USRE13304E - Friedr - Google Patents
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- Publication number
- USRE13304E USRE13304E US RE13304 E USRE13304 E US RE13304E
- Authority
- US
- United States
- Prior art keywords
- acid
- parts
- amino
- new
- germany
- Prior art date
Links
- 239000002253 acid Substances 0.000 description 8
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- -1 Aminobenzoylaminobenzoyl Chemical group 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000007859 condensation product Substances 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
- 229910052742 iron Inorganic materials 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 230000001264 neutralization Effects 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000001187 sodium carbonate Substances 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- QYFYIOWLBSPSDM-UHFFFAOYSA-N 6-aminonaphthalen-1-ol Chemical compound OC1=CC=CC2=CC(N)=CC=C21 QYFYIOWLBSPSDM-UHFFFAOYSA-N 0.000 description 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N Anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000003518 caustics Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 150000008049 diazo compounds Chemical class 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
Definitions
- FABBENFAIBRIKEN VORM. FBIEDR. BAYER & 00., OF ELB ERFELD, GERMANY, A COR- PORATION OF GERMANY.
- My invention relates to the manufacture and production of compounds valuable for the roduction of dyestufis which can be obtamed by condensing nitrobenzoylhalo- 'ds, such as ortho-, paraor meta-nitro oyl-chlorid with ortho-, metaor paraaminobenzoyl 2 amino 5 naphthol -7 sul- H are distinguished by the remarkable property, that they have the same afiinit for t e as the so-called substantive yes and that they can be fixed on the fiber in the same way as these colors.
- Cotton thus prepared can be combined with diazocompounds, or can be diazotized and combined with azo-dyestufl components.
- the new products are after being dried and pulverized in the she e of their alkalin salts whitish powders soluble in water, upon treatment with hot caustic alkali they are lit up into one molecule of 2-ammo-5- na hthol-7-sulfonic acid and into two molecu es of amino-benzene carboxylic acid.
- aminobenzoylaminobenzoyl-2-amino-5-naphthol-7-sulfonic acids of the formula:
Description
I WERE NEELMEIEB, OF LEVERKUSEN, NEAR COLOGNE, GERMANY, ASSIGNOR TO fonic acid and by reducing the condensation products thus 0 tained. These new products of the formula:
and usef .the parts UNITED STATES PATENT OFFICE.
FABBENFAIBRIKEN VORM. FBIEDR. BAYER & 00., OF ELB ERFELD, GERMANY, A COR- PORATION OF GERMANY.
Specification o! Beissued Letters Patent. Reissued Oct, 31, 1911.
lo Drawing. Original No. 984,420, dated June 6, 1911, Serial No. 610,505. Application for reissue filed Serial No. 647,291.
To all w it may concern:
Be it known that I, WILHELM NEELMEIER, doctor of hilosophy, chemist, citizen of the German mpire, residing at 'Leverkusen, near Colo e, Germany, have invented new Improvements. in Aminobenzoylaminobenzoyl 2-Amino-5-Na hthol 7 Sulfonic Acids, of which the ollowing is a specification.
My invention relates to the manufacture and production of compounds valuable for the roduction of dyestufis which can be obtamed by condensing nitrobenzoylhalo- 'ds, such as ortho-, paraor meta-nitro oyl-chlorid with ortho-, metaor paraaminobenzoyl 2 amino 5 naphthol -7 sul- H are distinguished by the remarkable property, that they have the same afiinit for t e as the so-called substantive yes and that they can be fixed on the fiber in the same way as these colors. Cotton thus prepared can be combined with diazocompounds, or can be diazotized and combined with azo-dyestufl components.
The new products are after being dried and pulverized in the she e of their alkalin salts whitish powders soluble in water, upon treatment with hot caustic alkali they are lit up into one molecule of 2-ammo-5- na hthol-7-sulfonic acid and into two molecu es of amino-benzene carboxylic acid.
In order to illustrate the new process more fulliethe following example is given,
ing by weight :A neutral solution prepared by dissolving 35.8 parts of meta aminobenzoyl 2 amino-5-naphthol-7- sulfonic acid in 500 parts of water containing 5.3 parts of sodium carbonate is heated to -60 0.; 14 parts of crystallized sodium acetate are added to it and then 18.6
parts of molten meta-nitrobenzoyl chlorid. The mixture is stirred at a temperature of about 5060 C. for 2 hours, the condensation product is filtered off and is then introduced into a boiling mixture of 20 arts of iron filings, 500 parts of water an 1 part of acetic acid (80 per cent). After about one hour the reduction is complete. The iron is after precipitation with sodium carbonate removed by filtration and the sodium salt of the new acid separates from the filtrate after the addition of so much hydrochloric acid that the liquid is neutral to litmus. On addition of an excess of acid the free acid having the formula:
. E separates.
I claim The herein described aminobenzoylaminobenzoyl-2-amino-5-naphthol-7-sulfonic acids of the formula:
which are after being dried and pulverized 1nthe shape of their'alkalin salts whitish powders which are soluble in water; the
- new com ounds can be fixed on the fiber and WILHELM NEELMEIER. 1. 8.] Witnesses CHAS. J. Wmorrr, L. Norma.
Family
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