PL24215B1 - A method of producing water-soluble pigment dyes. - Google Patents
A method of producing water-soluble pigment dyes. Download PDFInfo
- Publication number
- PL24215B1 PL24215B1 PL24215A PL2421536A PL24215B1 PL 24215 B1 PL24215 B1 PL 24215B1 PL 24215 A PL24215 A PL 24215A PL 2421536 A PL2421536 A PL 2421536A PL 24215 B1 PL24215 B1 PL 24215B1
- Authority
- PL
- Poland
- Prior art keywords
- water
- dyes
- producing water
- pigment dyes
- soluble pigment
- Prior art date
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- 239000000975 dye Substances 0.000 title claims description 13
- 239000000049 pigment Substances 0.000 title claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 150000003457 sulfones Chemical class 0.000 claims 1
- 239000000835 fiber Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- TZCXTZWJZNENPQ-UHFFFAOYSA-L Barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
- 229920000297 Rayon Polymers 0.000 description 2
- AKEJUJNQAAGONA-UHFFFAOYSA-N Sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000002964 rayon Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 2
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 2
- OXOBKZZXZVFOBB-UHFFFAOYSA-N 2-Diphenylmethylpyrrolidine Chemical compound C1CCNC1C(C=1C=CC=CC=1)C1=CC=CC=C1 OXOBKZZXZVFOBB-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- PZZYQPZGQPZBDN-UHFFFAOYSA-N Aluminium silicate Chemical compound O=[Al]O[Si](=O)O[Al]=O PZZYQPZGQPZBDN-UHFFFAOYSA-N 0.000 description 1
- 229960003563 Calcium Carbonate Drugs 0.000 description 1
- 229920003043 Cellulose fiber Polymers 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- VFNGKCDDZUSWLR-UHFFFAOYSA-N Disulfuric acid Chemical compound OS(=O)(=O)OS(O)(=O)=O VFNGKCDDZUSWLR-UHFFFAOYSA-N 0.000 description 1
- 210000002268 Wool Anatomy 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 150000004653 carbonic acids Chemical class 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- -1 for example Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
Description
Znane sa sposoby, wedlug których o- trzymuje sie nierozpuszczalne w wodzie barwniki pigmentowe o barwie od niebie¬ skiej do zielonej przez ogrzewanie do wyz¬ szych temperatur dwucyJanków ortoaryle- nów albo amidów kwasów ortocyjanoarylo- -karbonowych, jak np. nitrylu ftalowego [1,2 - dwucy janobenzenu) albo amidu kwa¬ su ortocyjanobenzoesowego, i to albo sa¬ mych tych zwiazków, albo tez w obecnosci metali albo zwiazków metali.Okazalo sie, ze barwniki pigmentowe otrzymane sposobami podanymi w paten¬ cie francuskim Nr 738 796 i patencie an¬ gielskim Nr 410 814 mozna uczynic roz¬ puszczalnymi w wodzie przez dzialanie w niskiej temperaturze srodkami o silnym dzialaniu sulfonujacym. Faktu tego nie mozna bylo przewidziec, poniewaz powyz¬ sze barwniki pigmentowe rozpuszczaja sie w kwasie siarkowym w temperaturze po¬ kojowej nie ulegajac zadnej zmianie, na¬ tomiast przy ogrzewaniu tego roztworu barwniki te rozkladaja sie. Jako srodki o silnym dzialaniu sulfonujacym, t. j. pole¬ gajacym na wprowadzaniu grup S0S do pierscienia benzenowego, naftalenowego i t. d., nalezy uwzglednic przede wszyst¬ kim kwas siarkowy dymiacy (o pewnej zawartosci bezwodnika kwasu siarkowego)i kwas chlorosulfonowy. Temperatura reak¬ cji, nie powinna znacznie przekraczac 20°C.Okazalo sie ponadto, ze otrzymane w ten spqsób rozpuszczalne w wodzie barw¬ niki posiadaja zdolnosc silnego barwienia zarówno wlókien zwierzecych (welny, je¬ dwabiu), jak i wlókien celulozy, np, ba¬ welny albo sztucznego jedwabiu wiskozo¬ wego, i wskutek odpornosci tych zabarwien na rózne czynniki maja duze znaczenie w technice. Mozna takze barwniki uczynione rozpuszczalnymi w wodzie wedlug wyna¬ lazku niniejszego osadzac w znany sposób na podlozach, jak na weglanie wapnia, siarczanie baru, glince, kaolinie i tym po¬ dobnych, i w tej postaci stosowac jako barwniki pigmentowe, 4 Przyklad. 194 czesci wagowe produk¬ tu, otrzymanego wedlug patentu angiel¬ skiego Nr 410 814 i patentu francuskiego Nr 738 796, o wzorze (C12H6NJ4Cu albo C48H24N8 Cu wprowadza sie malymi daw¬ kami dobrze chlodzac i mieszajac do 500 czesci wagowych dymiacego kwasu siarko¬ wego o zawartosci 20% bezwodnika siar¬ kowego. Mieszanie uskutecznia sie na zim¬ no w ciagu 2 godzin, po czym mieszanine ogrzewa sie do 20°C. Skoro tylko próbka mieszaniny reakcyjnej, rozcienczona woda z lodem, rozpusci sie klarownie w roztwo¬ rze sody, wylewa sie mieszanine na lód, zobojetnia soda albo wodorotlenkiem sodu i straca barwnik dodajac soli kuchennej.Po przesaczeniu i wysuszeniu pozostalosci otrzymuje sie zielony proszek, którego wodny roztwór barwi na zielono wlókna zwierzece i wlókna zawierajace celuloze.Zabarwienia te sa odporne na dzialanie swiatla, kwasu i lugów. PLThere are known methods according to which water-insoluble pigments of a blue to green color are obtained by heating to higher temperatures orthoaryl dicylates or amides of orthocyanoaryl carbonic acids, such as, for example, phthalic nitrile [1, 2 - dianobenzene) or orthocyanobenzoic acid amide, and either of these compounds alone, or in the presence of metals or metal compounds. It turned out that pigment dyes obtained by the methods described in French patent No. 738 796 and Ingredients No. 410 814 can be rendered water-soluble by treatment at low temperature with a highly sulfonating agent. This fact could not be foreseen, since the above pigment dyes dissolve in sulfuric acid at room temperature without undergoing any change, while when the solution is heated, these dyes decompose. Agents with a strong sulphonating effect, i.e., consisting in the introduction of SO S groups into the benzene, naphthalene ring, and so on, are primarily fuming sulfuric acid (with a certain content of sulfuric acid anhydride) and chlorosulfonic acid. The reaction temperature should not significantly exceed 20 ° C. It has also turned out that the water-soluble dyes obtained in this way have the ability to strongly dye both animal fibers (wool, whip) and cellulose fibers, e.g. cotton or rayon rayon, and due to the resistance of these colors to various factors, they are of great importance in the art. Dyes made water-soluble according to the present invention can also be deposited in a manner known per se on substrates such as calcium carbonate, barium sulphate, clay, kaolin and the like, and used in this form as pigment dyes. 194 parts by weight of the product, obtained according to the English patent No. 410 814 and French patent No. 738 796, of the formula (C12H6NJ4Cu or C48H24N8 Cu are introduced in small doses, cooling well and mixing up to 500 parts by weight of fuming sulfuric acid with 20% sulfuric anhydride. Stirring becomes cold for 2 hours, then the mixture is heated to 20 ° C. As soon as a sample of the reaction mixture, diluted with ice water, dissolves clearly in the soda solution, The mixture is poured on ice, neutralized with soda or sodium hydroxide and the dye is lost by adding table salt. After filtering and drying the residue, a green powder is obtained, the aqueous solution of which dyes animal fibers and fibers containing cellulose green. These colors are resistant to light, acid and lugów PL
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL24215B1 true PL24215B1 (en) | 1936-12-31 |
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