US1678611A - Process of - Google Patents
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- Publication number
- US1678611A US1678611A US1678611DA US1678611A US 1678611 A US1678611 A US 1678611A US 1678611D A US1678611D A US 1678611DA US 1678611 A US1678611 A US 1678611A
- Authority
- US
- United States
- Prior art keywords
- pyrazolone
- carboxylic acid
- silk
- acid ester
- fibre
- 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
- 238000000034 method Methods 0.000 title description 2
- 239000000835 fiber Substances 0.000 description 11
- 210000002268 wool Anatomy 0.000 description 8
- 239000002253 acid Substances 0.000 description 5
- 238000004043 dyeing Methods 0.000 description 5
- 239000000975 dye Substances 0.000 description 4
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 3
- 239000004753 textile Substances 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 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
- 150000001875 compounds Chemical class 0.000 description 2
- 150000008049 diazo compounds Chemical class 0.000 description 2
- -1 pyrazolone compound Chemical class 0.000 description 2
- ZRHUHDUEXWHZMA-UHFFFAOYSA-N 1,4-dihydropyrazol-5-one Chemical compound O=C1CC=NN1 ZRHUHDUEXWHZMA-UHFFFAOYSA-N 0.000 description 1
- 206010003805 Autism Diseases 0.000 description 1
- 208000020706 Autistic disease Diseases 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- VGURYVWLCVIMTF-UHFFFAOYSA-N methyl 2-amino-4-nitrobenzoate Chemical compound COC(=O)C1=CC=C([N+]([O-])=O)C=C1N VGURYVWLCVIMTF-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- RWZYAGGXGHYGMB-UHFFFAOYSA-N o-aminobenzenecarboxylic acid Natural products NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
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
- D06P3/34—Material containing ester groups
- D06P3/52—Polyesters
- D06P3/54—Polyesters using dispersed dyestuffs
-
- 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
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/39—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using acid dyes
-
- 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
- nmwingflap iicaaoa .iild was 28, 1926, Serial autism; giaiiff ia; Germany ret ial- 7, 1925..
- the wool and silk fibres are dyed even tints.
- the degree of the afiinity of the dyestufi's' for the silk fibre as compared with that for the wool fibre it should be considered that it is advantageous that the combinations of dyestuffs to be selected do not contain more acid groups, such as sulfoor free carboxylic groupsthan are necessary for rendering1 the 'dyestufi soluble in the usual dye bat.
- pyrazolone, t ere is also obtained a very pure yellow dyeing, the silk fibre as well as the wool fibre belng dyed a tint of even shade and intensity.
- the dyestufi' combinations specified in the foregoing examples are only to be regarded as representatives of the respective groups. They may, of course, be largely varied both in the diazo component and in the coupling I component.
- the ortho-c'hloroaniline may for instance be replaced by: aniline, ortho-metaand ara-toluidine or the like.
- the. diazo compounds do not contain any sulfo group, because ,inthis case the wool fibre is dyed more deeply thanthe silk fibre.
- the dye'stulfs of this kind are distinguished from the analogous dyestuffs in which. the sulfotphenylpyrazolonecarboxylic acid is not esteri ed, by the property of dyeing the silk fibre in mixed material more deeply.
- Example 2 For the pyrazolonesulfonic acid mentioned in Example 2 may be substituted any other sulfoaryl-3 methyl-5-pyrazolone but no sulfophenyl-5-pyrazolone-3-carboxylic acid.
- diazo. compounds mentioned in Examples 2and 3 may be replaced by. any other aminoarylcarboxylic acid ester, for instance by 4-nitro-2-aminobenzoic acid methyl ester etc;
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Dispersion Chemistry (AREA)
- Coloring (AREA)
Description
Patented July 24, 1928.
;,::RATENT .LOF ICE- HERMANN WAGNER; oFsonnmon 'rHE-TAo-nus, ilm) nsmz EICHWEDE-AND mun FISCHER; or ooHsr-oN-rirnmsnv, gnniaanmjassrenons ro GRASSELLI DYE- s'rurr CORPORATION, oannwyoitxnrt;A'coaroRArIoN ornnmiwnm.
PRbCESS. .OE; MIXED TEXTILE GOODS.
a. nmwingflap iicaaoa .iild was 28, 1926, Serial autism; giaiiff ia; Germany ret ial- 7, 1925..
It is already known that a number of pyrazolone azo dyestuffs possess a certain aflinity for the silkfibre.
when mixed with wool fibre, just as intensely as the wool fibre.
' ponent, or in both components simultaneously, one, or more carboxylic acid ester groups. The dyeings obtainable thereby,
which vary from yellow to orange, are dis tinguished by very good properties as to fastness. The wool and silk fibres are dyed even tints. Regarding the degree of the afiinity of the dyestufi's' for the silk fibre as compared with that for the wool fibre it should be considered that it is advantageous that the combinations of dyestuffs to be selected do not contain more acid groups, such as sulfoor free carboxylic groupsthan are necessary for rendering1 the 'dyestufi soluble in the usual dye bat.
The. following examples llustrate our invention:
(1) 1 kg. ofmaterial mixed ofr' wooland silk fibres is dyed in an appropriate manner in a dyebath containin g-2Ogr. of the dyephenyl-5-pyrazolone-3-carboxylic ethyl" ester,
while adding 10% of sodium sulfate and 4% of sulfuric acid. The dyeing thus obtained is not only distinguished for its great fastv 'ness but also for the fact that the woolas well as the silk fibres are dyed evenly and Lin an equal" shade. i
(2) By substituting for the dyestuffj'indicated in Exam le 1 an equal quantity of the dyestufi: ortho-aminobenzoic acid ethyl" ester'- 1--- 4'- sulfophenyl) 3 methyl- 5-.
pyrazolone, t ere is also obtained a very pure yellow dyeing, the silk fibre as well as the wool fibre belng dyed a tint of even shade and intensity.
. p (3) W'hen using the dyestufiz'm-aminobenzoic acid ethyl ester- 1-(4.-T-sulfo- However this aflinity is not sulficient to dye the silk fibre" esterfand operating thedyeingas, indicated .in Example 1: there are also obtained on the said'mate'rial very even tints.
The dyestufi' combinations specified in the foregoing examples are only to be regarded as representatives of the respective groups. They may, of course, be largely varied both in the diazo component and in the coupling I component.
Thus, for instance the pyrazolone compound mentioned in Examples'l and 3', may be replaced by the following combinations:
1) 1- (2- s'iilfophenyl) 5 pyrazolone 3- carboxylic acid ester.
(2) 1- (2'5-dichloro-4'-sulfophenyl) -5-pyrazolone-.3-carboxylic acid ester.
(3) l- (2'-chlor-5sul-fophenyl) -5-pyrazolone-3-carboxylic acid ester.
(4) 1- (2'-.methyl 6- chloro-' sulfophenyl)-5-pyrazolone-3-carboxylic acid ester.
(5) '1--(2- methyl 4fmethyl-5-sulfophenyl)-5-pyrazolone-3-carboxylic acid ester.
Furthermore in the. diazo component named in Example l the ortho-c'hloroaniline may for instance be replaced by: aniline, ortho-metaand ara-toluidine or the like.
However it is pre erable that the. diazo compounds do not contain any sulfo group, because ,inthis case the wool fibre is dyed more deeply thanthe silk fibre. In anycase, however, the dye'stulfs of this kind are distinguished from the analogous dyestuffs in which. the sulfotphenylpyrazolonecarboxylic acid is not esteri ed, by the property of dyeing the silk fibre in mixed material more deeply. W
For the pyrazolonesulfonic acid mentioned in Example 2 may be substituted any other sulfoaryl-3 methyl-5-pyrazolone but no sulfophenyl-5-pyrazolone-3-carboxylic acid.
In like manner, the diazo. compounds mentioned in Examples 2and 3 may be replaced by. any other aminoarylcarboxylic acid ester, for instance by 4-nitro-2-aminobenzoic acid methyl ester etc;
used to indicate the linkage of two components of an azod estufl'. Thus in the case of the dyestufi' o-c lor-anilinee 1- (4 sulfophenyl) -fi pyrazolone-ii-carboxylic ethyl ester the arrow indicates that fi-chlor-aniline has been diazotized and the diazo compound I It is to be understood that, in; the fore going description, the arrow ,is.
so formed has been coupled with the articular yrazolone compound stated. his use of tie arrow is described b Georgievics & Grandmougin, A Text-Boo of Dye Chemistry translated from the fourth German We claim; v
1. Process which comprises dyeing mlxed textile goods made of wool and sill: fibers with .a pyrezolone-ezodyestufi contain ng at least one carboxyl'ic acid ester group in the dyestufi' molecule, said pyrazolone-azo dye stufi conteining no free carboxylic acid edition by F. A. Mason, 1920, pages 87 and group linked to the carbon in the 3-position of the pyrazolone ring. w
2. As new products mixed wool and silk textile goods dyed with a pyrazolone-azo dyestufl containin at least one carboxylic acid ester group In the dyestuif molecule, said pyrazolone-azo, dyestufl containing no free carboxylic acid grou linked to the carbon in the 3-position of t e pyrazolone ring.
In testimony whereof, we aflix our signatures.
HERMANN WAGNER. HEINZ EICHWEDE. ERICH FISCHER;
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US1678611A true US1678611A (en) | 1928-07-24 |
Family
ID=3415676
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US1678611D Expired - Lifetime US1678611A (en) | Process of |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US1678611A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3033880A (en) * | 1959-06-01 | 1962-05-08 | Sandoz Ltd | Blue disperse dyestuffs of the anthraquinone series |
-
0
- US US1678611D patent/US1678611A/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3033880A (en) * | 1959-06-01 | 1962-05-08 | Sandoz Ltd | Blue disperse dyestuffs of the anthraquinone series |
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