BE633447A - - Google Patents

Description

       

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   S A N D O Z S. A.



    Dye! basic, their manufacturing processes and their applications.



    , Swiss patent application of May 3, 1963 in its favor.



  The present invention relates to basic dyes
 EMI1.1
 corresponding to the formula ni 1 A 1 y * N 1% X (X) it 3 1.-0, NB4 n in which A represents the radical of a dye free from carboxylic and sulfonic groups, represents an optionally substituted methylene group or a divalent or trivalent radical linked by such a group to the neighboring nitrogen atom,
 EMI1.2
 ai represents an optionally substituted alooy7, iquo, oyolo-alkyl, aralooyl or phenyl radical or, together with R2 and the neighboring nitrogen atom * a heterocyclic system or, together with the bridge element and the d atom 'neighboring nitrogen * a heterocyclic system or.

   together with y, A and the neighboring nitrogen atom, heterocyclic system,
 EMI1.3
 R2 represents a .lc01l1u radical. 'v.tu811.nt'.ubetituated or an optionally substituted oyolo-alooyl, aralkyl or phenyl radical or, together' with R1 and the neighboring nitrogen atom $ a heterocyclic system R3 represents a hydrogen atom or an alkyl radical optionally substituted or a

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 EMI2.1
 acyclic radical which can form a 07010 with zt4 and v or * when IR1 and R2 are other than a phenyl radical or a phenyl radical #
R4 represents a hydrogen atom or an optionally substituted alkyl radical or an acyl radical, n has the value 1 or 2, m has the value 1 or 2, if n is 1,

   and 2 if n is 2 and
X represents an anion corresponding to each cation of dye.



  The manufacturing process of these dyes consists of replacing or transforming a compound corresponding to the formula
 EMI2.2
 n substituents Z by grouped n corresponding to the formula
 EMI2.3
 in which B represents A or the radical of a compound capable of forming a dye and Z represents a substituent which can be replaced by a group corresponding to formula (III) or which can transform this into such a group and then transform the product of the reaction by dyeing if B represents the radical of a component capable of transforming into a dye.

   

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   One of the embodiments of this process is characterized by the reaction of 1 molecule of a compound corresponding to the formula
 EMI3.1
 in which E represents the acid radical of an enter with n molecules of a compound corresponding to the formula
 EMI3.2
 followed by the transformation of the reaction product into a dye, - when B represents the radical of a compound capable of transforming into a dye.



  We can also react 1 molecule of a component corresponding to the formula
 EMI3.3
 with n molecules of a compound corresponding to the formula
 EMI3.4
 quaternizing the reaction product and, when B represents the radical of a compound capable of transforming into a dye, transforming it into a dye, the quaterniaation and the transformation into a dye can be carried out in any order.



  The new basic dyestuffs corresponding to the formula CI) can also be obtained by reacting 1 molecule of a compound corresponding to the formula

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 EMI4.1
 in which the alkylene may or may not be pacified and contain 1 to 3 carbon atoms with 1 molecule of a compound of the formula
 EMI4.2
 and transforms the reaction product into a dye when B represents the radical of a compound capable of transforming into a dye, or when 1 molecule of a compound corresponding to the formula is reacted
 EMI4.3
 with 1 molecule of a compound corresponding to the formula
 EMI4.4
 and that the reaction product is converted into a dye when B represents the radical of a compound capable of transforming into a dye.



  One can also react 1 molecule of an amine responding to the
 EMI4.5
 formula B - 1,., R 1 (X) ",. Ra with II molecules of a halogen amine, quaternize the reaction product and transform it into a dye when B represents

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 EMI5.1
 a radical capable of 1.

   transforming into a coloring, or ut an reacts 1 molecule of a compote corresponding to the formula
 EMI5.2
 with n molecule of a * halogen amine, quaternize the product of the reaction and transform it into a dye when B represents a radical capable of transforming into a dye, quaternization and transformation into a dye can be done in any orde It is also possible to react 1 molecule of a compound corresponding to the formula
 EMI5.3
 
 EMI5.4
 aveo, toliaulee of a halogenated amine * quatify the reaction product and transform it into a dye when B represents a radical capable of transforming into an oolorant,

     quaternination and transformation into dye can be carried out in any order.
 EMI5.5
 



  L44 radioAUA of ao3orrnr which are taken into account Ion 'for example those of the oolorants nitrdoi etypyliqueut edthiniquois polyom4th1n1que., Anthraqu1non1qu .., quinophtaloniqueni aeomethines and, especially, azo, It is also possible to use radicals which contain azotic dye. co-ordinatively linked metal. Among the azo dye radicals are meant mainly those of mono- or disazo dyes

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 optionally substituted. The B components which appear suitable for the manufacture of the dye radical A are preferably those which can transform into asochous dye tele radicals by reaction with a diazonium salt or a compound capable of opulating.



  The azo coupling takes place in the usual way * preferably in a weakly alkaline medium to acids, if necessary in a buffered medium.



  Apart from cola, one can also take oas component B derivatives comprising a functional group or which can be transformed into such a group, one then reacts with a component used for the manufacture of the dye radical A to obtain the final dye corresponding to formula (I).



  The alkylating agents which make it possible to transform the products of the reaction of compounds corresponding to formulas (X), (XI) or (XII) and of the halogen amine in accordance with the invention into a colorant mixture or a product of the reaction of a compound of formula (IV) and a compound of formula (VI) are, e.g., esters
 EMI6.1
 aotdot m1n.rftux forte and aoidea sfoniqM * conical, chlorides 1'wigaye, alkyl bromides and) iodides of e, oox), e, halides of aralo0111., esters C & -1 \ 1101'n:

  l. low molecular weight fatty acids, dialoyl sulfates, alkyl esters of low molecular weight aloanesulphonic acids, such as methane-, thane- or butanesulphonic acid and esters of benzene acids -sulfonics which can carry other substituents! such as methyl, ethyl, propyl and benzene sulfonates

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 EMI7.1
 n * butyl, 2- or -methyl, methyl, ethyl, propyl and n-butyl 4-ohlorobenzane-sulfonates or 3- or
 EMI7.2
 Methyl, ethyl, propyl and n-butyl 4-nitrobenzenesulphonates, methyl ohloride, methyl bromide, methyl iodide or dimethyl sulfate,

   low molecular weight alkanesulfonic acid methylates or single benzene tallow acids *
The alkylation or quaternization preferably takes place in an inert drink or, where appropriate, in aqueous suspension or without solvent with an excess of alkylating agent and at temperature possibly raised in the presence of a buffer substance.



   X anions are both organic and inorganic ions such as, for example, methyl sulfate, ooze, di-sulfate, perohlorate, chloride, bromide, iodide, phosphomolybdate, phosphotungstomolybdate, benzenesulfate or 4-ohlorobenzene- ions. sulfonate.



   As the bridge element X, a methyl group is preferably chosen. lenic optionally substituted or a divalent or tri radical. are bonded through such a group to the neighboring nitrogen atom as, for example, the groups - (CH2) p- in which p represents a number
 EMI7.3
 number between 1 and 6, .CEI-GH-CIi3, MNH-00 CH2.0
 EMI7.4
 

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 EMI8.1
 However, y can also represent, together with R 1 and the neighboring nitrogen atom, a heterocyclic system of such aorta that it can result in oyol groups such as!
 EMI8.2
 Such compounds are obtained, for example, by reacting a compound corresponding to formula (VII) or (IX), for example.

   dihalogenated compounds, with a compound corresponding to the formula (VIII), e.g.
 EMI8.3
 

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 EMI9.1
 Like. rump. rather be linked to A, for example to the -oren of a mobro 1n "" d1a1re Y. lia oorresporu1ent in and where there is a troop corresponding to the formula
 EMI9.2
 wherein X represents a nitrogen atom or a CH group, the ring when X represents the CH group may still contain further hetero atoms, V may be part of the bridge element y.



  They can also be formed by% 'R1, the tertiary nitrogen atom in formula (XIII) is a part of A, for example in compounds corresponding to formula
 EMI9.3
 wherein D represents the radical of a ditcotation component and K may bear other substituents.



  However R1 and Rg can also form a heterocyclic system with the neighboring nitrogen atom but without y, thus.
 EMI9.4
 a piperaalc pyrralidic ring, morpholine or an ethyleneimine group, etc.

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 The resolves E radicals are broadly those of sul-
 EMI10.1
 furic acid (R - SOH), 4'an acid $ Ulfonlque (3 m $ 0t oo R 1'8- has an optionally substituted hydrocarbon radical), hydrosulfide (E - SH) but preferably those of $ halogenated acids (E represents Cl, Br, etc.).



  The acyl radicals R, and R are preferably those corresponding to the formula R6-SO2- or R6-CO where R6 represents a hydrogen atom or an aromatic radical or a saturated or unsaturated aliphatic cyclo-aliphatic radical which may form a nucleus with R4 and N.

   R- or R4 can be for example a group
 EMI10.2
 formyl, acdtyllic, propionyl, butyroyl, aoryloyl, cyanacetyl * dimethylaminacetyl, methyleultonyl or an optionally substituted phenylsulfonyl radical, R- and R4 together can represent, for example, a radical
 EMI10.3
 optionally substituted eucoinyl, maleinoyllic or phthaloyl Reaction of a component of formula (IV) with a hydrazine of formula (V) or (VI) or of a compound of formula (VII) or (IX) with a hydrazine corresponding to formula (VIII) is preferably carried out in an organic solvent and at temperatures of% between -5000 and +25000,

       The reaction can also be carried out in an aqueous medium, where appropriate in the presence of an organic solvent or even without any organic solvent at all at the temperatures indicated above * The reaction of an amine of formulas (X), (XI ) or (XII) with a halogen amine preferably takes place in an organic solvent.

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 picnic at temperatures between -50 C and +80 C.

   The reaction can also be carried out in an aqueous medium, optionally in the presence of an organic solvent, at the temperatures indicated above, the halogen amine being used either as a gas or in an organic solvent. , either in water or in a mixture of solvent and water.



   The dyes are isolated according to one of the usual basic methods by filtration, distillation and filtration, precipitation in a suitable medium and filtration.



   These new dyes are ideally suited for dyeing, webbing and printing articles of polymers containing more than 80% aorylonitrile, for example polyacrylonitrile such as "Orlon" (registered trademark) and copolymers comprising
80 to 90% acrylonitrile and 20 to 10% vinyl acetate, methyl arylate or methyl metaorylate.



   These products are known to be the following trademarks!
Aorilan (copolymer of 85% acrylonitrile and 15% vinyl acetate or vinyl pyridine), Orlon, Dralon, Cour tel,
Crylor, Dynel, etc.



   The dyes made on these materials are endowed with good fastnesses to light, washing, sweat, sublimation, pleating, decatising, ironing, water, sea water, bleaching, to dry cleaning, over dyeing and solvents.



   The dyeing with these dyes is preferably done in an aqueous medium, it is recommended to work in a neutral or acidic medium.

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 to the boil.



  The use of conventional braking agents does not cause any disturbance although these dyes make it possible to obtain very even dyes on the polymers mentioned above without it being necessary to resort to such agents. Of course, one can also dye in closed containers at high temperature under pressure because the new dyes are remarkably stable to prolonged boiling. They also make it possible to dye mixed fabrics based on polyaorylonitrile. Some of them are suitable for bulk dyeing of polyacrylonitrile in light and wet solid colors.

   Those which dissolve easily in organic solvents can also be used for coloring oils, varnishes, plastic mas @ s, as well as for mass dyeing of artificial fibers dissolved in organic solvents.



  In addition, some of these new basic dyes can be used for many other purposes, for example for dyeing mordano cotton, wool, silk, regenerated cellulose, synthetic polyamide fibers and paper in any way. stage of their manufacture. It has also been found that it is possible to advantageously use combinations of two or more dyes corresponding to formula (I).



  These new dyes can very well be combined with each other so that it is possible to use salts of dyes of the same class or of different classes to achieve the most diverse shades.

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   tens the following example, parts and percentages
 EMI13.1
 $ # mean by weight and temperatures in degrees entigre4toi Example a Heated for 24 hours at 100 17.6 parts of the compound of formula
 EMI13.2
 in a mixture of 100 partita of 2-ethoxy-ethanol and 4 parts
 EMI13.3
 of d1m4thll-hydra.1n ..

   After cooling, the mixture is diluted with 500 parts of water, filtered and the product precipitated by addition of sodium chloride.



  Polyacrylonitrile fibers are dyed in solid green-blue shades that are very light, wash and pleated.



  Example of dyeing 20 parts of the dye obtained according to example a are intimately ground with 80 parts of dextrin in a ticket mill for 48 hours * 1 part of the preparation is impregnated with 1 part of 40% acetic acid, 400 is poured parts of distilled water at 60 on this paste while stirring and then boil everything quickly. This solution is diluted with 7600 parts of distilled water, 2 parts of glacial acetic acid are added to it and introduced to 60-100 parts.

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 EMI14.1
 d "0rlon" (registered trademark),

   The material has been previously treated ** for 10 to 15 minutes at 60 in a bath composed of 8000 parts of water and 2 parts of glacial acetic acid, One goes up in 30 minutes to 100, one dyes 1 hour at this temperature and we rinse. We obtain a green-blue dye endowed * with a remarkable fastness to light and very good wet silidities Example of dyeing for the Belt on a scarf The toularding bath is prepared as follows
 EMI14.2
 50 part / liter of dye (corresponding to the dye preparation of the previous example)
3 parts / liter of sodium alginate 5 parts / liter of acetic acid conoc.

   



  20, parts / liter of a cationic softener, eg of a condensation product of 1 molecule of stearic acid and 1 molecule of tri-echanolamine 25 parts / liter of sodium sulfate
 EMI14.3
 A polyaorylonltrlle fabric is poularded 1 cold according to the usual method with a scarf with 2 or 3 rolls. The expressing rate
 EMI14.4
 eat by 80%. After a brief drying at 900 on a nécheung ream, a hotflue or using an infrared heater, one sets for 1 to 3 minutes between 170 and 1900 on a ream with nozzle, one rinses, one soap, one rinses with new.

   A remarkably light-fast green-blue dye is obtained.

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 EMI15.1
 Example d; printing The printing paste is made up of
75 parts of colorant (corresponding to the tinc- torial preparation of the first example)
10 parts of acetic acid conc.



   450 parts of sodium alginate thickener
25 parts of an aationic softener, eg of a condensation product of 1 molecule of stearic acid and 1 molecule of triethanolamine
25 parts of sodium sulfate
415 parts of water
1000 parts The polyacrylonitrile fabric is printed by hand using the usual method, the fabric is air dried, vaporized for 20 to 30 minutes with saturated steam in a star vaporizer, rinsed, soaped, we rinse it again. This gives a very solid green-blue impression.

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  Table 1 contains the description of other valuable dyes obtainable by the process which is the subject of the invention.



  They correspond to the formula
 EMI16.1
 
 EMI16.2
 in which the symbols R1, R2, R3 # R4 'R5' R6J "" 7, do not have the meaning indicated in the table.



  As anion x # comes in line immediately those of the description.
 EMI16.3
 



  The symbols Ki.9 K2 "K3, K, K, K6 * K.t, Ra, Kg which are indicated in tables 1 to 13 represent the following groups;
 EMI16.4
 

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 EMI17.1
 
 EMI17.2
 The symbol% lucid xx, K2 # y-3 "X, K, 5 $ kit x7. Kg, ru in the dyes indicated separately represent each time a choice of one of the groups mentioned ,, It is perfectly possible to replace the 'one of these groups in each dye by another of the groups indicated. Thus, for example., the symbols
 EMI17.3
 K2- 'K, K4 # K5 & X6,9 "7' à or K9 can very well varnish replace K1, eto. In principle, each K symbol shown can be replaced by any other K symbol.

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    TABLE 1
 EMI18.1
 8o7 "dS IV j rT râl R. Rs n6? S'8 Kim ce of 1 example Ri P-2 P-3 dyeing on 1 Br H 1fH () 3 HHHH blue 2 MH 2 Cl H NH () 3E2 HHHH blue 3 Br H NH (CH2) 2x1 HHHH blue 4 HHZ Cl H NH () 2 HHEH blue 5 nog COOC2B, .- x., H 1% HHBH blue 6 NH2 COOC2H ,. -Kg HHHHHH orange 7 NHp HB KH2 COOC2S.

   - BHH violet 8 MU HH nog H cooc2H, - HH violet 9 NA2 COOC3% -JC4 H Nog H 2 HH blue 10 Nog COOC2H, .- H on HHHH violet Il Nog CONH () 3-1C H NE2 HHHH reddish blue 12 Nog CCKH (C%) 3-K, HH 'HBHH orange 13 NH2 CONHC2H4- H N82 HHH If reddish blue 14 NB2 co # -o - Jtl H NHg HHHH blue 15 * m, CO - # g-Kj, !! H H H H H red orange 16 or H Ha NB 2 11 H H H blue rolled

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 EMI19.1
 i - Shade of the? * # ** -, -a dye on ex4! 'J1Ple ¯¯¯¯¯3 R2 2 R4 6 Jjji Rg Dralon 17 NH-Q-NHCO If HW -o-'mcocI' ' 2- Green HHHH 18 CE HH NH ¯. '"' G'NHCOCH2-K HHHH blue violet 39 N () 2 HH 5 ..,. 1 NHCOCH2 R. HHHH greenish blue 20 NHp CN H NH - (" V NHCOC- Kj HHHH id.



  21 NH H H NHC2H4NHCKl H H H H blue 22 Qg H H NH- ± V- NHCO # gNHCgH-Kg H H H H blue gray 23 OH H H NB -O-Wc # c3-K4 H H H H nest.



  24 OH NHCOCH2K3 HHHHHH yellow 25 CH NHC1 <2 H OH HHHH orange 26 CE NHCOCpHhKh H OH HHHH orange NgC f * ¯-¯¯3¯ orangc 27 CH NHCOc3 H OH HHHH orange 28 OH NHCOCH, 2K H NH -o-CH. 3 HHHH reddish blue 29 OH NHCgH H OH HHHH yellowish red 30 CH mro3 H oh HHHH will go.



  31 OH N (CB.3) C3% K- H CE H H H H id.



  32 OS V Z2 H # H H H H 14.



  C2H CH 33 NIl -0- COC- H H H H H H H Red violet

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 EMI20.1
 Grade No. of Example Rl R2 Rg R4 Rç Rg Ry Ra Dye! On Dralon 34 1i OCOC ,. H H OH H H H H violet 35}. SC2H4K H OH HHHH ruge bluish 36 FHg SC2H4 H NHC6Hs HHHH blue 37 ra S015 H NH-NHg HHHH blue green 38 1 SC2H, .X4 H NB -Q-WCI3 HHHH 1.d 39 NH2 OC2H4Ks H 1 HHHH purple 40 NHg 2% HS -0 HHHH red 4l NH2 S () 6-Kg H NBC6Hs HHHH blue green8t 2 2 S -0- CKa H 2 HHHH blue violet; <43 NHo S-Oa't red HHHHH red rr bluish 4 S # vyCHg H NBC6Hs HHHH greenish blue 45 SCgH H NH- @ HHHH blue. \ 6 2 -O-cH: 2-Kg H OH HHHH red 41 2 -o-cs2-cH-CH2- H OH HHHH id.



  '8 NHg -O-C-C-K6 H OH H H H H id.



  49 "" s o --eg OH H H id.



  '¯¯, ....... "".: ... \ - r, ... -' ".- ā,.; Ra-:! RSSa '<'! --- i'¯ r ... ¯ -.v. ¯ ... rv ¯ ... ¯ ¯

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 EMI21.1
 P. IT IT. ut c RA Shade of the 1 '8lJlP1e Il - 3 - R5 6 R8 dyeing on Driloa 50 HH2 -0 -1rs # H 11 red 51 NHg -p - - Cii-1C, 11 # red M3 52 UH2 -o - - p-cH3 H oH HHHHH red 53 NHg 'a -'-', g94 H oH HHHHH red 5k NB2 -o cH-x2 H EYE HHHHH red C.% - IK4 CHg-K 55 -Nn- * J-OE3 BH -NH-1% LeCH3 HHHHH green 59 -t # -o - 1ta HH -NH -x Il HHH green 57 NHo HH -NH CH .. g EE n blue Ctta-Ko reddish 58 N8-C HH H-CF -CH - x5 Ha HHH blue 59 1iH HH HE -,.-P-CH ^ H2 H il HE blue 0 greenish 1 x6'H2'2

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 EMI22.1
 ..

   - Grade l1exe from example R, 1 * 5 6 t * 8 dye gur Dralra 60 el H -HH-C-1tg HHHH blue 61 NEL, Br H -NH-C-X3 HHHH blue 62 OH HH -riH ' cH2'cH-x Na2 HH OH blue 63 -NH-1JH HHHH blue 64 ai HH NH -Hxi ai HH ti02 blue 65 KH2 CF3 H -NH-CHs-CHs- HHHH blue 66 OH HH -NH- at HO, HH OH blue so-NH 67 NE, -0-CHs-CHs-Ky H If OH HBHH blue.



  68 OH HH -NH-C-1C- NH-cxz-cH-x HH blue N02 j ### '69 NHjj-C HHHH N-CH2-CH2-CH2-l5 blue -C' 0 oh --çHQ ¯ 1C5 WHHHH Mr.



  0

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 EMI23.1
 No. of Ri RZ R3 Rh R5 R6 IL Ra Color shade for example on Dralon 0 CHa / 71 NHg -C -CH3C - HHHH green blue 0 -CH-CH-K -î CH 72 nu2.-Î N - CH 1 H green blue -cH 1 - SB green blue -C / N-CHg-CH-CHg-Kg NHg green blue JI 0 73 NH2 -a-rn-ca2-cx - x HHHHHH orange 74 NHg -co-Nx -cH2-cH-x HHHHHH orange 75 NH2 -CO-NU CH 2 -% -% H ce HHHH red 76 NH 2 -Co-tm-JC4 H NH-CHg Je HHH blue 77 NH2 -CO-NH-% ÎCH: 2-X7 H HH- @ HHHH blue 78 Nog -Co-Nn-C3-K H NH - a HHH blue CHa 79 M -Co-HB-C3H6- HHHHH reddish blue 80 NH 2 -CO-NH-C 1C5 H Nose HHHH blue 81 Uff2 -Co-NH-C3% -% H MH-CRg-CBL HHHH blue j

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 EMI24.1
 No. 11, "2 Rg R4 N5 1171 Rg dye sui 1 example Dralon s ia g H -NH-CH2-CH -% - K6 H H H H blue CE 83 jg, H -;

  -CN2'CR2'CN2N "t HHHH blue CHU 84 -co-NH-cc3- - H CH3 N% HHHH blue 85 HB -CO-NH-CHg-CH H NOg HHH il id. Cl 86 NN2 -CO-NH- C4 CH2-Xl H UH2 HHH fi blue 87, -cH-cHS-cs E -NA-cx-H-cx-s HEH violet 88 KHj, -S02-m-CB2'CR2-Kk HHHH red 89 -NH 04 H - oc2g, HH x B green <p blue 9OC% i Jb, ** <** <* - <*** HH s $ purple H NH-C3H-N $ H id.

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 EMI25.1
 



  1.of Ri F'2 R3 R P-5 P "6 it7 R8 Shade of the telatmbe example on l!) Ralon 92, ..... NH -A ftY9 -L - EHH blue 0 reddish 93 -NH -C3% - HH OH NOg HH violet 94 H-c3H- ce H CE B s H roap 95 iHG 5 HBBH SO () 3JCJJ H reddish violet 96 NHCHg HHHH sozm () 3 B nest.



  97 HB () 3 H B B H soaHtGH2) #xI B id.



  98 NH-Cyclohexyl H B H H S (11- H id.



  99 NHC HHHHH -SOpttH- B violet (eH2} 3X6 100 HH% ffl (CH2) 3X7 H sozm () 3 H red 101 NHg Bar HH chard 102 Mil (CH2) A blue Y02 Dr -HM () B <blue 103 M2 Br B -BN- (<33-5 11 blet z M Br H -HN-O-CCm! HH ble # - <} 31L ', 1 Br "HMa # () K6 B blue' 105 CORE (C% blu 106 1.05 III -0 COOl (CH? L - "1. blne 106 \" '"2 -..... A." ¯E!' '' F.1 "IC? Nailr! Tsxnw, a ,, p- m-0 blm

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 EMI26.1
 110 .. de RI R2 R3 ¯¯¯ RIF Rs B6 17 Ra Shade beyond 1.exeç1 dye on Dralon CCH-CH23 10 'NU2 Br H "BN-0 CH3 blue 108 (CH2) 3 HH OH WHO HB # blue ft1" dItN 109 () 3Ks HH NHCHg HHBH blue 110 NU2 HH OH RH () 3XS 9 HB blue 111 NH2 -OC2H4-X3 H -NHCe'7 "'BHB violet (CycïoÈxyl) 112 NE -OC04-Y-6 H NHC6Bs HBBB violet 113 M2 -1B # H MHc6H5 HHB violet cff2K, z NH2 -OC2H4Kr H P-NHC6H4C H violet 115 NH2 -OC4K.

   H NHC6H4Y-C B violet CH3 116 NHC-H- cam () 3!:. \ H 11 H H H red ..



  J.17 NHtcx2) 3cH c # a (C) 4 B '"r 1'¯,

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 EMI27.1
 'r¯¯ T 1 ¯ ¯¯¯ ¯¯ï Shade beyond --ww Shade of the Ho. of R- R2 R4 "5 6" 7 B8 dyeing on example Dralon 118 NHC6H1 COOB () 2Ks HHHHHH red 118 Mra "ii CMH (CH2) 2r "5 bluish 119 Br H N'rI-! H H B B blue ax (cH2) 3Kg 120 N32 Br il NHO-CONH (C) 2K. H H H H blue 121 SH2 Br H NH - CONH (CH2) 3Kg H n E H blue 122 jfflg. Br E NHCONHCH2HCH2 HHHH blue 123 NH2 Br H NH-Q éH3 HHHH blue CONH (C) 2K4 124 NR2 Br H NH-q) 3K H blue CONS 125 M Br H NH - {) <1) 4 HHHH blue --C ' 18 126 ilHCH3 HH NH {) 3K HHHH blue 127 HH NH () 2 HE a H blue 12S NHCH- HR Hg (ç) 3CH¯RZ B- HHH blue CH3 129 1iBC HHH [KH (CE2) 3K1 HHH red 129 'OEC83 NH (C%) 3'Cl bleultre 130 NH () 3 HHHHHBH reup

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 EMI28.1
 . dei.

   IL R- R- RJ "1 Shade of the No. of 'R3 R2 P3 R4 R6" 7 N8 dyeing on the example Dralon ¯¯¯¯¯ 131 HH HH (CH2) 3K4 HHHH reddish blue 132 NB () 2 # HH NB (C) 3 HHHH blue 133 iIHC6g11 HH NH () 3JC4 HHHH blue 134 NHC6PI. (p) HH NU () 3Kl HHHH greenish blue 135 HHH CH2 3Ki HHH red 3aur; ± tre 136 NB (cp'2) 2 # HHH NHfCH2) 3K2 HHH bluish red 137 NHC2P 5 HHH g H H&CH bordeaux 138 M 2 (0 ) 3 HH 1 bluish purple 139 HH OH NH (C) 3 HHH reddish purple 140 HFi2 HHI # - (J '' HHHH reddish blue 141 NH2 HH NH 1- CH2R $ HHHH id. Lez2 ira ph K.

   HHHH greenish blue 142 N $ CH3 HH NR CH2K3 H greenish blue z3 UN2 HH NH -'0 (CÜ2) 2ïC H nnn blue 144 HH NB -0- S () 2Kl HHHH blue z5 ni, HHJ "'¯ 802 - (Ci ) 2Kr HHHH blue C "3 -'- = --- <1.- -" "'' \ A '"' {l.me -...) .... "ZJfL ...! ¯. ' ft¯l "

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 EMI29.1
 Shade No. of Example Pi R- 5 6 Rr Ra Dye on Dralon 146 OH H H NH4.

   HHHH violet 147 NB -G :: CH3 HH NB -.y1 \ 6 HHHH green 148 NBL CH26 H NH- / 3r2'l H blue 0CIl) 149 NH () 2 # HH îni-QKy HHHH blue 150 NBL HH NH-C > -N - () 2K4 HHHH blue-green H3n cH-xfi .S.PbNH (CHp)., CH-! 151 NH-Q-CHj HH NH-'V- 3 HHHH green-eriMttre 152 NHCH3 HHH NH () 2X2 HHH bluish red 153! # () 3 HHHHHHH red Yellowish 15% KE2 HH NH (CI) 21 HHHH reddish blue 155 HF (G &) 2flH HH NH (CH2) HHHH blue 156! O'C6Hn HH NH (CH2) 2Ki HHHH blue 157 N '- cH3 HH NH (CH2) 3tS1 HHHH filter blue 158 HHH JIH () 2a HHH yellowish red 159 Im () 2 # HHH MB () 3 HHH bluish red

 <Desc / Clms Page number 30>

 
 EMI30.1
 I i "" "] '! UaTcedela Eiiture No. on example R- B R3 114 i Pl6 R- Rg Dralon 160 rsHC2H5 HHHH UH (CO4) X4 bordeaux 161 Na, H OH NR (CH2) 2K6 HH violet reddish 162 NRa H NH xH (cH2 HHH bluish purple '.'.

   I 1 1 #################! ########## - # - # "" '1 1 ### h

 <Desc / Clms Page number 31>

 Table 2 contains the description of other valuable dyes obtainable by the process forming the subject of the invention.



  They correspond to the formula
 EMI31.1
 
 EMI31.2
 in which the symbols R9 * R10 'Rll' R12 'Rl,' R14s R15 'R16'
R17 and R18 meet the definitions given in the table.



  The indications on pages 16 and 17 relating to table 1 on the anions and the meaning of the symbols K are also naturally valid *, ment for table 2.

 <Desc / Clms Page number 32>

 



  T A B L E A U 2
 EMI32.1
 No. of Il- RZO A1'I R12! T3 R4 R 3l6 R17 R18 Shade of the example 10 1 12 13 14 15 dye aur ¯¯¯¯¯¯¯¯¯¯ ¯¯¯¯¯ ¯¯¯ ¯ ¯¯¯ ¯-> ¯¯¯¯¯. ¯¯¯¯ Dralon 163 H H --COCB2Kg H H H H N (C) 2 H Cl orange-red 164 H H -COCH2ICg H H H H id. H CE3 red 165 H H -COC% K3 H H H H id. H CE3 red 166 HH -cocff2K7 HHH CH3 NIi2 H CH3 orange 167 HH -COCH2K1 HHHH NtC2HCN) 2 H CH3 orange 168 HH -COCH2Kl HHHH NH2 HC $ 3 orange 169 HH -COCK1 HHH CH3 NHZ C83 H orange yellow 170 HH-CH3 HK H NH2 H CH3 yellow brown 171 HH -cocH2K5 HHH oe3 NH2 H CK- id.



  172 HH -COCHgKg HHH CH3 rrH2 H Cl yellow 173 HH -Co% 'K2 HHH CE3 NHC2H5 HH orange red 174 HH -COCH2K HHHH NHCgHCN HH orange 175 HH -COCH2K HHH CH3 NHCgHCN HH orange NH 176 HH -CHHC CH3 CH3 HH orange 177 HH -COCH2x9 HHHH N ...- C "3 HH id.



  "C6Bs 178 H H -COCH2IC1 H H H H N (C.2H4 #) 2 H H orange 179 H H -ClC1 H H H H N (C2H0H) 2 H CH3 red 180 H H -cccH2x, 1 B H H H lq -e" 3 H H orange "" "C2H4CH

 <Desc / Clms Page number 33>

 
 EMI33.1
 '1 NO. of "11 11.2 Ruz HI5 H16 1'T H18 Rua 1ce of the example 119 Ric R13 R16 te1" 1ture on ¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯ ¯¯¯¯¯¯¯¯¯¯¯¯¯ Dralon 181 BH -COCH2K4 HHHHN â -7 HH orange C2HCN 182 HH -C! 6 HHHHNC 2 H 4 OEi HH ors 182 -coe% K6 C2H4CH 183 HH -CR7 HHHHN ( C4CH) 2 HH orange bzz HH -cocH2x? H H H H R-c4 # a CE3 red c crr les B H -cocH2x5 H H H H NCcC1 H Il orange 18b CH3 H H -COCA2 H H tCH3) 2 N (CH3) 2 H H orange 187 CH3 H H -COCHgKy H H H id. H Cl orange 188 CH2 H H -cocH2K9 H H H R () 2 H Mi3 brown 189 OCH3 H H -co% r, 8 H H H N (CH3) 2 H H orange 190 ccH3 H H -C0CB; H H H 1d. H Cl or & "1g8 red 191 Br H -cocH2x2 H H H H Id. H Cl red 192 Br H -CW% K2 H H H H.

   (C2%) 2 H Cl red 153 Br H -OCH2lCZ H H H H 1d. H CH, route violet 194 Br H -COML2% H H B H) I () 2 H H red 195 Br H -coe %% H Br H H id. H Cl wheel * 196 Br H -C1C H Br H H H (Cifs) 2 H ci red 197 Br if -C0C²1 H Br H H ld. H cH red-violet

 <Desc / Clms Page number 34>

 
 EMI34.1
 Grade of R .. R .. R .. R .. R ... R18 Grade of 1.'e! LlPle - "'5 -'" 1.0 Rii R12 13 1% R15 R16 R17 R18 dye on Illexemple ¯ ¯¯¯¯ DRALON 198 Br H -cocH2KT H Br H t CH3) 2 HH red i9g H ci -COCH2¯¯xz! H H H H H (e) 2 H ci orange-red 200 E Cl -COC% K5 H H H il !.

   H CH3 red 201 H cH3 -CK4 H cH3 HHH (CH.3) 2 HH orange-red 202 BH -COCH2Kb HHHH NHC2B, CH Cl H orange 203 BH -COO2HJ.K4 HHHHN (C2Hs) 2 H CH3 red 20 HB -COO3K HHHHN (C2Hs) 2 CH3 red 205 HH -CoC2H4y'l HHHB N'2H CN HB orange CH3 206 BH -CoqHK4 HHBN (C2H5) 2 B CE3 red CH3 CJ3t.CN orange 207 HH -CoîHK2 HHN "4 H orange 206 BH - COCAH - 3K HHBH NC2BJJC HH orange 209 B -cOc2H4K6 BBHB COQS '# HB yellow 210 Br B coc% N7 BH CH3 BN (C2B4 #) 2 H m red brown If COOC2H4 HH OH H CIi3 H yellow 211 C0002H4X3 reddish mz H CocH2x3 HHN / B3 H m orange '¯a

 <Desc / Clms Page number 35>

 
 EMI35.1
 #irj ltn # "[j '"' "'. 1 ¯ W # nee de la, l.tàemp1t Rq 19 --11 R12 -" "13 ¯ J.4 15 16 R17 RIS dyeing over the time DRALON 213 HH CK5 HH CH3 HN (C2Hs) 2 HH red 2i% HH C1t8 'H' lI 1mCOG} I ad.

   H H bluish red 215 CK ... '} I NH3 scarlet B r H M't -M "Xav, scarlet '21" 6, Jti 11 - "" -H ...., Xs - ... H. '11 'H H N :: CH3 R4S02NHC H CeH4NHS02CH3 217. HH ec4 HHHHN (C2) 2 HH orange 218 COOO²3 H eu HHHHN "" "2 4 4 HH red 3 'C2Hs 219 Cl H, ON: ... H' PHHN" "", C2H4 '"2 HH orange z5' ' '': ia} 1'1. CNX, N ", C2H41S. yellow -â H 5 s .. H '' 'CpH3CN H H yellow' 221 :. 1t ", ... Ho ;; ......... ...;" H, .HN "" 2 4 l H yellow -1> f 'i1 ""' "':>" "- 12 "Cl" "H 1 'eH3;'" H / "\ 'H - HN", C2H4Kl HH orange -;' * '"" # ..-- 25 "* 3" .t0 11 ..!' 11 .. - S4Cli H H H N -C2H4 K4 H H orange: (; ..... 1 '..... "", 2:, -.) H.'; * -If '; "' 't. ---.:s C -.-... r-. - N; 2CH3 H.> - .. 7 'in, # .1f 1 .... ¯ .... .. -...., .. 1' ..Sc¯.x, .¯ ¯ \ ¯ "" ".. - -'tLtm. Xat ¯.¯ ..., .... .. ¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯ ¯¯¯¯¯¯¯¯¯¯

 <Desc / Clms Page number 36>

 
 EMI36.1
 NO. of Re: R10 R11 R1 R13 Rl4.

   R15 R16 R1 l1.a 'fû1inè de la' ¯eU1pl dye Sralon 225 HHN "'" CH2-CH 3 MHH' H N '"E2-CE2-CN H CH3 yellow r'-CO-CÜ-K.' -CE2 -17 .226 # -: HH CH3 HHH i GHyCH-K9 HH yellow ",. ",: - .." r .. :: = "'" w ..., C%, - CHp-CN. 3 ".:;:;" - '<? .. -J1ftSe2- HHHHN "" CH 2 -CH x H r 'a.! Tr- "' fI4 Ê3i lêt 'H .... t: t6-'Q2 \. HHHH id. H'H ru1xhM- t" --2! I: V-: -'U "w Hi - f !! - il fI.- fi: te !!. - N age w4jt5 .... 1ft: -, '" ". ::" -2 't "1t -¯ .: H - H FI M. to leH3 --- wbt: ae.-231.: ¯l .. B -.: RC' - & .. 2- HHHHN 7B2 --CH2 -CN - H Cü3 Coil --J; - O --- ¯ CF-C- 3 23rd. Ci: "Jr - 1 'jM-mT li. HHH 1r''Gcx2- x H CH3 -on1! Ge- ôI.M '"-' 'c-cH3 red .435 ... -".,.;. L.2-C "' ') 11 H - HH nV6'61 "N CB3. ia.



  * - .:. 1. F ";" = g 2 ¯ -C J t. -,. H ¯ ¯ *. N Cii-CH3 -fez 34 1. '. '4B-SRSs) H H H H IS1 G-C- 11 C 1d.



  .¯¯ ¯ \ .NiJ8. () 2 -,. cx2 - ox -H2ooGA3 2 Cl.-H ÎU-fîHo-CCBp * H H H H N '"H 3Ho orange- #jggff # *' C -COOCCH3 H ¯ 3

 <Desc / Clms Page number 37>

 
 EMI37.1
 * # '# r #' '## "' 'rri # - #' '# ..- r --- # 1M | muence de No. * # Pq Rio 11 R12 Ri3 Ri4 R15 16, Ri7 R18 skin tone * ejwsple re 8 = 236 N0 H? 10 HHHE NC E CH3. roffl 237 N0. H N02 HHHHN - 'i H violet 238 Cl H N02 H Cl HHN ī-'3 xi 3 bzz 239 Cl H N02 H Cl HH NJCI "CH3. HH brown CH-CHg-Kg yellow 240 Cl H H00 HHHH Na C t2 'HH oe, * r4o 241 Cl H N02 HHHHN' G 0 '"' 9 CH3 scarlet CH-c; H2¯ ', 242 Cl H HOp HHHHT" '' -0 H CH3 tape 243 OH ï! H CH3 H H H -NH-G0-CHI a H yellowing 244 cm H CN H H H H 19 H Change 245 CF3 H H H H H H H N- *.

   CH2-% 'H H yellow ..c¯¯1 246 NO2 H NO2 H rr0, H !! 0-0 H H red

 <Desc / Clms Page number 38>

 
 EMI38.1
 Ru No. RIO 11 R12 R13 R14 R1, '1 ± J.7,' "Rl8 = example DI3'- ###. ##. ## - ##### - ### ### ####### ...,. t ....... ## "* # - '' <'" -' ". '. 9 <"-. #: ## '" ##' - "'#" *: # **' 247 ci H ci HHH le lcl% 7elk H 'orj & xïge 248 Br H CH 3 -Co- If H 1 <, * If re .. il '4) "" - 249 CH - CO- C-CHa 249 Br H CH3-Co- HHH Ir C'32 3 C' CH: 2-C- 250 Cl H K4CH2-CH2-CHI -) HHHH N - # 'H CH. "Orange- (H-so2-.'. Cn * 3 \ 'red 251 C1 H 5, CH2-C'H2-CH2-) H id. HH id.



  <'NHSO-' NH 252 Br H KO-CH2-CH2-) 'HKHHN, -A "id. -, NR-SO2->. ¯. - K 253 CF3 H èB: 2-CC-NH"'. S 2 HHHH idn .. - -. {. oN f iI 1J. routa 254 Y.7-CH2-co- N eCH2-ClÎ3 'H t H.



  254 K-CHp-CO- "" "CH21" 3 ruM.ne CH2 'ï $ 255 Br H iC-CH2¯CO- H H H H id. H H ld.



  256 CF3 H K-CH2-C0- H H H H id. H H violate 257 cH3-S0- H K5-cH2-c0- H H 11 H id. H H ribbon $ 25 CN H ICI-CH2-co- H H H H id. H -, 0, M.



  259 cm H K2-CR2-CO- H H H H id. H H id.

 <Desc / Clms Page number 39>

 
 EMI39.1
 



  ## Grade of the example Rc Rll R2 11.3 Rl4 11.5 R16 DRALON H m E ¯XfH 3 E red 260 bH .. -S02 - CH.3 -S -If .... FI3 red .x3 CH3-0% - -Cli2-NH-C - X1t: 261 Cl H N02 HHHH '<-cmC. (= H,) HH red' -Ci -NH-CO {C) 4 -K, "bluish 262 ci H --C % HHBB * faa 11 orange '-CH2- "6 CH2-CH2¯CN 263 ci H N02 H Cl -co-c Li2i H NH2 HH bordeaux 25 H OCHg HH OH H OH -COO-C4 -Kl HH yellow LOCH3 orange 265 S02Kl NRCOCH3 N, .COCOCH.3 orange SO, CH, CH, X, NHCCCH, CH2CH20C0CH 266 S02K4 N- (C2Hs) 2 orange 266 HH so2cH2cH2x HH CH3 H N-c2H52 reddish red! Be du = 267 S02C H3 H e2-5 H 1d.



  267 302CH2C% Y'2 H CE3 C2g -'.- C2 "40H 268 HH coc% N7 HHHHN (e) 2 HH brown 269 H COCHZK3 HH M3 H Id. H fi red 270 CpCg2 fi 11. H 1% H orange S70 cocR2K8 NI CH2C% CN star 271 1 CI HH CH3 lt (C2%) 2 H e

 <Desc / Clms Page number 40>

 
 EMI40.1
 Reg Rio No. R1I Rio R, 3 Ri & R15 R16 HIT H1.8 Shade of the example 'R18 dyeing on ¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯ ¯¯¯¯ Dralon 272 HH] LHHHHH 1 - 'HH yellow. '*' C "2c% CN yellow 273 HH cH2xs HHHH x (cH2cH2: x) 2 HH Yellow z HH CH2 HH CH3 HN (C2H5) 2 HH orange 275 HH C00C2HK HH CIi3 H id. HH reddish orange 276 HH COOC2H4X HH CH3 HN (#) 2 HH orange * reddish 277 HH OCHgCHgK HHHHN (C211s) 2 HH yellow 278 HH ocH2cHx2 HHHH rr (cH2cHococH HH yellow 279 8 H S02CH2OE2Kl HH CH3 HN (C) 2 HH3CH2 reddish orange id HH C CH. HH scarlet 281 HH COCH2CH2% HHHH id.

   HH brown orange 282 HH COCHgCHgKg HHHHN (CHZZCH2K) 2 HH brown 283 Cl B N02 HHHH 3ü -3 HH rubine CH2CHOCOCH2K> 28 Cl H S02CE3 HHHH N-3 HH orange ca2cH2 c cH2x2 285 Cl HgR5K) H HCO (NHH) Bordeaux

 <Desc / Clms Page number 41>

 
 EMI41.1
 No. of R ... IL IL iR, IL IL IL 'R .... RR Xunce 4th No. of R9 t 1%, 12 H13 P-14 RI5 '16 "17 R18 tetntureesur example ¯¯¯¯ ¯¯¯¯¯¯ ¯¯¯¯ Drtloa 286 Cl EN% eH.3 B 1I (²JC¯) 2 roaseltre brown 287 0. BH N0.2 CH3 a O-C2% reddish brown.



  288 CP'3 B 02 CE3 am, c2% roap -C2'1 289 Cl SO¯WR- 11 CR- 8 i (-j¯ H 8 orange rouselta 289 CH3 'C15 oesnge rougettm 290 Coocx3 HO, CH3 E N. * IPC2% E a brown * 291 go2çg S02CA3 Cl HH CE3 E y "CO5 a H roffl 292 Cl 13 cm a -'8 11 x" "" C? 'S orense - <' 293 OC83 B 0 c -R: -t E Il c8 E 1I.A "**" 294 ci a 302C XE CB: 3 a. "C2'Bs 8. X 0NnC8 YES C284T'3 2" BI \ HC "3 HB aa

 <Desc / Clms Page number 42>

 
 EMI42.1
 '** # *** -Nuance 4th No. of R11 R12 R .. R .. IL' the dyeing example 9 R1o Rii 2 Ra 5 --1.6 - "" l.7 - ""]. 8 n : r Dral # 296 WH3 HH io2 EHH t 'BH red CBCBCY6 297 Cl E * 02 BBBB Nez H bordeaux -ccHa 298 & 02 B) (lL Br) (.fl3 viol <ttt <298 M02 CH2C8 vlolotte 299 B NHCOCHK2 HBHHB i ¯ orange.



  3j oGH3 BH io2 HHH N'3 orange "% (CH2) 2X2 301 N0 B N02 B Br BB w" <: E1: 3 H red (CH2 bordeaux 302 M3 H N02 BHHH N- '3 orange 303 CHa H 02 HBHH 11 oran & 8.



  \) 3 z M3 E N02 B H CE3 a W3 orance 'CAI6

 <Desc / Clms Page number 43>

 
 EMI43.1
 No. of IL. R10 Ru Ri2 13 R1 15 R16 R17 R18 Tint of example -l dye 305 Cl H N02 HHBH - () 3Ka H red ....... () 3CH3 306 CN B CN BH CH3 HN C2 "5 red {) 2K 307 CN BH Cl H CH3 H tH '(CH2) 2K2 H orange 308 CN H CN HH CH3 H NH (GH2) 2IC HH orange red! Tre C 309 H Cl CN HH (.H3 H -IC2H5 H orange 309 CH3 N "-, c 2" 4y-2 310 Cl CN ci binds C2% red HCl CH3 "() 2Ks brick 311 CN Cl H N-e4 # 'orange 311 CH3 H, 2 g reddish 312 CIl H ci GH3 w. -c2Bs 1d. el2 tut3 '() 2Ks 313 H ci CN HH CH H HH2 H reddish yellow ... eC2E5 reddish 314 Cu HH Cs H CH3 B 11 / e B orange 315 CIl H Ct1 Ci CH3 H l':

  'C2Bs red -. 1 2-4-1

 <Desc / Clms Page number 44>

 
 EMI44.1
 example Rg RlO R1 R12 R13 14 H15 R6 R, 7 RI8 dye on ¯¯¯¯¯¯¯ ¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯ ¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯Dralon¯¯¯¯¯ 316 CN M02 HH CH3 HN OOM3 HH bordeaux C2H4Ks reddish 317 CH H C1 CN ci CBL HN, ç2H5 BH red CH3 "" C41C bluish 318 (3! B CN BHHHN 3 HH orange '(C%) 2X5 reddish 319 C1 H' .N 2 H C1 CH3 H IY2H5 HH brown \) 2xa orange 320 C1 H N02 B C1 HHN, C4Hg HH orange '<} 2!] Brownish 321 Cl H N02 HH CH3 H N' 'C2H5 HH red' () 2Xg bluish 322 C1 H N02 HHHHN> 4Hg HH red ICH2) Kt 323 ci H NQp HH CBL HN c2H OCH3 H brown N02 () 2KS red 32k Cl H 'g) 2 HHHHN - 3 BH red' t) 2Ks brownish

 <Desc / Clms Page number 45>

 
 EMI45.1
 No. RIO Rl, Aiz z3¯.

   R, 5 R16 IR,.,% 8! Lîwoce 1 example 12 R13 dyeing on Dralon 325 Ocfi3 8 H CM H CBg H x.- C2% HB Jauae 3 --- (CH2) 2% roKgsJttre 326 ci cy W -C % la orange - (CH2) 2X3 jametre 327 ci N02 R Cl CH, xoc2n4oe 3 H oeaffl% (CB2) 2r6 brown <t28 CNH OtHS x orenge 328 y --iCR2) 2X4 yellowish 329 CN H cm m ltci2 HH notch "yellowish 330 E crt CN S CH3 S2) A '331 Cl H CM H CH OE3 il UN (CH2) 2'r', brick red 332 H CO (CB2) 2X4 Il HHHM (CB3) 2 01 409 * 333 Il CO (CE2) 2X6 g HH m 2 4cu bzz

 <Desc / Clms Page number 46>

 
 EMI46.1
 ################## --- ## '# ¯tuancedeit Rl R13 Rl. \ R5 R16! I1 P-18 imnce lexemle Rio' Pl. i 1 Ri2? 13 R15 "17 dyeing On the example" ion on the example ¯¯¯ Dralon 334 Cl B SON B H H 11 / ²4 - g 8 scarlet 285 335 ci H E E E m # C2n% -Xl m m 14.



  335 N02 1% CO # -CI 336 ci H NQg H B H a x 2Hc 'B x nid.



  % .. C04-cx 337 Er H02 H Br H H. AH, -Je H CH- brown <c.



  M02 x% * C2H5 roffl brown 338 es B 11 B Br H B 19 --CO4-X2 B CE3 leS.



  339 Er H M02 B Br B H ltC2g''3 H cm, 2.cJ.



  340 Br H H! 02 H Br H H '2g H' H CE3 leS.



  C 341 Br H 11 H Br H H 1I. \ - Xs B cu, 342 M02 H02 1%. C2% CE3 3¯2 Br il N0, Br 11, C ,, - JI CIL ia.



  '2''5 z3 Br H M02 Br B x-'c2xx''l s ca3 lc1.

 <Desc / Clms Page number 47>

 
 EMI47.1
 



  I! 1 "¯1 1 Z Ir., 1 R, Q Shade beyond 1-qo. Ri0 gll R12 R13 8riz --15 R16 R1 Ris Grade No. P9" io Rii "12 13 R14 R15" l6 dyeing on the example dyeing the example ¯¯¯¯¯¯¯¯¯¯¯¯ Dralon iC2H, .K '$ 344 Br H N02 Oh Br HHN ,, c2 "4-K8 H CH3 red brown, C2" 5,345 Br H NOg H Br HHN, eC2Hb-N9 H CH3 id.



  \ C2H5 346 Br NO2 Br H H CH-CH # Ï-CHg-K H H id.



  346 NOg 'C2H5 347 Br H N02 H Br H H N sCA2-Ct-ZOH-CH-IC2 H H id.



  348 Br H N02 H Br H H N ..CFi2-CIiOH-CH2-K3 H n id.



  C2H5 349 Br H N02 H Br H H N OMCH2-CHOE'-CH2-X4 H H 1a.



  -2 5 H2-cHaH-cH2-xs 350 Br H N02 H Br H H N 1.1 H H id.



  351 Br N0, Br N iCH2-CH-CH id.



  351 M02 N ** - C2 "5,352 Br H N02 H Br H H 11, 'CH2-CHOH -% - Kt fl ia.



  -Ca? 5

 <Desc / Clms Page number 48>

 
 EMI48.1
 No. of 1 Nuanoe of No. of Rg 11.0 R! T2 Rit R, R15 R36 R1 8 teeth on Dralon J-OH-CH - !! ja 353 Br HN Br N-cH # -Xa H brown 353 N02 N% ..c2li red 35c Br B N02 H Br HH ll '-cH # -1Cg BH 1d.



  "" 'C2Hs 355 Br H No2 H Br H H N -CH # -x x sa.



  "C2Hs 356 Br H NOg H Br H H N B2'Cg-R2 H CH'3 id.



  C2H5 357 Cl N02 H Cl H H N-C2H4-Kl H CH3 Id.



  357 N02 C2H5 35d Cl B N02 H ci H H N 'C2R4 R2 H CH3 ias' -C2Hs 359 Cl B N02 H Cl H H N eCH2-CHOR-CH2-Xl H id.



  359 M02 C2H5 360 ci H N &, B Cl H B N'A2H2- g H id.



  N, 02 "'C2Hs 361 ci H N02 H Cl H H \ I \ -cH # - X3 H H 14.



  'C2Bs

 <Desc / Clms Page number 49>

 
 EMI49.1
 No. of B * *! <) 11.1 R12 R13 * 1 * 5 "16 T7 l1.8 Grade of the 1 example R9 P-10 R11 R14 R15 dyeing on DralOn 362 Cl H N02 B Cl HN -cB # - rusty brown 362 "" "'C2Hs t nia red 363 n H N02 H Cl HHN", C-cH # - HH Id.



  C2H5 364 Cl H N02 H Cl H H N --- cu # -16 H H M.



  364 N02 N C2% 365 in H NOg H Cl H H N :: - cBCH- H H 1d.



  365 NO2 5 366 Cl H N02 H Cl H H N ..-- cH # -Xs H H 14.



  366 C-1 N02 c 2% 367 Cl H N02 H Cl H H JI -cH # -Kg H 1d.



  367 2 -% C2% 368 Cl H N02 H Cl H H ......- cH -ca2- E CE3 ld.



  C2% 369 Cl H N02 H Cl H H HI 'c: -' "" 2 H CH- "'1.', * # 369 M02 J 'C M3'.



  370 Cl H Nog H Cl H H N -cHOa-cH-N3 H Id.

 <Desc / Clms Page number 50>

 
 EMI50.1
 



  ############################ tuance <te Rio No. Rl R2 R3 14 "15" l6 T7 Rs dye on Dralon example 311. Cl H NQ. H Cl H H -cu # - brown 3Tl M02 'c2Bs ciij red 372 Cl H N02 B Cl H B x a C 1d.



  373 ci H 11 H ci H H -cB # - a cH3 1d.



  31- ci B No2 B ci H B JI - -CH # -lt B CH- 14.



  374 "Eyelashes -: J 315 CI N0, H Cl II" "" -cH # - Xa CIL. her.



  C2H5 CH3 3'6 ci H N02 H Cl H H N-CH # -K9 a CIL. 1d.



  "2" 5 376a Cl B NO2 H Cl H Cl NHC2H¯ H.



  376b Cl H NOg H Cl B Cl HHCjI61C ld.



  376e Cl a N02 B Cl H ci NHC B Cl brown.



  376d ci H NQg B B B Cl tmC¯1tJ. scarlet 376e Cl N02 H H B Cl il C04 "2 rous8" "C2% 376 Cl N02 B Cl B Cl tmC2B¯ 1 B C83 brown

 <Desc / Clms Page number 51>

 Table 3 contains the description of the valuable coloring attractant obtainable by the process of the invention.



  They correspond to the formula
 EMI51.1
 
 EMI51.2
 in which the symbols R19 'R21' R22 "Bgy 4 'R2, 6' 1%,
R27, R28, R29 and R30 meeting the definitions given in the table.



  The indications on pages 16 + 17 concerning table 1 on anions. and the meaning of the symbols K are also naturally valid for this table 3.

 <Desc / Clms Page number 52>

 



  T A B L E A U 3
 EMI52.1
 J 1 HU! T.nce of example "19 -20 21 R22 R23 R2 R2 1 R28 9 6'30 on Dralon on Dralon 377 g H CHZK3 HHHHH N1- H - ruge 378 HH CH2r'9 HHHHHH -NaN-Q - # HH nest.



  OR 379 H H COC2H4Ks H H H H H H H orange 380 H COC2HKG B H H H H H H H H id.



  381 H COC2H4K4 H H H H H H H B CQOCH3 scarlet 382 H COC4K B H H H H H H H corm-C> ï ai red Il 383 H H COC2H4! C H H H H H H H H i. on red 38 B H H H H H H H H CONH -0- o 3H scarlet '24 385 B COC2B4 H H H H B H H H C03HC6FI5 red 386 H COC2H4Ks B H H H H H H OR H H id.



  387 COC2H41L H H H H H H H OH gOC2H4K H brown 388 H H CoCH2K3 H H H H H H NHC2H4 # H H red 389 B B N0. -S02-NHj yellow 389 N02 -f 6KI orange

 <Desc / Clms Page number 53>

 
 EMI53.1
 Rgo No. 21 22 2628 29 30 Teitture * ar Exemplc Dralon 390 SO2 H NOg H H H H H H H H -CO-I-CHZ -1C; OH orange 391 S02-C H NOg HHHHHHH -CO-H8 -CHy OR o 392 HH 1t.-CO- HHHHHH -. (CB3) 2 HH Y10lette 393 HH x-ca2-GO- HHHHHHHH KKg scarlet 394 HH Kg-CHg- CO- HHHHHHHB 1 # -C¯ # roo 395 HH! -CH2-C0- HHHHHHH 11 1mCB3 id.



  396 H H JI: 2-CO- H H H H H H H H m- @ M.



  397 H H K-CHg-CHg-CO H H H H H H H H KHg ias 398 H x xi '! - c3GH6-cGo- HHHHHHH H id.



  399 H H -c3H-co- B B H B H B Br H 1d.



  400 H H 1ts-CO- HHHHHHC1 H NHg id.



  401 CH3 H H 2 HHHBrHH H 1IH2 id.



  402 Cl H Kg-CBs-CO- H H H H H k H! 0 id.



  403 H K: 3-co- H H H H ca3 H H ia.



  40 * Br H 1rs-Co- Br H H H B? CH3 H H KHg id.



  405 H H 15-CO- H H H I H H ML, id.

 <Desc / Clms Page number 54>

 
 EMI54.1
 



  No. of R J ÏU 1L 2 t 27 a2s 29 30, c of the example * 9 '"-" 21 - c:,: c: 1i c ::; !.: - - {3O dye on ¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯ ¯¯¯¯¯¯¯¯¯¯ ¯ ¯¯¯¯¯¯¯¯¯¯Dralon¯¯¯¯¯¯ 406 H 3 X -COO-C4 -0- HHHHHHHH OH red 4 <xi H If xs-cH2-co 8 a H sa HHH #: 1d.



  406 N02 H H H H H H B 11 -NH-C4 H H id. zoos NOg R H H H H H H H -CCO-CE-K H H ld.



  410 HH C2B, - HHHBHH NMH2c% cu HH red kil HH S02 HHBHHH x c2as BH orange 302c3 cHlçH-OE2xl l: X '12 CH B! LO If ,, "C2! Ts violet 2 2 t OH 413 CE3 HN c 8 H x HHHS <? 'tf (CH-) 2 HH scarlet "" "C2K bzz HH COCCYX- HHHHHHH COOC2H¯1C OH orange 415 HH COOCH3 H 8 8 HHHH COOC4 Oh orange ci title wheel 416 HB COOC2H¯ HHHHHHB COOCHg OH orange bzz HH carx (cHZ) 35 HHHHHHHH CL young M3 kl8 EEC # BÇB - () 315 HHHHHH OH orange (cH2i3l oras

 <Desc / Clms Page number 55>

 
 EMI55.1
 ho. ae Ri R2o R21 R22 R23 R24 R25 26 R 2-1 J'2P- "29 R30 Huance e 1a example ### ### ¯¯¯ ¯¯¯ ¯¯¯ ¯¯¯ ¯¯¯¯ Dralon 41µ E .-, ilH (CH2) 3R HHHHHHHH OH red vr! CHa - j yellowish 420 E:

  5MD H .H H H H H H H OR orange (CH2) 3K]

 <Desc / Clms Page number 56>

 Table 4 contains the description of other valuable dyes which can be obtained according to the process forming the subject of the invention.



  They correspond to the formula
 EMI56.1
 
 EMI56.2
 in which the symbols B313 R, R3 'R, R35, R36 # R, B38
R39, R40, R41, R42, R43 and R44 meet the detentions given in the table.



  The indications on pages 16 and 17 concerning table 1 on anions and the meaning of the symbols K are also naturally valid for this table 4.

 <Desc / Clms Page number 57>

 
 EMI57.1
 ta B L E A
 EMI57.2
 oc * 4
 EMI57.3
 No. of 1 132 3 "34 5 6 R37 8 39 R # O R41 42 R43 fw Shade of the example ¯¯¯ ¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯ Dralon ##### ## - #### -. dec2u4x 1 korinth 421 EE OCE3 E OCE3 M CH3 E c 2H5 km-inth.



  422 CH- HHHH EL CE3 E CH3 HS "'c2% C2"' KIF EH orange 423 a EHHHHH HHCHgH HH "" 'C orange 424 H N02 CH3 HH CHg H OCR3 H CH3 H N' ** cO4XP- HH bordeaux N02 C 2 R 5 reddish 425 Cl H MO, H Cl OH- H OCH3 HHH 1fC4Xl a H kor1ntbe 426 CH H H02 HH OCH3 E OCK3 EHE id. H M brown% 27 CH H N0. H H OCH- H CCHg H CHg H H 246 id.



  427 Ciff N ') 2 W "3 OC" 3 C "3% .. C2E5 42E Cl H tKL H Cl OCH, H OCH, H CH, H JI, CJJ Je 5 #H .: H violet - -' - ' CH3 'e- # routestre 429 H * 02 il E 0% a OCE3 HBE. :: - kr, violet, J Cl red ¯¯¯¯¯¯¯¯

 <Desc / Clms Page number 58>

 
 EMI58.1
 No. of R31 32 33 I3- I35 "36 37 8 9 0 R4, Rg w R 4- Shade of the example ¯¯¯ ¯¯¯ ¯¯¯ ¯¯¯¯¯¯¯¯43 dye on 430 ci B N02 H Cl occ33 HZB OCH3 H ... fl2H.tX. \ HH violet 431 H N02 CH3 HH CH3 H oCH3 H oCH3 HN, c2H. \ 1t.3 MR3 H bordeaux% C2 '432 Oh H HOU H OCPg H OCHg OCB 'C2H4lLl HH brown 432 M02 OC \ i3 OCE3 *% C2 "5 raw 33 HH CH2K7 HH CH3 H tCH3 H OH BH (C2Hs) 2 HH red 434 HH CH2a3 HH cH3 HHH # HN (C2Hs) 2 HH red 435 HHBHH CH3 HH CH3 H N '"C2F'i5 H red ¯¯¯¯¯¯ ¯- #,

   # ¯ ## - # - ## # # # # 1> a # - # # - # #a - # # # # - ##### I * *

 <Desc / Clms Page number 59>

 Table 5 shows the deaorption of other valuable dyes obtainable by the process which is the subject of the invention,
 EMI59.1
 in which the symbols R45, R46, R47 and R48 meet the definitions given in the table.



  The indications on pages 16 and 17 concerning table 1 on the anions and the meaning of the symbols K are also naturally valid for this table 5.

 <Desc / Clms Page number 60>

 



  U
 EMI60.1
  C b4 T A B
 EMI60.2
 No. of R46 Ru R1I: 8 -¯¯ -¯.¯ ¯¯ ¯. Shade of the dye example R "5" 46 B * T on Dralon 436 H # * $ ¯ H C1 - GHyIC yellow 437 H 0- H - \ yo- (XM-X4 yellow 438 g, l H <¯ \ =! / - "0-CHo-CH9 - CHōKt yellow 439 H 0- H Yellow 440 HHH --o-cx-c-xl yellow 441 B OC H -0- OCC -Ka yellow 442 HHH O- % -Cll2-Clg2-lç5 yellow 443 HHH N2 3. yellow z44 HHH CE -CH2-CH2-r "2 yellow 112-Ç 445 H OCHg H - :;

  J yellow 446 H H H -CH2-> C% -% - "3 yellow 447 II H H -CHg-CHg-K yellow 448 H OC2X5 H -eH2-cti - x yellow

 <Desc / Clms Page number 61>

 
 EMI61.1
 ############## "######## **** '¯ ¯ ¯. Shade of example KitS R'6 R" 1 8 dye on example Dralon 49 H 003 '' c-c'x3 set 450 B #, Bg fi -1C Yellow 451 H M3 -CHjj-CHg-CH Yellow z H C4% H -15 yellow 453 C - T- "Jam CH3 leg 454 H 0 - H 't2-CH2 "2¯x yellow 455 tX2Bs -fi Yellow CHg-Kg 456 CSg H - /' # Yellow at 457 H IChCH-Câ2-0 HH at * = * 458 6-CBg HHH blade 459 H g3 ' JHH 38a 460 K7-CB2-CB2'Ca2 HB Yellow 461 H KC-CH-0- H -0 Jauoe

 <Desc / Clms Page number 62>

 
 EMI62.1
 ########## Ri. * Grade of teinitexempie R45 R47 "48 ture on Dralon 462 H Kk-CB2-CB2'CB2'O- yellow 462a x X2-C" 2-C% yellow 463% -C% 7 - yellow 464 I - CHg-CHg- yellow 465 IIC2% -C-CHg- C2 "5 reddish yellow 466 -CH2 -% - X4 yellow 467 -CH2-CH2-K2 CHg yellow 468 H -CH2 CHZ 'K,

   C2H5 yellow 469 x CH3 -C% -CI'2-X5 C2H5 yellow 470 H OC -ti2 Ci2-lc'I C2E5 Yellow 471 OCHg -CHg-CHg-K C2E5 Yellow 472 H -CH2 CK -% - c% -x2 yellow 473 a CH3 -CH2T9 C2H5 set 'C'c' 'yellow 474 H K.-CNg-CHg-O-

 <Desc / Clms Page number 63>

 Table 6 contains the description of other valuable dyes obtainable by the process forming the subject of the invention.
 EMI63.1
 lia correspond to the formula, R55 (3 'o R9., x CH - H - M # \ ¯7 "- Rc4 7C R54 R50' Y i R51 52 R53
 EMI63.2
 in which the symbols X, Y, Z, R49 # "50 #" 51 * R52 'R53 R54 and R55 meet the definitions given in the table.



  The indications on pages 16 and 17 concerning table 1 on the anions and the meaning of the symbols K are also naturally valid for this table 6.

 <Desc / Clms Page number 64>

 



  B L E A U 6
 EMI64.1
 44
 EMI64.2
 Shade of the example R49 R50% 1 1152 Rs3 B54 rP'55 dye on Dralon 475 SNN - -NE w i-f3CH CH H - Y - CB2-1Cl H blue -V-OCH3 CH, 3 -H greenish 476 SN x - SCH. CEL. H -, -cc- H violet 3 red .77 N C13 M3 H - ï 2 N2 red CH, ** - c4% blue 478 SNN - H3COVw- CHg H -., R'eH.3 OCR H blue YCC- 3 green 3-CO-C5 CX'2;: .... J 479 NHHB CH3 CH, H - N - red 479 '* C% -il-j bluish -' '! JI blue! tre.



  480 CH 3 H - H - ¯ 3. H red ....



  100 N '. red + $ 1 N N N CH3 H - KCH3 blueish IN.PI3 H purple 4u S N N - 3 CHg-CH-Kg red 483 CH3 H CH3 N'çH22 H blue red 483 S C N - 3 g2 R 'red

 <Desc / Clms Page number 65>

 
 EMI65.1
 example "" 9 '0 1 "52 3 the complexion ¯¯¯¯¯ ¯¯¯ ¯¯¯¯ ¯¯¯¯¯¯ ¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯ on Dralon 484 S - X02 CH CH3 - 'l P2 H young 2'c2 8 485 S c CH - cH3-co- HHH -12 violet --- ,: 5 3 486 c CH - cs3-co- X02 H t "' # * CH2 'CE3 blue r + 8 SC 3ri - G CH3 HRJ (..... eB2 H fileu -cH2-X3 violet 488 -so - CHp-CB-t: 1d.



  488 - CN3-302- CH3 M-OC% -CE3 id.



  "" '-12 489 seN - C & -CH-58- C "3 C 8 ¯ id.



  490 s c N - -S-cB2 3 H.-CH; H 14. x 491 8 c m - sc-so2- CE3 a a.-CR Il id.



  -92 Sc. - -s 0CH.3 H ..:. :: violet 492 -302-CE3 "2% M'3 '-CH, - blue

 <Desc / Clms Page number 66>

 
 EMI66.1
 Grade - of No. of Example y R. \ 9 Rso Rsl: 1s2 Rs3 R 5'1 55 rs wc 93 -S-cH- CIL. EYELASH. ! f- # violet 1493 - C 3 C "3 '% C% -Cla2-K6 ci blue JJ9JJ S 1f JI' 2. \ - blue 494 CE3" "C2HJJCH JJ95 sc Ji -s 11 H N'Ç2a # JI violet 495 -302-C% C2H5 blue. \ 96 11 N s tC - CB, - xWIC2H5 red 496 'C, -1) blue filter

 <Desc / Clms Page number 67>

 Table 7 contains the description of other. valuable colorant obtainable by the process forming the subject of the invention.



    It * correspond to the formula
 EMI67.1
 
 EMI67.2
 in which the symbols X, Z, R56 * R57 'R5g s R60, R61'
R62, R63, R64, R65 and R66 meet the definitions given in the table.



  The indications on pages 16 and 17 concerning table 1 on the anions and the meaning of the symbols K also naturally apply to this table 7.

 <Desc / Clms Page number 68>

 



  T A B L E A U 7
 EMI68.1
 ., ##. #####. ####### Shade No. of R Ry R6o 61 Afi2 63 64 65 66 the 3 e..eïe dye - ** on Dralon 437 SNHHHH CF3 HH -CH -CH-àC5 CH3 HH blue violet 498 SNHHH c OCH3 H -C-CH2-OC -C-Ke HH blue 499 SNH OCH3 HH CH3 HH -Co-cH2-K- C2Hs HH blue green 500 SNHHHH CH3 HH H-CO- Cf-Kl HHH blue greenAt # 501 SNH OCH- HH CH3 HH -C1: -1t C'H3 HH blue 502 SNH N02 HH CH3 HH -CHg-CHg-K C2Hs 1 H id.



  503 S N H c-se2- H H C2 H H -CHg-CHg-Kg id. H H id.



  504 S N H -S02-N (CH3) H H CHg H H -CH-CFi2-Kl id. H H id.



  505 S N H -S02-NH-CH3 H H CHg H H -CH2-CH2-K2 id H H id.



  506 S N H OCH3 H H CH3 H H -CH-CH2-I id. H H id.



  507 SNH CH3 HH CH3 HH C2Hs -CH2-CH-K2 HH blue 506 SN 8 OCH3 HH CH3 HH C2Hs -CH2-CH-X $ HH blue 509 SNHHHH CH3 HH C2Hs -CC-Kg HH blue 510 SNHHHHCHH C2H5 -CHZ-CH2 -K6 HH blue 511 SNHHHH -0 HH C2H5 -CH = -CH2-I HH blue 512 SNH OCH3 HH CH3 HH CH3 -CH-CH2-KT HH blue 513 SNH OCHg HH CHg HH C3ILr -CHg-CHg-Kg H li blue

 <Desc / Clms Page number 69>

 
 EMI69.1
 Triple XZ R56 1157% 8 59 0 N6I N62 3 64 5 66 ¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯re on ########### ####### ¯ ############# ¯ ######## ¯ ############ ¯ ###### #tln 5111 SNH MR3 HHHH C4% "22 HH tzsnue 515 SNH OCH3 HH CHg HHC% -CH2-cu '' cH'x If H blue 516 SNH OCH3 HR CH2 HH cH2-eH-acocH -cH-cx2 'HH blue 517 0 ra H CH3 HH CH3 HHC 'cr-cH' '1J Fui blue violet 518 0 n H Ache HH CH3 HH C2% -cFi! R5 HH 1d.



  519 S 1 H QCH3 HH CH3 CH3 B C2H5 22 HH blue 520 SNH OCH 3 HH CH3 H CH3 C -% - CH2-F..7 HH blue 521 SNH OCH3 HH CH3 HX "3 C -1t HH bl .... ae 522 s N 'U OCH3 HH cs3 ci s c2s5 -X5 HH blue 523 3 NHHH CH3 Br HC' cH'cH "; H H blue 52 S He He He He CE3 lff3 Co- H Eyelashes -Xg Il B blue 525 s N H OM3 H H CH3 C? 3 H c5 -IJ. Go blue 526 3 N H OCHg a H CHg H H -cx2xs -0 %% - X H blue 527 s m B 0% E H C H H C -cB2-K. B H purple 528. S 11 H H H CE3 H H C -CHg-C! L, - !: 6 B H roogeitre blue 529 8 v B H m a CH3 M E CH3 -16 B H M.

 <Desc / Clms Page number 70>

 
 EMI70.1
 



  : No. de - Nuance the example X Z Rs6 7 | 58 59 R60 1 61 * 62 1 H63 R65 R66 la tintaanr Datai.



  530 SNH -N8- HH C²3 HH CFi3 'CH2'C82-! 5 HH blue 531 SNH OCHg HH 11 H - HH blue 53 -GN3 -cet bzz2 -OC4-C 2H'x2 r-ougettre 532 SNH -CNS H n CE3 HH -C-CHg-CN -CI-CHg-OCO-CgH-Kg HH bluish red 533 SNH -SOCB3 HHH CH3 H C2Hs "11% BH id.



  534 S N H # 02 B H H cH3 Eyelashes -C2H¯Xs H H id.



  535 S N H SCN 8 8 H CH3 H C2Bs -C2H-1ca H H id.



  536 S N H cm H H B H H C -c2x- H H id.



  537 S M H X02 H H FI! B H C2H5 -C2H- - H H purple ¯¯¯¯ 1 ¯¯¯ bluish

 <Desc / Clms Page number 71>

 Table 8 contains the description of other valuable dyes * obtainable by the process forming the subject of the invention.



  They correspond to the formula
 EMI71.1
 
 EMI71.2
 in which the symbols R67, R68, R70, R71, R72, R73 and R74 correspond to the definitions given in the table ,, The indications on pages 16 and 17 relate to table 1 on anions and the meaning of the symbols K are also naturally valid for oe table 8.

 <Desc / Clms Page number 72>

 



  A U 8 wire L m T A
 EMI72.1
 No. of Re7 R R69 ¯- ¯ 170 R.1 2¯ ¯¯¯¯ R73 z-¯¯ ¯¯¯¯ R74 Shade of the example --l -l3 ¯ ¯ (dye on ¯¯¯¯ ¯¯¯¯¯¯¯ Dralon 538 HH K7-H 2C-Co- HH NHg -QH yellow 539 HH R-GH2-cH2-GO- HH NH2 .., 1 yellow 540 tI02 HH OH C6H12 yellow 541 N02 H. HH OH C6H12K 1 yellow 542 i0 H N02 8 H OH C6H12R6 orange 543 OCH3 H N02 EB OH C6H12JS. <3 reddish celi2xi yellow 544 OC13 H N02 HHH -CH2-CFI2-CÜ-Kl id.



  545 ao HHHH OH -GH2-aH2-xz g- yellow 546 u K7-CH2-e HHH OH -Ô M3 yellow 547 HH It9-GH2 Ca- HH OH B CH3 yellow z8 HH -GH-cH2-GO- HH OH m CH 3 yellow 549 x H KJ; -C3% -C0- H x OR H CH: 3 yellow 550 HH K2-ÇH-Co- HH OH H C13 yellow 55i 'rc2 G-CHA-CO- Yes Gas yellow 551 K2-CH2-Co- OH CH 3 yellow 552 Br B -C4 -co- HH OR H CH- yellow "" ### "" ### '* #####,;.,.;. - - .. :: -. :: t ... ::. q'7.: ':' ft - e: # 1 '' '- ,, ", ¯¯.1' '' Ic - "-." '± ... "'" * M '<C.). "" ##. Jt.-'-- J "###" tj .- ## .. ¯. -L. ... u

 <Desc / Clms Page number 73>

 
 EMI73.1
 Grade No. of the example '67 R68 9 0 71 172 T3 R74 te1nture or ¯¯¯¯¯¯¯¯¯¯¯¯¯ ¯¯¯¯¯¯¯ Dralon 553. Br H X -C-jl6-Co- H H OH - CE3 Yellow.



  554 CH3 H K-CH-CO- CH3 H or ¯% C93 .fauna Cl 555 CHg H Kb-t C- CE3 B OH B CE3 Yellow 556 Il Cl 15-C, -Co- HB oh H CE3 stess 557 H Cl Ir -co- HH OH - ^ 'CI C 3 Yellow 558 Br H -C3% -Co- H Br OH H al3 yellow 559 Br Xi' 3-CO- H Br Oi CE3 orange 560 N0- HHH CE '.- CB3 3au 560 2 # -Q CH3 Yellow NH-CO-C $ -1G 561 K0¯ HBH cvh -i) -NH-CO-C - 12 CH3 yellow 562 HO, B CH3 HH on f1 * '*! CE3 young red8tre 563 M02 a H on CE3 yellow -CO-C $ '564 * 0g H H B OS! TB-C-K CE3 0I'8Dp 565 H H 1c-CH2- B B # -0 CE3 Yellow

 <Desc / Clms Page number 74>

 
 EMI74.1
 Grade No. of Example 68 Rb9 R7 -i RT2 RT3 dye on Dralon 566 H NN-Co-c2H4-X7 HH OH sT \ C93 yellow 567 H H8-CO-C2B-l HH OH ¯ ± \ CHg yellow 568 HH pH-CO-CH, 1Gj HH ce C "3 CE3 Yellow 569 H NH-Cü-C2HX HEH ce -Ç C 3 yellow 570 H NB-COC04% H m OH ¯ / CH3 yellow 571 OCI So2-M3% 111 HHH OH -3 CH3 yellow 572 H -CHgK,

   H OH id CH yellow 573 H -COOC2H1C H H OH id. CH- yellow Here 574 HH Co-MC3% x9 HH OH -F \ C "3 greenish yellow 575 BH Co-NHC3H6a EH OH - CH3 yellow 576 Cl 01, CH, yellow 57 M¯cō (CF .2) 4 é Hearth /! H-CHp-OCO-CHp'H-'K- CHg-Kg / ÎEU-CHjj-OCO-CHo-CIîo-Ka 577 -à% -CH2-oco -% -% - x3 CE -VJ = \ CE3 orange t-CBO-CHg-CBg- xl # cB3 red

 <Desc / Clms Page number 75>

 
 EMI75.1
 No. of 7 R 9 --o R7, R'T2 -L3 R74 Shade of Example P-69 dyeing on ¯¯¯¯¯¯¯ ¯¯¯ ¯¯¯¯ ¯¯¯¯¯¯¯¯¯¯¯ ¯¯¯¯¯¯¯¯¯¯ ¯¯¯¯¯¯¯¯¯¯¯ ¯¯¯ ¯¯¯¯ ¯¯¯¯¯¯¯ ¯¯¯ Dralon 578 HH 'ocs2-cH2-oco-cH2- cH2- HH OH -0 CH3 young 579 HH -C <l # -C3-Ka HH OH -sC2- CB3 yellow% j-N8 02-D CE3 greenish 580 CH3 -H "" "C2Hs HHH -o- Yellow CH3 - M %% CO41rg * OCK3 'C2H41tg

 <Desc / Clms Page number 76>

 Table 9 contains the description of other valuable dyes obtainable by the process forming the subject of the invention.



  They correspond to the formula
 EMI76.1
 
 EMI76.2
 in which the symbols R75. R16 'R.r1' R78 # R.r9 and R meet the definitions given in the table.



  The indications on pages 16 and 17 relate to table 1 on the anions and the meaning of the symbols K are also naturally valid for this table 9.

 <Desc / Clms Page number 77>

 



  T A B L E A U 9
 EMI77.1
 Shade of Ro No. Shade d .. Example 77 7 Dralon 5bl -CO-CHg H j¯O yellow H 582 H -CO-CHp-K. HH p yellow elm * e 3 583 -CO -116 dF Yellow orane 584 HH -car-c-cg HHT¯Qî yellow -CO-C% -IK8 H reddish 13 585 BH -C-X9 BH m 3auna 3 Cl he

 <Desc / Clms Page number 78>

 
 EMI78.1
 ¯ - ###, #### t ### ï ### - "###### '" Ko BO Grade of Dralon i No. n76 R80 Grade of, 1'ex¯1e 5' T6 ## - ######## 1exemPZe ¯¯¯¯ ¯¯¯ ### - ########## *** 586 Ii H. 1 Ja- green ...



  -CO-CB- 587 H Ii -CO '2 Ni Ii -c -Co-CH * -Ki 3 -gaz¯ - # ar yellow 5g $ a -Co-c1l:! - Yellow f. #. yellow 589 '-Co-c1l:! - 1rs 589 CH3 ¯' C "3 Ji. yellow 59" -Co-c1l:! - L. --- ("} 59n H Cl -Cü'H2'l ./W CH3 3 H 591 -co-NR-c3% -1 (l: O.



  591 -CO-NH-C 3U6 Il, j3 yellow -.- a? F "7

 <Desc / Clms Page number 79>

 
 EMI79.1
 "" # - R - ,,, Nuance delateinl'exe'J1Ple - "1" "* 76 * 77? 8 R73" 80 Turkish on Dralon 592 1I2-m1:! - Co- Yellow 592 HH K2-CFi2-CO- HO alder.



  593 H H K1-C H-CO- H H id. Yellow 594 H H Kl-C3H6-CO- B H id. yellow 595 B "'- 8 K-r3CQ- HH id. yellow 596 HH IC3-CHZ-Cfl-. HH id yellow 597 HH 8-2- HH Jf / LOH yellow j \ greenish 598 HH K.-CH2-CO - HH d "G 'greenish H3 599 Br H b) x, .- C2H¯-Co- Br -O" 08 orange 8) 1-02-00- al orange 600 Br H - 3 11) - (orange b ) K # -CH3CQ-

 <Desc / Clms Page number 80>

 
 EMI80.1
 ¯ Shade of ## T 1 dye on No. of - '77 Rg "79 R80 Dralon aur bzz1178 Dralon example 75 76 77 ¯J¯¯¯¯¯¯¯¯¯¯¯¯¯¯ ### L - # ¯ ------ "" I -j. Red 601 X2-C-Co- orange 601 H VOfe-CO- XXCH3 "* 2H, .- eN" tfï scarlet Irt; -Co- scarlet 602 H - CHg-CO- ¯¯-3 Îj-Clî tVnV 08 red 603 HH g8-CH2-CO- HH # red 60Ii x ..- co- YY red 604 HH X7 HH H3c H ag5 bluish 3 21! S .Y red 605 Hey.

   H H H red 4119 / ni # PO # # lV / rNS; CH [H j bordeaux sos H - Ho H bordeaux 606 H H Kj-CHgW- s <- s! '

 <Desc / Clms Page number 81>

 
 EMI81.1
 Grade No. of Example R.r6 176 R # IU3 -19 Rao dye over 607 HH 1Cg-CFFO- BH --OB -anse J * HO 608 Bar H x, c2r, -co- HH .jg OMnR * 609 Br H "6-co- HH" iL / "01 * orange OR 610 Bar H Kg-CH-CO- HH ao 5 * tW # m 611 CHg H Es-Co- H J'1I ... rr * e Q OH 612 CHj H lC-CO- CB3 H ') C ** BO 613 Cl -c3a, .co- B, HO

 <Desc / Clms Page number 82>

 
 EMI82.1
 Grade No. of the example Rr5! L6 - (- 1 B78 Ff9 0 dye on Dralon OH 61 H Cl X - CH-CO- HH T5 orense IOB 615 Br H 1rs-Co- H Br JjC orange ses x5-c, -CO- aunt 616 Br H Kç-CjjH-CO- H Br Kgff J8UD * 617 HH xb-cx2-co- HH j, 1 <lcarlate at 618 HH x6-cH2-co- HH - # sa.



  ! 2H. \ - cI 619 H H x-cH2-co- H H y - ## / id.



  CgHCII 620 II H ca, H H "3 bzz

 <Desc / Clms Page number 83>

 
 EMI83.1
 ¯¯¯¯¯¯¯¯¯ Shade of the dye No. on DralOB No. of R.5 R76 "77 - -I8 179 Rao dye 8 on Dral" "the example ¯¯¯¯¯¯¯¯¯¯ ¯¯¯¯¯¯ - ¯ 621 -C00ll-C3% Ka BS w jO t reddish purple 6? '2 CE3 B CE 3 -CB2-NB-CO-CB: 2- CH2 Ho- -cH3 yellow 623 CH -NB -CO-CB: 2-K CB, II: 3C \ =: T "" Yellow 6211 CE, B cH3 -cg2-riH-co-cx-x3 CH 3 Hç 1 - - cH3 yellow paC-N - N G25 CE, H CH3 -cH2H-co-cx-x6 CH3 Be ## -CO- yellow = c, reddish 626 CR3 C "3" "- ¯¯'3 Bc 1 j C" 3 jame 626 -m-co-cll :!-\ . Young

 <Desc / Clms Page number 84>

 
 EMI84.1
 ¯¯¯¯¯¯¯¯.¯¯¯¯ -. ######. ##### r - ######## - #### j ¯ | Shade of ia of BSO dyeing on Iexple "75 '6' 7 Dralon on example 75 76" 78 ¯¯¯¯¯¯¯ # * # 62T M3 du -Ci tfi-C-CIi2-Xl CH3 FÏ 4 - C CE3 yellow ¯¯3 0 a- C, ...



  628 Cl CE3 -CH2 3H¯co, -CH2¯3 CH3 BÇ C - CH3 yellow 0-S CB-CH-CH 629 CH3 H CIL -CH-NH-CO-C8-iCl CH3 H .. N - C83 yellow 630 CH3 H CH3 -CH2-NH-co-cP12-x2 CH3 0-C # J - CBj 'yellow 631 -% - NH-CO-C% -K4 CH3 Hc c CH3 yellow 631 CH3 CH3 -CEa-HH-CO- K, CH3 -j "fauna

 <Desc / Clms Page number 85>

 
 EMI85.1
 No. wu "'- uance la exerle R, - -i R7.i? G ¯ lig R $ 0 1I 632 CH3 H cr3 Hg-CO-CB-Kj. CËL BC M3 yellow 0 cx 633 CEL CE - <' 0-Ctt-Kg CR3 HC # C - C8L iambe bzz 63 * OCH, -OU-KH-CO-CiÛ-K ,! ÎÏÇ tn * 634 OM3 -% - NE-co-C% - CE3 nuas C83 verditre T # # "0 - C, lî..Ox * b 302-C% 635 OCH- -CIIH-CO-CO C" 3 B &# C - CHj Id. P-3 0 -CJt sa2¯x32 636 OCE3 E -CB2- M-Co -% - C83 B ## C -Ct Id.



  ## * 0 - C.,

 <Desc / Clms Page number 86>

 
 EMI86.1
 zozo shade of 1 example R80 dye on 637 CCR, - (- 0-CH-Kj. CE3 -c- CE3 yellow Il ci reddish 638 OM3 9 - <- 0-C &, - KC "3 B (D ::: ;: g oe-ange 1 639 OC83 a -C-CO-C & '1C CH3 B -C -CH3 yellow 640 OCHg B -C'TFI-CO-C'f-l OE3 a O: -rf -0 0¯ - 641 1CH3 -G'Ftïi-CO-CB? -1C3 CH -C ## 3yellow 641 Or3.

   CE3 H3 cizQ yellow Cl 642 oeH3 m -cII:! -! III-CCl-Clf: -1I2 CH3 a.) A3 = .tre ¯- 3,643 OCHg --CO-CH-Ky CB WCY'O '643 -% -NH-co -% - lr7 CE3 days

 <Desc / Clms Page number 87>

 
 EMI87.1
 - Shade of l '; xe # ple R R7g 77 Rra 179 R80 dyeing on example 75 "77 -f8 1175 Dralon $ on 644 --¯3 CH3 ¯Cg2 NH¯CO¯CIīgI B. / Yellow H 645 OCH, CH3 ¯¯p0¯- HH - C-CO-CH3 il yellow 0 = Cî 6f WH 3 CH3 -CH2-NH-CO-CH2 -K5 H NC-ÇH-CO <) yellow 647 C "3 -C % -NH-CO -% - Y6 H NC - S02-o- yellow 646 OCH, --NB-Co - 1t WH3 H -HC - CE yellow ON reddish 649 '- -CHs-NH-CO-C- OCHg J red 650 3 H --II1I-C-Jr cg.3 IIII:! - (X) .SO:! - I1 () red

 <Desc / Clms Page number 88>

 
 EMI88.1
 Ho. R3e R Shade of the 3 'example Rc R? 6 77 78 79 0 dyeing on the example Dralon 651 OCH, -Hg-NH-CO-CH-Kg Cl PÀ3c-co-OE-co-NH red 651 OCH3 -NH-eo-c- e-Co-cH-CO-NH - orange range.



  652 OCHo -CHHH-CO-CEfe-Xj H3Ch.



  652 OCH -CH! H-CO-CHg-K 3 '> 652 WH3 -1'm-eO-C-K1 CI. I3C-Co-eH-CO-NHVC1 id.



  OCH- 653 0CH3 H --NH-Co-CH2-K Cl H 13ej- yellow -CH2-NH-CO-CH2-Kl H3C NH i-CH3 redfttre 654 HH -NH-eo-o-c2Hs -CH2-I3H- CO-C -K3 H H3C-co-ßH-eO-NH- (eH2) 5-c yellow 655 HH -rrH-co-o-c2H -CHg-NH-CO-CHg-Kg H H3C-CO-ÇH- CO-NH-CH2 yellow 656 HH -NH-CO-O-C2 -% - NH-C 0-CH2-lÇ6 H QCnhISh- red 657 HH -NH-CO-O-C2115 -cH2-riH-co-cH2- x7 H CjL ** * 2 reuge cl, C2H4-CH 658 HH la. -cH-rrH-co-cH- H I3c-co-bu-coO Yellow

 <Desc / Clms Page number 89>

 
 EMI89.1
 . ########################### '# "* #" ###############' Nuance of ...-: Ho. De B¯c R.6 77 8 179 0 e1nture in exile "76 '77 ¯ ¯t ¯ - f lon 659 HH -NH-CO-0-CHc -c -xx-co-cR H C-C0-cH-S02 JMM 660 HH -NH-Co-O-C21! s -CHg-NH-CO-CHg-K H .. 3Su.ne 661 H 1102 CHg -c r -co-cx-x OCHg R.3C-Co-Ca oran.



  662 H NO2 -cH, -. M-eo-CH, - OCH3 0- ./ CO 'es- yellow HI red! Be V 1I-Ci) -c <, r 663 H NO2 CH3 -.c-xA-co -c-x2 3 c-2 orange 664 H x CE3 --ë - - - "b OCH3 JJ. -C ...... CH- red! 'tre.' 1: 0/665 H 1 (c83 - I # -C-Xs OCHg xC - CO-0 CC! 1 Yellow 666 Cl H BC # C- J ..



  666 10-C.-N * \ Jas: 18 -H O-CT3 CH-MÎ-0-C% -KJ

 <Desc / Clms Page number 90>

 
 EMI90.1
 Lido. of/..,. R¯¯ R-. 3 p eacé d; example '"75 76" <T7 ..r the dye ¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯¯ ¯¯¯¯¯ on Ion 667 NH-CO-CH3 mi. - 0 c -CH3 young o - -N ----- 3 HtH-Cp-Cg¯I 668 H WH-Co-o-C2% H ne 8 cb Yellow 0 - c-.4 #, CH2-H- CO-- ,, 669 Co-o-C2H5 H HC ## S'CHa yellow o = C '' N '' 3i CH 3 -rx-CO-cH-xi CH-NH-CO-CH-K.



  610 Cl H N02 L) f3 red 670 N02 S <. blue HO OH 67i H ro2 CH3 -CH:! - NH-C-1I2 'OCH3 yellow

 <Desc / Clms Page number 91>

 Table 10 contains the description of other valuable dyes obtainable by the process which is the subject of the invention.



  They correspond to the formula
 EMI91.1
 
 EMI91.2
 in which the symbols IR8, # R82 Roy B840] R85 $ RQ6 'R37 and R88 meet the definitions given in the table *
The indications on pages 16 and 17 concerning table 1 on the anions and the meaning of the symbols K are also naturally valid for this table 10.

 <Desc / Clms Page number 92>

 



  T A B L E A U 10
 EMI92.1
 Shade of the example P'81 82 3 Ra4 z5 Ru Hg Raa dye on 672 HHHHH ONH () 3Ks HH yellow 673 HHHHH ONH (C) 2K HH yellow 674 HHHHH iH (cH2), KHH yellow 675 HHHHH 00 / C4H9 HH yellow 'CCHO! IC1C2,., CH3 676 HHHHH IC eCR3 HH yellow 676 () 3K6 677 HHHHH -COOC4 Kg H 1Í yellow 678 HHHHH cooçHCH2xg HH yellow Hq ÇH yellow 679 HHH CH3 H H -CCKHC2t ClHOE 6HH HH H yellow CONB () 3Kl HH Yellow 681 H Cl HHH COOC2H4Ks HH yellow 682 HHHH -NH (CHg) HHH yellow 683 H Br H Br -NH (CH2) 3K 4 HHH yellow 684 H Cl H CI -NH (CH2) 3X ,, HHH yellow 685 H Br HH -NH (C) 3JG HHH yellow 686 HH CI CH3 -NH () 3 HHE yellow 687 HHHHH -NH () 2Ks HH yellow.

 <Desc / Clms Page number 93>

 
 EMI93.1
 



  No. of F Ra- Roo Shade of the example pm Ra2 z83 Res Ru 1 dye on. # ¯.,, ¯ Dralon 688 H Br H Br H -mt () 216 HH yellow 689 H CI B Cl H -SH (C%) 2 "2 HH Yellow 690 H Br HHH -t'N2 HH set 691 HH Cl Cfi3 H -NB () 2 HH yellow 692 H 8 BB xcs2) 8 HH 3aUM 633 HHHH -! LHC () 2 HHB Yellow 694 HHHH -NH (%) 4x4 HH yellow 695 HHHH 'lox2 HHH Yellow 696 HHHH QH yellow 697 BHHH z cxox .Yellow

 <Desc / Clms Page number 94>

 Table 11 contains the description of other. valuable dye obtainable according to the process forming the subject of the invention.



  They correspond to the formula
 EMI94.1
 in which the symbols A, B and C meet the definitions given in the table.



   The indications on pages 16 and 17 concerning table 1 on the anions and the meaning of the symbols K are also naturally valid for this table 11.

 <Desc / Clms Page number 95>

 



  T A B L E A U 11
 EMI95.1
 No. of ABC Shade of No. dyeing on example dyeing example ¯¯¯ Dralon 698 HC 0 - --CH = CH-- '' fauna 698 "5C2 0-.G- CB = CH- \ W2115 yellow C} JCB ÇH-CHq.



  (; 3H63.K 3x6-i7.



  699 -c - \ s- '- 2 H2 lemon 3c; s -F> -s WeCH3 yellow -CH - # - CH - '=' = \ i -CH-CB3 golden OH oH C "orange 101 K2-C% H3C '%% 0, N ..- OE3 orange l \ 2-cH2 VI w "lez '1r1'" CB) bu -, j 7 # 117-CO -0- .. no orange 7'J3 -CO -0- / \ - i '"3 orange 703 E3-CH -CO -'ii% "orange C1 Hf. I \ ..- i

 <Desc / Clms Page number 96>

 
 EMI96.1
 ¯¯¯¯ - ## t ############## # - ######## "-" #### "# Color shade of ABC ture on Dralon example "" # / 3 -CH, -CO- llH3 f3 orange 7o4 IÇ9-c H2-Co lu3 orange fi3 HO H 715 r -0-0- J: i6Bs orange, Ci'4! C L2H4Xl C6H5 106 B -0- CH2 -0- \ - 16Hs. "Yellow:, 706 H5C6 \ == / 2 == / Ho yellow% J'-OH 'If' N C2A¯2 C2H4-.



  707 -0- "5C6 CH yellow # 34 701 -cI!:! / R \ # / C3% K- red j - <\ sunegtre 708 '<= /" yellowifter' 3

 <Desc / Clms Page number 97>

 
 EMI97.1
 No. of ABC Shade of the example dye on Dralon 709 H4e2 'N CH3 - <- NH- C2X4-K5 abalone C2 WH, put Tlo H3C / r "# /" H'i' 710 H3c P \ -c2HJF- Ki serte NOg Cil 711 C1 / === k NH-Coj; -K4 711 ON -o-C1) == <'' 'sriae ci Cl CHa ,, 2H4N1 T12 o -0- "([j3 -o-. , c IL. red '% C brlque 2H5 bluish Cl 113 Y ro :. brurie H 714 iL) ril id. bordeaux -0 K, Fec3m Cl bluish

 <Desc / Clms Page number 98>

 
 EMI98.1
 Shade No. of the Example ABC Tincture SUI "Dralon ..4.



  715 2N -0- \ -V '-Ó-w-Co-cB:! - X: 2 bordeaux H3CO HO ci 3 gOPS'V.



  716 \ = JL \ == C "2-Kl redness.



  O'E3 717 HO -0- CE borde! Tux 0-C - () \ NU CN2-xl CE2-'Kl K-CH C "3 / == C-! Q K2C2H4 '-¯-3' -Q- . ", C2H¯-% C2" 4 route "5C2 .-, N c2H5 letter" 3c 'boràaamc 719 yr' ('ù bordeaux 719 rC 3 -C3E6-Xl

 <Desc / Clms Page number 99>

 
A B L E A U 12 Other. Value dyes which are obtained according to the methods of the invention are described in the following table.
 EMI99.1
 



  Example No. CH 720 "###? A 2 E 5 ci 1- N,; - N - N W..A iW. Wheel-v101e + 721 a.r '' N 'N, ¯-I (\. ..- ,. / l'0, N / C2ü 1 zorn. - "CH2-1C6 01 'id.



  CH3? 02 722 2 a Ncx U.



  722 C-C "x C ', sul1 Hic 8 Y-- (t) Ci) 0' 3 1 C- 1 N m '1112-C -11 2 Gi blue.' CIi2-CH3 J) 724 724 - 'Nr, C2H5 G) (DH. -0- <C -Cil -Jtl 2CI CH3 rOUIe-violet 725 / - \, C2H5 00 725 -0- ", C2R5 t .. 2 CI roùse-violet LjLM 3 CHg-CHg-Kg pougw-violet

 <Desc / Clms Page number 100>

 
 EMI100.1
 No. of --N5 0 0 example N 2 5 '\ !; I 1 example CH3 t N N 01 726 N red violet' T2T 727 violet L). violet 'T red red HN 0 CH2-116 CH3 728 CH t! ** \ 728 HC #### N ..Cg¯, f \; 1 NCN - N -C% -C% -CH2-r'2 2 Cl violet CE3 H 729 -6²H 04 0 ('- "-0'! N 1 N H2-CH2'KI blue 1 -" "2 -" "2 blue CH3 730 0 NC CH 3 N"% -C "2- 0% -Kl 1 2 ci bordeaux

 <Desc / Clms Page number 101>

 
 EMI101.1
 Mo.dt <TV &, the specimen.



  1'1.> - o-N. No- <: (CIIa-K) 2 - j (X> -0 - '"' '-' Cl yellow 732 C2ff5.oe8oe" -:; N + #> zaza 25 Cl yellow N'CoN.No-CN lee .



  733 (: r 3 2 CI ci CH3 CH (D yellow 7J4 (: iN ".. -0- -0- N # eu, o 100, NN c's," (CH-L) H3G 2 2N-oN. 'Co ..NH-q yellow z arr-N H Si Ywl7i1 0 anion f anion Nn-CO-CH-CHo-! Wheel 7 <S ### NH 9 anion wf anim Xl-C2 "4-o CO-02HJ-Jel purple road

 <Desc / Clms Page number 102>

 
 EMI102.1
 No. do 0 0 l'wxotmpif # anion 737 îyCHg-CO - '"' ''. Violattt 737 X7 -%. Co) -U violet CH3 NEI2 z CH3 0 anion (D j == (<.t) Mien 738 x-CH2-CQ "NN N. N anion H, CO NH2 Cl \ / anion 7M. K-CIi-CO -" N'N R - Il violet Cul 740 JCl-H100, tY 1on 740 x H 0 anion 1 10 5 -EN 03 yellow CO 741 N- CH, anion 0 (TJLj 80-Nfi- (üi xl red NIl / Tr \ bleuit ...



  NH # \, Jr-CH NOa <.t) N02 anion 741 a 1 "CH2-CF-IN 80" NH "yellow

 <Desc / Clms Page number 103>

 Table 13 contains other components which are suitable for the manufacture of the dyestuffs which are the subject of the invention. These can be obtained by oopulation of the diazo compounds of amines of column A with the coupling components of column B then coupling of the diazo compounds of the amines of column C with the mono-azo compounds thus obtained.
 EMI103.1
 



  Ho. De Nuance of Example A ac dyeing 1 example AC Orlon 7.0-CNNH-C H.-K.CN 742 NC ¯0% ç) 2 4-K4 1! 2ND- ON gray-blue HO 7 CN -C2H4-K6 N - .. Cl C3 green-blue 74, 02N-o NI!:! Ç) 5 <.) - green-blue HO 744 NH -C2H4 -K6 CN grle-vort HO 745 V rL NH2 çô-CaH4-Ks "2" \ I) violet Cl liD NH-C2H4 -Kr Fin CN violet 746 Ide çô IIN-oN02 violet HO CN NH-112H 4-K3 CN 747 m2N. (- N% ç6 H2N- CN greenish bieu HO NH-C2H4 CN NH-02 H4-Kg CN 748 ne-d-NH 2 (j () H2N N02 blue L'OUgeit1'8 HO

 <Desc / Clms Page number 104>

 
 EMI104.1
 Mo. of * "" "'*" ## ** ## TT * ## .. example ¯, ¯¯¯.¯¯ ance of xemp3.a dyeing on z + 9 02N, .. 21 Nose NB .. 02 H4 -Xa 01 749 0 2 N - (% ÇI) .02H4-x8 lqo2 gray HO CN jm-Cs-Kg ci -o H brown nolre 750 02N-Q-NI!:! II; N -b- 002 black brown HO


    

Claims (1)

SUMMARY The present invention includes, in particular, 1 As an undue product! new: a) Basic dyes corresponding to the formula EMI105.1 in which A represents the radical of a dye free from carboxylic and sulphonic groups, represents an optionally substituted methylene group or a divalent or trivalent radical linked by such a group to the neighboring nitrogen atom, R1 represents an optionally substituted alkyl, cycloalkyl, aralkyl or phenyl radical or, together with R2 and the neighboring nitrogen atom, a heterocyclic system or, together with the bridge element y and the neighboring nitrogen atom, a heterocyclic system or, together with y, A and the neighboring atom, a heterocyclic system, <Desc / Clms Page number 106> R2 represents an optionally substituted alkyl radical or an optionally substituted cycloalkyl, oralcoyl or phenyl radical or, together with R1 and the neighboring nitrogen atom, a heterocyclic system, R- represents a hydrogen atom or an optionally substituted alkyl radical or an acyl radical which can form a ring with R and N or, when R1 and R2 signify other ohose than a phenyl radical, a phenyl radical, R4 represents a hydrogen atom or an optionally substituted alkyl radical or an acyl radical, n has the value 1 or 2, m has the value 1 or 2, if n is 1, and 2 if is 2 and X represents an anion corresponding to each dye cation, b) in particular nitrated, styrylic and methine dyes, EMI106.1 polymethenics, anihraquinone, quinophtalonlquee, azomethins and azo compounds corresponding to formula (I); c) articles based on polymers containing more than 80% aorylonitrile and copolymers composed of 95% acrylonitrile and 5% vinyl acetate, acrylate or methyl methacrylate dyed from aqueous solutions or aqueous suspensions of the dyes specified under a) and b); oils, varnishes, plastic materials, plastics * cellulose and polyacetates <Desc / Clms Page number 107> acrylonitrile dyed in the mass by means of the dyes specified by us a) and b) and salified by means of a fatty acid anion, the polyacrylonitrile and the cellulose acetates pigmented by means of the dyes specified noua a) and b) and soiled * fies by means of a complex inorganic acid anion. 2 A process for preparing the dyes under 1 a) and b) which consists of replacing or transforming into a compound corresponding to the formula B - y - Z) n (II) n substituents Z by n groups corresponding to the formula EMI107.1 in which B represents A or the radical of a compound capable of forming a dye and Z represents a substituent which can be replaced by a group corresponding to formula (III) or which can be transformed into such a group and then transform the product of the reaction er. dye if B represents the radical of a compound capable of transforming into a dye. 3 of the methods of carrying out the process specified in 2, having the following features taken separately or according to the various possible combinations: <Desc / Clms Page number 108> a) one of the embodiments of this process is characterized by the reaction of 1 molecule of a compound corresponding to the formula EMI108.1 in which E represents the acid radical of an ester with n molecules of a compound corresponding to the formula EMI108.2 followed by the transformation of the reaction product into a dye when B represents the radical of a compound capable of transforming into a dye. b) it is also possible to react 1 molecule of a compound corresponding to the formula EMI108.3 with n molecules of a compound corresponding to the formula EMI108.4 quaternizing the reaction product and, when B represents the radical of a compound capable of transforming into a dye, transforming it into a dye, the quaternization and the transformation into a dye being able to be carried out in a normal order. <Desc / Clms Page number 109> c) it is also possible to obtain the new basic dyes corresponding to the formula CI) when 1 molecule of a compound corresponding to the formula is reacted EMI109.1 in which the alkylene may or may not be branched and contain 1 to 3 carbon atoms with the molecule of a compound corresponding to the formula EMI109.2 and that the reaction product is converted into a dye when B represents the radical of a compound capable of transforming into a dye. d) one can react 1 molecule of a compound corresponding to the EMI109.3 formula / formula 8 ¯¯ i a (IX) elooyana .. 8 n with 1 molecule of a compound corresponding to the formula EMI109.4 and transforming the reaction product into a dye when. B represents the radical of a compound capable of transforming into a dye <Desc / Clms Page number 110> e) one can also react 1 molecule of an amine responding EMI110.1 à la t'orD1Ule / Rl.-j #,. <'*') with n molecules of a halogen amine, Quaternize the product of the reaction and transform it into a dye when B represents a radical capable of transforming into a dye or when 1 molecule of a compound is reacted answering the formula EMI110.2 with n molecules of a halogen amine, quaternize the reaction product and transform it into a dye when B represents a radical capable of transforming into a dye, quaternization and transformation into a dye which can be carried out in any order. f) it is also possible to react 1 molecule of a compound corresponding to the formula EMI110.3 with n molecule of a halogen amine, quaternize the reaction product. and transforming it into a dye when B represents a radical capable of transforming into a dye, the quaternization and the transformation into a dye which can be carried out in any order. <Desc / Clms Page number 111> 4 the application of the dyestuffs specified $ or 1 a) to the dyeing of articles based on polymers containing more than 80% aorylonitrile and copolymers composed of 95% aorylonitrile and 5% vinyl acetate, methyl acrylate or methycrylate dyed from aqueous solutions or aqueous suspension; to the dyeing in the mass of oil, varnish, plastic mass, plastics ;, cellulose acetates and polyacrylon @ trile if the dyes are salified by a fatty acid; to the pigmentation of cellulose acetates and polyaorylonitrile, if the dyes are salified with a complex inorganic acid, industrial applications of the dyed materials specified under 1 b). Process and products as described above with reference to the cited examples.