SE204674C1

SE204674C1 -

Info

Publication number: SE204674C1
Authority: SE
Publication date: 1965-01-01

Description

Uppfinnare: II Gunst Prioritet begard Iran den 12 augusti och 24 oktober 1960 (Schweiz) Foreliggande uppfinning hanfor sig till nya, vardefulla, for fargning av cellulosahaltiga material med fiberstruktur lampliga azofargamnen med formeln On- 1Cn- 2n-1 R—N \\/NH—X (1) S031-1 van i R betecknar en naftalenrest, som uppvisar tre sulfonsyragrupper, R, betecknar en benseneller naftaldnrest, n betecknar ett positivt helt tal med ett varde av hogst 2 och X betecknar en klorerad eller bromerad 1: 3: 5-triazinrest, som genom en ringkolatom at bnnden vid—NH-bryggan. Inventor: II Favor Priority requested Iran on 12 August and 24 October 1960 (Switzerland) The present invention relates to new, valuable, for dyeing cellulosic materials with fibrous structure suitable azo dyes of the formula On- 1Cn- 2n-1 R — N \\ / NH-X (1) SO 31-1 van in R represents a naphthalene residue, which has three sulfonic acid groups, R, represents a benzene or naphthalene residue, n represents a positive integer with a value of log 2 and X represents a chlorinated or brominated 1: 3 : 5-triazine residue, as through a ring carbon atom at the bond at — the NH bridge.

Sasom rester X ifragakomma exempelvis en. diklortriazinrest eller monoklortriazinrest, sasom den med formeln —C C—Cl I N N / van i Y betecknar en eventuellt ytterligare substituerad arninogrupp eller en fOretrad oxigrupp eller tiogrupp. As residues X, for example, one. dichlorotriazine residue or monochlorotriazine residue, as the one of the formula -C C-Cl I N N / van in Y represents an optionally further substituted arnino group or an ether oxy group or thio group.

De formeln (1) motsvarande fargamnena enligt uppfinningen ka,n man enligt i och f Or sig vanliga metoder framstalla av motsvarande fargamnen med formeln On_ 1Cn- 11-1 2n- 1 R—N=N—R1—N=N—/ /1/\NI-1, \X SOaH van i R, R, och 11 ha den under formeln (1) angivna betydelsen, t. ex. genom kondensation med dieller triklor- eller di- eller tribrom-1,3,5-triaziner. The formulas (1) corresponding to the dyes according to the invention can be prepared according to the usual methods of the corresponding dyes of the formula On_ 1Cn- 11-1 2n- 1 R — N = N — R1 — N = N— / / 1 / \ NI-1, \ X SOaH van in R, R, and 11 have the meaning given under formula (1), e.g. by condensation with di or trichloro- or di- or tribromo-1,3,5-triazines.

Sasom sadana triaziner ma exempelvis namnas cya,nurbromid, framforailt cya,nurklorid eller de primara kondensationsprodukter ay cyanurklorid, som innehalla tva kloratomer och i stallet for en tredje kloratom en. 1-12N-grupp eller en organisk rest. Sadana primara kondensationsprodukter av en mol cya,nurklorid och en mol av en reaktionsbenagen, organisk merkapto- eller hydroxylforening (t. ex. en mol av en fenol eller alkohol), en mol ammoniak eller en. mol av en organisk a.min med eller titan fargamneskaraktar (t. ex. metyl-, isopropyl-, cyklohexyl- eller fenylamin, climetylamin, etylamin, etanolamin, N-metylfenylamin, y-metoxipropylamin, morfolin, aminoetansulfonsyra, aminoattiksyra, o-, m- eller p-aminobensoe'syra, arninobensensulfonsyror, sasom fenolsulfon.- syror, o-, m- eller p-aminoben,sen.sulfonsyra. och 1- amin.obensen-2,5-disulfonsyra, aminonaftalensulfonsyra, t. ex. 2-aminonaftalen-4,8-disulfonsyra, (2) 2 d,essutom merkaptoforeningar, sasom 2-merka,ptobenstiazol, merkapto attiksyra) kunna, framstallas enligt i och for sig Undo, metoder. Man. kan a.ven med fordel exempelvis omsatta 2,4,6-tribrom- eller triklor-1,3,5-triazin a ena sidan med ett fargamne med formeln (2) till en dihalogentriazinkondensa- tionsprodukt ochan.dra, sidan omsatta, med ammoniak eller med en orga,nisk merkapto- eller hydroxylfarening eller med en. organisk, hogst sekundar monoamin. till en monohalogentriazinkondensationsprodukt. Such triazines may be called, for example, cya, nurbromide, precursor cya, nurchloride or the primary condensation products ay cyanuric chloride, which contain two chlorine atoms and instead of a third chlorine atom one. 1-12N group or an organic residue. Such primary condensation products of one mole of cya, nur chloride and one mole of a reactant, organic mercapto- or hydroxyl compound (eg one mole of a phenol or alcohol), one mole of ammonia or one. moles of an organic amine with or titanium dye character (eg methyl, isopropyl, cyclohexyl or phenylamine, climethylamine, ethylamine, ethanolamine, N-methylphenylamine, γ-methoxypropylamine, morpholine, aminoethanesulfonic acid, aminoacetic acid, o-, m- or p-aminobenzoic acid, aminobenzenesulfonic acids, such as phenolic sulfonic acids, o-, m- or p-aminobenzene, sen.sulfonic acid, and 1-aminobenzene-2,5-disulfonic acid, aminonaphthalenesulfonic acid, e.g. 2-Aminonaphthalene-4,8-disulfonic acid, (2) 2 d, in addition to mercapto compounds, such as 2-merka, ptobenstiazole, mercaptoacetic acid) can be prepared according to per se Undo, methods. MAN. may also advantageously react, for example, 2,4,6-tribromo- or trichloro-1,3,5-triazine on the one hand with a dye of the formula (2) into a dihalo-triazine condensation product and, on the other hand, reacted with ammonia or with an organic mercapto- or hydroxyl compound or with a. organic, highly secondary monoamine. to a monohalotriazine condensation product.

Konclensa,tionen enligt uppfinningen genomfor man lampligen under anvandning av syrabindande medel, sasom natriumkarbonat eller natriumhydroxid, och under sadana betingelser, att i slutprodukten fortfarande kvarbliva en eller tva utbytbara halogen atomer, clvs. exempelvis i organiska, losningsmedel eller vid relativt laga temperaturer I vattenhaltigt-organiska eller i va,ttenhaltiga medel. The concentration according to the invention is suitably carried out using acid-binding agents, such as sodium carbonate or sodium hydroxide, and under such conditions that one or two exchangeable halogen atoms still remain in the final product, i.e. for example in organic solvents or at relatively low temperatures in aqueous-organic or in aqueous means.

De acylerbara utgangsfargamnen.a med formeln (2) kunna erhallas genom koppling av 1-aminonaftalen-8-sulfonsyra, 2-metwd-1-aminonaftalen6-sulfonsyra eller framforallt 1-aminonaftalen-6- sulfonsyra och 1-aminonaftalen-7-sulfonsyra med cliazofareningar av ett fargamne med formeln R—N=N—R1—NH2(3) For framstallning av monoazofargamnena med formeln (3) kunna diazoterade 1- eller 2-aminonaftalen-trisulfonsyror, sasom 1-na,ftylamin-2,4,7- -2,4,8-, -2,5,7-, -3,6,8- eller -4,6,8-trisulfonsyra och 2-naftylamin-1,3,7-, -1,5,7-, -3,5,7-, -4,6,8- eller -3,6,8-trisulfonsyra i surt medium kopplas med oeller m-toluidin, kresidin, o- eller m-anisidin, 3- acetylaraino-1-aminobensen, 3-metansulfonylamino-1-aminobensen och a-naftylamin, framforallt med xylidiner eller med 1-amino-naftalen-6-, -7eller -8-monosulfonsyror. The acylatable starting dyes of formula (2) can be obtained by coupling 1-aminonaphthalene-8-sulfonic acid, 2-methyl-1-aminonaphthalene-6-sulfonic acid or especially 1-aminonaphthalene-6-sulfonic acid and 1-aminonaphthalene-7-sulfonic acid with Cliazo compounds of a dye of the formula R — N = N — R1 — NH2 (3) For the preparation of the monoazo dyes of the formula (3), diazotized 1- or 2-aminonaphthalene-trisulfonic acids, such as 1-na, phthylamine-2,4,7 -2,4,8-, -2,5,7-, -3,6,8- or -4,6,8-trisulfonic acid and 2-naphthylamine-1,3,7-, -,5, 7-, -3,5,7-, -4,6,8- or -3,6,8-trisulfonic acid in acidic medium is coupled with o or m-toluidine, cresidine, o- or m-anisidine, 3-acetylaraino- 1-aminobenzene, 3-methanesulfonylamino-1-aminobenzene and α-naphthylamine, especially with xylidines or with 1-amino-naphthalene-6-, -7 or -8-monosulfonic acids.

Diazoteringen av de for framstallningen av fargamnena med formeln (2) angivna aminomonoazofargamnena med formeln (3) kan ske enligt i och for sig Janda metoder, t. ex. med hjalp av mineralsyra, speciellt saltsyra, och natriumnitrit. Kopplingen a,v de pa sá satt erhallna diazoforeningarna med angivna 1-aminonaftalensulfonsyror, som kunna koppla i 4-stallning, sker likaledes enligt i och for sig kan.da metoder. The diazotization of the aminomonoazo dyes of formula (3) indicated for the preparation of the dyes of formula (2) can take place according to per se Janda methods, e.g. with the aid of mineral acid, especially hydrochloric acid, and sodium nitrite. The coupling of the diazo compounds thus obtained with the indicated 1-aminonaphthalenesulfonic acids, which can be coupled in the 4-position, also takes place according to methods known per se.

Isoleringen av de bildade fargamnena sker foretradesvis vid sa lag temperatur som mojligt genom utsaltning och filtrering. De filtrerade fargamn,ena kunna eventuellt torkas efter tillsats av utdrygningsmedel och/eller buffertmedel, sasom blandningar av lika delar mono- och dinatriumfosfat; foretradesvis faretages torkningen vid icke alltfor hoga, temperaturer och under forminskat tryck. Genom forstoftningstorkning av hela framstallningsblandningen kan man i vissa fall direkt framstalla de terra preparaten enligt uppfinningen, dvs. utan. mellanisolering av fargamnena,. The dyes formed are preferably isolated at as low a temperature as possible by salting out and filtration. The filtered dyes, one may optionally be dried after the addition of excipients and / or buffering agents, such as mixtures of equal parts of mono- and disodium phosphate; preferably the drying is carried out at not too high temperatures and under reduced pressure. By spray-drying the entire preparation mixture, it is possible in some cases to directly prepare the terra preparations according to the invention, ie. without. intermediate insulation of the dyes ,.

De nya fargamnena enligt uppfinningen aro lampliga for fargning och tryckning av de mest olika, material, sasom ylle, superpolyamid- och superpolyuretanfibrer och speciellt cellulosa,haltiga material med fiberstruktur, sasom lin, regenererad cellulosa eller framforallt bomull. De aro helt speciellt lampliga far fargning av cellulosa enligt det s. k. foulardfargningsforfarandet, enligt vilket va,ran impregneras med vattenhaltiga och eventuellt aven salthaltiga fargamneslosningar och fargamnena fixeras efter en alkalibehandling i kyla, om dihalogentriazinfargamnen anvanda,s, eller i varme, i handelse av monohalogentriazinfargamnen. Detta forfarande och direktfargningsmetoderna, som Even aro anvandbara vid manga av de ealigt foreliggande forfarande erhallna fargamnena, giva vardefulla, tvattakta fixerade fargningar, medan enligt tryckforfarandet akta tryck erhallas. The new dyes according to the invention are suitable for dyeing and printing the most diverse materials, such as wool, superpolyamide and superpolyurethane fibers and especially cellulose, containing materials with fiber structure, such as flax, regenerated cellulose or especially cotton. They are particularly suitable for dyeing cellulose according to the so-called scarf dyeing process, according to which the product is impregnated with aqueous and possibly also saline dye solutions and the dyes are fixed after an alkali treatment in cold, if the dihalogenetriazine dyes use, or in monohalogen, . This process and the direct dyeing methods, which are equally applicable to many of the dyes obtained in the present process, give valuable, two-stroke fixed dyes, while according to the printing process careful printing is obtained.

For forbattring av vataktheten är det lampligt att underkasta de pa sã satt erhallna fargningarna och trycken en grundlig skoljning med kallt och varmt vatten, eventuellt under tillsats av ett medel, som verkar dispergerande och som beframjar diffusionen av icke fixerade fargamn.esandela,r. To improve the watertightness, it is convenient to subject the dyes and pressures thus obtained to a thorough rinsing with cold and hot water, possibly with the addition of a dispersant which promotes the diffusion of non-fixed dyes.

De fargningar, som kunna erhallas med de nya farganmena pa polyhydroxylerade, speciellt cellulosahaltiga fibrer, utmarka sig i regel av hog bestanclighet lies fiber-fargamnesforeningen, genom lätt uttvattbarhet av fargamnesandelarna, som icke ha reagerat, genom god ljusakthet, genom ett gott forhallande vid skrynkelhardighetsbehandling och framfOrallt genom framtradande tvattakthet. The dyes which can be obtained with the new dyes on polyhydroxylated, especially cellulosic fibers, are generally distinguished by the high consistency of the fiber dye compound, by easy dilatability of the unreacted dye components, by good lightness, by good ratio in wrinkle hardness treatment. and above all through prominent water rate.

I foljande exempel beteckna delar, savida intet a,nnat angives, viktdelar, procent viktpro cent och temperaturerna Oro angivna, i celsiusgrader. vikt- och volymdelar bestar samma forhallande som mellan liter och kg. In the following examples, parts, unless otherwise indicated, denote parts by weight, percent by weight and temperatures are indicated in degrees Celsius. parts by weight and volume consist of the same ratio as between liters and kg.

Exempel 1. 18,6 delar cyanurklorid suspenderas i en bla,ndning av 300 delar is och 200 debar isva,tten. Till detta, atter man den pa pll 7 installda losningen av 74,9 delar av aminodisazofargamnet (framstallt genom koppling av diazoforeningen av 1-aminonaftalen-2,5,7-trisulfonsyra med 1-amino2,5-dimetylbensen, vidare-diazotering av det bildade aminomonoazofargamnet och koppling med 1-aminonaftalen-6-sulfonsyra) i 500 delar vatten. Under kondensationen hailer man temperaturen pa c:a 10-15° och pH-vardet mellan 4 och 6. Efter 2 timmar utskiljes fargamnet genom tillsa,ts av natriumklorid, franfiltreras och tvattas med natriumkloridlosning. Filterpresskakorna tillsattas 5 delar av en blanclnLng av lika debar mono- och dinatriumfosfat sasom buffertmedel och pressgodset torkas vid 30° i vakuum. Det pa sa satt erhallna fargamnet fargar bomull ur alkaliskt bad vid 25-35° i tvatt- och ljusakta, gulbruna fargtoner. Example 1. 18.6 parts of cyanuric chloride are suspended in a mixture of 300 parts of ice and 200 debar of ice water. To this, again, the solution of 74.9 parts of the aminodisazofar compound (prepared by coupling the diazo compound of 1-aminonaphthalene-2,5,7-trisulfonic acid with 1-amino2,5-dimethylbenzene) is further installed in Figure 7, further diazotizing the formed the aminomonoazophar gum and coupling with 1-aminonaphthalene-6-sulfonic acid) in 500 parts of water. During the condensation, the temperature is maintained at about 10-15 ° and the pH value between 4 and 6. After 2 hours, the dye is separated by adding sodium chloride, filtering off and washing with sodium chloride solution. The filter presses are added to 5 parts of a mixture of equally debar mono- and disodium phosphate as buffering agent and the press is dried at 30 ° in vacuum. The dye thus obtained dyes cotton from an alkaline bath at 25-35 ° in a watery and light yellow, yellow-brown color.

Exempel 2. 18,6 delar cyanurklorid suspenderas i en blandning ay 300 delar is och 200 debar is- 3 vatten. Till detta satter man Disningen av 85,1 delar av amino disazofargamnet (framstallt genom koppling av diazoforeningen av 1-aminonaftalen2,5,7-trisulfonsyra med 1-aminonaftalen-6-sulfonsyra., vidarediazotering av det bildade aminomonoazofargamnet och koppling med 1-aminonaftalen6-sulfonsyra) i 500 delar vatten. Vid c:a 10 hailer man pH-vardet mella,n. 5 och 7. Efter 2 timmar till-slitter man 300 delar ammoniak, omriir 4 timmar vid 40°, avskiljer fargamnet genom salttillsats, filtrerar framstallningsbla.ndningen och torkar erMina filterkakor. Det pa sa satt erhallna pulvret fargar bomull ir alkaliskt bad i tvatt- och ljusakta, rodbruna fargtoner. Example 2. 18.6 parts of cyanuric chloride are suspended in a mixture of 300 parts of ice and 200 debar of ice water. To this is added the distillation of 85.1 parts of the amino disazofar compound (prepared by coupling the diazo compound of 1-aminonaphthalene 2,5,7-trisulfonic acid with 1-aminonaphthalene-6-sulfonic acid., Further diazotizing the formed aminomonoazofar compound and coupling with 1-aminonaphthalene6 -sulfonic acid) in 500 parts of water. At about 10, the pH value is measured between, n. 5 and 7. After 2 hours, 300 parts of ammonia are consumed, stirred for 4 hours at 40 °, the dye is separated by salt addition, the production mixture is filtered and the filter cakes are dried. The powder thus obtained dyes cotton in an alkaline bath in watery and light, reddish-brown tones.

Exempel 3. 18,6 delar cyanurklorid suspenderas i en blandning av 300 delar is och 200 delar isvatten. Till detta atter man en losnin,g av 76,5 delar av ett amino disazof argamne (framsthllt genom koppling av diazoforeningen av 1-aminonaftalen-2,5,7-trisulfonsyra och 1-mety1-4-metoxi3-aminobensen, vidarediazotering av det bildade aminomonoazofargamnet och koppling med 1- aminonaftalen-6-sulfonsyra) i 500 delar vatten. Under kondensationen Hiles temperaturen pa c:a 0 och pH-vardet mellan 5 och 7. Efter 2 timmar tillsatter man 300 delar 2-n ammoniak, omrtir 4 timmar vid 40°, avskiljer fargamnet, filtrerar och torkar. Ur alkaliskt bad fargar det pa sa satt erhallna fargamnet bomull i tvatt- och ljusakta, rodbruna fargtoner, Ett fargamne med mycket liknande egenskaper erhalles, om man i stallet for 1-aminonaftalen2,5,7-trisulfonsyra anvander 1-aminonaftalen-4,6, S0,11 8-trisulfonsyra, medan 2-aminonaftalen-4,6,8-trisulfonsyra ger ett fargamne, som fargar bomull i nagot gulaktigare, bruna toner. Example 3. 18.6 parts of cyanuric chloride are suspended in a mixture of 300 parts of ice and 200 parts of ice water. To this is added again a solution of 76.5 parts of an amino disazof argamne (prepared by coupling the diazo compound of 1-aminonaphthalene-2,5,7-trisulfonic acid and 1-methyl-4-methoxy-3-aminobenzene, further diazotizing the formed the aminomonoazo compound and coupling with 1-aminonaphthalene-6-sulfonic acid) in 500 parts of water. During the condensation Hiles the temperature of about 0 and the pH value between 5 and 7. After 2 hours, 300 parts of 2-n ammonia are added, stirred for 4 hours at 40 °, the dye is separated, filtered and dried. From alkaline bath, the dye obtained in this way colors cotton in light and light brown, reddish-brown hues. A dye with very similar properties is obtained if 1-aminonaphthalene-4,6 is used instead of 1-aminonaphthalene 2,5,5-trisulfonic acid. , S0,11 8-trisulfonic acid, while 2-aminonaphthalene-4,6,8-trisulfonic acid gives a dye, which dyes cotton in slightly yellowish, brown tones.

Exempel 4. 18,6 delar cyanurklorid suspen.deras i en blandning av 300 delar is och 200 delar isvatten. Till denna blandning Otter man en pa pH 7 installd laming av 74,9 delar av ett 1-aminodisazofargamne (framstallt genom koppling av diazoforeningen av 1-amino-naftalen.-2,5,7-trisulfonsyra med 1-amino-2,5-dimetylbensen, vidarediazotering av det bildade aminomonoazofargamnet och koppling med 1-aminonaftaIen-6-sulfonsyra) I 500 delar vatten. Under kondensationen hales temp eraturen pa c:a 10-15° och pH-vardet mellan 4 och 6. Efter 2 timmar tillsatter man 300 delar 2-n ammoniak, omror 4 timmar vid 40°, omrOr kallt, faller fargamnet med natriumklorid, filtrerar och torkar. Ur alkaliskt bad fargar det pa sa sat erhallna fargamnet bomull i tvatt- och ljusakta gulbruna toner. Example 4. 18.6 parts of cyanuric chloride are suspended in a mixture of 300 parts of ice and 200 parts of ice water. To this mixture is added a pH 7-adjusted paralysis of 74.9 parts of a 1-aminodisazofar compound (prepared by coupling the diazo compound of 1-amino-naphthalene-2,5,7-trisulfonic acid with 1-amino-2,5 -dimethylbenzene, further diazotization of the aminomonoazofar compound formed and coupling with 1-aminonaphthalene-6-sulfonic acid) in 500 parts of water. During the condensation the temperature is kept at about 10-15 ° and the pH value between 4 and 6. After 2 hours 300 parts of 2-n ammonia are added, stirring for 4 hours at 40 °, stirring cold, the dye falls with sodium chloride, filters and dries. From alkaline bath, the dye obtained in this way colors cotton in watery and light yellow-brown tones.

Ett liknande fargamn,e erhalles, om man ersatier det anvanda aminodisa.zoffirgamnet med det disazofargamne, som man erhaller genom koppling av 1-amino-3-metylbensen med diazoterad 1-amino-naftalen-2,5,7-trisulfonsyra, vidarediazotering av det bildade aminomonoazofargamnet och koppling med 1-aminonaftalen-7-sulfonsyra. A similar dye is obtained by replacing the aminodisazole compound used with the disazo dye obtained by coupling 1-amino-3-methylbenzene with diazotized 1-amino-naphthalene-2,5,7-trisulfonic acid, further rediazotizing the aminomonoazofar formed and coupling with 1-aminonaphthalene-7-sulfonic acid.

Enligt metoden i exempel 2-4 erhaller man av cyanurklorid, de i spat Iii foljande tabell angivna foreningarna och de i spalt I angivna disazofargamnena liknande fargamnen, som fargar cellulosa i de i spalt III angivna fargtonerna. According to the method of Examples 2-4, cyanuric chloride, the compounds listed in Table Iii of the following table and the disazo dyes listed in column I are obtained, similar to the dyes which dye cellulose in the color shades given in column III.

—N=N—/\ —NH2ammoniakviolettbrun \—S031-1 HO2S—/\ \ S031-1 HO3S—/ /S0311 z—N=N—/\ p-metoxipropyla min /_N= N_ \/\ S0311 \/ \/ S0311 4_ 31-I /\—NH2ammoniakrodbrun HO BS—/ /\/—N=N—\/\ SO 3H \ / SO BH —NH2 \ /133H \/CH 3 \/ CHB— \N=.-N N-metylanilin etanolamin dietanolamin 2-aminobensoesyra fenol N-metylanilinsulfonsyra 1-amino-4(4'-amino- olivbrun fenylamino)-antrakinon-2,3'-disulfonsyra HO 3S—/ SO3H /—SOBH SO 3HHO NHB opak seharlakan \/\ —HOBS—SO BH / \/ /SO BH CHB ammoniakorangebrun HO 3S—/ N = \ —SO SO BH \/ piperidin morfolin Exempel 5. 2 delar av det enligt exempel 2 framstallda fargamnet ltisas i 100 delar vatten. Med derma %suing impregnerar man pa foulard vid 60-80° en bomullsvav och urpressar overskottet vatska pa sa satt, att tyget kvarhaller 75 procent av sin vikt fargamneslosning. —N = N - / \ —NH2 ammonia violet brown \ —S031-1 HO2S - / \ \ S031-1 HO3S— / / S0311 z — N = N - / \ p-methoxypropylene min / _N = N_ \ / \ S0311 \ / \ / S0311 4_ 31-I / \ - NH2ammoniakrodbrun HO BS— / / \ / - N = N - \ / \ SO 3H \ / SO BH —NH2 \ / 133H \ / CH 3 \ / CHB— \ N = .- N N-methylaniline ethanolamine diethanolamine 2-aminobenzoic acid phenol N-methylanilinesulfonic acid 1-amino-4 (4'-amino-olive brown phenylamino) -anthraquinone-2,3'-disulfonic acid HO 3S— / SO3H / —SOBH SO 3HHO NHB opaque seharlakan \ / \ —HOBS — SO BH / \ / / SO BH CHB ammonia orange-brown HO 3S— / N = \ —SO SO BH \ / piperidine morpholine Example 5. 2 parts of the dye prepared according to Example 2 are dissolved in 100 parts of water. With this% suction, a cotton swab is impregnated on the scarf at 60-80 ° and the excess liquid is squeezed out in such a way that the fabric retains 75 percent of its weight.

Den pa sa satt impregnerade varan torkas, impregneras darefter vid rumstemperatur i en lbsning, som per liter innehaller 10 gram natriumhydroxid och 300 gram natriumklorid, urpressas till 75 procent vatskeupptagning och angas 60 sekunder vid 100-101°. Darefter skoljes, behandlas i 0,5-procentig natriumbikarbonatlosning, skoljes, tvalas under 15 minuter i en 0,3-procentig losRing av ett jonfritt tvattmedel vid koktemperatur och torkas. Man erhaller en. rodbrun, tvatt- och ljusakta fargning. The impregnated product is then dried, then impregnated at room temperature in a solution containing 10 grams of sodium hydroxide and 300 grams of sodium chloride per liter, squeezed out to 75 percent liquid uptake and allowed to stand for 60 seconds at 100-101 °. It is then rinsed, treated in 0.5% sodium bicarbonate solution, rinsed, cooled for 15 minutes in a 0.3% solution of an ion-free detergent at boiling temperature and dried. You get one. reddish brown, watery and light-colored.

Exempel 6. 2 delar av det enligt exempel 2 framstallda fargamn,et losas i 100 delar vatten genom kort uppkokning. Den erhallna stamlosningen satter man till 2900 delar vatten av 20°. Efter tillsats av 30 delar trinatriumfosfat och 60 defer natriumklorid ingar man med 100 delar bomull, hojer temperaturen pa 45 minuter till 800, tillsatter annu en gang 60 delar natriumklorid och fargar ytterligare 30 minuter vid 90-95°. Darefter skoljes fargningen, och efterbehandla,s 15 minuter i en losning av 2 g/1 soda och 3 g/1 tval vid koktemperatur, skoljes och torkas. Man erhailer en kraftig, rodbrun fargning. Example 6. 2 parts of the dye prepared according to Example 2 are dissolved in 100 parts of water by short boiling. The resulting stock solution is added to 2900 parts of water of 20 °. After adding 30 parts of trisodium phosphate and 60 parts of sodium chloride, add 100 parts of cotton, raise the temperature in 45 minutes to 800, add 60 parts of sodium chloride once more and dye for a further 30 minutes at 90-95 °. Then rinse the dye, and finish, s 15 minutes in a solution of 2 g / l soda and 3 g / l sample at boiling temperature, rinse and dry. A strong, reddish-brown coloration is obtained.

SO ,H On_ AL_ 2n.. SO, H On_ AL_ 2n ..

HO 3S—R2—N=N—R1---N=N-7 SO ,H van i R, och R, vardera betecknar en naftalenrest, koholer, fenoler, merkaptaner, ammoniak eller ett Z betecknar vate och det a,ndra Z en. sulfon- organiska aminer. syragrupp, och eventuellt °matter ytterligare till3. FOrfarande enligt patentanspraket 1, kanne- monoklortriazinkondensationsprodukter med al- tecknat darav, att man anvander ett aminodisazo- fargamne med formeln SO,H HO 3S — R2 — N = N — R1 --- N = N-7 SO, H van in R 1 and R 2, each represents a naphthalene residue, coholes, phenols, mercaptans, ammonia or a Z denotes vate and the other Z and. sulfonic organic amines. acid group, and possibly ° mats further to3. Process according to claim 1, can monochlorotriazine condensation products, characterized in that an aminodisazo dye of the formula SO, H

Claims

Patent claim: 1. Modification of the process according to patent 189 382 for the preparation of the new azo compounds, characterized in that the azo compounds of the formula are prepared by condensation of the corresponding aminodisazo compounds with di- or trichloro- or tribromo-1,3,5-triazines: R 1 represents a naphthalene residue, which has three sulfonic acid groups, and R 1 represents a benzene or naphthalene residue, n represents a positive heft number with a value of log 2 and X denotes a halogenated 1,3,5-triazine residue.

2. Modification of the process according to claim 1, characterized in that in the molar ratio of about 1: 1, 2,4,6-trichloro-1,3,5-triazine is condensed, with an aminodisazofar compound of the form: /, \\ z — Nli 2 HO 3S — R2 — N = N — R3 — N = N— / SO, H / \ / - NH 2 6 van in R, denotes an n-agreement residue and R , fOretradesvis en. xylidia residue, which has both azo groups in opposition to each other, one Z denotes vate and the other Z a sulfonic acid group. 4. A process according to claim 2, characterized in that in the resulting dichlorium the triazinylamino-disazofar compound is replaced by a chlorine atom by condensation with ammonia or with an organic, at most seconds and preferably less than 13 carbon atoms having monoamine. 5. Process according to any one of claims 1-4, characterized in that the dyes of the formula (\ —N = N — R1 — N = N— 1 — NH, HO, S - SO, H SO, H \) z / van R denotes a benzene or naphthalene residue, one Z denotes vale and part Z denotes a sulfonic acid group.