CH139687A - Process for the preparation of a nitrogenous vat dye. - Google Patents
Process for the preparation of a nitrogenous vat dye.Info
- Publication number
- CH139687A CH139687A CH139687DA CH139687A CH 139687 A CH139687 A CH 139687A CH 139687D A CH139687D A CH 139687DA CH 139687 A CH139687 A CH 139687A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- vat
- works
- mol
- acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- 239000000984 vat dye Substances 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 title description 3
- 239000000975 dye Substances 0.000 claims description 4
- LLBIOIRWAYBCKK-UHFFFAOYSA-N pyranthrene-8,16-dione Chemical compound C12=CC=CC=C2C(=O)C2=CC=C3C=C4C5=CC=CC=C5C(=O)C5=C4C4=C3C2=C1C=C4C=C5 LLBIOIRWAYBCKK-UHFFFAOYSA-N 0.000 claims description 4
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 3
- ZYECOAILUNWEAL-NUDFZHEQSA-N (4z)-4-[[2-methoxy-5-(phenylcarbamoyl)phenyl]hydrazinylidene]-n-(3-nitrophenyl)-3-oxonaphthalene-2-carboxamide Chemical compound COC1=CC=C(C(=O)NC=2C=CC=CC=2)C=C1N\N=C(C1=CC=CC=C1C=1)/C(=O)C=1C(=O)NC1=CC=CC([N+]([O-])=O)=C1 ZYECOAILUNWEAL-NUDFZHEQSA-N 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 claims description 2
- 239000000835 fiber Substances 0.000 claims description 2
- 238000006396 nitration reaction Methods 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
- 235000013311 vegetables Nutrition 0.000 claims description 2
- VZMULMSIWMLZLC-UHFFFAOYSA-N 2-aminoanthra[9,1,2-cde]benzo[rst]pentaphene-5,10-dione Chemical compound C12=C3C4=CC=C2C2=CC=CC=C2C(=O)C1=CC=C3C1=CC=C2C(=O)C3=CC=C(N)C=C3C3=CC=C4C1=C32 VZMULMSIWMLZLC-UHFFFAOYSA-N 0.000 claims 1
- 239000011230 binding agent Substances 0.000 claims 1
- 230000002140 halogenating effect Effects 0.000 claims 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 description 1
- YWVPLPVOZCOMQA-UHFFFAOYSA-N 2,3,4-tribromo-2H-pyranthren-1-one Chemical compound C1=C2C(C(Br)=C(Br)C(C3=O)Br)=C3C=C(C=C3)C2=C2C3=CC3=C(C=CC=C4)C4=CC4=CC=C1C2=C34 YWVPLPVOZCOMQA-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 1
- 239000005751 Copper oxide Substances 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229910000431 copper oxide Inorganic materials 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 230000000802 nitrating effect Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- YKSGNOMLAIJTLT-UHFFFAOYSA-N violanthrone Chemical compound C12=C3C4=CC=C2C2=CC=CC=C2C(=O)C1=CC=C3C1=CC=C2C(=O)C3=CC=CC=C3C3=CC=C4C1=C32 YKSGNOMLAIJTLT-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfuhren zur Darstellung eines stickstoffhaltigen Küpenfarbstoffes.
EMI0001.0002
Im <SEP> Hauptpatent <SEP> ist <SEP> ein <SEP> Verfahren <SEP> zur
<tb> Darstdlllung <SEP> eines <SEP> stickstoffhaltigen <SEP> Küpen farb.stoffes <SEP> beschrieben, <SEP> bei <SEP> dem <SEP> man <SEP> 1 <SEP> Mol.
<tb> des <SEP> durch <SEP> Behandllung <SEP> von <SEP> Pyranthron <SEP> mit
<tb> Halogen <SEP> in. <SEP> Chlorsulfoansäure <SEP> erhältlichen
<tb> Tetrahalogenpyranthrons <SEP> mit <SEP> 3 <SEP> Mol. <SEP> des
<tb> durch <SEP> Nitrieren <SEP> von <SEP> Dibenzanthron <SEP> mit <SEP> Sal petersäure <SEP> in <SEP> Nitrobenzol <SEP> und <SEP> Reduktion <SEP> der
<tb> entstandenen <SEP> Nitroverbindung <SEP> erhältlichen
<tb> A.minoäibenzanthro#n.s <SEP> und <SEP> 1 <SEP> Mol. <SEP> 1-Amino anthrachinon <SEP> umsetzt.
<tb>
Es, <SEP> wurde <SEP> nun. <SEP> gefunden, <SEP> idass <SEP> man <SEP> einen
<tb> neuen <SEP> Kiipenfarbstoff <SEP> erhält, <SEP> wenn <SEP> man
<tb> 1 <SEP> Hol. <SEP> Trihalogenpyranthron, <SEP> erhältlich
<tb> durch <SEP> Hadagenieren <SEP> von <SEP> Pyranthron <SEP> in <SEP> Chlur sulfonsäure, <SEP> mit <SEP> 1 <SEP> Mal. <SEP> 1 <SEP> . <SEP> 5-Diaminoanthra chinon <SEP> und <SEP> 2 <SEP> Mol. <SEP> Aminoadibenzanthron, <SEP> er hältlich <SEP> duroh <SEP> Reduktion <SEP> desi <SEP> durch <SEP> Nitrieren
<tb> von <SEP> Dibenzanthranerhältlichen <SEP> Nitrodibenz anthrohs, <SEP> umsetzt.
<SEP> Die <SEP> Kondensation <SEP> führt
<tb> man <SEP> zweckmässig <SEP> in <SEP> hochsiedenden <SEP> Verdün nungsmitteln <SEP> und <SEP> unter <SEP> Zusatz <SEP> von <SEP> Säure-
EMI0001.0003
bindenden <SEP> Mitteln, <SEP> wie <SEP> Natriumacetat, <SEP> aus.
<tb> Vielfach <SEP> ist <SEP> es <SEP> von <SEP> Vorteil, <SEP> Katalysatoren,
<tb> b.eispäelisweise <SEP> Kupferverbindungen, <SEP> zuzu sietzen.
<tb>
Der <SEP> neue <SEP> Farbstoff <SEP> löst <SEP> sich <SEP> in <SEP> konzen trierterSchwefelsäure <SEP> mit <SEP> rotvioletter <SEP> Farbe
<tb> und <SEP> gibt <SEP> mit <SEP> alkalischer <SEP> Hydrosulfitlösung
<tb> eine <SEP> blaue <SEP> Küpenlösung, <SEP> aus" <SEP> der <SEP> die <SEP> pflanz liche <SEP> Faser <SEP> in <SEP> grauen <SEP> bis <SEP> schwarzen, <SEP> hervor ragend <SEP> echten <SEP> Tönen <SEP> gefärbt <SEP> wird.
<tb>
<I>Beispiel</I>
<tb> Eine <SEP> Suspension <SEP> von <SEP> 64 <SEP> Teilen <SEP> Tribrom pyranthron <SEP> (dargestellt <SEP> durch <SEP> Bromieren <SEP> von
<tb> Pyranthron <SEP> in <SEP> Clhlorsulfowäure), <SEP> 50 <SEP> Teilen
<tb> Naltriumiacetat, <SEP> 10 <SEP> Teilen <SEP> Kupferoxyd, <SEP> 2<B>5</B>
<tb> Teilen <SEP> 1. <SEP> 5-Diaminoanthrachinon <SEP> und <SEP> 94 <SEP> Tei len <SEP> Aminodibenzauthron <SEP> in. <SEP> 1000 <SEP> Teilen <SEP> Ni trabenzal <SEP> wird <SEP> unter <SEP> Rühren <SEP> so <SEP> lange, <SEP> ge kocht, <SEP> bis <SEP> (das <SEP> Reaktion[sprodukt <SEP> praktisch
<tb> bromfrei <SEP> ist. <SEP> Dann <SEP> wird <SEP> wie <SEP> üblich <SEP> auf gearbeitet.
Procedures for the representation of a nitrogenous vat dye.
EMI0001.0002
In the <SEP> main patent <SEP> <SEP> is a <SEP> method <SEP> for
<tb> Description <SEP> of a <SEP> nitrogen-containing <SEP> vat of dye <SEP> described, <SEP> for <SEP> the <SEP> man <SEP> 1 <SEP> mol.
<tb> of the <SEP> by <SEP> treatment <SEP> of <SEP> pyranthrone <SEP> with
<tb> Halogen <SEP> in. <SEP> chlorosulfoanic acid <SEP> available
<tb> Tetrahalogenpyranthrons <SEP> with <SEP> 3 <SEP> Mol. <SEP> des
<tb> by <SEP> nitrating <SEP> of <SEP> dibenzanthrone <SEP> with <SEP> nitric acid <SEP> in <SEP> nitrobenzene <SEP> and <SEP> reduction <SEP> der
<tb> resulting <SEP> nitro compound <SEP> available
<tb> A.minoäibenzanthro # n.s <SEP> and <SEP> 1 <SEP> Mol. <SEP> 1-amino anthraquinone <SEP>.
<tb>
It, <SEP> became <SEP> now. <SEP> found, <SEP> i that <SEP> man <SEP> one
<tb> receives new <SEP> jar dye <SEP>, <SEP> if <SEP> man
<tb> 1 <SEP> Hol. <SEP> Trihalogenpyranthron, <SEP> available
<tb> by <SEP> hadagening <SEP> of <SEP> pyranthrone <SEP> in <SEP> chlorosulfonic acid, <SEP> with <SEP> 1 <SEP> times. <SEP> 1 <SEP>. <SEP> 5-diaminoanthraquinone <SEP> and <SEP> 2 <SEP> Mol. <SEP> Aminoadibenzanthrone, <SEP> available <SEP> duroh <SEP> reduction <SEP> desi <SEP> by <SEP> nitration
<tb> from <SEP> dibenzanthrane available <SEP> nitrodibenz anthrohs, <SEP> implements.
<SEP> The <SEP> condensation <SEP> leads
<tb> one <SEP> useful <SEP> in <SEP> high-boiling <SEP> thinners <SEP> and <SEP> under <SEP> addition <SEP> of <SEP> acid
EMI0001.0003
binding <SEP> agents, <SEP> such as <SEP> sodium acetate, <SEP>.
<tb> In many cases <SEP> is <SEP> it <SEP> of <SEP> advantage, <SEP> catalysts,
<tb> for example <SEP> copper connections, <SEP> to be added.
<tb>
The <SEP> new <SEP> dye <SEP> dissolves <SEP> <SEP> in <SEP> concentrated sulfuric acid <SEP> with <SEP> red-violet <SEP> color
<tb> and <SEP> give <SEP> with <SEP> alkaline <SEP> hydrosulfite solution
<tb> a <SEP> blue <SEP> vat solution, <SEP> from "<SEP> the <SEP> the <SEP> vegetable <SEP> fiber <SEP> in <SEP> gray <SEP> to <SEP> black, <SEP> outstanding <SEP> real <SEP> tones <SEP> is colored <SEP>.
<tb>
<I> Example </I>
<tb> A <SEP> suspension <SEP> of <SEP> 64 <SEP> parts <SEP> tribromopyranthrone <SEP> (represented <SEP> by <SEP> bromination <SEP> of
<tb> pyranthrone <SEP> in <SEP> chlorosulfonic acid), <SEP> 50 <SEP> parts
<tb> Naltrium acetate, <SEP> 10 <SEP> parts <SEP> copper oxide, <SEP> 2 <B> 5 </B>
<tb> Divide <SEP> 1. <SEP> 5-diaminoanthraquinone <SEP> and <SEP> 94 <SEP> divide <SEP> Aminodibenzauthron <SEP> in. <SEP> 1000 <SEP> parts <SEP> Ni trabenzal <SEP> becomes <SEP> with <SEP> stirring <SEP> so <SEP> long, <SEP> boiled, <SEP> to <SEP> (the <SEP> reaction [product <SEP> practical
<tb> is bromine-free <SEP>. <SEP> Then <SEP>, <SEP> is opened as usual <SEP>.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE139687X | 1927-10-18 | ||
| CH138317T | 1928-10-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH139687A true CH139687A (en) | 1930-04-30 |
Family
ID=25713138
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH139687D CH139687A (en) | 1927-10-18 | 1928-10-01 | Process for the preparation of a nitrogenous vat dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH139687A (en) |
-
1928
- 1928-10-01 CH CH139687D patent/CH139687A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH139687A (en) | Process for the preparation of a nitrogenous vat dye. | |
| CH139719A (en) | Process for the preparation of a nitrogenous vat dye. | |
| CH139666A (en) | Process for the preparation of a nitrogenous vat dye. | |
| CH139698A (en) | Process for the preparation of a nitrogenous vat dye. | |
| CH139700A (en) | Process for the preparation of a nitrogenous vat dye. | |
| CH139701A (en) | Process for the preparation of a nitrogenous vat dye. | |
| CH139664A (en) | Process for the preparation of a nitrogenous vat dye. | |
| CH139662A (en) | Process for the preparation of a nitrogenous vat dye. | |
| CH139680A (en) | Process for the preparation of a nitrogenous vat dye. | |
| CH139696A (en) | Process for the preparation of a nitrogenous vat dye. | |
| CH139689A (en) | Process for the preparation of a nitrogenous vat dye. | |
| CH139703A (en) | Process for the preparation of a nitrogenous vat dye. | |
| CH139674A (en) | Process for the preparation of a nitrogenous vat dye. | |
| CH139713A (en) | Process for the preparation of a nitrogenous vat dye. | |
| CH139707A (en) | Process for the preparation of a nitrogenous vat dye. | |
| CH139715A (en) | Process for the preparation of a nitrogenous vat dye. | |
| CH139710A (en) | Process for the preparation of a nitrogenous vat dye. | |
| CH139699A (en) | Process for the preparation of a nitrogenous vat dye. | |
| CH139685A (en) | Process for the preparation of a nitrogenous vat dye. | |
| CH139659A (en) | Process for the preparation of a nitrogenous vat dye. | |
| CH139695A (en) | Process for the preparation of a nitrogenous vat dye. | |
| CH139704A (en) | Process for the preparation of a nitrogenous vat dye. | |
| CH139675A (en) | Process for the preparation of a nitrogenous vat dye. | |
| CH139679A (en) | Process for the preparation of a nitrogenous vat dye. | |
| CH139718A (en) | Process for the preparation of a nitrogenous vat dye. |