US1023977A - Dye. - Google Patents
Dye. Download PDFInfo
- Publication number
- US1023977A US1023977A US58085910A US1910580859A US1023977A US 1023977 A US1023977 A US 1023977A US 58085910 A US58085910 A US 58085910A US 1910580859 A US1910580859 A US 1910580859A US 1023977 A US1023977 A US 1023977A
- Authority
- US
- United States
- Prior art keywords
- acid
- pyrazolone
- methylene
- dyeing
- dye
- 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
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000002253 acid Substances 0.000 description 6
- 238000004043 dyeing Methods 0.000 description 6
- 235000011121 sodium hydroxide Nutrition 0.000 description 6
- 239000000975 dye Substances 0.000 description 5
- 210000002268 wool Anatomy 0.000 description 5
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 4
- MGWMGDQIOPGJFX-UHFFFAOYSA-N 3-[3-(3-carboxy-2-hydroxyphenyl)propyl]-2-hydroxybenzoic acid Chemical compound C(CC=1C(=C(C=CC1)C(=O)O)O)CC=1C(=C(C=CC1)C(=O)O)O MGWMGDQIOPGJFX-UHFFFAOYSA-N 0.000 description 3
- 229940051880 analgesics and antipyretics pyrazolones Drugs 0.000 description 3
- -1 methylene oxycarboxylic acids Chemical class 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- QELUYTUMUWHWMC-UHFFFAOYSA-N edaravone Chemical compound O=C1CC(C)=NN1C1=CC=CC=C1 QELUYTUMUWHWMC-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- NHLAPJMCARJFOG-UHFFFAOYSA-N 3-methyl-1,4-dihydropyrazol-5-one Chemical compound CC1=NNC(=O)C1 NHLAPJMCARJFOG-UHFFFAOYSA-N 0.000 description 1
- CWJQQASJVVAXKL-UHFFFAOYSA-N 4-(3-Methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl)benzenesulfonic acid Chemical compound O=C1CC(C)=NN1C1=CC=C(S(O)(=O)=O)C=C1 CWJQQASJVVAXKL-UHFFFAOYSA-N 0.000 description 1
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 description 1
- IMZSHPUSPMOODC-UHFFFAOYSA-N 5-oxo-1-phenyl-4h-pyrazole-3-carboxylic acid Chemical compound O=C1CC(C(=O)O)=NN1C1=CC=CC=C1 IMZSHPUSPMOODC-UHFFFAOYSA-N 0.000 description 1
- RHBHJNSTEIEPGS-UHFFFAOYSA-N 5-oxopyrazole-3-carboxylic acid Chemical compound OC(=O)C1=CC(=O)N=N1 RHBHJNSTEIEPGS-UHFFFAOYSA-N 0.000 description 1
- FYEHYMARPSSOBO-UHFFFAOYSA-N Aurin Chemical class C1=CC(O)=CC=C1C(C=1C=CC(O)=CC=1)=C1C=CC(=O)C=C1 FYEHYMARPSSOBO-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- 150000001845 chromium compounds Chemical class 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000000835 fiber Substances 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
- 238000000034 method Methods 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/18—One oxygen or sulfur atom
- C07D231/20—One oxygen atom attached in position 3 or 5
- C07D231/22—One oxygen atom attached in position 3 or 5 with aryl radicals attached to ring nitrogen atoms
- C07D231/26—1-Phenyl-3-methyl-5- pyrazolones, unsubstituted or substituted on the phenyl ring
Definitions
- My invention relates to the manufacture and production of new dyestuffs of the aurin series, which are obtained by condensing in the presence of oxidizing agents methylene oxycarboxylic acids, especially 1nethylene-di-salicylic acid and methylenediortho-cresotinic acid with pyrazolones containing probably in their molecule the following group:
- Methylene-di-ortho-cresotinic acid may be replaced by methylene-di-salicylic or methylene-di- 2. l-dioxybenzoic acid, etc., or by mixed methylene-di-hydroxy acids.
- Methylene-di-ortho-cresotinic acid may be replaced by methylene-di-salicylic or methylene-di- 2. l-dioxybenzoic acid, etc., or by mixed methylene-di-hydroxy acids.
- the hydrogenes of the two carboxylic-benzene nuclei may be further substituted by the methyland hydroxyl group.
- the new dyes are dark powders soluble in dilute caustic soda lye generally with a red color, dyeing wool from acid baths generally from red to violet to brown shades, which can be chromed on the fiber.
- the parts being by weight :21.1 parts of methylene-di-ortho-cresotinic acid and 12.8 parts of 3-methyl-l-phenyl-5-pyrazolone are mixed with 320 parts of strong sulfuric acid and the necessary quantity of nitrosyl sulfuric acid and then stirred at from 20- 45" C. until the quantity of the dyestuff produced is not further increased and the evolution of nitrogen oxids ceases.
- the product of the reaction is poured on ice and the dyestuff is filtered off.
- pyrazolones may be employed, 6. g. 3-methyl-5-pyrazolone, 3-methyl-1- para-sulfophenyl-5-pyrazolone, 3-methyl- 5- pyrazolone-l-beta napht-hyl 4.8 disulfonlc acid, 3 carboxy 1 phenyl-5-pyrazolone, 3- carboxy 5 pyrazolone 1 phenyl para-sulfonic acid, etc.
- the dyeing can be done in the usual ways.
- 001 is either dyed and treated with bichroinates after dyeing, or wool mordanted with chromium compounds is dyed, 0r uninordanted wool is dyed and niordanted in one operation from a bath containing both dyestutt and chrome niordant.
- R means an aryl radical which dyestuffs are dark powders soluble in dilute caustic soda lye generally with a red color, dyeing wool from acid baths generally from red to violet to brown shades, which can be chromed after dyeing, substantially as described.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Umrnn srarns PATENT OFFICE.
MAX WEILER, OF ELBERFELD, GERMANY, ASSIGNOR TO FARBENFABRIKEN VORlVL FRIEDR. BAYER & 00., OF ELBERFELD, GERMANY, A CORPORATION OF GERMANY.
DYE.
No Drawing.
Specification of Letters Patent.
Application filed September 7, 1910.
To aZZ whom it may concern Be it known that I, MAX WEILER, doctor of philosophy chemist, citizen of the German Empire, residing at Elberfeld, Germany, have invented new and useful Improvements in New Dye, of which the following is a specification.
My invention relates to the manufacture and production of new dyestuffs of the aurin series, which are obtained by condensing in the presence of oxidizing agents methylene oxycarboxylic acids, especially 1nethylene-di-salicylic acid and methylenediortho-cresotinic acid with pyrazolones containing probably in their molecule the following group:
0 R meaning the phenylor naphthyl radical,
fuming sulfuric acid may be used. Methylene-di-ortho-cresotinic acid may be replaced by methylene-di-salicylic or methylene-di- 2. l-dioxybenzoic acid, etc., or by mixed methylene-di-hydroxy acids. Instead of 3-methyl- 1-phenyl-5-pyrazolone mentioned in the exand R the methylor carboxyl group; the hydrogenes of the two carboxylic-benzene nuclei may be further substituted by the methyland hydroxyl group.
The new dyes are dark powders soluble in dilute caustic soda lye generally with a red color, dyeing wool from acid baths generally from red to violet to brown shades, which can be chromed on the fiber.
In order to illustrate the new process more fully the following example is given, the parts being by weight :21.1 parts of methylene-di-ortho-cresotinic acid and 12.8 parts of 3-methyl-l-phenyl-5-pyrazolone are mixed with 320 parts of strong sulfuric acid and the necessary quantity of nitrosyl sulfuric acid and then stirred at from 20- 45" C. until the quantity of the dyestuff produced is not further increased and the evolution of nitrogen oxids ceases. The product of the reaction is poured on ice and the dyestuff is filtered off. It is a yellowish-brown powder soluble in hot water with an orange color, in dilute caustic soda lye with an orange-red color, capable of dyeing wool in orange shades which on chroming turn into an intense brownish-orange and is probably obtained according to the following formula:
ample other pyrazolones may be employed, 6. g. 3-methyl-5-pyrazolone, 3-methyl-1- para-sulfophenyl-5-pyrazolone, 3-methyl- 5- pyrazolone-l-beta napht-hyl 4.8 disulfonlc acid, 3 carboxy 1 phenyl-5-pyrazolone, 3- carboxy 5 pyrazolone 1 phenyl para-sulfonic acid, etc.
The dyeing can be done in the usual ways.
001 is either dyed and treated with bichroinates after dyeing, or wool mordanted with chromium compounds is dyed, 0r uninordanted wool is dyed and niordanted in one operation from a bath containing both dyestutt and chrome niordant.
I claim 1. The herein described new dyestuffs, being condensation products of methylene-dioxycarboxylic acids and pyrazolones containing probably in their molecule the following characteristic group:
OH O R COOH (X91 pyrazolone in which R means an aryl radical which dyestuffs are dark powders soluble in dilute caustic soda lye generally with a red color, dyeing wool from acid baths generally from red to violet to brown shades, which can be chromed after dyeing, substantially as described.
2. The herein described new dyestuff having probably the following formula:
on 0H3 my hand in the presence of two subscribing witnesses.
MAX WEILER. [n s] Witnesses CHAS. J. WRIGHT,
lVALTER VONNEGUT.
Copies of this patent may be obtained for five cents each, by addressing the Commissioner of latents, Washington, D. C.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US58085910A US1023977A (en) | 1910-09-07 | 1910-09-07 | Dye. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US58085910A US1023977A (en) | 1910-09-07 | 1910-09-07 | Dye. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US1023977A true US1023977A (en) | 1912-04-23 |
Family
ID=3092274
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US58085910A Expired - Lifetime US1023977A (en) | 1910-09-07 | 1910-09-07 | Dye. |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US1023977A (en) |
-
1910
- 1910-09-07 US US58085910A patent/US1023977A/en not_active Expired - Lifetime
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