US1853501A - Uniform dyeing of viscose - Google Patents
Uniform dyeing of viscose Download PDFInfo
- Publication number
- US1853501A US1853501A US338891A US33889129A US1853501A US 1853501 A US1853501 A US 1853501A US 338891 A US338891 A US 338891A US 33889129 A US33889129 A US 33889129A US 1853501 A US1853501 A US 1853501A
- Authority
- US
- United States
- Prior art keywords
- viscose
- acid
- dyeing
- nitraniline
- sulfonic acid
- 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
- 229920000297 Rayon Polymers 0.000 title description 17
- 238000004043 dyeing Methods 0.000 title description 12
- 239000002253 acid Substances 0.000 description 16
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 7
- 230000008878 coupling Effects 0.000 description 7
- 238000010168 coupling process Methods 0.000 description 7
- 238000005859 coupling reaction Methods 0.000 description 7
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 6
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 6
- 239000000975 dye Substances 0.000 description 6
- 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 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 4
- 150000008049 diazo compounds Chemical class 0.000 description 4
- 230000005404 monopole Effects 0.000 description 4
- 239000000344 soap Substances 0.000 description 4
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 150000001555 benzenes Chemical class 0.000 description 3
- 229950011260 betanaphthol Drugs 0.000 description 3
- 239000003638 chemical reducing agent Substances 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000010446 mirabilite Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- 125000005337 azoxy group Chemical group [N+]([O-])(=N*)* 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- ZMCHBSMFKQYNKA-UHFFFAOYSA-N 2-aminobenzenesulfonic acid Chemical compound NC1=CC=CC=C1S(O)(=O)=O ZMCHBSMFKQYNKA-UHFFFAOYSA-N 0.000 description 1
- QWUXRYXQSXFJFZ-UHFFFAOYSA-N 3-(2-methylpropyl)naphthalene-1,2-disulfonic acid Chemical compound C1=CC=C2C(S(O)(=O)=O)=C(S(O)(=O)=O)C(CC(C)C)=CC2=C1 QWUXRYXQSXFJFZ-UHFFFAOYSA-N 0.000 description 1
- 229920002955 Art silk Polymers 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000001035 methylating effect Effects 0.000 description 1
- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical compound C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- STZCRXQWRGQSJD-UHFFFAOYSA-M sodium;4-[[4-(dimethylamino)phenyl]diazenyl]benzenesulfonate Chemical compound [Na+].C1=CC(N(C)C)=CC=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 STZCRXQWRGQSJD-UHFFFAOYSA-M 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
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
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/08—Preparation of azo dyes from other azo compounds by reduction
- C09B43/10—Preparation of azo dyes from other azo compounds by reduction with formation of a new azo or an azoxy bridge
-
- 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
-
- 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
- the present invention relates to the uniform dyeing of viscose silk of different origin.
- R stands for the residue of any coupling component and R stands for a benzene nucleus which may be substituted by a sulphonic or 'carboxylic acid group, to which the azo group is attached in meta or para position to m, and m' stands for an azo or azoxy group.
- the dyestuffs used for the purpose of my invention are obtainable by the combination of tetrazo compounds of mand p-azoxyaniline and substitution products thereof with any desired coupling components, or by couplin g the diazo compounds of 3- and ii-nitroaniline or substitution products thereof with any desired component and subsequent reduction of the resulting monoazo dyestuffs with alkaline reducing agents, for example, grape sugar in alkaline solution, to the disazo-azoxy dyestuffs or trisazo dyestuffs.
- the dyeing is carried out in the usual man nor as outlined in the examples, by dissolving the dyestuffs in hot water and adding to the dye-bath Glaubers salt and monopol soap (a water soluble salt of sulfonated castor oil) if desired with the addition of a wetting agent, f. i. an. alkyl-naphthalene-sulfonio acid, such as isobutyl-naphthalene-disulfonic acid.
- a wetting agent f. i. an. alkyl-naphthalene-sulfonio acid, such as isobutyl-naphthalene-disulfonic acid.
- the viscose is introduced into the bath at about 30 G., then the bath is slowly heated to about 80 (3., at which temperature the viscose is dyed for about 4 to 1 hour. Then the viscose is washed and dried.
- the dyeings thus obtained are distinguished by their uniformity.
- Emample 1.-10 kgs. of knitted viscose are dyed in 300 liters of water. are added 200 gms. of the dyestuff, obtained by coupling the diazo compound of 4-nitraniline-2-sulfonic acid with 2-naphthylaminesulfonic acid and linking two molecules of the resulting monoazo dyestuff by treatment with alkaline reducing agents; 200 gms. of monopol soap (a water soluble salt of sulfonated castor oil and 2 kgs. of Glaubers salt are added. yeing is effected for one hour at about 80 C. and is followed by rinsing" and drying. The fabric is dyed uniformly a reddish blue shade.
- Example 2 The dye-bath is prepared with 200 gms. of the dyestuif, obtained by coupling the diazo compound of 3-nitraniline with 2-naphthol-S-monosulfonic acid and linking two molecules of the resulting monoazo dyestuff by treatment with alkaline reducing agents, in 300 liters of water. 10 kgs. of knitted viscose are introduced into the dye-bath, which is then heated, 200 gms. of monopole soap and 2 kgs. of Glaubers salt are added, and the dyeing is completed within an hour at about 80 C. The fabric is dyed a uniform orange.
- Example '3.10kgs. of knitted viscose are dyed in 300 liters of water.
- To the dye-bath are added 200 gms. of the dyestuif, obtained by coupling the diazo compound of 4-nitraniline-Q-sulfonic acid with phenol, methylating the hydroxy group of the monoazo dyestuff and linking two molecules of the resulting monoazo dyestufi' by treatment with grape sugar in alkaline solution to the corresponding disazo-azoxy dyestufl, having probable the formula:
- R stands for the residue of any coupling component
- B stands for a benzene nucleus which may be substituted by a sulfonic or carboxyhcacid group and which benzene nucleus is in one of the positions consisting of the para and meta positions to m
- :1: stands for one of the groupings consisting of the azoand azoxy-groups.
- I 801R o cn,o-O ONQNON NOO on.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Patented Apr. 12, 1932 UNITED STATES PATENT OFFICE ANILINE WORKS, INC.,. OF NEW YORK,
N. Y., A CORPORATION OF DELAWARE UNIFORM DYEING OF VISGOSE The present invention relates to the uniform dyeing of viscose silk of different origin.
It is known that it is very difficult to obtain even shades in the dyeing of viscose of different origin, for example of knitted artifi cial silk.
According to the present invention these difliculties are overcome by dyeing viscose with azo dyestuffs of the general formula:
wherein R stands for the residue of any coupling component and R stands for a benzene nucleus which may be substituted by a sulphonic or 'carboxylic acid group, to which the azo group is attached in meta or para position to m, and m' stands for an azo or azoxy group.
The dyestuffs used for the purpose of my invention are obtainable by the combination of tetrazo compounds of mand p-azoxyaniline and substitution products thereof with any desired coupling components, or by couplin g the diazo compounds of 3- and ii-nitroaniline or substitution products thereof with any desired component and subsequent reduction of the resulting monoazo dyestuffs with alkaline reducing agents, for example, grape sugar in alkaline solution, to the disazo-azoxy dyestuffs or trisazo dyestuffs.
The dyeing is carried out in the usual man nor as outlined in the examples, by dissolving the dyestuffs in hot water and adding to the dye-bath Glaubers salt and monopol soap (a water soluble salt of sulfonated castor oil) if desired with the addition of a wetting agent, f. i. an. alkyl-naphthalene-sulfonio acid, such as isobutyl-naphthalene-disulfonic acid. The viscose is introduced into the bath at about 30 G., then the bath is slowly heated to about 80 (3., at which temperature the viscose is dyed for about 4 to 1 hour. Then the viscose is washed and dried.
The dyeings thus obtained are distinguished by their uniformity.
No Drawing. Application filed February 9, 1929, Serial No. 338,891, and in Germany February 17, 19 28.
The invention is illustrated by the following examples, without being limited thereto:
Emample 1.-10 kgs. of knitted viscose are dyed in 300 liters of water. are added 200 gms. of the dyestuff, obtained by coupling the diazo compound of 4-nitraniline-2-sulfonic acid with 2-naphthylaminesulfonic acid and linking two molecules of the resulting monoazo dyestuff by treatment with alkaline reducing agents; 200 gms. of monopol soap (a water soluble salt of sulfonated castor oil and 2 kgs. of Glaubers salt are added. yeing is effected for one hour at about 80 C. and is followed by rinsing" and drying. The fabric is dyed uniformly a reddish blue shade.
Example 2.The dye-bath is prepared with 200 gms. of the dyestuif, obtained by coupling the diazo compound of 3-nitraniline with 2-naphthol-S-monosulfonic acid and linking two molecules of the resulting monoazo dyestuff by treatment with alkaline reducing agents, in 300 liters of water. 10 kgs. of knitted viscose are introduced into the dye-bath, which is then heated, 200 gms. of monopole soap and 2 kgs. of Glaubers salt are added, and the dyeing is completed within an hour at about 80 C. The fabric is dyed a uniform orange.
Example '3.10kgs. of knitted viscose are dyed in 300 liters of water. To the dye-bath are added 200 gms. of the dyestuif, obtained by coupling the diazo compound of 4-nitraniline-Q-sulfonic acid with phenol, methylating the hydroxy group of the monoazo dyestuff and linking two molecules of the resulting monoazo dyestufi' by treatment with grape sugar in alkaline solution to the corresponding disazo-azoxy dyestufl, having probable the formula:
SOaH SOaH 200 gms. of monopol soap and 2 kgs. of Glaubers' salt are added. Dyeing-is efl'ected for one hour at about 80 C. and is followed by rinsing and drying. The fabric is dyed uniformly a gold orange shade.
To the dye-bath 4 i n1tranlline+2.5 gminonaphthol 4 nitranil ne+2.8 aininonaphthol Disazoazoxy compound or trisazo dyestuff from the monoazo dyestui! Dyes uniformly 4 nitraniline --2 sulfonic acid+1 Reddish blue naphthyl-- amine 4 sulfonic acid.
4 nitmniline 2 'sulfonic acid +2 Reddish blue na hthyl amine 6- sulfonicacld.
4 n traniline 2 sulfonic acid 1 Bordeaux naphtholi-sulfonic acid.
4 mtraniline 2 suitonic acid 2 Wi d na hthoi-7-sulfonic acid.
4 n tr'aniline 2 sulfonic acid 2 Blue methyiamino naphthaline 7 sultonic acid.;-
4 nitraniline+2 naphthol 3:7 R ddish blue disulfonic acid.
4 nitraniline+2 naphthol 6.8 Violet disuifonic acid.
4 nitraniline 2 naphthol 8 mono- Wine red sulfonic acid.
3 nitraniline+1 naphthylamine Orange 4.7-disulfonic acid.
8 nitraniline 1 naphthol 3.6 di- 'sulfonic acid.
4 nitraniline 2 aulfonic acid +pyrazolone from dehydrothiotoluidinemonosulfonic acid.
4 nitmniline 2 carboxylic acid pyrazclone from dehydrothiotoiuidinemonosulfonic acid.
4 nitraniline 1.8 dihydroxy naphthaline 4 sultonic acid.
Beddish orange.
Orange Orange Violet Bordeaux Blue 7 disulfonic ac 4 nitrani1ine 2 sultonic acid+ 2.5 aminonaphthoi- 7 sulfonic acid (acid cou ling). 1
3.6 disulfonic acid -(acid coupling).
I claim: 1.-The
which comprises dyeing the viscose in the customarymanner with a dyestufi of the general formula:
wherein R stands for the residue of any coupling component, B." stands for a benzene nucleus which may be substituted by a sulfonic or carboxyhcacid group and which benzene nucleus is in one of the positions consisting of the para and meta positions to m, and :1: stands for one of the groupings consisting of the azoand azoxy-groups.
2. The process for the uniform dyeing of viscose of various origin, which comprises dyeing the viscose in the customary manner process for the uniform dyeing of viscose of various ongi' '11,
attached to the azo group which comprises 4. As new products of manufacture knitted viscose dyed with a dyestufi' as claimed in claim 1.
5. As new products of manufacture knitted viscose dyed with a dyestufi as claimed in claim 2.
6. As new products of manufacture knitted viscose dyed with the dyestufl' claimed in claim 3.
In testimony my hand,
z 'KARL BORMANN. [n 8.]
whereof I have hereunto set sou: I 801R o cn,o-O on.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1853501X | 1928-02-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US1853501A true US1853501A (en) | 1932-04-12 |
Family
ID=7746104
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US338891A Expired - Lifetime US1853501A (en) | 1928-02-17 | 1929-02-09 | Uniform dyeing of viscose |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US1853501A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2466245A (en) * | 1944-06-27 | 1949-04-05 | Geigy Ag J R | Azo-azoxy dyes |
| US4591634A (en) * | 1980-06-12 | 1986-05-27 | Bayer Aktiengesellschaft | Trisazo/azoxy dyestuff mixtures |
-
1929
- 1929-02-09 US US338891A patent/US1853501A/en not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2466245A (en) * | 1944-06-27 | 1949-04-05 | Geigy Ag J R | Azo-azoxy dyes |
| US4591634A (en) * | 1980-06-12 | 1986-05-27 | Bayer Aktiengesellschaft | Trisazo/azoxy dyestuff mixtures |
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