US1824671A - Treatment of cotton and artificial silk - Google Patents
Treatment of cotton and artificial silk Download PDFInfo
- Publication number
- US1824671A US1824671A US248269A US24826928A US1824671A US 1824671 A US1824671 A US 1824671A US 248269 A US248269 A US 248269A US 24826928 A US24826928 A US 24826928A US 1824671 A US1824671 A US 1824671A
- Authority
- US
- United States
- Prior art keywords
- cotton
- fibres
- acid
- dyed
- parts
- 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
- 229920000742 Cotton Polymers 0.000 title description 12
- 229920002955 Art silk Polymers 0.000 title description 3
- 239000002253 acid Substances 0.000 description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- 239000003086 colorant Substances 0.000 description 12
- 238000000034 method Methods 0.000 description 11
- 239000003960 organic solvent Substances 0.000 description 8
- 238000009877 rendering Methods 0.000 description 7
- 229920003043 Cellulose fiber Polymers 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 150000007530 organic bases Chemical group 0.000 description 5
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- 229920000297 Rayon Polymers 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000004627 regenerated cellulose Substances 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000000020 Nitrocellulose Substances 0.000 description 2
- 150000001555 benzenes Chemical class 0.000 description 2
- VQLYBLABXAHUDN-UHFFFAOYSA-N bis(4-fluorophenyl)-methyl-(1,2,4-triazol-1-ylmethyl)silane;methyl n-(1h-benzimidazol-2-yl)carbamate Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1.C=1C=C(F)C=CC=1[Si](C=1C=CC(F)=CC=1)(C)CN1C=NC=N1 VQLYBLABXAHUDN-UHFFFAOYSA-N 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 229920001220 nitrocellulos Polymers 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- RXXCIBALSKQCAE-UHFFFAOYSA-N 3-methylbutoxymethylbenzene Chemical compound CC(C)CCOCC1=CC=CC=C1 RXXCIBALSKQCAE-UHFFFAOYSA-N 0.000 description 1
- IHZXTIBMKNSJCJ-UHFFFAOYSA-N 3-{[(4-{[4-(dimethylamino)phenyl](4-{ethyl[(3-sulfophenyl)methyl]amino}phenyl)methylidene}cyclohexa-2,5-dien-1-ylidene)(ethyl)azaniumyl]methyl}benzene-1-sulfonate Chemical compound C=1C=C(C(=C2C=CC(C=C2)=[N+](C)C)C=2C=CC(=CC=2)N(CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=CC=1N(CC)CC1=CC=CC(S(O)(=O)=O)=C1 IHZXTIBMKNSJCJ-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- -1 aromatic sulphonic acid chlorides Chemical class 0.000 description 1
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- FRYHCSODNHYDPU-UHFFFAOYSA-N ethanesulfonyl chloride Chemical compound CCS(Cl)(=O)=O FRYHCSODNHYDPU-UHFFFAOYSA-N 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000005517 mercerization Methods 0.000 description 1
- UWGCNDBLFSEBDW-UHFFFAOYSA-M sodium;4-[[4-(diethylamino)phenyl]-(4-diethylazaniumylidenecyclohexa-2,5-dien-1-ylidene)methyl]naphthalene-2,7-disulfonate Chemical compound [Na+].C1=CC(N(CC)CC)=CC=C1C(C=1C2=CC=C(C=C2C=C(C=1)S([O-])(=O)=O)S([O-])(=O)=O)=C1C=CC(=[N+](CC)CC)C=C1 UWGCNDBLFSEBDW-UHFFFAOYSA-M 0.000 description 1
- FTUYQIPAPWPHNC-UHFFFAOYSA-M sodium;4-[[4-[benzyl(ethyl)amino]phenyl]-[4-[benzyl(ethyl)azaniumylidene]cyclohexa-2,5-dien-1-ylidene]methyl]benzene-1,3-disulfonate Chemical compound [Na+].C=1C=C(C(=C2C=CC(C=C2)=[N+](CC)CC=2C=CC=CC=2)C=2C(=CC(=CC=2)S([O-])(=O)=O)S([O-])(=O)=O)C=CC=1N(CC)CC1=CC=CC=C1 FTUYQIPAPWPHNC-UHFFFAOYSA-M 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
- D06P5/22—Effecting variation of dye affinity on textile material by chemical means that react with the fibre
- D06P5/225—Aminalization of cellulose; introducing aminogroups into cellulose
Definitions
- the process can also be carried out by treating the above mentioned fibres with the products of reaction of the above mentioned acid halides with tertiary organic bases.
- the reaction may be carried out at lower or higher temperatures (for instance at 70 C. up to 110 0.).
- the new effect is very surprising.
- fibres may be obtained by the interaction of alkalized cotton and aromatic sulphonic acid chlorides, which are refractory against direct cotton dyes and-which.
- the duration of the interaction may also be diminished for instance to one hour and the pyridine may be replaced by a mixture of pyridine homologues, quinoline or triethylamine.
- Example 2 3.9 parts of mercerized cotton are heated at 110 C. for three hours with a mixture of 7.8 parts of p-toluene-sulphonic chloride, 10 parts of pyridine and 20 parts of nitrobenzene. The yarn then washed and dried shows the mercerization lustre unaltered and can easily be dyed with acid colors.
- the nitrobenzene can be replaced by another indifferent organic solvent having the desired dissolving properties, such as carbon tetrachloride for example.
- the reaction may also be carried out in presence of an indifferent organic solvent, such as nitrobenzene or carbon tetrachloride.
- an indifferent organic solvent such as nitrobenzene or carbon tetrachloride.
- a process for rendering cotton and regenerated cellulose fibres capable of being dyed byacid colors consisting in treating these fibres simultaneously with an aromatic sulphonic chloride and a tertiary .organic base.
- a process for rendering cotton and regenerated cellulose fibres capable of being dyed by acid colors consisting in treating these fibres simultaneously with an aromatic sulphonic chloride and a tertiary organic base in presence of an inert organic solvent. 7
- a process for rendering cotton and re-- generated cellulose fibres capable of being dyed by acid colors consisting in treating these fibres simultaneously with an aromatic sulphonic chloride of the benzene series and a tertiary organic base in presence of an inert organic solvent.
- a process for rendering cotton and regenerated cellulose fibres capable of being dyed by acid colors consisting in treating these fibres simultaneously with an aromatic sulphonic chloride of the benzene, series and a heterocyclic tertiary organic base in presence of an inert organic solvent.
- a process for rendering cotton and regenerated cellulose fibres capable of being dyed b acid colors consisting in treating these fi res simultaneously with an aromatic sulphonic chloride of the benzene series and.
- a process for rendering cotton and renerated cellulose fibres capable of being yed by acid colors consistlng in treating these fibres simultaneously with p-toluenesulphonic chloride and pyridine in presence of an inert organic solvent.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Description
Patented Sept. 22, 1931 UNITED STATES PATENT QFFICE PAUL KABRER, OF ZURICH, AND WALTER WEHRLI, OF BINNINGEN, NEAR BASEL, SWITZERLAND, ASSIGNORS TO THE FIRM OF CHEMICAL WORKS FORMERLY SA NDOZ,
OF BASEL, SWITZERLAND TREATMENT OF COTTON AND ARTIFICIAL SILK No Drawing. Application filed January 20, 1928, Serial No.248,269, and in Germany January 28, 1927.
It has been found, that if cotton or artificial silk fibres (viscose, cuproammonium and nitrocellulose silk) are simultaneously treated at elevated temperatures with a halide (chloride or bromide) of any of the aliphatic oraromatic sulphonic acids (for instance toluene-, benzene-, benzylor ethylsulphonic acid chloride) and a tertiary, alihatic, aromatic or heterocyclic organic ase, like triethylamine, dimethylaniline, pyridine, its homologues, quinoline and like substances, improved fibres can be obtained, which contrary to the original ones, show a good affinity for acid dyestuffs and yield fast shades. The process can also be carried out by treating the above mentioned fibres with the products of reaction of the above mentioned acid halides with tertiary organic bases. The reaction may be carried out at lower or higher temperatures (for instance at 70 C. up to 110 0.). The new effect is very surprising. According to the process of the United States Letters Patent No. 1,523,742, fibres may be obtained by the interaction of alkalized cotton and aromatic sulphonic acid chlorides, which are refractory against direct cotton dyes and-which.
are only dyedby certain acid colors, As against this the improved process allows to produce fibres which can be dyed by acid colors quite generally.
The following examples illustrate the improved process, the parts being by weight.
Example 1.3.7 parts of cotton are treated in a convenient closed vessel with 7.4 parts of benzene-sulphonic chloride and 40 parts of pyridine. The temperature is kept during one hour and a half at 110 C. The yarn is then washed with water and can be dyed after this treatment with acid colors in fast and level shades.
The duration of the interaction may also be diminished for instance to one hour and the pyridine may be replaced by a mixture of pyridine homologues, quinoline or triethylamine.
Example 2. 3.9 parts of mercerized cotton are heated at 110 C. for three hours with a mixture of 7.8 parts of p-toluene-sulphonic chloride, 10 parts of pyridine and 20 parts of nitrobenzene. The yarn then washed and dried shows the mercerization lustre unaltered and can easily be dyed with acid colors. In this example, the nitrobenzene can be replaced by another indifferent organic solvent having the desired dissolving properties, such as carbon tetrachloride for example.
Ewample 3.5.7 parts of viscose silk (or ammoniumcuproxide silk or nitrocellulose silk) are immersed into a mixture of 11 parts of p-toluene-sulphonic chloride and 35 parts of pyridine. The yarn is then kept a quarter of an hour at ordinary temperature and the mixture is then heated at 110 C. for half an hour. The washed and dried viscose silk thus treated returns its lustre fully, but contrary to the untreated fibre,
it can be dyed with acid colors of any kind,
such as for example lanafuchsine 6B (color index No. 54), acid violet GBS (color index No. 717), patent blue A (color index No. 714) and naphthalene green V (color index No. 735), in level and fast shades. In this example, the reaction may also be carried out in presence of an indifferent organic solvent, such as nitrobenzene or carbon tetrachloride. Furthermore the fibres as well as the reacting compounds are advantageously water-free.
at we claim is:
1. A process for rendering cotton and regenerated cellulose fibres capable of being dyed byacid colors, consisting in treating these fibres simultaneously with an aromatic sulphonic chloride and a tertiary .organic base.
2. A process for rendering cotton and regenerated cellulose fibres capable of being dyed by acid colors, consisting in treating these fibres simultaneously with an aromatic sulphonic chloride and a tertiary organic base in presence of an inert organic solvent. 7
3. A process for rendering cotton and re-- generated cellulose fibres capable of being dyed by acid colors, consisting in treating these fibres simultaneously with an aromatic sulphonic chloride of the benzene series and a tertiary organic base in presence of an inert organic solvent.
4. A process for rendering cotton and regenerated cellulose fibres capable of being dyed by acid colors, consisting in treating these fibres simultaneously with an aromatic sulphonic chloride of the benzene, series and a heterocyclic tertiary organic base in presence of an inert organic solvent.
5. A process for rendering cotton and regenerated cellulose fibres capable of being dyed b acid colors, consisting in treating these fi res simultaneously with an aromatic sulphonic chloride of the benzene series and.
15. pyridine in presence of an inert organic solvent.
6. A process for rendering cotton and renerated cellulose fibres capable of being yed by acid colors, consistlng in treating these fibres simultaneously with p-toluenesulphonic chloride and pyridine in presence of an inert organic solvent.
7 A process for rendering viscose silk capable of being dyed by acid colors, consisting in treating these fibres simultaneously with p-toluenesulphonic chloride and pyridine in presence of an inert organic solvent.
In witness whereof we have hereunto signed our names this 5th day of January,
PAUL KARRER. WALTER WEHRLI.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE1824671X | 1927-01-28 |
Publications (1)
Publication Number | Publication Date |
---|---|
US1824671A true US1824671A (en) | 1931-09-22 |
Family
ID=7744886
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US248269A Expired - Lifetime US1824671A (en) | 1927-01-28 | 1928-01-20 | Treatment of cotton and artificial silk |
Country Status (1)
Country | Link |
---|---|
US (1) | US1824671A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2990234A (en) * | 1959-03-13 | 1961-06-27 | Klein Elias | Production of strong, rot-resistant benzyl cellulose fibers |
-
1928
- 1928-01-20 US US248269A patent/US1824671A/en not_active Expired - Lifetime
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2990234A (en) * | 1959-03-13 | 1961-06-27 | Klein Elias | Production of strong, rot-resistant benzyl cellulose fibers |
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