DE2020295C3 - Dye preparations, processes for their production and their use - Google Patents

Description

F-. have been various FarhstolTpräparate suggested that mainly from a solution of a dye in an organic solvent exist. These preparations have the π The advantage that, in contrast to the otherwise customary dye powders, they do not dust and those contained therein Dyes do not have to be ground and conditioned as finely as dye powders Case is. But since the admixture of solvents ίπ Inevitably, the water fouling increases and the solvents used with the dyes are used can practically not be recovered, there was a need for dye preparations. which contain as high a proportion of dye r> as possible.

It has now been found that dye preparations with phosphorus! Solvents, in particular with lle \ amethvlphosphoric acid triamide. the above mentioned Fulfill the requirement and, moreover, are practically non-combustible, which makes the handling of the Preparations made easier.

The subject of the present Spring is therefore Farhsiol'fpräparate. those from a) 20 to 50 "» (related on the weight of the finished preparation) of a dye tr> sioifs. hi HcxaiiiclMylphosphoisäuiciriaiiiid as a solvent, el optionally a dispersant, dl optionally a further Tcvtilhilfsmittcl and

e) optionally consist of a further solvent.

The dye preparation preferably contains 25 to 50%! Based on the weight of the finished F'arhsloff preparation) Dye, if you use a liquid dispersant with good dissolving power. bis / u 50 "ii ties present Pliosphortriamids through the disperser can be replaced.

Representatives of the most varied classes come into consideration as dyes, namely a) those containing sulfo groups substantive dyes, acidic wool dyes and above especially acidic fiber-reactive dyes and b) preferably metal complex dyes free of sulfo groups. internalized dyes, for spin dyeing of Cellulose acetate suitable and paint-soluble dyes and especially disperse dyes, which also fiber-reactive groups have oiler can be free of them.

The above mentioned dye delineations correspond in tier cone use the one in the color index! en terms.

The dyes can be of the most varied classes of dye like ilen classes of mono-, dis- and polyazo dyes. Aiilhraquinone-. Perinoii. Chinophlhalon-. Oxazine, nitro, phthalocyanine, stilbene and methine dyes including the styryl. Azamelhin-. Polvmethiii- and Azosl \ r \ lfarbsloffen.

From the particularly preferred series of disperse dyes The azo dyes of the mono- and disazo series are particularly suitable, as examples be the dyes of the formula

DN = NA-NR ₁ R ₃

wherein I) the remainder of a diazo component, A the remainder an optionally substituted p-aryl moiety and R, and Ri each optionally substituted alkyl radical c are, which can be the same or different from one another, and the dyes of the formula

D-N =

where D is the same as above and B is the remainder of an enolic coupling component such as a pyrazolone or aminopyrazole or a naphthol or phenol. Then come the Disazo dyes in question, especially those that differ from the p-Phcnyüi / o-azobenzene of the formula

N- N

derive.

Examples of suitable anthraquinone dyes are /. B. the optionally substituted 1,4-diamino, l-hydroxy-4-amino- and 1.5-dihydroxy-4, X-diaminoanthraquinone c called.

The azo dyes can be derived from the following diazo component !! D NH> derive:

Aminobenzene,

- A mino-4-chloro benzene.
-Amino-4-bronihcnzol.
-Amino-4-methylhenzene.
-Amino-4-nitrobenzene.
-Amino-4-cyaiibenzol.
-Amino-2,5-dicyanhcnzt) l.
-Amino-4-methylsulfonyl benzene. -Amino-4-caralkoxybenzene.
- / \ miiio-2,4-dichlorobenzene.
-Amino-2,4-dibromobeiizole.
-. \ mino-2-methyl-4-chlorobenzene.

- A mi no-2-lri fluor met hjl-4-ch Io r benzol. -Aminoe-cyaii ^ -ehlorbenzene. -Amino-2-carbonielhi) xy-4-chlorobenzene, -Amino ^ -carbomclhoxy ^ t-nitrobenzene. -Amino-2-ChIoM-CVaHbCHZoI. -. \ mino-2-chloro-4-nitrobenzene. -Aminoe-brom ^ -nilrohenzol.

-A mino-2-chloro-4-carbalho \\ benzene.

-Amiiu> -2-chloro-4-mcth> lsuiron_s! Benzene.

-Aniiiio-2-methylsulfone) l-4-chlorobenzene.

-A mino-2,4-dinitro-6-melh \ Isu Ifony! Benzene.

-Amino-2,4-dinitro-ft- (2'-h) hydroxyethylsilfoil) -bcnzene,

-A mino-2,4-ilinitro-ft- (2-chloral h ν! Sulfonyl) -benzene.

- \ mi η ο-2-niel In Isu I fön \ 1-4-11 it ro benzol. - / \ mino-4-nieth> lsiiiron \ l-2-nitrobenzene, - ■ \ miiio-2,4-iliiiilrobcnzol.

- \ mino-2,4-dic> anbeiizol.

- A miiio-2-cyano-4-meth \ isulphone \! Benzene. - ■ \ niiiio-2.ft-dichloro-4-c> anlu ⁱ nzol. - ■ \ mino-2,6-dicblor-4-nilnibenzene. -. ■ \ mino-2,4-dic> an- (i-chlorlu '! IZ (> l.

4-.Amiiio-benzoesiiiire-c \ elohe \ slestcr.

l-amino-2,4-dinitro-6-chlorobenzo! and iiiheson-

l-Amino-2-cyano-4-nitrobenzo |, also I-aminobenzenes-, -'S- or ^ -sulfonic acid amides, like that

N-methyl- or Ν, Ν-dimethyl- or -diiithylamid,

N,; - Isopropyloxypropyl-2-amino-naphthalene-

6-sulfonic acid camide,

N ^ -Isopropyloxypropyl-1-aminobenzenes-, -3- or -4-sulfonsaiircamid,

N-isopropyl-1-aminobenzene-2-, -3- or -4-sulfonic acid amide,

N.y-methoxypropyl-l-aminobenzoie-, -3- or -4-sulfonic acid amide,

N, N-bis (/) - hydroxyethyl) -l-aminobenzene-2-.

-3- or -4-sulfonic acid amide, l-amino ^ -chlorobeiizole-i-sulfoiisäureamiti.

and the N-substituted derivatives 2,3- or 4-ammopheny! su! famat.

2-amino-4-, -5- or -6-meth> phenylsilfamate.

2-Aniino-5-niethoxyphenylsulfamate.

.i-Aniino-o-chlorophenylsilfamate.

3-amino-2,6-dichlorophen isulfaniate.

4-amino-2 or -3-mclhoxyphenyl sulfamate.

N.N-dimethyl-2-arjinophene> isilfamate.

N.N-Di-ii-bulyl-2-aminophen \ isulfaniate.

N, N-Diniethyl-2-amino-4-chlorophenyl sulfamate.

N.ii-Prop> l-3-aminophen> lsiilfaniat.

N, N-di-n-butyl-3-aminophen> isulphanate.

O-I.VAniinophenjll-N-morpholine-N-sulfonal.

() - | 3-Aiiiinophen> l) -N-piperidiii-siilfoiiat.

N-Cyclohexjl-iH.Vaiiiinopheinll-sulfamal.

N- (N-melhylaniline) -0-3- | aminopheiiyl) -sulfoiiai.

N.N-diethyl-3-aniiiio-6-nielh> lphen \ l-siiiniiiKil.

N-Ethy! Cniinin - () - (4-aminophenjl) -siilfonai.

N.N-Diniethyl ^ -aminophenslsnlfamal.

i) - (n-l'ropyl) - () - (3-aniinophen \ l) -s: 'lfonai.

O.,; - chloroethyl - () - (2-aminophenvli-siilfonai.

() -Benz \ l - () - (3-aminophen \ l) -siilf () iiat and

f) -Ath> i-O- (4-Amino-2.ft-.limeih> l-phen> l | - sulfonate.

4- aminoazobeiizole.

3.2'-dimeth) 1-4-aminoazobenzene.

2-meth> l-5-metho \> - 4-aminoazohenzene.

4- \ mino-2-nilroazobenzene.

2.5-dimelhii-4-aminoazobenzene.

4'-Melho \ v-4-aniiiioazobeiizole.

2-methyl-4'-melho \\ - 4-aminoaz <) henzene.

3.6.4-1 rimelho \ v-4-amiuoazohcnzol.

4 '- ("chloro-4-aminoazobenzene.

2- oiler .t'-C'hloM-amimnizobenzol.

3-Nilro-4-amino-2'.4'-dichlorazobeiizole uihI 4-A m in oazobenzene-4'-SIiIfOHSaU ream id.

2-aminolhiazole.

2- Amino-S-nitroihiaznl.

2-Amino-5-methylsilef (iii \ l-thiazole.

2 -. \ Niiiio -? - L'vanlliiazol.

2- A mino-4-meth \ 1-5-11 il red hiazole.

2-Aniiiio-4-melh \ llhiazole.

2-amino-4-phe! Ivllhiazole.

2-Amino-4-14'-chloro (-phcH \ It hiazol.

2- Amino-4-f4'-nitrol-phenvltliiazole.

3-aminop) rilin.
3-minoquinoline.
3-aminopazole.

3- \ niino-l-phcii_ \ lp \ razol.
3-Amiiioiiiilaznl.

3-amino- |, 2,4-triazo |,

5- (Me (hy | -, ethyl, phenyl or benzyl 1-1,2,4-triazole,

3-atnino- | - (4'-methoxyphenyl) -pyrazo |, 2-aminobenzothiazole,

2-amino-6-methoxybenzthiazole, 2-amino-6-methoxybenzthiazole, 2-amino-6-chlorobenzothiazole,

2-amino-6-cyanobenzothiazole,

3-amino-5,7-dibromobenzlhiazole, 3-amino-benzisothiazole.

S-Amino-S-nitro-T-bromobenzisolhiazole, i-Amino-S-nitro-benzisothiazole, i.S-Diamino-S-nitro-benzisothiazole, S-amino-S-chlorobenzisothiazole, i-Amino-S-chloro-T-bromo-benzisole-thiazole.

2-amino-6-thiocyanthiazole,

2-Amino-6-nitrobeιιzthiazoI.

2-amino-6-caΓboätho.xybenz! Hiiι / ol, 2-amino- (4- or 6) -methyisiilfonylbi ^> n / lhi:! Zol, 2-amino 1,3,4-thiadiazole,

2-amino-1,3,5-thiadiazole.

2-Amino-4-phen> 1- or ^ -methyl-1.3.5-thiadiazole,

2-Amino-5-phenyl-1.3.4-thiadia? Ol.

2-Amino-3-nitro-5-methylsulfo-lhiophene.

2-Amino-3,5-bis- (methylsuiro) -thiophene.

S-aminoO-methyl-isothiazole.

3- or 4-aminophthalimide.

The water-soluble azo dyes can contain fasrrreaklive groups, such as. B. s-triazinyl radical c. which carry 1 or 2 chlorine or bromine atoms on the triazine ring. Pyrimidyl cstc. the one or two chlorine atoms b / w. one or two arylsilphonyl or alkanesulfonyl groups protrude from the pyrimidine ring. Mono- or bis - (; - halogen - // - hydroxy propy I) -amine ι! Groups. // - halogenated sulfamic acid, / - '- halogenated ethoxy groups. i'i - Halogenäthylmcrcaptognippcn. 2-chloro-benzothiazolyl-6-a / ouruppcn. 2 - chlorine - thia / olyl-6-a / o groups. 2-chlorobenzene / thiazoly 1-6-amino groups. ; · · Halogen - // - hydroxy - propy'siilfamylrcstc. Chloroacctylamino groups. \ .// - dibromopropionyl groups. Vinyl sulfony groups and 2,3-poxy groups.

(iccignetc fascrrcaklivc diazo component !! /. I !.

N./(-Chlorälhyl-3chlor-4-amino-bcn/olsulfamid (Hydrochloride).

N./i-Chlorälhvl-^-aininoben/ol-siilfamid (Hydrochloride). 3-Bromo-4-aniino-C »-chloracclophonone.

N.; '- ChU) r- / i-hydrox \ propyl-4-amiiiobciiznI-Milfamid.

N./i-Chloräthyl-l-amino-4-iiaphlhylsiiironamid.

N./Z-Chlorathyl-l-amino-.^.S-dichlor-bcn/olsulfamid and

4 - (; - C'hIor - / .'-hydrox \ -propoxy (-aniline. Coupling components are /. B. gcnannl:

N./i'- Cyaiiälhyl-N-methNl-aniline.

N.N-Bis-l / i'-eNanälhjII-aiiilin.

N-Ethyl-N-dimctlivlaniinoalhyll-aniline.

N.N-l) i - /; - h \ drox \ äth \ l-aniline.

N-Athvl-N-I / Mrimcthylainmoiiii.imätlnllanilin.

N-Athsl-N-l / i'-psrimidiniiimalhyll-aniline.

i -N - />'-(') aniline v ^r -N-iiiii> i-iiiiiiini-3-iiiciiivl ben / ol.

-N-zZ-cyano-ethyl-amino-S-methylbenzene,

benzene,

N - // - Cyanäihyl-naphthsuliam- (l, 8),
^r i lNN-Di-zi-cyanoethyl ^ -methyl-aminobenzene,

N ^ i-Cyanathyl-N ^ i'-hydroxyathyl-aminohenzol,

N, // - Cyai! Äthyl-2-mclhyl-indole,

N./Z-Cyanathyl-tetrahydroquinoline,

N-phenyl-aminobenzene,
in 4-hydroxy-l-melhylehinolin- (2),

l-hydroxy-3-methylbenzene,

8-hydroxyquinoline,

S-cyano ^ o-dihydroxy ^ -mclhylpyridine,

1,3-dioxybenzene,
ι> 2-naphthylamine-5-sulfomethylamide,

l-oxy-3-cyanomethylbenzene,

1-phenyl-methyl-S-pyrazoIon,

Acotcssigcster. as well as anilines of the formula

-N

where c and d are hydrogen Tatomc, lower alkyl-. Alkoxy or alkyl captor chains or optionally substituted phenyl, phenoxy or Are cylinals.

The group e can, in addition to the groups mentioned above, also a chlorine or bromine atom, a Ί rifluormclhylgriippe and ciiu- possibly am Nitrogen atom alkylicrtc, preferably methylicrlc acylamino group, in which the acyl residue the remainder of an organic monocarboxylic acidc. an organic monosulfonic acid such as methane. Athanodcr p-Toluene monosiiIfonsäiirc, or the remainder of one Carbamic acid or a carbonic acid mono-amide or monoamide. such as phenoxycarbonyl. Methoxyjtirbonyl and is aminocarbonyl.

The groups R ₁ and R ₂ can be hydrogen atoms or lower, ie 1 to 4, preferably 2 to 4 alkyl groups containing carbon atoms, such as methyl. Be ethyl, n-propyl or n-Butylgruppcn, which can be substituted in the usual way, such. B. Benzyl-, // - Phenäthy I-. halogenated alkyl groups. like / i'-Chloräthyi-. /<'./'./'-Ί rifluorät hy 1-, / »',; ■ -Dich lor pro py I-odcr3-chloro-2-hydroxypropyl -, /; - cyanoethyl-alkoxyalkyl, such as / i -Athoxyäthyl- or Λ-Mclhoxyhutyl-. Hydroxyalkyl-. like, i-hydroxyethyl-, //, ^ - dihydroxypropyl-, nitroalkyl-. like // - nitroethyl-, acylaminoalkyl-. like // - (acetyl- or formyl) -aminoethyl-, l'cllsäureacyloxyalkyl-, like formyloxy alkyl -, // - Acclyloxyät hy I-. /i'.^- diacctoxypr.ipyl- and; -Biilyryloxypropyl-, // - (alkyl or aryl) -sulfonylalkyl-. like // - Mclhansulfonyläthyl-, / <- Ath; insiiironyiäthyl-, Vinylsul (onylalk \ l-, Phenylsulfonylalkyl- and // - (p-Chlorbcn / olsulfonyl) -äthyl-. Alkyl-1 Jcr Arylcarbamoyloxyalkyl-. like // - Me-Ihylcarbamyloxyäthyl-, Butylcarbamyloxyäthyl- and / i'-Phcnylcarbamyloxyäthyl-, Alkyl- or Aryloxycarbonyloxyalkyl- such as // - (Methoxy-. At'noxy-. / "" - Chloraelhoxy-, Isopropyloxy- or p-'l'oliiyloxy ) -carbonyioxyälhyl-, ^ -Acctamidopropyl-, // - (p-Nitrophcnoxy) -älhyl-, / i- (pl lvcii: i \ y plu'noxyt-iilhyl-, // - (// '- AcctyläthoxycarbonyD-iilhyl -. // - [(// '- Cyano-, Hydroxy-. Metli ii \ y- iiiler AteioX \ i-iiilu> \\ LiiriuiMyl] -äiliyi-, cyanoalkoxyalkyl-, / i-Cai bowälhvl-, /. '-Acelaläthvl-. // - Diethylaminoäthyl-. /.'- Cyanoacetoxyäthyl-. // - Bcnzoyl-

owällnl- mill / i '- (p- \ lko \\ uler l'henow -hen / cnll- niclil nielir ills IX kohleiiNloH; ilome ox \ iil h \ IC iruppcti.

The (inippen R, and Rj enllinllen in general mihI /. 15 the! '' Iirh ^ loffc the I ornieln

Cl

.hl in

ΙτΓιικΙιιιιμΝμαηϋΗ / ιι using A / ufni-bsiorie 5 the I- "iir

(MI ₄ OII

N N

CN

O, N

N N

CN Ο., Ν- NN

CN O, N • -NN

(MI ₄ CN

(MI ₄ CN N

(WED _{4 OCOCH 1}

NICjII ₄ OCOCH ₁ Ij CjII ₄ OCO ' ₍₎

C, H ₄ CN

OjN NN N (CjH ₄ CN) J

(I NIICOCH ₁

(H, SO,

C N N

(Ml,

/ ■ ιι C ₂ IU CN

CjIU C ',, H ₅

O, N ^] .. ^; N N- ^x - N

Cl

(MJ ₄ CN

OjN < _x ,. · NN / N (C ₂ H ₄ CN),

C ₂ H ₄ CN

C ₂ H ₄ OCOC ₁ H ₅

Cl

O ₂ N ^ _x > -NN < _N )

"■ i '

Cl Cl

O ₂ N <> -N --- N- <^ -N (C ₂ H ₄ OCOCH,), NHCOQ ₁ H,

Climbing up

• arhsiolTe

I) N N HC

X C

lei formulas

C R

N I

ir

I) N N Λ

e. in which X OH ("the Nile,. K 'II.

(IK. CONII. Or C () O (\ II _S. R "Il

or ("ils and Λ a phenol or naphmoiresi isi. which can be further substituted.

F.rfiiulungKgcmül.1 styryl dyes to be used are those of the formula

NC

C (11

NR ₁ R,

v \ .. hei Rι and R, have the same meaning as above. C is a hydrogen talom or a methyl group lsi. and Y is a ("van, carhalkoxy oiler aryl sulfoniy! group. like /. U is a carbalhow oiler l'henv isulfone group
(IeiK may be / H. the dyes of animal formulas:

NC

C CII

N (CH-CHa) COCH ₁ ),

πι,

NC

NC

NC

NC

CII

ΝΙ (ΊΙ, (ΊΙ, (Κ '() (· ,, ΙΙ,),

πι,

CNII ₅

CII

ClU

cn,

CH

C "CH

CH, C, H ₁ OCON J I,

IO

(The appropriate anthraquinone dyes are /. H. IaIogciiicningsproduklc des 1.5-dihydro \ Y-4.X-dianiinoanthraquinone. how /. U.

2- oiler 3-IJiOm-1,> dihulro \ y-4.X-diamino-

anthraquinone.

3. 7- di bromine-1,5-tlih ν ilrox ν -4.8-dianiino-

anlhraquinone. further

l.4-l) iamino-2..Vdichlor-antlirachiiion.

l.4-l) ianiinii-5-nilro-anlhraquinone.

l-Aniino-2-riheno \\ - 4-h> dro \ Y-anthrachinoii.

I- \ inino-2-pheuvlmeieaplo-4-hvdro \ v-

■ iiiiliraihinou.

I- \ mino-2 - ((i'-hvdro \ yäthvlo \ y) -4-h> dro \> -

antlirachinon and

l - / \ mino-2 - (/ i-nielho \\ älhvlo \> ) -4-hvdio \ v-

aiilhniL'hinon.

l.5-l) ihvdriixy-4, K-diamiiHi-2- oiler

-.1 - (. V-nielhoxy-4'-hydnix \ phenyh-anthrachiiion.

l.v |) ih \ droxy-4.X-dianiinii-2- or -3- (4'-li> -

ilrow- and / or 4'-nielho \ v-phen> l) -anilira-

chiiuui.

l. ^ - l) ih \ dro \> - 4.K-dianiino-2- or -3- (4-h ν-

dro \\ - 2- -methylplieiivD-anlhraehinon,

l.5-l) ihvdro \ y-4-amino-S-acelo \ yäthvlamiin> -2- or -V (4'-hvilro \ vphenvl) -anlhraquinone.

1.4-l) iainino-2.3-anthraquinone-dicarbo \ imid.

I-I lvdio \ v-4-amino-2.3-anthraquinone-dicarbo \ - imid.

I.X-nihvdri) xy-4- (p-nielhoxyphenylaniini)) -

5-nilro-anthraquinone.

l-ll \ droxy-4- | 4 '- (p \ rrolidon-2-) l-l | -phenvl-

amino-anlhraquinone and

p-nitro-p'-phenylaniiniia / ohen / ol.

The ErlinduiigsgemiiK used water-soluble Reactive dyes can be used as fiber-reactive Reslc /. IJ. have the following radicals iiiul substituents:

Chlormaleinylaminognippen. the l'ropiolgroup-ΐΊίημ. Mono- and dichlorocrotonvlaniinocrupncn. Urom or chloroacrylamino groups. Aerylaniino groups. Vinyl silicone handles and especially the a group containing a labile syllable, which while taking along the pair of Hindimgsclcktronen are easily split, /. H. aliphatically bound sulfuric acid or thiosulfuric acid ester groups and aliphatically bonded sulfonyl or sulfonyloxy groups or halogen atoms, in particular an aliphatically bound chlorine atom, / wake-wise these unstable substituents are in \ - or / i-separation of an aliphatic radical, deep above an aminocarbonyl or aminosulfonyl group is attached to the dye molecule; with those in Petracht Coming dyes which contain halogen atoms as stable substituents can make these interchangeable Halogen atoms also e.g. B. in an Acctylrstcs or in the \ - and / (- position of a Propionylrstcs stand. Examples of such residues are e.g. B. chlorine or \, // - dichloro or dibromopropionylamino groups or i-chloroacelylamino groups. Preferably located however, the halogen atoms which can be split off are in a preferably 2 to 3 ring hydrogen atom, in particular Heterocyclic radical containing ring nitrogen atoms, e.g. B. in a phthalazine, pyridazine, Pyridazone, quinoxaline, quinazoline, oxazole, thiazole, but especially in a pyrimidine or in particular Triazine ring. z. B. in a grouping of

ormel

Il

n; i c c /

! P.

N N

I laloucn

wherein Z is a hydrogen atom. cine possibly subsl with linked amino group, a veriilherlc oxy- or ι Mercapto groups or a ll; ilogen; itome or a Alkyl-. Means aryl or aralkyl group. Pie HaIo-

IICIMUMIIÜ Sii'iu / .. IJ. IiI üllKluHTiC, ν'ϋΓ / ügS WCiSC jcut "iCn

(hloratome. The usage is of particular interest of dyes representing the grouping of the formula

Nile C C /.,

I Il

N N

i laloueii

contain, where Z, a chloraloma. an NH, group or denotes the remainder of an aliphatic or aromatic amine, and also those speed-reactive groups, whose removable substituent is, in particular, on a carbon atom of a heterocyclic radical bound qualernary ammonium or hydra / inium group represents, d. H. a group of the formula

N N

i il

Nile C C ΝΚΊΙ., Ι, ΝΙΙ

means substituted amino group or an etherified oxy or mercapto group.

The dyes to be used according to the invention are known in large numbers. You can post at established using the usual methods. ζ B. (. by acylation of primary or secondary amino groups containing dyes of the most varied classes, but especially the anlhracliinon-. l'hlhalocwiiiiii- or A / o series with acidifying agents. which contain one or more reactive groups. As such \ e \ lieningsmiuel let / B the anhulridc or chlorides of those cited above acids corresponding to aliphatic amino residues, z. B. acrylic acid. Propiolic acid. Chloromaleic acid. (Hloracrs! acid. \., ■ '- Dibromopropionic acid. , -'- ("chlorpropioin! acid etc .. \ above all but the den hetero-esclic reactions corresponding halo

: ι. ι ι. . η r. ι ι

'-LIIIIIL. U. II. /. If. 11'IUCMtILII LLt- II ₁ 1 IIIII

Nile C

N C

C C

II
Cl

Cl

NiCH ₁ I ₂ NH,
Cl

wherein Z, a hydrogen atom. a usefulness 2-lliil () geiiben / thia / ol- or -oxa / olcarbon- or sulfonic acid chloride.

3. f) -Dich loi "p \ rida / in-5-cai'hon säurechlor id.
relrachlorp \ ridazin.

4.5-1) ichloi "p \ rida / on- | (i | - \ l-propionic acid chloride.

4.5- The h Io r-1 -phenslpsrida / on-c.iihon- or
sulfonic acid chloride.

4.> Dii: hlorp \ rida / propionic acid chloride.
l ^ -Dichlorphthala / incarhoii- or -sulfonsäurechlorid.

2 ..'- D i Io rch mo \ a I in car hon- or -sulfonic acid chloride.

2.4 Dich loichi na / oil near honey or sulfonic acid chloride.

2.4.ii-Trichloro-oiler 2.4. (Ν l'ribronipx rimidin and its deri \ .ile. Die /. H. in> Posnion a C \ an-. Nitro-. Meth \ l-. AtInI-. Carb.mml -. Sulfaniid-. Carbometho \\ -. Carlxilkow-. \ E \ l- (/.H. Ben- / o \ l-. \ Cet \ l- or I'ropioinl-I. \ Lken> l- I / B. VlIv 1 - or chlorine \ lI. Or a subsituierie \ lk \ l-1 /. B. Carbow-metal, chlorometal or Brinnietln I) carry.
2.4.5. (I-Tetrachloro- or 2.4.5.d-Tetrahromp> rimidine.

2. (vDichlor- or 2. ('- Dihiom-4-cai hoälhowp > rimidin.

2.4.5-1 riehlorp \ rimidin.
5-Nilro- (i-meth \ l-2.4-dichlorop \ rimidin.
2.4- Dich Io rp \ rim id i η -h-carho n acid chloride.
2.4-Diclilorp \ rimidine-5-carboxylic acid chloride.
2. (il) chloro- or 2. (i-Dihroinp-riniiilin-4- or -5-carboiic acid- oiicr -.sulfonsäureamide i> / ».
-4-oiler-i-carboxylic acid or sulfonic acid chloride. 2.4-dichloroprimidine-5-sulfonic acid.
2.4-dichlo! -5-chlorometh>l-6-nieth>ip> rimidine.
2.4-Dihroni-5-bromnieth \ l-6-meth \ lp> rimidin.
2.4-dichloro-5-chloromethane> lp \ rimidin.
2.4-Dibroni-5-brommeih>lp> rimidin.
2.5.6-Tri <; hlor-4-melh \ lp \ rimidin.
2.6-dichloro-4-triehlormeihJp \ rimidin or especially TC

2-Mclhansuiron \ 1-4.5-d i lor-6-meih \ lpv rimidin.

2.4-dimethanesulfone \ l-5-chloro-fi-meth \ lp \ rimidin.

2.4.f> -Tridilor-l.3.5-tria / in b / u. 2.4.6-trihrom-1.3.5-tria / in.
4.6-dichloro-1.3.5-1 ria / ine.

which are substituted in the 2-position by an aryl or alkyl radical. z. B. a phenyl, methyl or ethyl radical. or by the remainder of an aliphatic or aromatic mercapto b / w bonded via the sulfur atom. Hydroxyl compound bonded via the oxygen atom, or in particular by a ··· ■ NIIi-C inippe or by the remainder of an aliphatic, heterocyclic or aromatic amino compound bonded via the nitrogen atom. Such compounds, the radicals of which can be bonded to the Triazinkcrn in the 2-position by reaction with Trihalogentria / inen, are, for. B. Mentioned the following: aliphatic ^ ¹ or aromatic mercapto or hydroxyl compounds. like thio alcohols. Thioglycolic acid. Thiourea. Thiophenols. Methyl-. Ethyl-. Isopropyl alcohol. Glycolic acid. Phenol. Chlorophenols or nitrophenols. Phenolcarboniiiiu -SülK'M vi UrCi'l

üpü

p p

etc .. but in particular compounds containing ammonia and acylatable amino groups, such as hydroxylamine. Hydrazine. Phylhydrazine. Phenylhydra- / insulphonic acids. Carbamic acid and its derivatives. Semi- and thiosemicarbazides and -carbozones. Methyl-. Ethyl-. Isopropyl. Methoxyethyl, methoxyoxypropylamine. Dimethyl-. Diethyl. Methylphenyk ethylphenylamine. Chloroethylamine. Ethanolamines. Propanolamines. Benzylamine. Cyclohexylamine. Morpholine. Piperidine. Piperazir aminocarbonate. Ethyl aminoacetate. Aminoethanesulfonic acid. N-methylaminoethanesulfonic acid. but above all aromatic Amines, such as aniline. N-methylaniline. Toluidines. Xylidines. Chloranilines. p- or m-aminoacetanilide. Nilraniline. Aminophenols. Nitrotoluidines. Phenylenediamines. Toluenediamines, anisidine. Phenetirfine. Diphenylamine. Naphthylamine. Aminonaphthols. Diaminonaphthalenes and especially acidic groups containing anilines, such as Sulfanil-, Mctani! -. Orthanilic acid. Aniline disulfonic acid aminobenzylsulfonic acid. Aniline, ω-methanesulfonic acid, aminodibenzoic acid c. Naphthylamine mono-, di- and trisulfonic acids. Aminobenzoic acids such as 1- or 2-Oxv-5-aminobenzoic acid. Aminonaphtholnionn-. -di and irisulphonic acids. Amiiiobenzoic acid-milfoilic acid etc .. also also colored connections or connections with color sauce. z. B. 4-nitro-4'-aminostilbene disulfonic acid and Aminoazofarbsloffe the Aminoanthraquinones or Phthalocyanine, which still at least a reactive amino group.

The introduction of the in 2-Slelhmg by the rest of a hydroxyl. Mercapto or. \ Niino \ erbinding u / w. ΑπΊΠΙΟΠΚί K StiifSi iiüiCi'tOii l riii / irifCSlC iwiiiM also expediently done in such a way that one replaces a halogen atom in the chromic acid dye produced by condensation by surrounding it with one or more of the above-mentioned compounds.

It can also be prepared as indicated Dyes that have a, / - Chlorpropionyl-. v / i'-dichlorodcr Have Dibromopropionylrcsl, this according to the invention subsequently by splitting off hydrogen halide mit'.cls alkaline reacting agents in an unsaturated acyl group. z. B. an acrylic, a Convert chlorine or bromoalkyl residue.

[The water-soluble fiber dyes that According to the present invention, the following fibrous groups can also be used exhibit:

2-Me (hvlthio-4-fluoropyrimidine-5-carbon \ l-. 2.4-bis- (phen y Isn I fön> I) -triazinyl-ft-. 2- (3 '- (' arbo \\ plienyl) - siilfon \ l-4-chlorlriaziii \ l-ft-,
2 - (. V-Siilfophenyl) -sulfoii \ l-4 chloi-

2.4-Bis-I.V-carboxyphene> l-sulfone \ l-l I-lriazine \ l-6-,

2-C "arboxyniclhy1sulfon \ l-pyrimidine \ l-4-. 2-methyl-sulfonyl-fi-methyl-pyriniidin \ 1-4. 2.ft-Uismethylsulfon \ l-p \ rimiiiin> l-ft-. 2. fi-bis-methylsilfoil-? - chloro-pyrimidine \ 1-4. 2.4-His-n; elhylsiiironyl-p \ rimitlinyl-Vsulfon \ l-. 2-Meth \ lsilfonyl-pyrimidine \ 1-4. 2-Phen \ lsulfoiiyl-pyrimidinyl-4-. 2-Trichloromethylsulfoii) l-ft-meth \ lp \ rimiclin> I-4-.

_- IVH-tll N I.MIMIMI ^ I -.'- *. !!!! *! -W-MIL Ul WJM MItIKIlIlN I-Ι ".

2-Melh \ lsilfiinyl-5-bromo-ft-methylp> riiiiidinyl-4-,

2-Melh \ lsiilfonyl -. 'I-chl () r-6-äthvl-p \ iimiilin \ l-4-.

2-Meth \ lsilfonyl-. 'I-chloro-6-chloronielh \ l-

p \ rimid "inyl-4-.

2-Melh \ lsulfonyl-4-chloro-ft-mclh \ lp \ rimidin-5-Milfon \ l-.

2-methylsilphonyl-5-iiiin> -f> -methylp \ ι iinicliiivl-4-.

2.?.ft-Ti"ismethylsuironyl-p\rimidin\l-4-.

2-methylsuironyl-5,6-dimethyl-pyrimidine \ 1-4.

2-Älh \ lsulfonyl-5-chloro-ft-nielhyl-p \ riniiclin \ l-4-.

2-Metli \ lsilfonyl-ft-chloro-pyrimidinsl-4-.

2.ft-bis-methylsulfonyl-5-chloro-p \ rimidin \ l-4-.

2-Melh> lsulfonyl-ft-carbo \\ - p \ rimidin> l-4-.

2-Meih \ lsiilfi) nyl-5-siilfo-p \ rimidin \ l-4-.

2-methylsulfonyl-ft-carbomethox> p \ rimidinyl-4-.

2-meth \ lsulfonyl -. '> - carboxy-p \ rimidin \ 1-4.

2-Melh \ lsuifonyl-5-eyan-6-methox; -p \ rimidinyl-4-.

2-Melh \ lsilfonyl-5-chloro-pyrimidine \ 1-4.

2-sulfoethylsulfonyl-ft-meth \ l-pyrimidine \ l-4-.

2-Melh \ lsulfonyl-ii-broni-p \ riniidiii \ l-J-.

2-Phen \ lsulfonyl-5-chloro-pyrimidiiiyl-4-.

2 - ('arbo \ ymethyl-sulfonyl-5-clilor-6-meth \ lpyriiiiidinyl-4-,

2-meth \ isuironyl-ft-chloi-pyriniidin-4-unil -5-caronyl-.

2. (i-Bis- (mclhylsullonyl) -p \ rimidin-4-oiler -5-carbonyl-.

2-ethylsulfonvl-ft-chloro-pyriniidin-5-carbon> 1-.

2.4-His- (methylsulfonyl) -pyrimidine-5-sulfone \ l-.

2-MelhvlsiilK) iiyl-4-t "l'ili> r-6-meinyip \ riniidiii-5-sulfonyl- or -carbonyl-, 2-ChIoTbCiIzIhJaZoI-S- or -6-carboiiyl- or -5- or -6-siilfonyi-,

2-Arylsulfonyl- or 2-Alkylsulfonvlbcnzlhiazol-5- or -6-earbonyl- or -5- oiler -6-sulfonyl-,

"Ic 2-Methylsilfonyl- or 2-Ethylsilfonyl-benzothiazole-5- or -6-sulfonyl- or -carbonyl-.

2-Phenylsilfonyl-bcn7.lhia7.ol-5- or -6-sulfonylodcr -carbonyl- and the corresponding derivatives of 2-SIiIfOiIyIbCnZ-IhIaZIiI-S- or -6-carbonyl- or -sulfonyl-,

which contain suifo groups on the condensed Bcnzoiring, such as

2-ChIoTbCnZIhIaZoI-S- or -ft-earbonyl- or -siilfiinvl-.

16

2-carbonyl chloride / imidazole-5- or -6-carbonyl- or -sulfonyl-,,

2-ChloΓ-I-methyIbenzimidazol-5- or -6-carbonyl- ode: -sulfonyl-,

2-chloro-4-methylthiazole (l, 3 | -5-carbonyl or ι -4- or -5-sulfonyl radicals
and the N-oxide of the chlorine or nitroquinoline-S-irrhonyl radical. Also mentioned are the

2,2,3,3-TelrafIuor-cyclobulancarbonyl-l- or m -sulfonyl-1-,

2-fluoro-2-chloro-3,3-dinuorcyclobutanl-carbonyl- and

/'-(2.2,3,3-Telranuor-cyclobutyl-1) -acryloyl-, \ - or // - bromoacryloyl- and ■> - or, / - alkyl- π or -arylsulfonylacryloyl residues.

Crlinduiijispemäß is used as metal complex dyes preferably such eggs. which as heavy metals iron, cobalt. Nickel, cent Chromium and copper contained in complex bindmiu.

Such complex dispersion dyes are used above all azo dyes in question, which in nichlmetallisicrtcm State a group of the formula special :; important are dyes that are present in the meta H-freeii State atom groupings of the formulas

oüer

X,

X,

COOH

N-

H-O

OH

> —N

H-O

N ---?

N N

contain, where X, and Xi
NH R. and COOH are "

OH.

NH ,.

contain.

Examples are the cobalt and chromium complexes of the following dyes (R = —NH- .. κι -Alk \ l. —NH-alkyl. -NfAlkylj ,: the arrows indicate the Kiipplungsrichtiing to):

SO ₂ COOH
i , / Ί) / NH ₂ R. K ( OH SO, Nile, R. /, < SO, SO, Nile, R. Oll (
N R. N

CH,

NII, l'yrazolone

Pyrazolone

2-naphthol

I-acylamino-7-naphthol

Pyrazolone
> !! - Naphthol

4-methyl-fi-nilro-2-aminophenol 4-Nilro-2-aminophi.'nol

4 - ('chloro-2-aminophenol

4- ('chloro-S-nitro-2-aniinophenol

R SO,

5- N it ro-2-aminophynol

<- 4-nitro-2-aminophenol

as well as the following complex dyes:

Oh Oll

Copper complex and nickel complex

OH

N N-C

Cl

OH

C N

CN
[
COOII

Kiipferkoniplex

Oll

N N C

II, N SO,

OH

C N C N

!
eil., S (KNII,

Kiipferkoniplex

In i · r; ι μ c · also come complexes free of sulfo groups dyes of the IMiI halocya η series and the 1.5-DiiiiyHiirmaAin series.

The qiiaternis used in accordance with the invention ILT ten l-arhsioffc contain at least its η torrent Nitrogen atom, which is either aliphatic, cyclic or tone of structural type ties C'hi non im ins derived scm can. d. H. is bound directly to the aromatic ring.

Use! preferably the customary Sal / e Mi) (I metal halides, for example / inkch Io rid-I) onnelsal / eder known kai ionic substances. in particular the methine or azamcthine dyes. which den liulolinium-, pyra / oliuni-. Imida / o | ium-, Tria / olium, Tetrazolium, Oxdia / olium, I hiadia / olium-. Oxa / oliiini-, Ihia / oliiim-. Pyridinium, Comply with pyrimidinium and pyra / inium rings. The mentioned I lelerocyclen can be substituted and / or be condensed with aromatic rings. Furthermore, there are also potassium dyes of diphenylmethane. Triphenylniellian, Oxazine and Tria / in series in Irage and finally l'arbsal / e of the Aryla / oiiiiil Anlhraquinone series with external onium flu. (ienannl be /. IJ. the larbslofTe of the I-Ornieln:

C.I. Basic Yellow 13

CH

[η— / V ^ / \

- ¹ I [CN = NNC V-NO, \ y \ _N '/ I V- /

CH, CH,

HC
Ι! 0 CJ-N = Il
N CIIj - - N-CHj C-N --- N
ι I.
C. / \ - / -
= Ν ^^ Ν- < N-N-Y

CH ₂ CH ₂ OH

CH,

V-NfCIUl,

ZnCl, "

HCI

H, N

NH,

(CH.,)., N CII ₂ OC <

(CMU) HN Γ ⁷ H ₁ CNN -C-- r

Il j

H ₁ C-CI

N '' Il

j NII (CMU)

CHj

COOCMU

Cl

I C CH CII ■ · <

CIIj ClI, CII, Cl

CH,

(SME

Cl

((MU) ₂ N

Cl

NHC ₂ H ₅

N (C ₂ H ₅ ),

NHCH, CT

N (C ₂ H ₅ ),

HSO, "

Ji-N = N--

Ν C ¹ H,

-NH, ZnCl.r

O, N

C-N = N - C --- N --Ν -C-

Il I

N-CH, CH, H ₃ CN

CH.,

CH,

ZnCI,

O NH,

CO

CO

O NH,

CH,

CH,

CH ₁ OSO,

O, N

Cl

N N-

C ₂ W,

C ₂ H ₄ N (CH.,).,

Cl

CM,

NN Cl I, O - · - ',; - NN

and their mixtures.

PmUt the acid substantival larbsloflen are \ above all those which differ from Mcn / idin. Derive diamylicstilhen and delmlin thiotoluidine as dialysis components. From Hedeutiinu are also KüppliiiigspriKliii,! ·. · Dir (; ■ Nmisio-! -Iiiiphlhnl 3 si:! Fiuisüure siiuie condensation products ans / uei i / iiraibslcirfen mil l'liosijen or ('\ ainir-

OCH, J, "
. / N (C ₂ Ii ₅ J ₂

Cl

eh Io rid.

The sal / c of the sulpho group hallijia also come along l'arbsldffe mil aliphalic primary, secondary and terli'.tren Amineu eier l'etlzeile. how /. 15th Dodecylamine. in l'rage.

c, .ir. '.,., .. "".,., r _r ,.;,. \ λ in, .. "" i ", r. ,, i" i ,, rr ,. i,.: i .., <

. Hill »'£ ;! ti ι f | 'V ^ l Ml \ - l \ _ i »n.l <ui (\ i' | i || .n..iiiii ir.m-MV n_ i \ .n

haiiptsäehlich from Λ / ofai bsloilen. in which see two to Koriiplcxhikliinj! beHihiyle noun

tiienleii. especially llvdroxv-. Carboxyl groups or cvelically bound nitrogen atoms either in orlho- or peri-position in an aromatic or helcroaromatischeii radical or else in the ortho-sielluugeii of two linked by an agreement ' aromatic or hctcroevclic residues heliiulen. Furthermore, the metal complexes of formazan are open called, in which see the / uei / iir Capable of forming complexes (groups in the orllio-Stelluiigen two by a 1.2.4.5 Telrn / apenlamet In lenkctle associated aromalisehcr or liclcroaroniatischer Leftovers.

I osuugsmillel that can also be used as a facultative. which can be added to the phosphorus rival are /. B the hvdrophobes. Called I ösinu'smillel, such as acetophenone, which is not or only to a limited extent miscible with water. Cyclohexanol. Benzv! Alcohol, window. like Athv! acetal. Propv! Acetal. Uni \ Licclat. Hydrocarbons such as Bcn / ol. \\ lol or toluene, and halogenated hydrocarbons such as carbon tetrachloride. ('Hloroform. Mclhv lenehlorid. Trichloräthvlen.Pcrchloräthvlen.Triehloriilhan. I ctrachloräthan. [) ibromiilli> leii or chlorobenzene.

Hydrophilic solvents which are miscible with water form a particularly preferred class of solvents, such as, for example, aliphatic alcohols. like methanol. Ethanol. n-propanol. Isopropanol. Ketones such as acetone. Met In läthv I ketone. Cv el ο he \ aiion. Ethers and acetals like l) iisoprop_ \ liillier. Diphenv lenoxyd. I) io \ an. I etrahv drofin; ni. (ilvcennlormal and (ihcolformal.such.Aceloiütnl and Pv ridiu. diacetone alcohol. also higher-boiling (ilvcolderivatives. such as Ath \ lenul> eolnioiionietli \ l-. -allnatherl- and -hui \ lather and I) iäth> leiighcolmonomerither -ätln ln ln . ThiodigKcol. L'ol \ ath \ leiigl \ cole. As far as they are liquid at / alwayslempcraliir. Aih \ lenearhonal.; - Hui \ rolacloii and especially the (inippe of the water-miscible active solvents such as NN Dimetlnlformaniid. NN-Diinetlulacetamid. His-ldimeth \ lamiilol-niethanphosl'iiiii. 71 i> -iuiiiieiii \!> Iiinuoi- |>iio> piiiti. N-'vieiii \ ip \ r raw den. L.5-l) imeth \ lp \ rrolitlon. NN-I) imeth> lmethow acetamid. NNN .N-I'etramet In I urea. Telramelh \ leiisulfon and 3-MellnlMilfohin and Dimeth \ lsulfo \ '. d.

The Erlindtingsgemiihen dye preparations can Contain Dispergaloren. With water-soluble l'arbsloffen if tier / usat / \ on is not dispersants necessary if the preparation / u contains a mainly water-oiler water as a discrete phase dyebellotte is to be given. Likewise, you can, if appropriate, from the use of dispersants refrain from dissolving water-insoluble dyes in an organic liquor. In other cases, namely whenever the Dyes will be present at least / by part in the dispersed state in the dye liquor Presence of dispersants indicated.

Important representatives of such dispersants belong in particular to the following non-ionic compounds:

al Polvgheoherbindungen such as polvoxalkvlierlc Fatty alcohol c. pol \ o \ aikylated polvole. polvoxalkylicrte Mercaptans and aliphatic amines. pol \ o \ alkylated alkylphenols and naphthols. pol \ o \ alkalized alkaline> lmereaptanes and \ lk \ lar \! amines.

hl fatty acid esters of ethylene and polyethylene lycoles. as well as propylene and butylene glycol. des (ilvcerins or <\ · - ··: polyglycernia and de-l'eiiiaeiy thrils. as well as of sugar alcohols. such as sorbitol, sorbitol and sucrose

el N-I Iy ilroxy alky l-carbo-.iamide. polvoxalky lated ('arboiianiide and Siilfonaunile.

dl Liquid polyalkylene glycols. especially PoIyälhv lenglycole.

For example, as a precautionary usable dispensers in this (iruppeii called ¹ \ nstockuiiL'sprodukl of N moles of ethylene oxide to 1 mole of p-oil. OcH! Phenol, of 15 or ( 1 mole of AlIn leuox yd to castor oil. \ Nn 20 Mol .A'lhylenovyd au den \ lkohol (, "!! ,, Uli. - \ lhv lenoxvil- \ nlagerungspi odukte an I) iI \ - pheiiy lälliy ll-phenole. Polyethylenes d-lert.-dodecy llhioether. I OIv a now-. Po I v glycoläiher oder \ nlagei imgsprodukle ν a I ^ b / w. 3 (1 Mol ■ \ lhvleno \ vd Sn I Mol \ min C ₁ -Il- Nil, .del C ₁ JI. NIL

N.iiiiumsi are particularly valuable dispergalores 11 los iicci na I. NaI r tu ma Ik y I ar ν NuI lon a Ic. \ inni-.dky I-ai \ N υ Hol la I c. F el I acid esters ν on sorbitan. al ho χ ν lierle \ lkanolaii: iile. älhoxylierle phenols and älhoxvlleilc

The present preparations durltcii im. hl at the same time al dyes in which see primary, secondary or larynx basic nitrogen atoms in l hl adhere to an amount of an acid which is at least equivalent to the nitrogen atoms.

The manufacture of the farhsinil preparations, which are cut to size, is usually carried out by simple means. where you stir / wake-up, or by grinding i \ cv components / B m in a ball mill.

The dye preparations described above are suitable for the production of conventional ones Chosen pair of children and especially for the production of dyebaths based on organic solutions. in vveicnen never lainstone ius |> et uici ι iniei are preferably solved.

In the following examples, the Ί hurry means unless otherwise stated, (iewiclitsleile. the percentages (weight percent. and the temperatures suit! given in degrees Celsius.

Example I.
2 File of an ailrachinon fiber of the FOrnie

O NHCH.,

O NH (CFF)., - ΝΙΓΗ., Ι:

3 parts of hexamethylphosphoric acid triainide and 1 part an addition product of 5 moles of Atlnlenowd of castor oil are finely ground in a ball mill. A low-viscosity dye preparation is obtained, This can be seen in the addition to a foulard liquor made from tetraehloräthvlen immediately to a homogeneous one I.ösun »distributed.

25th

Ii c ι s ρ ι c I

ΙΟΊ hurry one f; iseiTe; ikli \ en I Jispeisioiislarhsioffe the I ormel

OH H eis ρ ie I 20 parts of the acidic full raw material of the formula

N N

NII

HrC 11. CMHi (O NII

NN SO, K

CII,

are in a mixed with overheating ·.! \ on M * I hurry pasture with cooling in M) parts I le \ amelh \ lphosphorsäiirelriamid entered. The mixture is stirred for 2 hours at 35 to 40. whereby the dye goes into solution. ) anaeh cools down to 10. gives 10 parts of trieths

lle \ anielli. \ lphosphorsäiireiriamid and 2 leile Sor- ι, gl \ kolmonoinetlnlather / u and liltiiert \ on low hitannionolaiirat registered and stirred for so long. Sal / quantities from. You get a thin liquid. clear until a clear 1 solution emerged lsi. from the home dye preparation.

\ bkuhlen aiii Mi no i arbsioif auskrisiaiiisie. ι. More iarbsioifpräpaiaie. which according to> ucii Λπύ, ίΙχΜ

If you hear the disperser iSorbilannionolaiirati of Hebeispiele I to 3, are in the

path. You also get a clear preparation. : listed in the table below.

urea parts Solution millel

Dispergaloren

C. I. Basic Yellow (as ΛΐΛ-lal} 20 parts

Cl. Acid Orange IaK K-SaI /) 2 parts

C i. Solvent Yellow 1 part

O, N · - N N

Ci

C ₂ H,

C ₂ H ₄ OCOC ₁ H-

33 parts

NC C ₂ H,

C CH ■ / N (XII,

NC C ₂ H ₄ N

Hexamelhylphosphoric iriamide 1 5 parts

Alhylene glycol monomethyl ether

1 5 parts

Hexamethylphosphoric ynamide

2 parts

Pyridine 1 part

Hexamethylphosphoric iriamide I part

Sulfolane I part

Hexamethylphosphoric iriamide 67 parts

Hexamethylphosphoric iriamide 40 parts

Addition product of 40 mol of ethylene oxide with castor oil 30 parts

30 parts

C. I. Direct Red 3 parts hexamethylphosphoric triamide 5 parts

Diethylene glycol monomelhyl ether 3 parts

Triethanolammonium salt of

Kükosfelläure

I part

CICH ₂ CO- <"> —Ν _Λ

O = C

20 parts

Cl. Basic Blue 3.8 parts hexamethylphosphoric triamide 65 pieces

Hexamethylphosphoric triamide 6.2 parts

Sodium oleate 15 parts

21

28

larbsloff parts

solvent

Dispersants

HO

9 O ₁ S
33 parts 2.3 parts X) J -NHC HN - c ' N O OCH ₂ ClC ₁₂ H ₂₁ NH ₁ ' ^N N C.
j Hexamylphosphorus
Iriamide
67 parts Coconut fatty acid ethanolamic
Part 1 10 CI Aeid Orange (K:
2 parts λ lium salt) CO OC ₂ H ₁ OC ₂ Hs Hexamethylphosphorus
triamid
3 parts CICH ₂ COHN \
N
I.
N C ₂ H ₁ OCOCH ₁ Il Cl / V-N ----- N y _y - ν O Hexamelhylphosphorus Γ
CN C ₂ H ₄ OCOCH ₁
Cl K ^]
Cu N
N 7.7 parts - c ' N Anlaccruniisproduki \ on
¹ J mol of ethylene oxide
Nonylphenol
25 parts 12th ι lex, methylphosphorus
liiamid
50 parts

NO ₂ O ₂ N _χ > -NH \ N- NH \

I SO ₂ NHC ₂ H ₁ Cl

Parts

(CIC ₂ H ₄ ) INSO ₂

Parts

-N ■ - = N-χ> -Ν - = - Ν — τ

Hexamethylphosphorriamide 5 parts

Telrachlorethylene 10 parts

Hexamelhylphosphoric triamide 4 parts

Stearyl alcohol + 20 moles

Ethyl oxide

5 parts

C ₁₆ H ₁₃ O (CH ₂ CH ₂ O) ₂₀ OSO;

HN (C ₂ H ₁ OH), 2 parts

Claims (15)

Patent claims: 1. Dye preparation, characterized in that that they from a) 20 to 50% | based on the weight of the finished preparation) one Dye, b) methylphosphoric triamide as a solvent, c) optionally a dispersant, d) optionally a further auxiliary textile agent and e) optionally a further ι ο solvent. 2. dye preparations according to claim I, characterized in that they contain 25 to 50% dye (based on the weight of the finished preparation). 3. Dye preparations according to Claims I and 2, characterized in that up to 50% of the hexamethylphosphoric acid ciriamide are replaced by the dispersant. 4. Fa r bs to ffprä parate according to the claims! . · » to 3. characterized in that they contain a dye free of sulfo groups. 5. dye preparations according to claim 4, characterized in that they are a disperse dye contain. . '"> 6. dye preparation according to claim 5, characterized in that it consists of disperse dyes, Hexamelhylphosphoric acid eliamide and dispergaloren anionic and / or nonionic Type exist. , κι 7. Colourant preparations according to claim 6, characterized in that they do not contain any free acids contain. S. dye preparations according to claim 4, characterized in that they have an at least r> a dye containing an iiaternary nitrogen atom contain. 9. dye preparation according to claim K, characterized characterized in that they also contain a leveling agent for coloring acrylic fibers with quaternized dyes. 10. dye preparation according to claim 4. characterized characterized as having a Mclall complex dye contain. 11. Dyestuff preparations according to claim 4, characterized characterized in that they are a lacquer-soluble or for the dyeing of Ccllulose Acetat-Spinnmasscn contain suitable dye. 12. Colourant preparations according to the claims I to 3, characterized in that they contain an acidic nylon dye containing sulfo groups or Wool dye, nouns cotton dye, or contain an acidic fiber-reactive dye !!. 13. Dyestuff preparation according to claims I to 3, characterized in that they are at the same time A) a water-insoluble dispersion dye and B) a water-soluble acidic, contain fiber-reactive dye. 14. Process for making the dye preparation e according to Claims I to 13, characterized in that the components a) and b) either alone or, if present, ground with components c) and d). 15. Use of the dye preparation «: according to Claims I to 13 for the production of dye liquors, wherein the dye preparation with an organic solvent, with an aqueous liquor, oiler mi! an emulsion Gentiles mixed up.