US881158A - Dark-blue-violet dye. - Google Patents
Dark-blue-violet dye. Download PDFInfo
- Publication number
- US881158A US881158A US35842007A US1907358420A US881158A US 881158 A US881158 A US 881158A US 35842007 A US35842007 A US 35842007A US 1907358420 A US1907358420 A US 1907358420A US 881158 A US881158 A US 881158A
- Authority
- US
- United States
- Prior art keywords
- parts
- dark
- blue
- acid
- violet
- 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.)
- Expired - Lifetime
Links
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 239000003518 caustics Substances 0.000 description 5
- 230000005484 gravity Effects 0.000 description 4
- 229960000443 hydrochloric acid Drugs 0.000 description 4
- 235000011167 hydrochloric acid Nutrition 0.000 description 4
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 3
- 235000005811 Viola adunca Nutrition 0.000 description 3
- 240000009038 Viola odorata Species 0.000 description 3
- 235000013487 Viola odorata Nutrition 0.000 description 3
- 235000002254 Viola papilionacea Nutrition 0.000 description 3
- 244000172533 Viola sororia Species 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 210000002268 wool Anatomy 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- -1 acetylaminophenol carboxylic acid Chemical class 0.000 description 2
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241001237728 Precis Species 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000002832 nitroso derivatives Chemical class 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- JCBJVAJGLKENNC-UHFFFAOYSA-M potassium ethyl xanthate Chemical compound [K+].CCOC([S-])=S JCBJVAJGLKENNC-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 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
- C09B7/10—Bis-thionapthene indigos
Definitions
- KARL SCHIRMACHER AND BERNHARD D IoKia or HocHsr-oN-THEMAIN, GSERMIANQY, ASSIGNORS To raR wEaKE VORM.
- This invention relates to new vat dyestuffs the constitution of which corresponds to the formula:
- R means ethyl and methyl
- the method to obtain the new dyestuffs is, for instance, as follows:
- Example: 15.3 parts of aminophenolcarboXylic acid (OH:XH :COOH 522:1 are boiled with 50 parts of glacial acetic acid for 12 hours in a reflux apparatus, half of the glacial acetic acid is then distilled and some water added. The acetylaminophenol carboxylic acid separates. It is obtained in a pure state by crystallizing' from water. Then 19,5 parts of this acid are dissolved in 20 parts of caustic soda-lye of 40 Be. and 200 parts of water, 15 parts of dimethylsulfate being added while stirring. After stirring for some hours, care being taken to keep the liquid alkaline, the methylation is complete; parts of caustic soda-lye of 40 B.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
KARL SCHIRMACHER AND BERNHARD D IoKia, or HocHsr-oN-THEMAIN, GSERMIANQY, ASSIGNORS To raR wEaKE VORM. MEISTER LUCIUS & BRUNING, or HOCHST-ON- THE-MAIN, cERiLiNYjA CORPORATION OF GERMANY.
DARK-B LUE -VIOLET DYE.
Specification of Letters Patent.
Patented March 10,- 1908.
Application filed February 20, 1907. Serial No. 358,420.
many, have invented certain new and useful Improvements in Dark-Blue-Violet Dyes, of which the following is a specification.
This invention relates to new vat dyestuffs the constitution of which corresponds to the formula:
wherein R means ethyl and methyl.
The new dyestuffs may be obtained by oxidizing 5-alkyl-oxy-oxythionaphthene carboxylic acids (R :8 :C :2 :1) obtained from 5-alkyloxyphenylthioglyc ollicortho-carb oxylic acids -(RO:SCH CO()H:COOH= 5:2:1) by heating with alkali. They are violet powders, insoluble in water, soluble in hot alcohol, benzene, glacial acetic acid and chloroform with a violet color, in concentrated sulfuric acid with a green color. With alkaline hydrosulfite they yield yellow colored vats dyeing wool and cotton dark blue-violet shades.
The method to obtain the new dyestuffs is, for instance, as follows:
Example: 15.3 parts of aminophenolcarboXylic acid (OH:XH :COOH= 522:1 are boiled with 50 parts of glacial acetic acid for 12 hours in a reflux apparatus, half of the glacial acetic acid is then distilled and some water added. The acetylaminophenol carboxylic acid separates. It is obtained in a pure state by crystallizing' from water. Then 19,5 parts of this acid are dissolved in 20 parts of caustic soda-lye of 40 Be. and 200 parts of water, 15 parts of dimethylsulfate being added while stirring. After stirring for some hours, care being taken to keep the liquid alkaline, the methylation is complete; parts of caustic soda-lye of 40 B. specific gravity are then added and to effect hydrolysis the whole is boiled in a reflux apparatus till a test portion with hydroc hloric acid shows no more a precipitate of unchanged acetyl compound. 'hen cold it is acidified; there are then added 20 parts of hydrochloric acid of 20 Be. specific gravity and 6.9 parts of nitrite. The obtained and filtered diazo solution is run at 2025 (hintoa solution of 18 parts of potassium Xanthogenate and parts of sodium carbonate till no further nitrogen is evolved. Then are added 16 parts of sodium ohloracetate and 25 parts of caustic soda-lye of B. specific gravity and the whole is boiled. After 12 hours it is allowed to cool and on adding a mineral acid the 5 methoxyphenylthioglycollic ortho carboxylic acid (OCH :SCH COOH :COOH 5 :2 :1)
is preci itated. It is a yellowish powder difficult y soluble in cold Water crystalli'zing; from hot water in yellowish prisms of the melting point 198199.
To manufacture 5-1nethoXy-oxythionaphthene carboxylic acid 20 parts of 5-methoXyphenylthioglycollic ortho carboxylic acid are heated to 180-200 C. for some time with a mixture of 100 parts of caustic sogia and 10 parts of water. The fusion becomes yellow and gradually brittle. 'hen cold the mass is dissolved in water and by adding a mineral acid the 5-methoxyoxythionaphthene carboxylic acid is precipitated. It is soluble in acetates and a-lkalies, yielding, when treated with hydrochloric acid and nitrite, a nitroso compound crystallizing from water in reddish yellow needles. On boiling the afore described 5-1nethoxy-oxythionaphthene carboxylic acid with hydrochloric acid the 5- niethoxy-oxythionaphthene is obtained; it is volatile with steam and crystallizes in white needles.
To convert into the dyestuff, 23 parts'of 5- methoxy-oxythionaphthene carboxylic acid or 18 parts of 5-methoxy-oxythionaphthene and 22 parts of caustic soda-lye of 40 B. specific gravity are dissolved in 1000 parts of water and then is added a solution of potassium ferri cyanid till no further dyestufi' is formed. flakes, being, when dry, a violet-black powder. With an alkaline hydrosulfite solution it yields a vat from which itdyes wool. and cotton dark blue-violet tints. From the 5 methoxy oxythionaphthene carboxylic The dyestuif separates in violet acid a very like dyestuff may be obtained I As roduots the dyestnffs having the forum a:
inconcentrated sulfuric acid with a green.
'10 color with alkaline hydrosnlfite they yield yellow colored .vats dyeing wool and cotton dark blue-violet shades.
In testimony that we claim the foregoing as our invention,f.we have signed our names in presence of two subscribing witnesses.
KARL SOHIRMAOHER. BERNHARD DEICKE.
lVitnesses:
, JEAN GRUND, CARL GRUND.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US35842007A US881158A (en) | 1907-02-20 | 1907-02-20 | Dark-blue-violet dye. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US35842007A US881158A (en) | 1907-02-20 | 1907-02-20 | Dark-blue-violet dye. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US881158A true US881158A (en) | 1908-03-10 |
Family
ID=2949598
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US35842007A Expired - Lifetime US881158A (en) | 1907-02-20 | 1907-02-20 | Dark-blue-violet dye. |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US881158A (en) |
-
1907
- 1907-02-20 US US35842007A patent/US881158A/en not_active Expired - Lifetime
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