US501160A - Benfabriken - Google Patents
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- Publication number
- US501160A US501160A US501160DA US501160A US 501160 A US501160 A US 501160A US 501160D A US501160D A US 501160DA US 501160 A US501160 A US 501160A
- Authority
- US
- United States
- Prior art keywords
- acid
- fiber
- cotton
- black
- acids
- 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
- 239000002253 acid Substances 0.000 description 24
- 238000000034 method Methods 0.000 description 20
- 239000000835 fiber Substances 0.000 description 18
- 229920000742 Cotton Polymers 0.000 description 16
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 10
- 238000004040 coloring Methods 0.000 description 10
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-Naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 8
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-Naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 8
- VWDWKYIASSYTQR-UHFFFAOYSA-N Sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 8
- 150000007513 acids Chemical class 0.000 description 8
- 229950011260 betanaphthol Drugs 0.000 description 8
- 150000008049 diazo compounds Chemical class 0.000 description 8
- 238000004043 dyeing Methods 0.000 description 8
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 6
- 239000000975 dye Substances 0.000 description 6
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-Naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 4
- YGSDEFSMJLZEOE-UHFFFAOYSA-N Salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 235000010344 sodium nitrate Nutrition 0.000 description 4
- 239000004317 sodium nitrate Substances 0.000 description 4
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-Naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N Resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 125000003368 amide group Chemical group 0.000 description 2
- -1 amido naphthol Chemical compound 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000000987 azo dye Substances 0.000 description 2
- 230000003796 beauty Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 239000005018 casein Substances 0.000 description 2
- 235000021240 caseins Nutrition 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- 238000005755 formation reaction Methods 0.000 description 2
- 235000011167 hydrochloric acid Nutrition 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 150000004780 naphthols Chemical class 0.000 description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-M nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 2
- 150000002828 nitro derivatives Chemical class 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 229960004889 salicylic acid Drugs 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 235000002639 sodium chloride Nutrition 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
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
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/02—Disazo dyes
- C09B35/039—Disazo dyes characterised by the tetrazo component
- C09B35/04—Disazo dyes characterised by the tetrazo component the tetrazo component being a benzene derivative
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/916—Natural fiber dyeing
- Y10S8/918—Cellulose textile
Definitions
- My invention relates to the production of black azo dyes on the fiber and depends on a peculiar property of coloring matters which are obtained by combining one molecular proportion of tetrazodiphenyl, or as equivalents therefor in this process tetrazoditholyl, tetrazomethoxydiphenyl, tetrazoethoxydiphenyl, tetrazodiphenoldi methyl ether, tetrazodiphenoldiethylether or tetrazostilbene either with two molecular proportions of amidonaphtholmonosulfo acid G or as equivalents therefor in this process of the amidonaphtholdisulfo acid formed by melting with alkalies the alphanaphthylamine trisulfo acid which results when the nitro compound of the naphthalenetrisulfo acid described in the German Patent No.
- dye-stulfs when fixed on fiber, are capable of being diazotized and the thus produced diazo compounds of the aforesaid coloring matters may directly be combined on fiber with phenols or as equivalents thereforin this process with naphthols, amines, amid ophenols or amidonaphthols, di-
- unmordanted cotton are at first colored in a boiling bath prepared by dissolving in two hundred liters of water about one kilo of common salt and 0.6 kilos of the dye-stuff which is for example resulting by the combination of one molecular proportion of tetrazodiphenyl chlorid with two molecular proportions of amidonaphtholmonosulfo acid G; thereupon the cotton after having been washed with water is introduced into a solution of one kilo of sodium nitrate in two hundred liters of cold water on addition of two kilos of muriatic acid (20 Baum).
- the diazo compound which likewise remains fixed on the fiber and is fast to washing to which the cotton after its re moval out of the solution of sodium nitrate by preference is to be subjected.
- the shades which are produced when on the fiber the coloring matter formed from one molecule of tetrazodiphenyl chloridand two molecules of amidonaphtholmonosulfo acid G is diazotized and combined with betanaphthol especially differ by their absolute fastness to soaping from those which result when the said tetrazo dyestuff is employed without being further diazotized and combined with betanaphthol.
Description
U ITE ST -Ins "PATENT OFFICE.
.WILLIAM PFITZINGER, .OF ELBERFEIJD, GERMANY, ASSIGNOR TO THE FAR- BENFAB RIKEN, VORMALS FR. BAYER'& (10., OF SAME PLACE.
PROCESS OF DYEING BLACK.
I SPECIFICATION forming m of Letters Patent No. 501,160, dated July 11, 1893.
Application filed November 19,1891. $erial No. 412,438. (No specimens.) Patented in Germany April 1, 1890, No. 53.799; in
England June 2, 1890 No. 8,530; in Belgium October 29, 1890, No. 92,5l7iin Italy January 31, 1891, XXV, 29.122, and in I Austria-Hungary January 23, 1891, No. 4,929 and No. 22,349.
To all whom it may concern:
Be it known that I, WILLIAM PFITZINGER, chemist, (assignor to the FARBENFABRIKEN,
' VORMALS FR. BAYER 8: 00., of Elberfeld,) a
subject of the Emperor of Germany, residing at Elberfeld, Germany, have invented a new and useful Improvement in Producing Black Az'o Dyes on Fiber, (for which the aforesaid FARBENFABRIKEN has already obtained Letters Patent in Germany, No. 53,799, dated April 1, 1890; in England, No. 8,530, dated June 2, 1890; in Austria-Hungary, No. 4,929 and No. 22,849, dated January 23, 1891; in' Italy, XXV, No. 29,122, dated January 31, 1891, and in Belgium, No. 92,517, dated October 29, 1890,) of which I give in the following a clear and exact description.
' My invention relates to the production of black azo dyes on the fiber and depends on a peculiar property of coloring matters which are obtained by combining one molecular proportion of tetrazodiphenyl, or as equivalents therefor in this process tetrazoditholyl, tetrazomethoxydiphenyl, tetrazoethoxydiphenyl, tetrazodiphenoldi methyl ether, tetrazodiphenoldiethylether or tetrazostilbene either with two molecular proportions of amidonaphtholmonosulfo acid G or as equivalents therefor in this process of the amidonaphtholdisulfo acid formed by melting with alkalies the alphanaphthylamine trisulfo acid which results when the nitro compound of the naphthalenetrisulfo acid described in the German Patent No. 38,281, dated September 2, 1885, is reduced, or as equivalents therefor in this process with one molecular proportion of any of the two aforesaid amidonaphthosulfo acids and with one molecular proportion of a phenol, or as equivalents therefor in this process a naphthol or the sulfo and carboxylic acid of aphenol or naphthol or naphthylamine or the sulfo acid thereof. The last named dye-stulfs, when fixed on fiber, are capable of being diazotized and the thus produced diazo compounds of the aforesaid coloring matters may directly be combined on fiber with phenols or as equivalents thereforin this process with naphthols, amines, amid ophenols or amidonaphthols, di-
hydroxynaphthalenes or the sulfo acids of these compounds.
In carrying out my process practically I proceed as follows: About ten kilos, by weight,
of unmordanted cotton are at first colored in a boiling bath prepared by dissolving in two hundred liters of water about one kilo of common salt and 0.6 kilos of the dye-stuff which is for example resulting by the combination of one molecular proportion of tetrazodiphenyl chlorid with two molecular proportions of amidonaphtholmonosulfo acid G; thereupon the cotton after having been washed with water is introduced into a solution of one kilo of sodium nitrate in two hundred liters of cold water on addition of two kilos of muriatic acid (20 Baum). In this manner there is formed the diazo compound which likewise remains fixed on the fiber and is fast to washing to which the cotton after its re moval out of the solution of sodium nitrate by preference is to be subjected. By introducing the cotton thus prepared into an alkaline solution of about 4.5 kilos of beta naphthol the formation of the dye-stud takes place on the fiber and the end of this reaction may easily be recognized as the cotton gradually assumes a deep bluish-black color while that produced on it by the said diazo compound is a pure blue-black. When the intensity of the color does no more increase the cotton is carefully washed with water; it shows after the treatment described a deep bluish-black, which is very fast to alkalies and acids and which as to its intensity, brightness and beauty surpasses by far the shades produced by the coloring matter derived from one molecule of tetrazodiphenyl chlorid and two molecules of amidonaphtholmonosulfo acidG. The shades which are produced when on the fiber the coloring matter formed from one molecule of tetrazodiphenyl chloridand two molecules of amidonaphtholmonosulfo acid G is diazotized and combined with betanaphthol especially differ by their absolute fastness to soaping from those which result when the said tetrazo dyestuff is employed without being further diazotized and combined with betanaphthol.
According to this process many reactions may be carried out in a very simple way and directly on the fiber. A great Variety of black shades with reddish, bluish or violet tones results as on the one hand the tetrazodiphenyl chlorid may be replaced with the similar result by the analogous compounds: tetrazoditolyl chlorid, tetrazomethoxydiphenyl chlorid, tetrazoethoxydiphenyl chlorid,tetrazodiphenoldimethylether,tetrazodiphenoldiethylether or tetrazostilbene and as on the other hand instead of betanaphthol there may be employed also alphanaphthol, the sulfo and carboxylic acids of both, dihydroxnaphthalenes or their snlfo acids, alphaand betanaphthylamine or their sulfo acids, phenol, resorcine, salicylic acid, metaphenylene diamnaphtholethers, amidonaphtholsulfo acids in what manner the same is to be performed, that which I claim as new, and desire to secure by Letters Patent, is-- The process of dyeing cotton, which consists, first, in dyeing said cotton by a coloring matter such as is obtained by the combination of one molecule of tetrazo diphenyl or analogous compounds thereof with two molecules of amido naphthol monosulfo acid G; second, in diazotizing on the fiber the dyestufi thereon which contains one or two free amido groups; and, third, combining the resulting diazo compound with phenol, substantially as described.
In testimony whereof I have signed my name in the presence of two subscribing wit- WILLIAM PFITZINGER.
nesses. ine, chrysoidlne,amldonaphthols and amido- Witn esses:
WM. ESSENWEIN, RUDODPH FRICKE.
It ishereby certified that in Letters Patent No. 501,160, granted J my 11., 1893, upon the application of William Pfitzinger, of Elberfeld, Germany, for an improvement in Processes of Dyeing Black, errors appear in the printed specification requiring the following correction, viz: In lines 64 and 70, page 1, the word nitrate should read nitrite and that the said Letters Patent should be read with these corrections therein that the same may conform to the record of the casein the Patent Office. Signed, countersigned, and sealed this 1st day of August, A. D. 1893. i I
[SEALJ .r JNO. M. REYNOLDS,
Assistant Secretary of the Interior. Gountersigned JOHN S. SEYMOUR,
Commissioner of Patents.
Publications (1)
Publication Number | Publication Date |
---|---|
US501160A true US501160A (en) | 1893-07-11 |
Family
ID=2569995
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US501160D Expired - Lifetime US501160A (en) | Benfabriken |
Country Status (1)
Country | Link |
---|---|
US (1) | US501160A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4973672A (en) * | 1985-09-28 | 1990-11-27 | Cassella Aktiengesellschaft | Water-soluble aminonaphthol disazo dyestuffs, their preparation and their use |
-
0
- US US501160D patent/US501160A/en not_active Expired - Lifetime
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4973672A (en) * | 1985-09-28 | 1990-11-27 | Cassella Aktiengesellschaft | Water-soluble aminonaphthol disazo dyestuffs, their preparation and their use |
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