US1739879A - Dyeing mixed textile goods made - Google Patents
Dyeing mixed textile goods made Download PDFInfo
- Publication number
- US1739879A US1739879A US1739879DA US1739879A US 1739879 A US1739879 A US 1739879A US 1739879D A US1739879D A US 1739879DA US 1739879 A US1739879 A US 1739879A
- Authority
- US
- United States
- Prior art keywords
- textile goods
- pyrazolone
- wool
- silk
- goods made
- 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
- 239000004753 textile Substances 0.000 title description 26
- 238000004043 dyeing Methods 0.000 title description 14
- 210000002268 Wool Anatomy 0.000 description 24
- 239000000835 fiber Substances 0.000 description 20
- 125000001033 ether group Chemical group 0.000 description 16
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 12
- 230000001808 coupling Effects 0.000 description 10
- 238000010168 coupling process Methods 0.000 description 10
- 238000005859 coupling reaction Methods 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 239000002253 acid Substances 0.000 description 6
- 239000000975 dye Substances 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- CWJQQASJVVAXKL-UHFFFAOYSA-N 4-(3-methyl-5-oxo-4H-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 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
- XYIBRDXRRQCHLP-UHFFFAOYSA-N Ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 2
- 229940051880 analgesics and antipyretics Pyrazolones Drugs 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 2
- 125000005324 aryloxy alkyloxy group Chemical group 0.000 description 2
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 description 2
- 230000000875 corresponding Effects 0.000 description 2
- 150000008049 diazo compounds Chemical class 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 150000002429 hydrazines Chemical class 0.000 description 2
- 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 2
- PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 2
- 238000009877 rendering Methods 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000002194 synthesizing Effects 0.000 description 2
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/02—Material containing basic nitrogen
- D06P3/04—Material containing basic nitrogen containing amide groups
- D06P3/14—Wool
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/34—Material containing ester groups
- D06P3/52—Polyesters
- D06P3/54—Polyesters using dispersed dyestuffs
-
- 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
- Y10S8/917—Wool or silk
Definitions
- Patent 1,678,611 it has been set forth that such pyrazolone azo dyestuffs as contain one or more carboxylic'acid ester groups are dis glpguished by an increased afiinity for the silk Now we have found that pyrazolone-azo 1n .dyestufl's containing one or more of the ether oreoni groupsa'lkyloxy-,' aryloxyand aralkyl-' oxyare also eminently suitable for producing very even tints on mixed textile goods made of wool and silk fibers.
- the dyeing thus obtained is not only remarkable for its great general fastness but also for the fact that the wool fibersas well as the silk fibers are dyed evenly and one and the same shade.
- the dyestufi' has the following constitution:
- the dyestufi's. are prepared in known manner by causing the diazo compounds to act upon the pyrazolones obtainable from the corresponding hydrazines and acetoacetic ester.
- the afiinity of the dyestuffs for the silk fiber is enhanced if both the diazo component and the coupling component contain one or more of the ether groupscon'sisting of alkyloxy-, aryloxyand aral-kyloxy-or if one of the components contains an ether group and the other a carboxylic acid ester group.
- the above-cited monoazo dyestuffs there may also advantageously be used disazo dyestuffs obtained in a suitable mixed textile goods made of wool an 40 fibers with a pyrazolone-azo dyestuflI' con--.
- ether group is to be understood as including alkyloxy,; aryloxy and aralkyloxy groups.
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Dispersion Chemistry (AREA)
- Coloring (AREA)
Description
Patented Dec. 17, 1929 UNITED STATES PATENT OFFICE.
HERMANN WAGNER, OE SODEN-ON-THE-TAUNUS, A ND HEINZ EIGHWEDE AND ERICH FISCHER, OF HOCHST-ON-THE-MAIN, GERMANY, ASSIGNORS TO GENERAL ANILINE WORKS, INC., OFINEW YORK, N. Y., A CORPORATION OF DELAWARE DYEING MIXED TEXTILE GOODS MADE OF WOOL AND SILK FIBERS No Drawing. Application-filed March 17, 1927, Serial No. 176,298, and in Germany March 22, 1926.
As is known only a few acid azo dyestuffs possess the property of dyeing evenly wool and silk fibers in a single bath. In U. S.
Patent 1,678,611, it has been set forth that such pyrazolone azo dyestuffs as contain one or more carboxylic'acid ester groups are dis glpguished by an increased afiinity for the silk Now we have found that pyrazolone-azo 1n .dyestufl's containing one or more of the ether oreoni groupsa'lkyloxy-,' aryloxyand aralkyl-' oxyare also eminently suitable for producing very even tints on mixed textile goods made of wool and silk fibers.
In the following examples the mark signifies that-the amino body standing before the arrow is diazotiz'ed and coupled with the component standing in the direction of the arrow. These examples serve to illustrate our invention but the 'are not intended to limit it; the parts are y'weight:
(1) 1 kg. of a fabric of mixed wool and silk fibers is dyed in an appropriate manner in a dyebath containing 20g. of the dyestuif:
ortho-aminoani'sole 1- (4 -sulfophenyl) -3- methyl-5-pyrazolone, while adding 10% of sodium sulfate and 4% of sulfuric acid. The dyeing thus obtained is not only remarkable for its great general fastness but also for the fact that the wool fibersas well as the silk fibers are dyed evenly and one and the same shade. The dyestufi' has the following constitution:
there is obtained the same result as in Exam- The combinations specified in the forego ing examples may be largely varied both as regards the diazotizin'g component and the coupllngcomponent. I t is, however, advantageous to prepare the dyestuif in such a manner that its molecule does not contain more acid groups than are necessary for rendering the dyestuff soluble.
Besides the dyestuffs used in Examples 1 and 2 there may also advantageously be used the following dyestuffs:
S-amirio-l-methyl 4 phenylbenzylether-a l-(t'-sr1lfopl1enyl) -3-methyl-5-pyrazol0ne of the following constitution:
CHa
Ortho-aniline-sulfonic acid- 1- (4-methoxyphenyl) -3-n1etl'1yl-5-pyrazalone of the following constitution: 7
son oH-c= a a /N O-OCHs =N=N H-CO Para Jaminocliphenylether-ortho sulfonic acid- 1-phenyl-3-methyl-5-pyrazo1one of the oH,-=N OON=N eH CO following constitution:
or the like.
SOIH
The dyestufi's. are prepared in known manner by causing the diazo compounds to act upon the pyrazolones obtainable from the corresponding hydrazines and acetoacetic ester.
The afiinity of the dyestuffs for the silk fiber is enhanced if both the diazo component and the coupling component contain one or more of the ether groupscon'sisting of alkyloxy-, aryloxyand aral-kyloxy-or if one of the components contains an ether group and the other a carboxylic acid ester group. Besides the above-cited monoazo dyestuffs there may also advantageously be used disazo dyestuffs obtained in a suitable mixed textile goods made of wool an 40 fibers with a pyrazolone-azo dyestuflI' con--.
manner by synthesis. c
In the appended claims the term ether group is to be understood as including alkyloxy,; aryloxy and aralkyloxy groups.
We clalm: "1. The process which comprises dyeing mixed textile goods made of wool and silk fibers with a pyrazolone-azo dyestufi containing both in its diazo component and in its coupling component several ether groups.
2. The process which comprises dyeing 9. As :new products, mixed wool and silk textile oods dyed with a pyrazolone-azodyestu of the followingformula:
textile goods dyed with a pyrazolone-azodyestufl of the following formula:
' ONZZiEZEQ Q 11. As new products, mixed wool and silk textile goods dyed with the pyrazolone-azodyestuif of the following formula:
mixed textile goods made of wool and silk fibers with a'pyrazolone-azo dyestufl' containing' in one of its two components several ether groups.
3. The process which comprises d eing silk taining both in its diazo component and in its coupling component an ether group.
4. The process which comprises dyeing mixed textile goods made of wool and silk fibers with a pyrazolone-azo dyestufi containing in one. of its two components an ether group. p
5. As new products, mixed wool and silk textile goods dyed with a water-soluble pyrazolone-azo dyestufl' containing both in.
its diazo component and inits coupling componentseveral ether groups.
6.'As new products, mixed wool and silk textile goods dyed with a water-soluble pyrazolone-azo dyestuff containing in one of its two components several ethen groups.
7. As ne w products nixed 'WOOIjaDd silk textile goods dyed with a water-soluble pyrazolone-azo dyestuff containing both in its diazo component,and in its coupling component an ether group.
' In testimony tures.
HERMANN WAGNER. HEINZ EICHWED-E. ERICH FISCHER.
8. As new products, mixed wool and silk textile goods dyed with a water-soluble. pyrazolone-azo dyestuflt' containing in one of its two components an other group.
' whereof, we afiix our signa-
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US1739879A true US1739879A (en) | 1929-12-17 |
Family
ID=3419571
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US1739879D Expired - Lifetime US1739879A (en) | Dyeing mixed textile goods made |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US1739879A (en) |
-
0
- US US1739879D patent/US1739879A/en not_active Expired - Lifetime
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