US1945221A - Printing of textile fibers - Google Patents
Printing of textile fibers Download PDFInfo
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- US1945221A US1945221A US1945221DA US1945221A US 1945221 A US1945221 A US 1945221A US 1945221D A US1945221D A US 1945221DA US 1945221 A US1945221 A US 1945221A
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- United States
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- printing
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- sodium
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- 239000000835 fiber Substances 0.000 title description 4
- 239000004753 textile Substances 0.000 title description 4
- -1 alkali metal salt Chemical class 0.000 description 72
- 239000011780 sodium chloride Substances 0.000 description 64
- 229910052783 alkali metal Inorganic materials 0.000 description 62
- 238000002360 preparation method Methods 0.000 description 44
- 229920000742 Cotton Polymers 0.000 description 40
- 159000000000 sodium salts Chemical class 0.000 description 40
- 239000000975 dye Substances 0.000 description 38
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 34
- 235000011187 glycerol Nutrition 0.000 description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 28
- 239000002253 acid Substances 0.000 description 26
- 238000000034 method Methods 0.000 description 24
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 20
- 229940092714 benzenesulfonic acid Drugs 0.000 description 18
- 238000007792 addition Methods 0.000 description 16
- SRSXLGNVWSONIS-UHFFFAOYSA-N Benzenesulfonic acid Chemical group OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 14
- YGSDEFSMJLZEOE-UHFFFAOYSA-N Salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 14
- 125000004663 dialkyl amino group Chemical group 0.000 description 14
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical group C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 14
- 125000000217 alkyl group Chemical group 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- 239000000843 powder Substances 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 229940097275 Indigo Drugs 0.000 description 10
- 241001062009 Indigofera Species 0.000 description 10
- 235000000177 Indigofera tinctoria Nutrition 0.000 description 10
- XWGJFPHUCFXLBL-UHFFFAOYSA-M Rongalite Chemical compound [Na+].OCS([O-])=O XWGJFPHUCFXLBL-UHFFFAOYSA-M 0.000 description 10
- 150000001735 carboxylic acids Chemical class 0.000 description 10
- 150000002790 naphthalenes Chemical class 0.000 description 10
- 229940077386 sodium benzenesulfonate Drugs 0.000 description 10
- 239000001187 sodium carbonate Substances 0.000 description 10
- 229910000029 sodium carbonate Inorganic materials 0.000 description 10
- 235000017550 sodium carbonate Nutrition 0.000 description 10
- 229940001593 sodium carbonate Drugs 0.000 description 10
- MZSDGDXXBZSFTG-UHFFFAOYSA-M sodium;benzenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC=CC=C1 MZSDGDXXBZSFTG-UHFFFAOYSA-M 0.000 description 10
- 150000008107 benzenesulfonic acids Chemical group 0.000 description 8
- 238000005984 hydrogenation reaction Methods 0.000 description 8
- 239000011734 sodium Substances 0.000 description 8
- 229910052708 sodium Inorganic materials 0.000 description 8
- BGLLQCPSNQUDKF-UHFFFAOYSA-N 1,2,3,4-tetrahydronaphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)CCCC2=C1 BGLLQCPSNQUDKF-UHFFFAOYSA-N 0.000 description 6
- QXRBXMKEMUAWPM-UHFFFAOYSA-N 1,2,3,4-tetrahydronaphthalene-2-sulfonic acid Chemical compound C1=CC=C2CC(S(=O)(=O)O)CCC2=C1 QXRBXMKEMUAWPM-UHFFFAOYSA-N 0.000 description 6
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical group C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 description 6
- KZVBBVPCVQEVQK-UHFFFAOYSA-N 4-(dimethylamino)benzenesulfonic acid Chemical compound CN(C)C1=CC=C(S(O)(=O)=O)C=C1 KZVBBVPCVQEVQK-UHFFFAOYSA-N 0.000 description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Chemical group OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
- CXJFOLNGBMNALC-UHFFFAOYSA-N C(C1=CC=CC=C1)OS(=O)(=O)NC1=CC=CC=C1.[Na] Chemical compound C(C1=CC=CC=C1)OS(=O)(=O)NC1=CC=CC=C1.[Na] CXJFOLNGBMNALC-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- LSNNMFCWUKXFEE-UHFFFAOYSA-M bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 239000001184 potassium carbonate Substances 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 229960004889 salicylic acid Drugs 0.000 description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
- 238000005728 strengthening Methods 0.000 description 6
- 150000003460 sulfonic acids Chemical class 0.000 description 6
- QALBBKSSPZLLJH-UHFFFAOYSA-N CN(C=1C(=CC(=CC1)S(=O)(=O)O)C)C Chemical compound CN(C=1C(=CC(=CC1)S(=O)(=O)O)C)C QALBBKSSPZLLJH-UHFFFAOYSA-N 0.000 description 4
- NZNMSOFKMUBTKW-UHFFFAOYSA-N Cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 4
- FYGDTMLNYKFZSV-MRCIVHHJSA-N Dextrin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)OC1O[C@@H]1[C@@H](CO)OC(O[C@@H]2[C@H](O[C@H](O)[C@H](O)[C@H]2O)CO)[C@H](O)[C@H]1O FYGDTMLNYKFZSV-MRCIVHHJSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- PANJMBIFGCKWBY-UHFFFAOYSA-N iron tricyanide Chemical compound N#C[Fe](C#N)C#N PANJMBIFGCKWBY-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
- 229910052700 potassium Inorganic materials 0.000 description 4
- 239000011591 potassium Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- 239000011593 sulfur Substances 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- YXHILBWQUILXRY-UHFFFAOYSA-N 2-(dimethylamino)benzenesulfonic acid Chemical compound CN(C)C1=CC=CC=C1S(O)(=O)=O YXHILBWQUILXRY-UHFFFAOYSA-N 0.000 description 2
- UKIMGCJPCFNHHF-UHFFFAOYSA-N 2-methylpropyl naphthalene-1-sulfonate;sodium Chemical compound [Na].C1=CC=C2C(S(=O)(=O)OCC(C)C)=CC=CC2=C1 UKIMGCJPCFNHHF-UHFFFAOYSA-N 0.000 description 2
- TYXZQVMCGZKDEK-UHFFFAOYSA-N 3-(diethylamino)benzenesulfonic acid Chemical compound CCN(CC)C1=CC=CC(S(O)(=O)=O)=C1 TYXZQVMCGZKDEK-UHFFFAOYSA-N 0.000 description 2
- BOTGCZBEERTTDQ-UHFFFAOYSA-N 4-Methoxy-1-naphthol Chemical compound C1=CC=C2C(OC)=CC=C(O)C2=C1 BOTGCZBEERTTDQ-UHFFFAOYSA-N 0.000 description 2
- YJISHJVIRFPGGN-UHFFFAOYSA-N 5-[5-[3,4-dihydroxy-6-(hydroxymethyl)-5-methoxyoxan-2-yl]oxy-6-[[3,4-dihydroxy-6-(hydroxymethyl)-5-methoxyoxan-2-yl]oxymethyl]-3,4-dihydroxyoxan-2-yl]oxy-6-(hydroxymethyl)-2-methyloxane-3,4-diol Chemical compound O1C(CO)C(OC)C(O)C(O)C1OCC1C(OC2C(C(O)C(OC)C(CO)O2)O)C(O)C(O)C(OC2C(OC(C)C(O)C2O)CO)O1 YJISHJVIRFPGGN-UHFFFAOYSA-N 0.000 description 2
- 241000416162 Astragalus gummifer Species 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- PRMHXMVBYLVTRC-UHFFFAOYSA-N C1(=CC=CC2=CC=CC=C12)OC1=C(SC=C1)C(=O)O Chemical compound C1(=CC=CC2=CC=CC=C12)OC1=C(SC=C1)C(=O)O PRMHXMVBYLVTRC-UHFFFAOYSA-N 0.000 description 2
- XQGDNRFLRLSUFQ-UHFFFAOYSA-N C1=C(C2=C3C4=C56)C=CC3=CC5=C3C=CC=CC3=CC6=CC=C4C=C2C2=C1C(=O)CC=C2 Chemical compound C1=C(C2=C3C4=C56)C=CC3=CC5=C3C=CC=CC3=CC6=CC=C4C=C2C2=C1C(=O)CC=C2 XQGDNRFLRLSUFQ-UHFFFAOYSA-N 0.000 description 2
- HAUIVYFKVTYMIX-UHFFFAOYSA-M CN(C=1C(=CC(=CC1)S(=O)(=O)[O-])C)C.[Na+] Chemical compound CN(C=1C(=CC(=CC1)S(=O)(=O)[O-])C)C.[Na+] HAUIVYFKVTYMIX-UHFFFAOYSA-M 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N P-Toluenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N Phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- JVBXVOWTABLYPX-UHFFFAOYSA-L Sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 2
- ABBQHOQBGMUPJH-UHFFFAOYSA-M Sodium salicylate Chemical compound [Na+].OC1=CC=CC=C1C([O-])=O ABBQHOQBGMUPJH-UHFFFAOYSA-M 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N Tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 2
- 229920001615 Tragacanth Polymers 0.000 description 2
- 229940116362 Tragacanth Drugs 0.000 description 2
- 240000008529 Triticum aestivum Species 0.000 description 2
- 229940100445 WHEAT STARCH Drugs 0.000 description 2
- NWUQSRFTWWZVKD-UHFFFAOYSA-N [K+].[K+].CC(O)=O.[O-][Cr]([O-])(=O)=O Chemical compound [K+].[K+].CC(O)=O.[O-][Cr]([O-])(=O)=O NWUQSRFTWWZVKD-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical class [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- ISXSFOPKZQZDAO-UHFFFAOYSA-N formaldehyde;sodium Chemical compound [Na].O=C ISXSFOPKZQZDAO-UHFFFAOYSA-N 0.000 description 2
- 229920000591 gum Polymers 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 2
- 230000002035 prolonged Effects 0.000 description 2
- 239000003638 reducing agent Substances 0.000 description 2
- 229960004025 sodium salicylate Drugs 0.000 description 2
- DMZUWZNMZRSBOK-UHFFFAOYSA-M sodium;4-(dimethylamino)benzenesulfonate Chemical compound [Na+].CN(C)C1=CC=C(S([O-])(=O)=O)C=C1 DMZUWZNMZRSBOK-UHFFFAOYSA-M 0.000 description 2
- 238000010025 steaming Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 235000010487 tragacanth Nutrition 0.000 description 2
- 239000000196 tragacanth Substances 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- 235000021307 wheat Nutrition 0.000 description 2
Definitions
- the present invention relates to improvements in the printing of cotton with vat or sulfur dyestuffs.
- cotton is printed according to any desired method with printing pastes of vat or sulfur dyestuffs containing besides the different ingredients, known for the preparation of such printing .pastes, an alkali metal salt of an unsubstituted sulfonic or carboxylic 'acid of the benzene or naphthalene series or, a hydrogenation product thereof, or a benzene or naphthalene sulfonic acid substituted by alkyl groups or dialkylamino groups, or a benzene or naphthalene carboxylic acid, substituted by alkyl-, hydroXy-, or dialkylamino groups.
- printing pastes is intended to include all kinds of pastes usually applied for cotton printing purposes, such pastes for example as are obtainable by mixing vat dyestuffs with thickenings, water, glycerine or another similar water soluble alcohol, potassium carbonate, sodium carbonate, sodium formaldehyde sulfoxylate, sodium hydrosulfite or a mixture of the latter with sodium formaldehyde
- the alkali metal salts of the sulfonic or carboxylic acids above specified may be added to the printing pastes at any stage of the preparation of the same.
- the printing of.c otton with said printing pastes may be performed in the usual manner, for example, with the aid of a printing engine, whereupon the printings are dried to a certain extent, steamed with wet steam (e. g. in a Mather-Flatt) and developed 'by oxidation, e. g., with an aqueous solution of an alkali metal bichromate and acetic acid, rinsed and soaped while boiling.
- wet steam e. g. in a Mather-Flatt
- oxidation e. g., with an aqueous solution of an alkali metal bichromate and acetic acid
- pastes containing the sulfonic or carboxylic acids above specified in sloppadding processes, and it may be mentioned that the best results are generally obtained when working with pastes which are reduced only on the fiber while steaming, which pastes generally do not contain hydrosulfites, but,- e. g., sodium formaldehyde sulfoxylate as the reducing agent.
- alkali metal salts of the kind above referred to may be mentioned by way of example: Alkali metal salts of benzoic acid, ortho-toluylic acid, salicylic acid, phthalic acid, benzene sulfonic acid, para-toluene sulfonic acid, naphthalene-alphaand beta-sulfonic acid, dialkylaniline sulfonic acids, such as sodium dimethylor diethyl-metanilate, sodium dimethylsulfanilate, sodium dimethyl-2-toluidine-4-sulfonate, furthermore, the sodium salt of cyclohexane carboxylic acid, .sodium tetrahydronaphthalenebeta-sulfonate and so on.
- One or more of such salts may be added to the dyestuff preparations with a good effect.
- Example 1 20 parts by weight of '6.6'dichlor0-4.4'-di- 1 methylbisthio naphthene indigo (in form of an aqueous paste) 15 parts by weight of the sodium salt of dimethylmetanilic acid 40 parts by weight of glycerine are evaporated in a plain pan until the paste has a dyestuff content of 18%.
- the dyestuff preparation thus obtainable is of permanent durability
- the printing pastes thus obtainable are used for printing purposes in the ordinary manner.
- the printings are steamed whilst moist, developed with potassium chromate-acetic acid and soaped while boiling.
- the printings produced in this manner on cotton are considerably more powerful than those obtainable by the same directions but without the addition of the alkali metal salts mentioned.
- Example 2 20 parts by weight of the finely divided dyestufi, obtainable in accordance with example 1 of British Patent No. 15,60'7/07 from naphtho-oxythiophen-carboxylic acid, in form of an aqueous paste 15 parts by weight of sodium benzene sulfonate and 40 parts by weight of glycerine are evaporated on the water bath with stirring until a paste of 20% dyestufi content is obtained.
- the dyestufi preparation thus obtainable does not dry up and can be worked up immediately by the customary processes to printing pastes,
- Example 3 3 parts by weight of a 60% dyestufi powder obtainable by drying parts by weight of a 10.33% paste of the d'yestufi obtained in accordance with Example 1 of'U. S. Patent No. 1,667,848, in the presence of 2 parts by weight of calcined sodium carbonate and parts by weight of the sodium salt of dimethyl-metanilic acid in an enamelled drying dish on the water bath or on a roller dryer, heated by means of steam at 1 /q--2 atmospheres pressure or by some other means, are mixed for printing purposes with parts by weight of water and parts by weight of a thickening as described in Example 1, B.
- the printings obtainable with this paste in the usual manner are without stippling, they are fixed better and show a strengthening of shade compared with the printing'obtainable according to the same method but without the addition of the sodium salt of dimethylmetanilic acid.
- Example 4 3 parts by weight of a 60% dyestuff powder, obtainable by drying 484 parts by weight of an aqueous paste of the dyestufi specified in Example 1, together with parts by weight of the sodium salt of dimethyl-metanilic acid and 2 parts by weight of sodium carbonate in the manner described in Example 3, are used for printing purposes as described in Example 3.
- the printings on cotton even in printing processes without previous reduction are' considerably stronger thanthe printings obtainable from a normal aqueous paste of the same dyestuff material without the addition of the sodium salt of dimethylmetanilic acid.
- Example 5 v 30 parts by weight of the dyestufi of Example 1 in form of an aqueous paste 19 parts by weight of the sodium salt of dimethylmetanilic acid 0.5 parts by weight of sodium carbonate and 0.5 parts by weight of sodium isobutylnaphthalenesulfonate (as' wetting agent) are evaporated to dryness in the manner described in Example 3.
- the powder is finely ground and sieved and can be used without further treatment for printing in the manner described in Example 3.
- the sodium salt of dimethylmetanilic acid can also be replaced by the sodium salt of dimethyl- 2-toluidine-4-sulfonic acid.
- Example 6 30 parts by weight of the dyestuff specified in Example 1,- in form of an aqueous paste 18 parts by weight of the sodium salt of tetra-- hydro -naphthalene beta sulfonic acid and 2 parts by weight of sodiumcarbonate are worked up to a dry dyestufi preparation, as described in Example 3 and display the same advantages in printing as described in the preceding examples.
- Example 7 30 parts by weight of 3.3'-dichloro-N-dihydro-1.2-2'.1-anthraquinone-azine (in the form of an aqueous paste) 18 parts by weight of the sodium salt of Example 8
- the dyestufi specified in Example 1 is replaced by flavanthrone and sodium benzene sulfonate is used instead of sodium dimethylmetanilate, a preparation likewise yielding stronger printings is obtained.
- Example 9 tion likewise yielding stronger printings than a normal aqueous paste of the same dyestuff without the addition of. sodium benzene sulfonate, is obtained.
- Example 10 In Example 1 the dyestuff can be replaced by dimethoxy-dibenzanthrone (Color Index page 265 No. 1101) and as the addition sodium salicylate or sodium dimethylmetanilic acid can be used, in which case dyestufi preparations valuable in cotton printing are likewise obtained.
- Example 11 When the dyestuff specified in Example 9 is replaced by that of the German Patent No. 242,621, a preparation likewise yielding stronger printings is obtained.
- Example 12 From the dyestuff obtainable according to Example 3 (first dyestufi) of British Patent No.
- dyestuif preparations can be produced in accordance with Examples 1 or 2, said vdyestuif preparations also yielding especially strong printings.
- Example 15 partsby weight of an aqueous paste containing 11% of 6.6-diethoxy-2.2'-bis thionaphtheneindigo (Color Index No.
- printing pastes comprising a vat dyestuil zene sulfonic acid.
- Example 16 I 356. 5 parts by weight of an aqueouspaste containing 11.2% of the dyestuif obtained from bromo-1-chloro-2.3 naphthisatin' and 4 -methoxy-1-naphthol in accordance with the example of Brit. Patent No. 289,154
- Example 1 parts by weight of 4.7-4'-7'-tetramethyl- 5.5-dichlorobisthionaphthene indigo (in the form of an aqueous paste) parts by weight of crude glycerine .parts byweight of the sodium salt of benzene sulfonic acid are concentrated to a dyestuif content of 17%.
- the dyestufi preparations obtainable in accordance with the last examples also display, when used for printing purposes after working up to printing pastes in any desired manner, the valuable properties already described.
- I Process which comprises printing cotton with a printing paste comprising a vat dyestuff and an alkali metal salt of a compound of the group consisting of unsubstituted sulfonic and carboxylic acids of the benzene and naphthalene series, hydrogenation products thereof, benzene and naphthalene sulfonic acids substituted by alkyl groups or dialkylamino groups, and benzene or naphthalene carboxylic acids substituted by a1kyl;, hydroxyor dialkylamino groups.
- Process which comprises printing cotton with printing pastes comprising a vat dyestuff and an alkali metal salt of a dialkylamino benzene sulfonic acid.
- Process which comprises printing cotton with printing pastes derived from vat dyestuffs, said pastes comprising an alkali metal salt of tetrahydronaphthalene sulfonic acid.
- Vat dyestufi preparations consisting of a vatdyestuff, water, glycerine and an alkali metal salt of a compound of the group consisting of unsubstituted sulfonic and carboxylic acids -of the benzene and naphthalene series, hydrogenation products thereof, benzene and naphthalene sulfonic acids substituted by alkyl groups or dialkylamino groups, and benzene or naphthalene salt of an unsubstituted benzene or naphthalene sulfonic acid.
- Vat dyestuff preparations consisting of a vat dyestufi, water, glycerine and an alkali metal salt of a dialkylamino benzene sulfonic acid.
- Vat dyestufi preparations consisting of a vat dyestufi', water, glycerine and an alkali metal salt of a dimethylamino benzene sulfonic acid.
- Vat dyestufi preparations consisting of avat dyestufi, water, glycerine and an alkali metal salt of benzene sulfonic acid.
- Vat dyestuff preparations consisting of a.
- vat dvestufi water, glycerine and an alkali metal salt of tetrahydronaphthalene sulfonic acid.
- Printing pastes suitable for printing cotton which comprise a vat dyestuif, a; thickening and an alkali metal salt of a compound of the group consisting of sulfonic and carboxylic acids of the benzene and naphthalene series, hydrogenation products thereof, benzene and naphthalene sulfonic acids substituted by alkyl groups or dialkylamino groups, and benzene and naphthalene carboxylic acids substituted by alkyl-, hydroxyor dialkylamino groups.
- Printing pastes suitable for printing cotton which comprise a vat dyestufi, a thickening and an alkali metal salt of an unsubstitutedbenzene or naphthalene sulfonic acid.
- Printing pastes suitable for printing cotton which comprise a vat dyestufl', a thickening and an alkali metal salt of a dialkylamino benzene sulfonic acid.
- Printing pastes suitable for printing cotton which comprise a vat dyestuff, a thickenand an alkali metal salt of tetrahydronaphthalene sulfonic acid.
- a printing paste comprising 6.6'-dichloro 4.4 dimethylbisthionaphthene indigo and an alkali metal salt of a compound selected from the group consistingof dimethylmetanilic acid, dimethyl-sulfanilic acid and salicylic acid.
- a printing paste comprising the dyestufi obtainable from naphtho-oxythiophene carboxylic acid by oxidation with potassium ferric cyanide in caustic soda solution, and an alkali metal salt of benzene sulfonic acid.
- a printing paste comprising 3.3'-dichloro- N-dihydro-1.2.2.'.1'-anthraquinone azine and an alkali metal salt of tetrahydronaphthalene-betasulfonic acid.
- a vat dyestuif preparation consisting of 6.6'-dichloro-4.4'-dimethyl-bisthionaphthene indigo, water, glycerine and an alkali metal salt of a compound selected from the group consisting of dimethyl-metanilic acid, dimethylsulfanilic acid and salicylic acid.
- a vat dyestufi preparation consisting of the dyestuff obtainable by reacting upon naphthoxythiophene-carboxylic acid with potassium ferric cyanide in caustic soda solution, water, glycerine and an alkali metal salt of benzene sulfonic acid.
- a vat dyestufi preparation consisting of 4 3.3 dichloro-N-dihydro-l.2.2'.1' -anthraquinone azine, water, glycerine, and an alkali metal salt of tetrahydronaphthalene-beta-sulfonic acid.
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Description
' sulfoxylate and the like.
Patented Jan. 30, 1934 v PRINTING OF TEXTILE FIBERS- Sebastian- Gassner and Herman Berthold, Leverkusen-on-the-Rhine, Germany, assign'ors to General Aniline Works, Inc.,. New York, N. Y', a corporation of Delaware No Drawing. Application May 19,- 1930, Serial No. 453,855, and in Germany May 29, 1929 27 Claims.
The present invention relates to improvements in the printing of cotton with vat or sulfur dyestuffs.
In accordance with the invention cotton is printed according to any desired method with printing pastes of vat or sulfur dyestuffs containing besides the different ingredients, known for the preparation of such printing .pastes, an alkali metal salt of an unsubstituted sulfonic or carboxylic 'acid of the benzene or naphthalene series or, a hydrogenation product thereof, or a benzene or naphthalene sulfonic acid substituted by alkyl groups or dialkylamino groups, or a benzene or naphthalene carboxylic acid, substituted by alkyl-, hydroXy-, or dialkylamino groups.
It may be mentioned that the term printing pastes is intended to include all kinds of pastes usually applied for cotton printing purposes, such pastes for example as are obtainable by mixing vat dyestuffs with thickenings, water, glycerine or another similar water soluble alcohol, potassium carbonate, sodium carbonate, sodium formaldehyde sulfoxylate, sodium hydrosulfite or a mixture of the latter with sodium formaldehyde The alkali metal salts of the sulfonic or carboxylic acids above specified may be added to the printing pastes at any stage of the preparation of the same. The printing of.c otton with said printing pastes may be performed in the usual manner, for example, with the aid of a printing engine, whereupon the printings are dried to a certain extent, steamed with wet steam (e. g. in a Mather-Flatt) and developed 'by oxidation, e. g., with an aqueous solution of an alkali metal bichromate and acetic acid, rinsed and soaped while boiling. It will also be possible to use the pastes containing the sulfonic or carboxylic acids above specified in sloppadding processes, and it may be mentioned that the best results are generally obtained when working with pastes which are reduced only on the fiber while steaming, which pastes generally do not contain hydrosulfites, but,- e. g., sodium formaldehyde sulfoxylate as the reducing agent.
Numerous advantages result from the presence of the alkali metal salts mentioned in the printing of cotton. In the first place it is possible in this manner to obtain concentrated dyestuff pastes, which do not settle or separate even on prolonged storing; in the second place it is frequently possible to obtain dyestufi powders of a high degree of dryness, which can be worked up immediately to very uniform printing pastes; thirdly, the addition of the alkali metal salts described above produces in most cases a considerable strengthening of the printings obtainable, which strengthening amounts in some cases to 40% and which by far exceeds the action of sodium benzylaniline sulfonate, or other similar salts which are known as additions to printing pastes.
As alkali metal salts of the kind above referred to may be mentioned by way of example: Alkali metal salts of benzoic acid, ortho-toluylic acid, salicylic acid, phthalic acid, benzene sulfonic acid, para-toluene sulfonic acid, naphthalene-alphaand beta-sulfonic acid, dialkylaniline sulfonic acids, such as sodium dimethylor diethyl-metanilate, sodium dimethylsulfanilate, sodium dimethyl-2-toluidine-4-sulfonate, furthermore, the sodium salt of cyclohexane carboxylic acid, .sodium tetrahydronaphthalenebeta-sulfonate and so on. One or more of such salts may be added to the dyestuff preparations with a good effect.
The following examples will illustrate our in-' vention without restricting it thereto:
Example 1 A. 20 parts by weight of '6.6'dichlor0-4.4'-di- 1 methylbisthio naphthene indigo (in form of an aqueous paste) 15 parts by weight of the sodium salt of dimethylmetanilic acid 40 parts by weight of glycerine are evaporated in a plain pan until the paste has a dyestuff content of 18%. The dyestuff preparation thus obtainable is of permanent durability,
does not settle as the aqueous paste, neither B. 10 parts by weight of the dyestuff preparations thus obtainable are mixed with 10 parts by weight of water and 80 parts by weight of a thickening containing in parts by weight 6 parts by weight of wheat starch 6 parts by weight of British gum powder 16 parts by weight of gum 1:1 17 parts by weight of tragacanth 65:1000 10' parts by weight of glycerine 15 parts by weight of potassium carbonate 15 parts by weight of sodium formaldehyde sulfoxylate and 15 parts by weight of water.
The printing pastes thus obtainable are used for printing purposes in the ordinary manner. The printings are steamed whilst moist, developed with potassium chromate-acetic acid and soaped while boiling. The printings produced in this manner on cotton are considerably more powerful than those obtainable by the same directions but without the addition of the alkali metal salts mentioned.
C. 20 parts by weight of the dyestufi preparations according to A. v10 parts by weight of glycerine 2 parts by weight of sodium-benzylaniline sulfonate 15 parts by weight of potassium carbonate 12 parts by weight of sodium formaldehyde sulfoxylate 41 parts by weight of a thickening containing in 100 parts by weight 35 parts by weight of British gum powder 13 parts by weight of wheat stare 2 parts by weight sodium benzylaniline sulfonate 50 parts by weight water are used for printing in the same manner as under B.
Example 2 20 parts by weight of the finely divided dyestufi, obtainable in accordance with example 1 of British Patent No. 15,60'7/07 from naphtho-oxythiophen-carboxylic acid, in form of an aqueous paste 15 parts by weight of sodium benzene sulfonate and 40 parts by weight of glycerine are evaporated on the water bath with stirring until a paste of 20% dyestufi content is obtained. The dyestufi preparation thus obtainable does not dry up and can be worked up immediately by the customary processes to printing pastes,
which on printing, for example, according to the process mentioned in Example 1, 3., yield more powerful printings than are obtainable without the addition of sodium benzene sulfonate.
Example 3 3 parts by weight of a 60% dyestufi powder obtainable by drying parts by weight of a 10.33% paste of the d'yestufi obtained in accordance with Example 1 of'U. S. Patent No. 1,667,848, in the presence of 2 parts by weight of calcined sodium carbonate and parts by weight of the sodium salt of dimethyl-metanilic acid in an enamelled drying dish on the water bath or on a roller dryer, heated by means of steam at 1 /q--2 atmospheres pressure or by some other means, are mixed for printing purposes with parts by weight of water and parts by weight of a thickening as described in Example 1, B. The printings obtainable with this paste in the usual manner are without stippling, they are fixed better and show a strengthening of shade compared with the printing'obtainable according to the same method but without the addition of the sodium salt of dimethylmetanilic acid.
Example 4 3 parts by weight of a 60% dyestuff powder, obtainable by drying 484 parts by weight of an aqueous paste of the dyestufi specified in Example 1, together with parts by weight of the sodium salt of dimethyl-metanilic acid and 2 parts by weight of sodium carbonate in the manner described in Example 3, are used for printing purposes as described in Example 3. The printings on cotton even in printing processes without previous reduction are' considerably stronger thanthe printings obtainable from a normal aqueous paste of the same dyestuff material without the addition of the sodium salt of dimethylmetanilic acid.
Example 5 v 30 parts by weight of the dyestufi of Example 1 in form of an aqueous paste 19 parts by weight of the sodium salt of dimethylmetanilic acid 0.5 parts by weight of sodium carbonate and 0.5 parts by weight of sodium isobutylnaphthalenesulfonate (as' wetting agent) are evaporated to dryness in the manner described in Example 3. The powder is finely ground and sieved and can be used without further treatment for printing in the manner described in Example 3.
The sodium salt of dimethylmetanilic acid can also be replaced by the sodium salt of dimethyl- 2-toluidine-4-sulfonic acid.
Example 6 30 parts by weight of the dyestuff specified in Example 1,- in form of an aqueous paste 18 parts by weight of the sodium salt of tetra-- hydro -naphthalene beta sulfonic acid and 2 parts by weight of sodiumcarbonate are worked up to a dry dyestufi preparation, as described in Example 3 and display the same advantages in printing as described in the preceding examples.
Example 7 30 parts by weight of 3.3'-dichloro-N-dihydro-1.2-2'.1-anthraquinone-azine (in the form of an aqueous paste) 18 parts by weight of the sodium salt of Example 8 When the dyestufi specified in Example 1 is replaced by flavanthrone and sodium benzene sulfonate is used instead of sodium dimethylmetanilate, a preparation likewise yielding stronger printings is obtained.
Example 9 tion likewise yielding stronger printings than a normal aqueous paste of the same dyestuff without the addition of. sodium benzene sulfonate, is obtained.
Example 10 In Example 1 the dyestuff can be replaced by dimethoxy-dibenzanthrone (Color Index page 265 No. 1101) and as the addition sodium salicylate or sodium dimethylmetanilic acid can be used, in which case dyestufi preparations valuable in cotton printing are likewise obtained.
Example 11 When the dyestuff specified in Example 9 is replaced by that of the German Patent No. 242,621, a preparation likewise yielding stronger printings is obtained.
Example 12 From the dyestuff obtainable according to Example 3 (first dyestufi) of British Patent No.
201,786, glycerine, and the sodium salt of diethylmetanilic acid or the sodium salt of ortho- -toluylic acid, dyestuif preparations can be produced in accordance with Examples 1 or 2, said vdyestuif preparations also yielding especially strong printings.
Example 13 From the dyestufi known in the literature (Scholl, Berichte der deutschen Chemischen Gesellsehaft Vol. 43, page 349) as pyranthrone,
in combination with the sodium salt of naphthalene-beta-sulfonic acid or dimethylmetanilic acid or dimethyl-2-toluidine-4-sulfonic acid valuable printings are obtainable in accordance with the method described in Example 1.
Erample 14 The printing capacity of the dyestuif specified in Brit. Patent No. 23179/03 isimproved by the addition of, for example, the sodium salt of cyclohexane carboxylic acid, the sodium salt of tetrahydronaphthalene-beta-sulfonic acid, the sodium salt of naphthalene-alpha-or beta-sulionic acid.
Example 15 partsby weight of an aqueous paste containing 11% of 6.6-diethoxy-2.2'-bis thionaphtheneindigo (Color Index No.
1217) v 40 parts by weight of crude glycerine 88% 1 15 Parts by weight of the sodium salt of bencontaining sodium benzene sulfonate.
with printing pastes comprising a vat dyestuil zene sulfonic acid.
I 3 Example 16 I 356. 5 parts by weight of an aqueouspaste containing 11.2% of the dyestuif obtained from bromo-1-chloro-2.3 naphthisatin' and 4 -methoxy-1-naphthol in accordance with the example of Brit. Patent No. 289,154
parts by weight of glycerine and parts by weight of the sodium salt of di- 7 methylmetanilic acid are concentrated until the paste again shows a dyestuff content of 11.2%.
Example 1? parts by weight of 4.7-4'-7'-tetramethyl- 5.5-dichlorobisthionaphthene indigo (in the form of an aqueous paste) parts by weight of crude glycerine .parts byweight of the sodium salt of benzene sulfonic acid are concentrated to a dyestuif content of 17%.
The dyestufi preparations obtainable in accordance with the last examples also display, when used for printing purposes after working up to printing pastes in any desired manner, the valuable properties already described.
We claim: I 1. Process which comprises printing cotton with a printing paste comprising a vat dyestuff and an alkali metal salt of a compound of the group consisting of unsubstituted sulfonic and carboxylic acids of the benzene and naphthalene series, hydrogenation products thereof, benzene and naphthalene sulfonic acids substituted by alkyl groups or dialkylamino groups, and benzene or naphthalene carboxylic acids substituted by a1kyl;, hydroxyor dialkylamino groups.
2. Process which comprises printing cotton and an alkali metal salt of an unsubstituted benzeneor naphthalene-sulfonic acid.
3. Process which comprises printing cotton with printing pastes comprising a vat dyestuff and an alkali metal salt of a dialkylamino benzene sulfonic acid.
4. Process which comprises printing cotton with printing pastes comprising a vat dyestufi, and an alkali metal salt of a di'methylamino ben- 5. Process which comprises printing cotton with printing pastes comprising a vat 'dyestuif and an alkali metal salt of benzene sulfonic acid.
6. Process which comprises printing cotton with printing pastes derived from vat dyestuffs, said pastes comprising an alkali metal salt of tetrahydronaphthalene sulfonic acid.
' -'7. Vat dyestufi preparations consisting of a vatdyestuff, water, glycerine and an alkali metal salt of a compound of the group consisting of unsubstituted sulfonic and carboxylic acids -of the benzene and naphthalene series, hydrogenation products thereof, benzene and naphthalene sulfonic acids substituted by alkyl groups or dialkylamino groups, and benzene or naphthalene salt of an unsubstituted benzene or naphthalene sulfonic acid.
9. Vat dyestuff preparations consisting of a vat dyestufi, water, glycerine and an alkali metal salt of a dialkylamino benzene sulfonic acid.
- 10. Vat dyestufi preparations consisting of a vat dyestufi', water, glycerine and an alkali metal salt of a dimethylamino benzene sulfonic acid.
'11. Vat dyestufi preparations consisting of avat dyestufi, water, glycerine and an alkali metal salt of benzene sulfonic acid.
12. Vat dyestuff preparations consisting of a.
vat dvestufi, water, glycerine and an alkali metal salt of tetrahydronaphthalene sulfonic acid.
13. Printing pastes suitable for printing cotton, which comprise a vat dyestuif, a; thickening and an alkali metal salt of a compound of the group consisting of sulfonic and carboxylic acids of the benzene and naphthalene series, hydrogenation products thereof, benzene and naphthalene sulfonic acids substituted by alkyl groups or dialkylamino groups, and benzene and naphthalene carboxylic acids substituted by alkyl-, hydroxyor dialkylamino groups.
14. Printing pastes suitable for printing cotton, which comprise a vat dyestufi, a thickening and an alkali metal salt of an unsubstitutedbenzene or naphthalene sulfonic acid.
15. Printing pastes suitable for printing cotton, which comprise a vat dyestufl', a thickening and an alkali metal salt of a dialkylamino benzene sulfonic acid.
16. Printing pastes suitable for printing cotton, which comprise a vat dyestuff, a thickenand an alkali metal salt of tetrahydronaphthalene sulfonic acid.
19. The process which comprises printing cotton with aprinting paste comprising 6.6- dichloro-4.4'-dimethyl bisthionaphthene indigo, and an alkali metal salt of a compound selected from the group consisting of dimethylmetanilic acid, dimethylsulfanilic acid and salicyclic acid.
20. The process which comprises printing cotton with a printing paste comprising the dyestufi cotton with a printing paste comprising 3.3-di- I chloro-N-dihydro-1.2.2.'.1-anthraquinone azine and an alkali metal salt of 'tetrahydronaphthalene-beta-sulfonic acid.
22. A printing paste comprising 6.6'-dichloro 4.4 dimethylbisthionaphthene indigo and an alkali metal salt of a compound selected from the group consistingof dimethylmetanilic acid, dimethyl-sulfanilic acid and salicylic acid. I
23. A printing paste comprising the dyestufi obtainable from naphtho-oxythiophene carboxylic acid by oxidation with potassium ferric cyanide in caustic soda solution, and an alkali metal salt of benzene sulfonic acid.
24. A printing paste comprising 3.3'-dichloro- N-dihydro-1.2.2.'.1'-anthraquinone azine and an alkali metal salt of tetrahydronaphthalene-betasulfonic acid. I
25. A vat dyestuif preparation consisting of 6.6'-dichloro-4.4'-dimethyl-bisthionaphthene indigo, water, glycerine and an alkali metal salt of a compound selected from the group consisting of dimethyl-metanilic acid, dimethylsulfanilic acid and salicylic acid.
26. A vat dyestufi preparation consisting of the dyestuff obtainable by reacting upon naphthoxythiophene-carboxylic acid with potassium ferric cyanide in caustic soda solution, water, glycerine and an alkali metal salt of benzene sulfonic acid.
27. A vat dyestufi preparation consisting of 4 3.3 dichloro-N-dihydro-l.2.2'.1' -anthraquinone azine, water, glycerine, and an alkali metal salt of tetrahydronaphthalene-beta-sulfonic acid.
SEBASTIAN GASSNER. HERMANN BERTHOLD.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US1945221A true US1945221A (en) | 1934-01-30 |
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ID=3426098
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US1945221D Expired - Lifetime US1945221A (en) | Printing of textile fibers |
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| US (1) | US1945221A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4383865A (en) * | 1981-06-08 | 1983-05-17 | Basf Wyandotte Corporation | Soft textured high strength alkali blue pigment |
-
0
- US US1945221D patent/US1945221A/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4383865A (en) * | 1981-06-08 | 1983-05-17 | Basf Wyandotte Corporation | Soft textured high strength alkali blue pigment |
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