US2138457A - Process fob improving the fastness - Google Patents
Process fob improving the fastness Download PDFInfo
- Publication number
- US2138457A US2138457A US2138457DA US2138457A US 2138457 A US2138457 A US 2138457A US 2138457D A US2138457D A US 2138457DA US 2138457 A US2138457 A US 2138457A
- Authority
- US
- United States
- Prior art keywords
- fastness
- improving
- dyeings
- parts
- water
- 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 12
- 239000000047 product Substances 0.000 description 20
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 239000000463 material Substances 0.000 description 12
- 239000002585 base Substances 0.000 description 10
- 229920002678 cellulose Polymers 0.000 description 10
- 239000001913 cellulose Substances 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 238000005406 washing Methods 0.000 description 8
- CSVFWMMPUJDVKH-UHFFFAOYSA-N 1,1-dichloropropan-2-one Chemical compound CC(=O)C(Cl)Cl CSVFWMMPUJDVKH-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 238000004043 dyeing Methods 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 150000002829 nitrogen Chemical group 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 6
- 229940044174 4-phenylenediamine Drugs 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N Chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 4
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N Dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 4
- CBCKQZAAMUWICA-UHFFFAOYSA-N P-Phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- QQUIOPPOYYOSSQ-UHFFFAOYSA-N 1-chlorochloranuidylpentadecane Chemical compound CCCCCCCCCCCCCCC[Cl-]Cl QQUIOPPOYYOSSQ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-O Pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000004432 carbon atoms Chemical group C* 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 125000000853 cresyl group Chemical class C1(=CC=C(C=C1)C)* 0.000 description 2
- 230000002349 favourable Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 230000001376 precipitating Effects 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 239000001187 sodium carbonate Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 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
- 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
-
- 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
- Our present invention relates to a process for improving the fastness of dyeings which have been prepared on cellulose materials by means of substantive dyestufis.
- Such bases are capable of improving the fastness to water and to cross dyeings and-as far as they contain pentavalent nitrogen-to perspiration, but they can not substantially improve the fastness to washing which is of considerably more importance.
- Our present invention has for its object the after-treatment of such dyeings with solutions containing products containing a pyridine radicle the ring nitrogen atom of which is converted into the pentavalent state, and a member of the group consisting of a radicle of dichloro-diacetyl-L4- phenylenediamine and of symmetrical dichloroacetone.
- the favorable effect of the present compounds is obtained by the fact that they do not contain a long aliphatic chain and that therefore their reaction products with dyestuif acids are insoluble not only in water but also in solutions of soaps.
- they contain the nitrogen atom of basic character in the highest valency the fact is obtained that the salts of these compounds with the dyestufl-acids of the used substantive dyestuffs are not decomposed by the alkali used for washing the dyeings.
- Example 1 54 parts of 1.4-phenylenediamine are dissolved in 500 parts of water. Then parts of sodium carbonate are added and 120 parts of chloracetyl chloride are slowly poured in at about 0 to 5 C. The precipitate formed which is the dichlorodlacetyl-1.4- phenylene-diamine of the following formula:
- Example 2 parts of 2.6-diaminopyridine (see German Patent No. 399,902) and 46 parts of symmetrical dichloro-acetone are dissolved in chloro-benzene and the solution obtained is heated tountil the precipitation is finished.
- the precipitate formed is washed withchlorobenzene and the hydrochloride of the base thus obtained is dissolved in water.
- the solution obtained is treated with 400 parts of dimethyl sulfate in the presence of an excess of alkali at room temperature until the dimethyl sulfate is decomposed.
- the new base exhibits a similar effect to dye. ings obtained by means of substantive dyestuffs as the above described product.
- Example 3 A dyeing obtained on cotton with 3% of Brillantbenzoviolett BBH (Schultz, Farbstofitabellen, 7th edition, supplement vol. I, page 73) is treated for half an hour at 30 with a solution of 1 gr. per liter of a pyridinium base (described in the German Patent No. 551,872, Example 4) of a resin which is obtained by starting from a technical cresol mixture and by acting thereupon with formaldehyde inthe presence of hydrochloric acid.
- Brillantbenzoviolett BBH Schotz, Farbstofitabellen, 7th edition, supplement vol. I, page 73
- the dyeing thus treated exhibits a considerably increased fastness to washing.
Description
Patented Nov. 29, 1938 UNITED STATES PATENT OFFICE PROCESS FOR IMPROVING THE FASTNESS OF DYEINGS No; Drawing. Original application March 27, 1936, Serial No. 71,172. Divided and this-application September 24, 1937, Serial No. 165,482. In Germany April 3, 1935 3 Claims.
The present application is a division of our application Serial No. 71,172, filed March 27, 1936 relating to Expedients useful for improving the fastness of dyeings.
Our present invention relates to a process for improving the fastness of dyeings which have been prepared on cellulose materials by means of substantive dyestufis.
It is well known that dyeings obtained on cellulose materials by means of substantive dyestuffs can be improved as regardsu-fastness by treatment with salts of certain organic bases. A great number of such bases has already been proposed for this purpose. Most of them are characterized by the fact that they contain in the molecule a long aliphatic carbon chain of at least 7 carbon atoms.
Such bases are capable of improving the fastness to water and to cross dyeings and-as far as they contain pentavalent nitrogen-to perspiration, but they can not substantially improve the fastness to washing which is of considerably more importance.
Our present invention has for its object the after-treatment of such dyeings with solutions containing products containing a pyridine radicle the ring nitrogen atom of which is converted into the pentavalent state, and a member of the group consisting of a radicle of dichloro-diacetyl-L4- phenylenediamine and of symmetrical dichloroacetone.
The favorable effect of the present compounds is obtained by the fact that they do not contain a long aliphatic chain and that therefore their reaction products with dyestuif acids are insoluble not only in water but also in solutions of soaps. By the fact that they contain the nitrogen atom of basic character in the highest valency the fact is obtained that the salts of these compounds with the dyestufl-acids of the used substantive dyestuffs are not decomposed by the alkali used for washing the dyeings.
In order to further illustrate our invention the following examples are given, the parts being by weight and all temperatures in degrees centigrade. We wish it, however, to be understood that our invention is not limited to the particular products nor reaction conditions mentioned therein.
Example 1 54 parts of 1.4-phenylenediamine are dissolved in 500 parts of water. Then parts of sodium carbonate are added and 120 parts of chloracetyl chloride are slowly poured in at about 0 to 5 C. The precipitate formed which is the dichlorodlacetyl-1.4- phenylene-diamine of the following formula:
NH-OOCHPCl NELCOC Hz-Cl is washed with cold and hot water and alcohol.
50 parts thereof are mixed with 100 parts of pyridine and the mixture is heated to about 100 for 20 hours. The precipitate formed is washed with alcohol and dried. It may be freed from unaltered initial material by redissolving in water, filtering the solution thus obtained and precipitating it by the addition of sodium chloride or alcohol. A dyeing obtained on cotton by means of 3% of Sirius blue BR (Schultz, Farbstofftabellen, 7th edition, vol. 2, page 197) which is aftertreated for half an hour at about 30' with a solution containing 2 grs. of the above product per liter exhibits a very good fastness to washing. The new product is when dry a light brown powder easily soluble in water and insoluble in alcohol.
Example 2 parts of 2.6-diaminopyridine (see German Patent No. 399,902) and 46 parts of symmetrical dichloro-acetone are dissolved in chloro-benzene and the solution obtained is heated tountil the precipitation is finished. The precipitate formed is washed withchlorobenzene and the hydrochloride of the base thus obtained is dissolved in water. The solution obtained is treated with 400 parts of dimethyl sulfate in the presence of an excess of alkali at room temperature until the dimethyl sulfate is decomposed.
The new base exhibits a similar effect to dye. ings obtained by means of substantive dyestuffs as the above described product.
Example 3 A dyeing obtained on cotton with 3% of Brillantbenzoviolett BBH (Schultz, Farbstofitabellen, 7th edition, supplement vol. I, page 73) is treated for half an hour at 30 with a solution of 1 gr. per liter of a pyridinium base (described in the German Patent No. 551,872, Example 4) of a resin which is obtained by starting from a technical cresol mixture and by acting thereupon with formaldehyde inthe presence of hydrochloric acid.
The dyeing thus treated exhibits a considerably increased fastness to washing.
We claim:
1. Process for improving the tastness oi dyeings which have been prepared on cellulose materials by means of substantive dyestuffs by ai'tertreating them with solutions containing products containing a pyridine radicle the ring nitrogen atom of .which is converted into the pentavalent state, said products being obtained by the action 01 pyridine on a member 01' the group consisting of dichloro-diacetyl-1.4-pheny1enediamine and symmetrical dichioroacetone.
2. Process for improving the tastness of dyeings which have been prepared on cellulose materials by means of substantive dyestuffs by aftertreating them with solutions containing a product obtained by the action of pyridine on dichlorodiacetyl-1.4-pheny1enediamine of the formula:
mr-ooom-m NH-COCHr-Cl which product is when dry 9, light brown powder easily soluble in water and insoluble in alcohol.
3. Process for i proving the Iastness bi dyeings which have been prepared on cellulose materials by means of substantive dyestuffs by aftertreating them with solutions containing a product obtained by condensing 2.6-diaminopyridine with symmetrical dichloroacetone and acting on the reaction product with dimethylsuliate in an alkaline medium.
mnmanp Mtinz. KARL KELLER- o'rro mosxmr,
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2138457A true US2138457A (en) | 1938-11-29 |
Family
ID=3429809
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US2138457D Expired - Lifetime US2138457A (en) | Process fob improving the fastness |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2138457A (en) |
-
0
- US US2138457D patent/US2138457A/en not_active Expired - Lifetime
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