CS252596B1 - Grey to black 1 to 2 chromocomplex azo-dye stuffs - Google Patents
Grey to black 1 to 2 chromocomplex azo-dye stuffs Download PDFInfo
- Publication number
- CS252596B1 CS252596B1 CS861522A CS152286A CS252596B1 CS 252596 B1 CS252596 B1 CS 252596B1 CS 861522 A CS861522 A CS 861522A CS 152286 A CS152286 A CS 152286A CS 252596 B1 CS252596 B1 CS 252596B1
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- Czechoslovakia
- Prior art keywords
- dyes
- dyeing
- metal complex
- black
- complex
- Prior art date
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- 239000000987 azo dye Substances 0.000 title abstract description 4
- 239000000975 dye Substances 0.000 claims abstract description 17
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052804 chromium Inorganic materials 0.000 claims abstract description 7
- 239000011651 chromium Substances 0.000 claims abstract description 7
- 238000004043 dyeing Methods 0.000 abstract description 7
- 210000002268 wool Anatomy 0.000 abstract description 5
- 150000004696 coordination complex Chemical class 0.000 abstract description 3
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 abstract description 3
- 239000002253 acid Substances 0.000 abstract description 2
- 238000006467 substitution reaction Methods 0.000 abstract 3
- 229910052751 metal Inorganic materials 0.000 abstract 2
- 239000002184 metal Substances 0.000 abstract 2
- 239000000434 metal complex dye Substances 0.000 abstract 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 abstract 1
- 150000001450 anions Chemical class 0.000 abstract 1
- 229910017052 cobalt Inorganic materials 0.000 abstract 1
- 239000010941 cobalt Substances 0.000 abstract 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 abstract 1
- NFMHSPWHNQRFNR-UHFFFAOYSA-N hyponitrous acid Chemical group ON=NO NFMHSPWHNQRFNR-UHFFFAOYSA-N 0.000 abstract 1
- 238000010348 incorporation Methods 0.000 abstract 1
- JCCNYMKQOSZNPW-UHFFFAOYSA-N loratadine Chemical compound C1CN(C(=O)OCC)CCC1=C1C2=NC=CC=C2CCC2=CC(Cl)=CC=C21 JCCNYMKQOSZNPW-UHFFFAOYSA-N 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 238000012876 topography Methods 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 5
- 229950011260 betanaphthol Drugs 0.000 description 5
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 4
- 239000000725 suspension Substances 0.000 description 3
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- SJEYSFABYSGQBG-UHFFFAOYSA-M Patent blue Chemical compound [Na+].C1=CC(N(CC)CC)=CC=C1C(C=1C(=CC(=CC=1)S([O-])(=O)=O)S([O-])(=O)=O)=C1C=CC(=[N+](CC)CC)C=C1 SJEYSFABYSGQBG-UHFFFAOYSA-M 0.000 description 1
- 239000000980 acid dye Substances 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
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- Coloring (AREA)
Abstract
Vynález se týká šedých až černých 1:2 chromkomplexnich azobarviv. V barvířství a tiskařství vlny a PAD se v posledních letech prosazují sortimenty kyse lých, sulfosubstituovaných 1:2 kovokomplexnřch o,o* 1 * * -dihydroxyazobarviv, která se vyznačují vysokými stálostmi, vysokou rozpustností za studená, výbornou egalitou a vytažlivostí a uni verzálním použitím. Jsou to koordinační komplexy 1 atomu kovu s koordinačním číslem 6 (nejčastěji chrómu nebo kobaltu) se dvěma stejnými nebo různými o,o'-dihydroxy-, o-hydroxy-o1-karboxy- nebo o-hydroxy-o'-aminoazobarvivy. Vodorozpustnost těchto 1:2 kovokomplexních azobarviv je zvyšována vhodnou substitucí. Známá jsou 1:2 kovokomplexní barviva solubilizovaná neionogenními, hydrofilnost zvyšujícími substituenty, jako například skupinami sulfamoylovými nebo methansulfonylovými. Výroba těch to barviv je však poměrně nákladná. Stejné kvality vybarvení se podařilo docílit i použitím barviv solubiíizovaných sulfo- skupinami. Vpravení sulfoskupin do molekuly 1:2 kovokomplexního barviva není však bez pro blémů. Zatímco neionogenně substituované 1:2 kovokomplexy jsou v podstatě solemi jednosyt- ných kyselin, zvyšuje substituce sulfoskupinami záporný náboj barevného aniontu· a tím pocho pitelně může nepříznivě ovlivnit jeho barvířské schopnosti, zejména egalitu vybarvení a vy- tažlivost. Barvířské chování je navíc ovlivněno nejen elektrickým nábojem, ale i substituční topografií a prostorovým uspořádáním molekuly barevného komplexu.The invention relates to gray to black 1: 2 chromium-complex azo dyes. In the dyeing and printing of wool and PAD, the assortment of clubs has been promoted in recent years 1: 2 metal complex o, o * 1 * * dihydroxyazo dyes, which are characterized by high stability, high cold solubility, excellent levelness and elongation and uni versal use. They are coordination complexes of 1 metal atom with coordination number 6 (most commonly chromium or cobalt) with two identical or different o, o'-dihydroxy-, o -hydroxy-o-carboxy- or o-hydroxy-o'-aminoazo dyes. The water solubility of these 1: 2 metal complex azo dyes is enhanced by appropriate substitution. 1: 2 metal complex dyes solubilized by non-ionic hydrophilicity are known substituents such as sulfamoyl or methanesulfonyl groups. Production of those however, dyes are relatively expensive. The same dyeing qualities have been achieved by using sulfonated dyes groups. However, incorporation of sulfo groups into the 1: 2 molecule of the metal complex dye is not without problems. While the non-ionic substituted 1: 2 metal complexes are essentially the salts of the mono- acid, increases the substitution of the sulfo groups with a negative charge of the colored anion · and thus pox may detrimentally affect its dyeing properties, in particular the dyeing \ t ductility. Moreover, dyeing behavior is influenced not only by electric charge, but also by substitution topography and spatial arrangement of the color complex molecule.
Description
Nyní byla nalezena šedá až černá 1:2 ohromkomplexní azobarviva sestávající podle vynálezu ze směsi monosulfonovaného (I) a disulfonovaného (II) 1:2 chromkomplexuWe have now found gray to black 1: 2 aromo-complex azo dyes consisting of a monosulfonated (I) and disulfonated (II) 1: 2 chromium complex according to the invention
II kdeII where
M = Na, K, NH4 M = Na, K, NH 4
v poměru I:II = 0,05 až 0,95:0,9.5 až 0*05 a připravitelná koordinační chromací směsi nesulfonovaného a sulfonovaného o,o1-dihydroxyazobarviva a 1:1 chromkomplexu o,o'-dihydroxyazobarviva obsahujícího v molekule jednu sulfoskupinu, nebo přímo míšením I a II za mokra resp. za sucha.in a ratio of I: II = 0.05 to 0.95: 0.9.5 to 0 * 05 and obtainable by coordination chromatization of a mixture of unsulfonated and sulfonated o, o 1 -dihydroxyazo dye and 1: 1 chromo complex o, o'-dihydroxyazo dye containing one molecule sulfo or directly by wet mixing I and II respectively. dry.
Zvýšením obsahu disulfonovaného 1:2 chromkomplexu (II) podle vynálezu lze příznivě ovlivnit barvířské vlastnosti monosulfonovaného 1:2 chromkomplexu: barviva s vyšším podílem disulfonované složky (II) vykazují výrazné zlepšení rozpustnosti za studená při zachování da'lšíoh barvířských vlastností jako je například vytažlivost a egalita; vlnu a PAD vybarvují ze slabě kyselé až neutrální lázně, lze je dobře kombinovat s jinými barvivý stejného nebo i jiného kovokomplexního sortimentu, případně s běžnými kyselými barvivý.By increasing the disulfonated 1: 2 chromcomplex (II) content of the invention, the dyeing properties of the monosulfonated 1: 2 chromium complex can be favorably influenced: dyes with a higher proportion of disulfonated component (II) exhibit a marked improvement in cold solubility while retaining further dyeing properties egalita; wool and PAD stain from a weakly acid to neutral bath, they can be well combined with other dyes of the same or even other metal-complex assortment, or with conventional acid dyes.
PřikladlHe did
49,2 g (0,1 mol) chromitého 1:1 komplexu monoazobarviva 6-nitro-2-aminofenol-4-sulfokyselina-.>· 2-naftol ve formě pasty se vnese do 70 °C teplé alkalické suspenze 19,2 g (0,06 mol) monoazobarviva ze 2 dílů 4,S-nitro-2-aminofenolu a 1 dílu 4-nitro-2-aminofenolu—fr 4 díly 2-naftolu a 1 dílem 1,7-acetaminonaftolu ve formě pasty nebo kopulační suspenze a 15,6 g (0,04 mol) monoazobarviva 6-nitro-2-aminofenol-4-sulfokyselina—>» 2 naftol ve formě pasty nebo kopulační suspenze. Po několika hodinách zahřívání na 85 až 95 °C vznikne roztok směsného 1:2 chromitého komplexu černě. Odpařením se získá 130 g silného barviva, které barví vlnu a PAD černým odstínem.49.2 g (0.1 mol) of chromic 1: 1 monoazo dye complex 6-nitro-2-aminophenol-4-sulfoacid -> 2-naphthol in the form of a paste is introduced into a warm alkaline suspension of 19.2 g at 70 ° C (0.06 mol) monoazo dyes of 2 parts of 4, S-nitro-2-aminophenol and 1 part of 4-nitro-2-aminophenol-fr 4 parts of 2-naphthol and 1 part of 1,7-acetaminonaphthol in the form of a paste or coupling suspension and 15.6 g (0.04 mol) of 6-nitro-2-aminophenol-4-sulfoacid → 2 naphthol monoazo dye in the form of a paste or coupling suspension. After a few hours of heating to 85-95 ° C, a 1: 2 mixture of chromium complex was formed in black. Evaporation gave 130 g of a strong dye which stained wool and PAD with a black tint.
Příklad 2 g ostalanové černě FBGL a 30 g chromitého 1:2 komplexu monoazobarviva 6-nitro-2-aminofenol-4-sulfokyselina — 2-naftol se zhomogenizuje. Získá se 100 g barviva, které barví vlnu a PAD šedým až černým odstínem.Example 2 g of ostalanic black FBGL and 30 g of chromic 1: 2 monoazo dye complex 6-nitro-2-aminophenol-4-sulfoacid-2-naphthol are homogenized. 100 g of dye are obtained which stains wool and PAD with a gray to black shade.
Příklad 3 g ostalanové Černě FBGL a 20 g chromitého komplexu 1:2 komplexu monoazobarviva 4-nit ro-2-aminof enol-6-sulfokyselina—^ 2-naftol se zhomogenizu je. Získá se 100 g barviva, které barví vlnu a PAD šedým až černým odstínem. jExample 3 g of ostalanic black FBGL and 20 g of chromium complex 1: 2 monoazo dye complex 4-nitro-2-aminophenol-6-sulfoacid-2-naphthol are homogenized. 100 g of dye are obtained which stains wool and PAD with a gray to black shade. j
PŘEDMĚT VYNÁLEZUSUBJECT OF THE INVENTION
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS861522A CS252596B1 (en) | 1986-03-05 | 1986-03-05 | Grey to black 1 to 2 chromocomplex azo-dye stuffs |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS861522A CS252596B1 (en) | 1986-03-05 | 1986-03-05 | Grey to black 1 to 2 chromocomplex azo-dye stuffs |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS152286A1 CS152286A1 (en) | 1987-02-12 |
| CS252596B1 true CS252596B1 (en) | 1987-09-17 |
Family
ID=5349807
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS861522A CS252596B1 (en) | 1986-03-05 | 1986-03-05 | Grey to black 1 to 2 chromocomplex azo-dye stuffs |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS252596B1 (en) |
-
1986
- 1986-03-05 CS CS861522A patent/CS252596B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS152286A1 (en) | 1987-02-12 |
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