US2218924A - Aftertreatment of dyed textile fibers - Google Patents
Aftertreatment of dyed textile fibers Download PDFInfo
- Publication number
- US2218924A US2218924A US254010A US25401039A US2218924A US 2218924 A US2218924 A US 2218924A US 254010 A US254010 A US 254010A US 25401039 A US25401039 A US 25401039A US 2218924 A US2218924 A US 2218924A
- Authority
- US
- United States
- Prior art keywords
- compound
- dyed
- textile fibers
- dyeings
- aftertreatment
- 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
- 239000000835 fiber Substances 0.000 title description 15
- 239000004753 textile Substances 0.000 title description 8
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 16
- 238000004043 dyeing Methods 0.000 description 14
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 14
- 239000002253 acid Substances 0.000 description 13
- 150000001875 compounds Chemical class 0.000 description 10
- 238000000034 method Methods 0.000 description 9
- 150000003839 salts Chemical class 0.000 description 9
- 229940123208 Biguanide Drugs 0.000 description 8
- 150000004283 biguanides Chemical class 0.000 description 7
- 239000005749 Copper compound Substances 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 150000001880 copper compounds Chemical class 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 5
- 150000002736 metal compounds Chemical class 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- -1 metal complex compounds Chemical class 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- XRPLBRIHZGVJIC-UHFFFAOYSA-L chembl3182776 Chemical compound [Na+].[Na+].NC1=CC(N)=CC=C1N=NC1=CC=C(C=2C=CC(=CC=2)N=NC=2C(=CC3=CC(=C(N=NC=4C=CC=CC=4)C(O)=C3C=2N)S([O-])(=O)=O)S([O-])(=O)=O)C=C1 XRPLBRIHZGVJIC-UHFFFAOYSA-L 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- ZILVNHNSYBNLSZ-UHFFFAOYSA-N 2-(diaminomethylideneamino)guanidine Chemical compound NC(N)=NNC(N)=N ZILVNHNSYBNLSZ-UHFFFAOYSA-N 0.000 description 1
- XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- IQFVPQOLBLOTPF-HKXUKFGYSA-L congo red Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(/N=N/C3=CC=C(C=C3)C3=CC=C(C=C3)/N=N/C3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)N)=CC(S([O-])(=O)=O)=C21 IQFVPQOLBLOTPF-HKXUKFGYSA-L 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 229910000366 copper(II) sulfate Inorganic materials 0.000 description 1
- 229940045803 cuprous chloride Drugs 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 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
- 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
- D06P1/44—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 insoluble pigments or auxiliary substances, e.g. binders
- D06P1/64—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 insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
- D06P1/642—Compounds containing nitrogen
- D06P1/649—Compounds containing carbonamide, thiocarbonamide or guanyl groups
- D06P1/6495—Compounds containing carbonamide -RCON= (R=H or hydrocarbons)
-
- 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
- D06P5/02—After-treatment
- D06P5/10—After-treatment with compounds containing metal
Definitions
- dyeings 'of organic dyestufis can be improved by causing the said dyestufis to interact on the dyed material with organic bases like amines, quaternary ammonium compounds or soluble salts thereof.
- organic bases like amines, quaternary ammonium compounds or soluble salts thereof.
- the said treatment has been carried out either by aftertreating the dyed material or by pretreating the material and thereafter dyeing it with direct or acid dyestuffs.
- metal complex compounds to be used according to our invention we may men- 40 tion the metal complex compounds of biguanide or guanidino guanidine, of substituted biguanides and of thiourea.
- the metals suitable for preparing the compounds to be used according to .our invention are of the type which easily forms 5 complex compounds with organic bases, for instance, chromium, iron and especially copper.
- the process of our invention may be carried out by aftertreating the dyed fibers with an, aqueous solution of one of the said complex metal 50 compounds;. if desired, the solution may be weakly acid or alkaline.
- the process forming of the metal complex compound and aftertreating of the dyeing is performed in one and the same bath.
- Our invention will be apparent in more detail from the fol- Divided and this applicalowing examples without, however, being limited thereto.
- Example 1 Cotton yarn is dyed in the usual manner with 6% of Direct Deep Black EW extra (comp. 001. Ind. 1st edition, No. 581) washed and aftertreated with an aqueous solution of the sulfate of 1.1'- dimethyl-biguanide-copper at 30 C. for half an hour, again washed and dried.
- the sulfate of 1-1'-dimethyl-biguanide-copper is obtainable by causing cupric sulfate, an aqueous solution prepared from dimethylamine and dicyanidiamide to react together at an elevated temperature and under superatmospheric pressure.
- the substance is soluble in water on adding sodium chloride or another neutral salt, if
- Example 2 On aftertreating dyeings on cotton of Direct Deep Black EW extra in the usual manner with the solution of the complex salt prepared from 1 mol cuprous chloride and 3 mols thiourea, the fastness to water and to light increases.
- the modification which comprises causing the dyed fibers to interact with a complex copper compound of a compound of the urea group being selected from the group consisting of thiourea and the biguanides, which copper compound is capable of forming salts with acids.
- Textile fibers dyed with organic dyestuffs containing free acid groups said dyed fibers being. combined with a complex metal compound of a compound of the urea group being selected from the group consisting of thiourea and the biguanides, which metal compound is capable of forming salts with acids.
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
Description
Patented Oct. 22, 1940 UNITED s'mrizs PATENT OFFICE AFTERTREATMIENT F DYED TEXTILE FIBERS Siegfried Petersen, Cologne-Mulheim, and Otto Bayer and Carl Taube, Lcverkusen-I. G.-Werk,
Germany, assignors to General Aniline & Film Serial No. 143,726.
tion February 1, 1939, Serial No. 254,010.
Germany May 30, 1936 Claims.
The present invention relates to a process of improving dyeings on textile fibers and similar material. This is a division of our copending application Ser. No. 143,726, filed May 20, 1937, Patent No. 2,190,848, February 20, 1940.
It is known that in many cases dyeings 'of organic dyestufis, especially such as contain free carboxylic or sulfonic acid groups, can be improved by causing the said dyestufis to interact on the dyed material with organic bases like amines, quaternary ammonium compounds or soluble salts thereof. By such processes the dyestufis are more solidly fixed on the dyed material so that the dyeings will be of better fastness to water, to washing and the like. The said treatment has been carried out either by aftertreating the dyed material or by pretreating the material and thereafter dyeing it with direct or acid dyestuffs. 9
We have now found that still better results are obtained by employing for the said purpose a compound of the urea group being selected from the group consisting of thiourea and the biguanides which compound has combined therewith a metal in complex form but is still capable of forming salts with acids. By our new process,
for instance, in many cases the fastness of the 'dyeings to water will be materially increased whilst in these and other cases the treated dyeings will be much faster to the action of light.
The process of our invention has proved to be especially suitable for improving dyeings of substantive dyestufis on cellulosic textile fibers like cotton or artificial'silk from regenerated cellulose.
These and other objects and results of our in-- vention will be more fully illustrated by the following description thereof.
As examples of metal complex compounds to be used according to our invention we may men- 40 tion the metal complex compounds of biguanide or guanidino guanidine, of substituted biguanides and of thiourea. The metals suitable for preparing the compounds to be used according to .our invention are of the type which easily forms 5 complex compounds with organic bases, for instance, chromium, iron and especially copper.
The process of our invention may be carried out by aftertreating the dyed fibers with an, aqueous solution of one of the said complex metal 50 compounds;. if desired, the solution may be weakly acid or alkaline. In another modification of our process forming of the metal complex compound and aftertreating of the dyeing is performed in one and the same bath. Our invention will be apparent in more detail from the fol- Divided and this applicalowing examples without, however, being limited thereto.
Example 1 Cotton yarn is dyed in the usual manner with 6% of Direct Deep Black EW extra (comp. 001. Ind. 1st edition, No. 581) washed and aftertreated with an aqueous solution of the sulfate of 1.1'- dimethyl-biguanide-copper at 30 C. for half an hour, again washed and dried.
The fastness to water and to washing of the dyeings thus treated are,.in comparison with the non-treated dyeings, essentially improved.
, If a 2% dyeing of Congo Red (comp; Col. Ind., No. 370)" is treated in the same manner, the shade becomes somewhat bluer and the fastness to water and to washing is at the sametime increased. The aftertreatment'can also be performed in a warm bath.
The sulfate of 1-1'-dimethyl-biguanide-copper is obtainable by causing cupric sulfate, an aqueous solution prepared from dimethylamine and dicyanidiamide to react together at an elevated temperature and under superatmospheric pressure. The substance is soluble in water on adding sodium chloride or another neutral salt, if
necessary with the addition of a small quantity of sodium carbonate.
Example 2 Example 3 On aftertreating dyeings on cotton of Direct Deep Black EW extra in the usual manner with the solution of the complex salt prepared from 1 mol cuprous chloride and 3 mols thiourea, the fastness to water and to light increases.
We claim:
1. In the process of improving dyemgs of organic dyestufis containing free acid groups on textile fibers the modification which comprises causing the dyed fibers to interact with a complex metal compound of a compound of the urea group being selected from the group consisting of thiourea and the biguanides, which metal compound is capable of forming salts with acids.
2. In the process of improving dyeings of or-' ganic dyestuiis containing free acid groups on textile fibers the modification which comprises causing the dyed fibers to interact with a complex copper compound of a. compound of the urea group being selected from the group consisting of thiourea and the biguanides, which copper compound is capable of forming salts with acids.
3. In the process of improving dyeings of organic dyestuffs containing free acid groups on cellulosic fibers the modification which comprises causing the dyed fibers to interact with a complex copper compound of a compound of the urea group being selected from the group consisting of thiourea and the biguanides, which copper compound is capable of forming salts with acids.
4. Textile fibers dyed with organic dyestuffs containing free acid groups, said dyed fibers being. combined with a complex metal compound of a compound of the urea group being selected from the group consisting of thiourea and the biguanides, which metal compound is capable of forming salts with acids.
5. Cellulosic textile fibers dyed with organic dyestuffs containing free acid groups, said dyed fibers being combined with a complex copper compound of a compound of the urea group being selected from the group consisting of thiourea and the biguanides, which copper compound is capable of forming salts with acids.
SIEGFRIE'D PETERSEN. OTTO BAYER. I CARL TAUBE.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US254010A US2218924A (en) | 1937-05-20 | 1939-02-01 | Aftertreatment of dyed textile fibers |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US143726A US2190848A (en) | 1936-05-31 | 1937-05-20 | Dyeings |
| US254010A US2218924A (en) | 1937-05-20 | 1939-02-01 | Aftertreatment of dyed textile fibers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2218924A true US2218924A (en) | 1940-10-22 |
Family
ID=26841339
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US254010A Expired - Lifetime US2218924A (en) | 1937-05-20 | 1939-02-01 | Aftertreatment of dyed textile fibers |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2218924A (en) |
-
1939
- 1939-02-01 US US254010A patent/US2218924A/en not_active Expired - Lifetime
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