- ORFSSYGWXNGVFB-UHFFFAOYSA-N sodium 4-amino-6-[[4-[4-[(8-amino-1-hydroxy-5,7-disulfonaphthalen-2-yl)diazenyl]-3-methoxyphenyl]-2-methoxyphenyl]diazenyl]-5-hydroxynaphthalene-1,3-disulfonic acid Chemical compound COC1=C(C=CC(=C1)C2=CC(=C(C=C2)N=NC3=C(C4=C(C=C3)C(=CC(=C4N)S(=O)(=O)O)S(=O)(=O)O)O)OC)N=NC5=C(C6=C(C=C5)C(=CC(=C6N)S(=O)(=O)O)S(=O)(=O)O)O.[Na+] ORFSSYGWXNGVFB-UHFFFAOYSA-N 0.000 description 5
- QPKNFEVLZVJGBM-UHFFFAOYSA-N 2-aminonaphthalen-1-ol Chemical class C1=CC=CC2=C(O)C(N)=CC=C21 QPKNFEVLZVJGBM-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 235000013877 carbamide Nutrition 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000000984 vat dye Substances 0.000 description 2
- OYJNIYAGHTZTMD-UHFFFAOYSA-N 2,3-dioxo-n-phenylindole-1-carboxamide Chemical compound O=C1C(=O)C2=CC=CC=C2N1C(=O)NC1=CC=CC=C1 OYJNIYAGHTZTMD-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- 150000004780 naphthols Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000004753 textile 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
- C09B7/00—Indigoid dyes
- C09B7/08—Other indole-indigos
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Description
Gegenstand des Patentes 292360 ist ein Verfahren zur Darstellung - schwarzer indigoider Farbstoffe durch Kondensation reaktionsfähiger Isatin-a-derivate mit Aryla'minonaphtholen oder Naphtimidazolen mit freier o-Stellung zur Hydroxylgruppe.. .The subject of patent 292360 is a process for the representation - black indigoid Dyes by condensation of reactive isatin-a-derivatives with Aryla'minonaphtholen or Naphtimidazoles with a free o-position to the hydroxyl group ...
Es wurde nun · weiter gefunden, daß echteIt has now been found that real
Küpenfarbstoffe, die in wertvollen, tiefblauen bis schwarzen Nuancen ausfärben, . erhaltenVat dyes that color in valuable, deep blue to black nuances,. obtain
ίο werden, wenn man in der Aminogruppe durch andere Gruppen substituierte Aminonaphthole, nämlich Acidylderivate oder Harnstoffe ausίο be when you get through in the amino group other groups substituted aminonaphthols, namely acidyl derivatives or ureas
■ heteronuklearen Aminonaphtholen oder ihre Substitutionsprodukte und Homologen '. unter Ausschluß ■ des i-Acetylamino-5-oxynaphthalins mit den Isatin-a-derivaten kondensiert. Daß die lediglich in der-Aminogruppe substituierten Aminonaphthole zu technisch sehr wertvollen, . echten Farbstoffen von schwarzer Nuance führen, war nicht aus bekannten Tatsachen abzu-■ heteronuclear aminonaphthols or their substitution products and homologues '. with the exclusion of i-acetylamino-5-oxynaphthalene condensed with the isatin-α-derivatives. That the aminonaphthols, which are only substituted in the amino group, are technically very valuable. real dyes of black nuances could not be deduced from known facts.
'. leiten. '..' . s . . x '. conduct. '..'. s . . x
■ ':Beispiel.:'- ' .■ ': Example.:' - '.
2,6 Teile 2-Benzoylamino-5-oxynaphthalin2.6 parts of 2-benzoylamino-5-oxynaphthalene
. 25 werden zusammen mit 2,2 Teilen Isatin-a-anilid und 25 Teilen Essigsäureanhydrid gekocht, bis die Farbstoffbildung vollendet ist. Nach dem Abkühlen wird filtriert, der erhaltene Färbstoff ·■. mit Alkohol gewaschen und getrocknet. Er '· färbt aus der Küpe die. Textilfaser in echten schwarzen Tönen an.... 25 together with 2.2 parts of isatin-a-anilide and 25 parts acetic anhydride boiled until dye formation is complete. After this Cooling is filtered, the resulting dye · ■. washed with alcohol and dried. He '· colors from the vat. Textile fiber in real black tones on ...
Statt 2,6 Teile 2-Benzoylamino-5-oxynaphthalin kann man auch 1,7 -Teile 5-5'-Dioxy-2<2/-dinäphthylharnstoff anwenden, wobei ein blauschwarzer Küpenfarbstoff entsteht.Instead of 2.6 parts of 2-benzoylamino-5-oxynaphthalene, 1.7 parts of 5-5'-dioxy-2 < 2 / -dinaphthylurea can also be used, a blue-black vat dye being formed.
Die erhaltenen. Produkte lassen sich mit ..'
Halogen nachbehandeln und werden dadurch in ihren Echtheitseigenschaften noch verbessert.
Es sei noch bemerkt, daß' selbstverständlich
an Stelle der gewöhnlichen unsubstituierten.. Isatin-a-derivate deren Substitutionsprodukte,
z. B. die bromierten, oder-Homologe oder Analoge verwendet werden können, .wesentlich ist
nur, daß die Verbindungen die leicht austauschbare α-substituierte Gruppe enthalten, die sie
zur Kondensation mit den Naphtholen befähigt. Homologe sind hier Verbindungen, die an Stelle
eines Wasserstoffatomes einen Köhlenwasserstoffrest enthalten, / Analoge solche, bei denen
der Benzolkern mit anderen Ringen verschmolzen
derivate.The received. Products can be post-treated with .. 'Halogen and their fastness properties are further improved as a result. It should also be noted that 'of course, instead of the usual unsubstituted .. isatin-a-derivatives, their substitution products, e.g. B. the brominated, or homologues or analogs can be used. It is only essential that the compounds contain the easily exchangeable α-substituted group that enables them to condense with the naphthols. Here, homologues are compounds that contain a hydrocarbon radical instead of a hydrogen atom / analogues are those in which the benzene nucleus fused with other rings
derivatives.
ist, wie z. B-,'' die" Naphtisatin-a-is, such as B-, '' the "Naphtisatin-a-
Aus der nachstehenden Tabelle· sind die Eigenschaften einer Reihe unter 'das vorliegende Verfahren fallender Farbstoffe ersieht-· 40 lieh: . . ■ . ·From the table below, the properties of a number under 'are the present Process of falling dyes see- · 40 borrowed:. . ■. ·
.,-, . i y. - £.-:! Λ el ■-<
'-■ -'i'■ 1 ■ -v et "* 1, **«' v. "«. ('»' R
., -,. i y. - £ .- :! Λ el ■ - <'- ■ -'i
des
Farbstoff
pulversAppearance : l
of
dye
powder
·■■■■. ,heißem
Nitrobenzol .St ■■ " " Solubility
· ■■■■. , hot
Nitrobenzene.
'-■ kon
zentrierter
Schwefel-,
säureit in
'- ■ con
more centered
Sulfur-,
acid
. lin+Isatinanilid .i-Benzoyl'amino-5-oxynaphtha-.
. lin + isatin anilide.
bronzierendreddish
bronzing
blaueasily soluble,
blue
lin+Isatinanilid . . . ■·a-Benzoylamino-S-oxynaphtha-
lin + isatin anilide. . . ■ ·
schwarz. reddish
black
rotblaueasily soluble,
Red Blue
lin + Isatinanilid; bromiert
zum Dibromprodukt2-benzoylamino-5-ox'ynaphtha-
lin + isatinanilide; brominated
to the dibromine product
violettblau-; deep
violet blue
rein blau 'easily soluble,
pure blue '
harnstoff + Isatinanilid,5 5'-dioxy-2 2'-dinaphthyl-
urea + isatin anilide,
blauroteasily soluble,
blue red
naphthalin+ Isatinanilid .w-PKenylacetyl-2 ~ amino-5-oxy-
naphthalene + isatin anilide.
. ■ blaurot jeasily soluble,
. ■ blue red j
lin-f Isatinanilid2-benzoylamino-8-oxynaphtha-
lin-f isatin anilide
schwarzbrownish
black
rein blau'easily soluble,
pure blue '
harnstoffrf- Isatinanilid8 8'-dioxy-2 2 ' : dinaphthyl-
urea rf- isatin anilide
schwarzviolet
black
blaueasily soluble,
blue
Claims (1)
wobei unter Isatin-a-derivaten auch deren
Kernsubstitutionsprodukte, Homologe und 75 Analoge verstanden werden, und die erhaltenen Farbstoffe gegebenenfalls, mit Halogen behandelt. .Exclusion. of the i- ^ acetylamino-5-oxynaphthalene condensed with the isatin-a-derivatives,
under isatin-a-derivatives also their
Nuclear substitution products, homologues and analogs are understood, and the resulting dyes, if appropriate, treated with halogen. .
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE292569C true DE292569C (en) |
Family
ID=547321
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT292569D Active DE292569C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE292569C (en) |
-
0
- DE DENDAT292569D patent/DE292569C/de active Active
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