US2053821A - - Google Patents
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- US2053821A US2053821A US2053821DA US2053821A US 2053821 A US2053821 A US 2053821A US 2053821D A US2053821D A US 2053821DA US 2053821 A US2053821 A US 2053821A
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- bath
- baths
- dyed
- dyeing
- hydrosulfite
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- 239000000463 material Substances 0.000 description 26
- 238000004043 dyeing Methods 0.000 description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 125000004432 carbon atoms Chemical group C* 0.000 description 14
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 14
- 239000004753 textile Substances 0.000 description 14
- 230000035507 absorption Effects 0.000 description 12
- 238000010521 absorption reaction Methods 0.000 description 12
- 239000003513 alkali Substances 0.000 description 12
- 229920002678 cellulose Polymers 0.000 description 12
- 239000001913 cellulose Substances 0.000 description 12
- 125000001931 aliphatic group Chemical group 0.000 description 10
- 229910052799 carbon Inorganic materials 0.000 description 10
- -1 cyclic amidines Chemical class 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 159000000000 sodium salts Chemical class 0.000 description 10
- 229920000742 Cotton Polymers 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 8
- 125000004433 nitrogen atoms Chemical group N* 0.000 description 8
- JVBXVOWTABLYPX-UHFFFAOYSA-L Sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 6
- 241001584775 Tunga penetrans Species 0.000 description 6
- KOTVVDDZWMCZBT-UHFFFAOYSA-N Vat Violet 1 Chemical compound C1=CC=C[C]2C(=O)C(C=CC3=C4C=C(C=5C=6C(C([C]7C=CC=CC7=5)=O)=CC=C5C4=6)Cl)=C4C3=C5C=C(Cl)C4=C21 KOTVVDDZWMCZBT-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 150000001409 amidines Chemical class 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
- 239000000975 dye Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000004744 fabric Substances 0.000 description 6
- 239000000835 fiber Substances 0.000 description 6
- 239000003638 reducing agent Substances 0.000 description 6
- 238000006277 sulfonation reaction Methods 0.000 description 6
- 150000003460 sulfonic acids Chemical class 0.000 description 6
- GJBZRASGBXVGID-UHFFFAOYSA-N 2-heptadecyl-1-methylbenzimidazole Chemical compound C1=CC=C2N(C)C(CCCCCCCCCCCCCCCCC)=NC2=C1 GJBZRASGBXVGID-UHFFFAOYSA-N 0.000 description 4
- 210000002268 Wool Anatomy 0.000 description 4
- 150000001447 alkali salts Chemical class 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 150000001556 benzimidazoles Chemical class 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 230000002950 deficient Effects 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 150000002460 imidazoles Chemical class 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 230000000979 retarding Effects 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 229920002955 Art silk Polymers 0.000 description 2
- 240000008564 Boehmeria nivea Species 0.000 description 2
- KFGNBLKDBMEHRO-UHFFFAOYSA-N CN1C(=NC2=C1C=CC=C2CCCCCCCCCCCCCCCCC)S(=O)(=O)O Chemical compound CN1C(=NC2=C1C=CC=C2CCCCCCCCCCCCCCCCC)S(=O)(=O)O KFGNBLKDBMEHRO-UHFFFAOYSA-N 0.000 description 2
- 240000000218 Cannabis sativa Species 0.000 description 2
- 229940097275 Indigo Drugs 0.000 description 2
- 240000007871 Indigofera tinctoria Species 0.000 description 2
- 235000000177 Indigofera tinctoria Nutrition 0.000 description 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N O-Phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 2
- VXMKYRQZQXVKGB-CWWHNZPOSA-N Tannin Chemical compound O([C@H]1[C@H]([C@@H]2OC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)O[C@H]([C@H]2O)O1)O)C(=O)C1=CC(O)=C(O)C(O)=C1 VXMKYRQZQXVKGB-CWWHNZPOSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 150000004056 anthraquinones Chemical class 0.000 description 2
- 229940058303 antinematodal Benzimidazole derivatives Drugs 0.000 description 2
- 125000004429 atoms Chemical group 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- 235000009120 camo Nutrition 0.000 description 2
- 235000005607 chanvre indien Nutrition 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 238000009967 direct dyeing Methods 0.000 description 2
- 239000002657 fibrous material Substances 0.000 description 2
- 235000021323 fish oil Nutrition 0.000 description 2
- 239000003292 glue Substances 0.000 description 2
- 230000005484 gravity Effects 0.000 description 2
- 239000011487 hemp Substances 0.000 description 2
- 235000012765 hemp Nutrition 0.000 description 2
- 235000012766 marijuana Nutrition 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000003801 milling Methods 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N oxygen atom Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 125000004430 oxygen atoms Chemical group O* 0.000 description 2
- 239000004627 regenerated cellulose Substances 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 2
- 235000018553 tannin Nutrition 0.000 description 2
- 229920001864 tannin Polymers 0.000 description 2
- 239000001648 tannin Substances 0.000 description 2
- 230000003313 weakening Effects 0.000 description 2
Definitions
- the absorption of dyestufis by fibrous material is retarded by means of a dispersing agent containing, on the one hand, at least one basic nitrogen atom and at least one sulfo-group, which may be linked to a carbon atom or otherwise, e. g. to an oxygen atom, and, on the other hand, an aliphatic or cycloaliphatic radical containing at least 8 carbon atoms.
- a dispersing agent containing, on the one hand, at least one basic nitrogen atom and at least one sulfo-group, which may be linked to a carbon atom or otherwise, e. g. to an oxygen atom, and, on the other hand, an aliphatic or cycloaliphatic radical containing at least 8 carbon atoms.
- dispersing agents examples include the sulfonic acids of cyclic amidines, such as are described in applications Serial No. 667,133 and No. 743,483, or obtained by sulfonation of the amidines described in the application Serial No. 727,584, as well as mixtures of such sulfonic acids.
- the absorption capacity results, on the one hand, in an improvement of the levelness of the dyeings obtained, and, on the other hand, in an increase in the capacity for alkaline reducing baths to strip dyeings produced with vat-dyestufis.
- the addition to the bath of a compound used in accordance with the invention has the result that the dyeings undergo a pronounced weakening which renders it possible to improve the levelness oi. unlevel defective vat-dyeings.
- Example 1 There is added to the dye-bath, containing 0.5 per cent. of trichloroisodibenzanthrone, vatted in the usual manner in an alkaline hydrosulfite bath, the sulfonated cyclic amidine, obtained by sulfonation of N-methyl-,uheptadecylbenzimidazole, in quantity amounting to 0.25 gram per liter of dye-bath.
- the absorption of the dyestuff from the bath is appreciably retarded, so that the dyeings obtained are more level and the material is better through-dyed than is the case in the absence of the sulfonated amidine.
- the N-alkyl, N-propyl or N -buty1- .-heptadecylbenzimidazolesulfonic acids behave quite similarly.
- Example 2 A material which has been dyed with 1.5 per cent. of Cibanone Blu'e 3G (Schultz, Farbstoi ftabellen No. 1,279) but which is defective owing to unlevelness, is treated for half-an-hour at 60 C. in a bath-containing per liter, 16 cc. of an aqueous solution of sodium hydroxide of B. and 2 grams of sodium hydrosulfite.
- the sulfonated cyclic 'amidine prepared by sulfonation of the mixture of N-methylated imidazoles from ortho-phenylenediamine and hydrogenated fish oil, the reabsorption of the reduced dyestuff which has been removed .is retarded, whereby the dyeing is levelled.
- the product may also be used for stripping vat-dyeings.
- Example 4 A padding bath is prepared with 50 grams of Cibanone Violet 2R double paste (Schultz, Farbstoiltabellen, 7th edition, 1931, No. 1,265) and 5 grams of the product of the suli'onatlon of a mixture of 25 per cent. oi N-methyl- -heptadecylbenzimidazole and '75 per cent. of N.N-methylethyl- L-heptadecylbenzimidazolium chloride.
- a linen fabric is passed repeatedly through the bath and intermedlateiy between squeezing rollers.
- the dyeing is then developed in a Jigger by treating the fabric at 60 C. with a liquor containing per liter 16 cc. of sodium hydroxide solution of 36 B. and 2 grams of sodium hydrosulfite.
- the fabric is thus dyed very levelly and is well through-dyed. Similar results are obtained when using other quantitative proportions than indicated in the first paragraph of this example, e. g. 30 to 70, 50 to 50 or 70 to 30.
- Example 5 For dyeing kilos of loose wool, a dye-bath of about 1000 liters and having a temperature of 55 C. is prepared with the aid of 500 grams of glue, 500 cc. of ammonia of specific gravity 0.9, 300 grams of sodium hydrosulfite and 500 grams of the sodium salt of suii'onated N-methyl- -heptadecylbenzimldazole. Thereupon'there are added 2.5 kilos of Ciba Blue' 2B (Schultz, Farbstofltahellen, 7th edition, No. 1,314) which have previously been vatted in the customary manner. 1
- suii'onated benzimidazole derivative has the effect of retarding appreciably absorption of the dyestufi so that the whole batch is dyed much more levelly than in the absence of such a derivative.
- the bcnzimidazole-sullonic acids alkyiated at the N-atom mentioned at the end of Example 1 behave similarly.
- Example 6 For dyeing mercerized bead yarn there is added to the dye-bath. containing 0.5 per cent. of Cibanone Violet 2R (Schultz, Farbstofltabellen, 7th edition, No. 1,265) or 0.5 per cent. 01 Cibanone Blue 3G (Schultz, Farbstoiltabellen, 7th
- Cotton piece goods are dyed in a jigger with an alkaline hydrosulfite bath containing 0.5 per cent. of Cibanone Violet 2R (Schultz, Farbstofitabelien, 7th edition, 1931, No. 1,265), with the addition, per liter of dye-bath, of 0.5 gram of the sodium salt of the-product prepared by suitonating the quaternary hexadecyl-phenyl-dimethyl-ammonium-methylsuliate.
- the dyeings are appreciably more level than those obtained without this addition.
- Cotton drapery material is dyed by means of 20 per cent. of Pyrogene Indigo (Schultz, Farbstofitabellen, 'lth edition, No. 1,110) in a bath containing besides the usual additions, 0.3 gram per liter of the sodium salt of N-methyl-heptadecylbenzimidazol-sulfonic acid.
- the dyestuil is appreciably more slowly absorbed; the dyeing is much more level and the material is better through-dyed. Furthermore, the dyeing shows no tendency towards bronzing.
- Baths used for treating textile materials containing cellulose which baths are characterized by a content of alkali, a reducing agent, and a sulfonated benzimidazole substituted at the -carbon atom by an aliphatic chain having at least 8 carbon atoms.
- Baths used for treating textile materials containing cellulose which baths are characterized by a content oi alkali, hydrosulfite, and a sulfonated benzimidazole substituted at the u-carbon atom by an aliphatic chain having at least 8 carbon atoms.
- Baths used for treating textile materials containing cellulose which baths are characterized by a content of alkali, hydrosulfite, and a sullonated benzimidazole substituted at the -carbon atom by the heptadecyl radical.
- Baths used for treating textile materials containing cellulose which baths are characterized by a content of alkali, hydrosulflte, and a suli'onated benzimidazole substituted at the -carbon atom by the heptadecyl radical and at at least one nitrogen atom by an alkyl radical containing not-more than 4 carbon atoms.
- Baths used for treating textile materials containing cellulose which baths are character ized by a content of alkali, hydrosulfite and an alkali salt of the sultonated Nmethyl- -heptadecylbenzimidazole.
- Baths used for treating textile materials containing cellulose which baths are characterized by a content 01 alkali, hydrosulfite and an alkali salt oi a sultonated mixture 01 N-methyl- -heptadecylbenzimidazole and N-methyl-N'- ethyl- -heptadecylbenzimidazoiium chloride.
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Description
Patented Sept, 8, 1936 U l'l'E l) ST 3.,1
PROCESS FOR RETARDING THE ABSORP- TION F DYESTUFFS BY THE FIBER No Drawing. Application September 10, 1934, Serial No. 743,484. 1111 Switzerland September 6 Claims.
According to this invention the absorption of dyestufis by fibrous material is retarded by means of a dispersing agent containing, on the one hand, at least one basic nitrogen atom and at least one sulfo-group, which may be linked to a carbon atom or otherwise, e. g. to an oxygen atom, and, on the other hand, an aliphatic or cycloaliphatic radical containing at least 8 carbon atoms. By the expression aliphatic or cycloallphatic radical containing at least 8 carbon atoms there are to be understoodnot only chains merely consisting of carbon atoms, but also chains which are interrupted by an oxygen-, sulfuror nitrogen-bridge.
Examples of such dispersing agents are the sulfonic acids of cyclic amidines, such as are described in applications Serial No. 667,133 and No. 743,483, or obtained by sulfonation of the amidines described in the application Serial No. 727,584, as well as mixtures of such sulfonic acids.
If a water-soluble compound of this kind is added to a dye-bath the absorption of the dyestuii is verysubstantiallyretarded,so that in many cases there is a substantial improvement in the levelness of dyeings produced with the aid of such dyestuffs which would otherwise be rapidly absorbed. This eiiect can already occur in dyeing with basic dyestuffs cotton which has been mordanted with tannin or in some other suitable manner. The improvement in the levelling capacity may further be observed in the case of such direct-dyeing dyestuffs which are used for dyeing cellulosic fibers, such as cotton, artificial silk from regenerated cellulose, hemp, and ramie. It is also clearly observed in the case of dyestufis intended for'dyeing animal fibers, such as wool or silk, particularly also in the case of acid dyestuffs which are rapidly absorbed, such as dyestufis fast to milling, which must be dyed in an 40 acetic acid bath. However, this effect is of particularly great practical importance in the case of alkaline baths containing hydrosulfite or other reducing agents having a similar action, and dyestuffs capable of being dyed in the reduced state, 45 such as sulfuror vat-dyestuffs, particularly vatdyestuffs of the anthraquinone series being rapidly absorbed by the fibers. the absorption capacity results, on the one hand, in an improvement of the levelness of the dyeings obtained, and, on the other hand, in an increase in the capacity for alkaline reducing baths to strip dyeings produced with vat-dyestufis. Thus Whilst many vat-dyestuff dyeings are scarcely affected by alkaline reducing baths, the addition to the bath of a compound used in accordance with the invention has the result that the dyeings undergo a pronounced weakening which renders it possible to improve the levelness oi. unlevel defective vat-dyeings. When used in dye-baths containing reducing agents those The retardation of among the above cited products have proved particularly eifective which contain such sulionated benzimidazole derivatives which are substituted at the ,u-CZLIbOIl atom or at the N-atom by a longer aliphatic chain which may be interrupted. Among these, as is the case quite generally, the monosulfonic acids are particularly .valuable. Further such sulfonic acids in which imidazoles, represent valuable new agents which are used both for dyeing vat dyestufis and for stripping textile materials dyed with vat-dyestuffs.
The following examples illustrate the invention:-
Example 1 There is added to the dye-bath, containing 0.5 per cent. of trichloroisodibenzanthrone, vatted in the usual manner in an alkaline hydrosulfite bath, the sulfonated cyclic amidine, obtained by sulfonation of N-methyl-,uheptadecylbenzimidazole, in quantity amounting to 0.25 gram per liter of dye-bath. The absorption of the dyestuff from the bath is appreciably retarded, so that the dyeings obtained are more level and the material is better through-dyed than is the case in the absence of the sulfonated amidine. The N-alkyl, N-propyl or N -buty1- .-heptadecylbenzimidazolesulfonic acids behave quite similarly.
Example 2 A material which has been dyed with 1.5 per cent. of Cibanone Blu'e 3G (Schultz, Farbstoi ftabellen No. 1,279) but which is defective owing to unlevelness, is treated for half-an-hour at 60 C. in a bath-containing per liter, 16 cc. of an aqueous solution of sodium hydroxide of B. and 2 grams of sodium hydrosulfite. By the addition of 1 gram per liter of the sulfonated cyclic 'amidine, prepared by sulfonation of the mixture of N-methylated imidazoles from ortho-phenylenediamine and hydrogenated fish oil, the reabsorption of the reduced dyestuff which has been removed .is retarded, whereby the dyeing is levelled. The product may also be used for stripping vat-dyeings.
'- Example 3 "A shirting material which has been dyed with 0.5 per cent. of Cibanone Blue (3CD (Schultz, Farbstofitabeilen, 7th edition, 1931, No. 1,234) and is unsuitable for making up into clothing owing to unievcl dyeing, is treated in a jigger for half-an-hour at 60" C. with a solution containing per liter 15 cc. of an aqueous solution of sodium hydroxide of 36" B., 5 grams of sodium hydrosuifite and 0.2 gram of the product prepared by suifonating a mixture of 25 per cent. of N-methyl- -heptadecylbe'nzimidazole and per cent. of NzN- methyl-ethyl- .-heptadecylbenzimldazoiium chloride.
There is obtained in this manner a piece material which is dyed uniformly throughout and is suitable for making up into clothing. Similar resuits are obtained when using other quantitative proportions than indicated in the first paragraph of this example, e. g. 30 to 70, 50 to 50 or 70 to 30.
Example 4 A padding bath is prepared with 50 grams of Cibanone Violet 2R double paste (Schultz, Farbstoiltabellen, 7th edition, 1931, No. 1,265) and 5 grams of the product of the suli'onatlon of a mixture of 25 per cent. oi N-methyl- -heptadecylbenzimidazole and '75 per cent. of N.N-methylethyl- L-heptadecylbenzimidazolium chloride.
A linen fabric is passed repeatedly through the bath and intermedlateiy between squeezing rollers. The dyeing is then developed in a Jigger by treating the fabric at 60 C. with a liquor containing per liter 16 cc. of sodium hydroxide solution of 36 B. and 2 grams of sodium hydrosulfite.
The fabric is thus dyed very levelly and is well through-dyed. Similar results are obtained when using other quantitative proportions than indicated in the first paragraph of this example, e. g. 30 to 70, 50 to 50 or 70 to 30.
Example 5 For dyeing kilos of loose wool, a dye-bath of about 1000 liters and having a temperature of 55 C. is prepared with the aid of 500 grams of glue, 500 cc. of ammonia of specific gravity 0.9, 300 grams of sodium hydrosulfite and 500 grams of the sodium salt of suii'onated N-methyl- -heptadecylbenzimldazole. Thereupon'there are added 2.5 kilos of Ciba Blue' 2B (Schultz, Farbstofltahellen, 7th edition, No. 1,314) which have previously been vatted in the customary manner. 1
The addition of the suii'onated benzimidazole derivative has the effect of retarding appreciably absorption of the dyestufi so that the whole batch is dyed much more levelly than in the absence of such a derivative. The bcnzimidazole-sullonic acids alkyiated at the N-atom mentioned at the end of Example 1 behave similarly.
Example 6 For dyeing mercerized bead yarn there is added to the dye-bath. containing 0.5 per cent. of Cibanone Violet 2R (Schultz, Farbstofltabellen, 7th edition, No. 1,265) or 0.5 per cent. 01 Cibanone Blue 3G (Schultz, Farbstoiltabellen, 7th
edition, No. 1,279) vatted in the customary man- Example 7 Cotton piece goods are dyed in a jigger with an alkaline hydrosulfite bath containing 0.5 per cent. of Cibanone Violet 2R (Schultz, Farbstofitabelien, 7th edition, 1931, No. 1,265), with the addition, per liter of dye-bath, of 0.5 gram of the sodium salt of the-product prepared by suitonating the quaternary hexadecyl-phenyl-dimethyl-ammonium-methylsuliate. The dyeings are appreciably more level than those obtained without this addition.
A like effect is obtained it instead of the aforesaid addition there is added, per liter of dyebath, 1 gram of the sodium salt of sulfonated methyl-hexadecyl-aniiine, or 2 grams of the sodium salt of sulfonated hexadecyl-aniiine.
Example 8 Cotton drapery material is dyed by means of 20 per cent. of Pyrogene Indigo (Schultz, Farbstofitabellen, 'lth edition, No. 1,110) in a bath containing besides the usual additions, 0.3 gram per liter of the sodium salt of N-methyl-heptadecylbenzimidazol-sulfonic acid.
Owing to the addition or this substance the dyestuil is appreciably more slowly absorbed; the dyeing is much more level and the material is better through-dyed. Furthermore, the dyeing shows no tendency towards bronzing.
What we claim is:-
1. Baths used for treating textile materials containing cellulose, which baths are characterized by a content of alkali, a reducing agent, and a sulfonated benzimidazole substituted at the -carbon atom by an aliphatic chain having at least 8 carbon atoms.
2. Baths used for treating textile materials containing cellulose, which baths are characterized by a content oi alkali, hydrosulfite, and a sulfonated benzimidazole substituted at the u-carbon atom by an aliphatic chain having at least 8 carbon atoms.
3. Baths used for treating textile materials containing cellulose, which baths are characterized by a content of alkali, hydrosulfite, and a sullonated benzimidazole substituted at the -carbon atom by the heptadecyl radical.
4. Baths used for treating textile materials containing cellulose, which baths are characterized by a content of alkali, hydrosulflte, and a suli'onated benzimidazole substituted at the -carbon atom by the heptadecyl radical and at at least one nitrogen atom by an alkyl radical containing not-more than 4 carbon atoms.
5. Baths used for treating textile materials containing cellulose, which baths are character ized by a content of alkali, hydrosulfite and an alkali salt of the sultonated Nmethyl- -heptadecylbenzimidazole.
6. Baths used for treating textile materials containing cellulose, which baths are characterized by a content 01 alkali, hydrosulfite and an alkali salt oi a sultonated mixture 01 N-methyl- -heptadecylbenzimidazole and N-methyl-N'- ethyl- -heptadecylbenzimidazoiium chloride.
CHARLES GRAENACHER. FRANZ ACKERMANN. ALBERT LANDOLT. WILHELM GEIGY.
Publications (1)
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US2053821A true US2053821A (en) | 1936-09-08 |
Family
ID=3428157
Family Applications (1)
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US2053821D Expired - Lifetime US2053821A (en) |
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2892668A (en) * | 1956-02-14 | 1959-06-30 | Celanese Corp | Coloring of cellulose-cellulose triacetate textiles |
-
0
- US US2053821D patent/US2053821A/en not_active Expired - Lifetime
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2892668A (en) * | 1956-02-14 | 1959-06-30 | Celanese Corp | Coloring of cellulose-cellulose triacetate textiles |
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