DE2837121A1 - ORGANIC COMPOUNDS - Google Patents

Description

where D is the remainder of a standard used in the chemistry of disperse dyes

Diazo component,
K is the remainder of a coupling component of the 1,4-phenylene or 1,4-

Naphthylene series,
' R is hydrogen, alkyl or alkenyl or, if K is a radical of the 1,4-phenylene series, also by halogen, hydroxy, alkoxy, acyloxy, phenyl, phenoxy, cyano, alkenyloxy, alkynyloxy or alkoxyalkynyl

oxy-substituted alkyl or optionally alkenyl substituted by halogen, R ₂ hydrogen, acyl or optionally a halogen, alkoxy, phenyl, hydroxyl,

Alkyl bearing phenoxy, benzyloxy or acyloxy as substituents, R ₃ and R ^ independently of one another are hydrogen or alkyl or, if R is hydrogen, together and with that bonded to them

Carbon atom also cyclohexylene,

R is a group of the formula -C ⁵ CR ₁ . or if K is 1,4-naphthylene, also a group of the formula R R '

, 6, 6

_ Γ * - ■ C «" D

U ~~ O ß._ j

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R is hydrogen or a group of the formula

- C - 0 - R ₉ ,

R and R 'one hydrogen, the other hydrogen or halogen, ο ο

R hydrogen or alkyl,

R and R 'independently of one another are hydrogen or alkyl ο ο

and R is hydrogen, acyl or optionally alkoxy, alkoxyalkoxy or Acyloxy denotes alkyl bearing substituents

and the molecule only bears those substituents that are found in disperse dyes are common.

As acyl radicals, especially the radicals of the formulas R'-RX and Y are concerned, where R is alkyl, preferably C alkyl, [Wlydroxyäthyl, p- or / ^J-hydroxy-

propyl, ß,) j'-diliydroxypropyl, haloalkyl, phenyl, toluyl or benzyl, X is a radical of the formula -0-CO- (where R is bonded to the oxygen atom) or -SO -,
R ^{1 is} hydrogen or R,
Y is a radical of the formula -CO-, -NR "-C0- or -NR" -SO (where R "is

the nitrogen atom is bound) and R "is hydrogen or R.

All of the alkyl radicals mentioned (including those in alkoxy and alkylcarbonyl) generally contain 1 to 6, preferably 1 to 4, especially 1 or 2 carbon atoms. Unless otherwise specified, they are unsubstituted or wear one of the mentioned substituents, as a second substituent may also come a hydroxyl group into consideration. The alkenyl and alkynyl radicals contain im generally 2 to 6, preferably 2 to 4, in particular 2 or 3 carbon atoms, Alkenyl can carry one or two halogen atoms, but they are preferably unsubstituted.

Ilalog means fluorine, chlorine, bromine or iodine, in particular chlorine or bromine to adjust.

The radicals D can belong to the phenyl, nophthyl or heterocyclic series and also contain another azo group.

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The symbols in formula I preferably mean independently of one another

D Phenyl, which can have up to four substituents, including up to four Chlorine or bromine, up to two from the group cyano, iodine, trifluoromethyl, C "-Aükylsulfonyl and nitro and / or one from the group methyl, Methoxy, formyl, C -alkylcarbonyl, C -iUkoxy-carbonyl, amino carbonyl, C -alkyl-aminocarbonyl, di- (C -alkyl) -aminocarbonyl, phenyl, benzoyl, Benzylcarbonyl, phenylsulfonyl, toluylsulfonyl, aminosulfonyl, C -alkylaminosulfonyl, C1-4 alkoxycarbonyl, rhodan, di- (C1-4 alkyl) aminosulfonyl and / or phenylazo, which can carry up to three substituents, including up to three chlorine or bromine, up to two methyl, C -alkoxy, Cyano and / or nitro and a phenyl,

Benzthiazolyl, which can carry up to two substituents, namely up to to two from the group chlorine, bromine, cyano and nitro and / or one from the group methyl, C -alkylsulfonyl, aminosulfonyl and rhodan,

1–2

Benzisothiazolyl, which can carry up to two substituents, namely up to two from the group chlorine, bromine and cyano and / or one from the group nitro and C -alkylsulfonyl,

Thienyl, which can have up to three substituents, including up to two from the group chlorine, bromine, cyano and nitro and / or one from the group methyl, phenyl, C -alkyl-carbonyl, methoxycarbonyl and hydroxyl,

Thiazolyl, which can carry up to two substituents, up to two from the group chlorine, bromine and cyano and / or one from the group methyl, nitro and C -alkylsulfonyl, 3-phenyl-l, 2,4-thiadiazolyl (5) or 2-phenyl-1,3,4-thiadiazolyl (5),

in particular a radical of the formula III

(III),

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1837121

where R is hydrogen, chlorine, bromine, iodine, nitro, cyano, methylsulfonyl, ethyl

sulfonyl, methoxycarbonyl or ethoxycarbonyl, R nitro, aminosulfonyl or di (C -alkyl) -aminosulfonyl, R hydrogen, chlorine, bromine, iodine, cyano, methylsulfonyl or ethyl

sulfonyl

and R 'is hydrogen or, if R is hydrogen, also chlorine or bromine, especially a radical of the formula III a

(III a) Ί " VV

^R 14 wherein R is nitro or cyano

R chlorine, bromine, cyano or methylsulfonyl,

K unsubstituted 1,4-naphthylene or a radical of the formula II

R hydrogen, chlorine, bromine, C alkyl, C alkoxy, hydroxyethoxy, Methoxyethoxy or cyano-C -alkoxy, especially hydrogen, C "-alkoxy or hydroxyethoxy, especially methoxy or ethoxy,

R hydrogen, chlorine, bromine, C alkyl, C alkoxy, C alkyl -carbonylamino, bromo- or chloroethylcarbonylamino, cyano, formylamino, C -Alkoxy-C -alkyl-carbonylamino, C -alkoxycarbonylamino, Phenoxy-C ^^ - alkyl-carbonylamino, C -alkoxy-C -alkoxy- -carbonylamino, C _ -alkoxy-carbonyl-C _ -alkylamino-carbonylamino, Benzoylamino or phenyl-C-alkyl-carbonylamino, in particular

L ~ JL

Hydrogen, methyl, formylamino or C alkyl-carbonylamino, especially C ₁ _ "- alkyl-carbonylamino,

R, if K is 1,4-naphthylene, hydrogen or C-alkyl, otherwise also once by chlorine, bromine, hydroxy, C ₂ ~ alkoxy, formyloxy, C ._, - alkyl-carbonyloxy, C "-alkoxycarbonyloxy, C - Alkylaminocarbonyloxy, phenoxy, phenyl, benzoyloxy or cyano substituted C -alkyl, ß-hydroxy-V'-chloropropyl, benzyl, allyl, 2- or 3-

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1837121

Chlorine or bromine allyl or a group of the formula

-CH CHOHCH OCH C = CH or -CH CHOHCH OCH C = CCH OCH, in particular

£ - Z * Z ~ fm Z * Δ, Zt 3

if K is 1,4-naphthylene, hydrogen or C -alkyl, otherwise also substituted once by C -alkyl-carbonyloxy or cyano C -alkyl, especially hydrogen,

R-hydrogen, C -alkyl, which optionally carries a chlorine, bromine, C- alkoxy, phenoxy, formyloxy, C _1- -alkyl-carbonyloxy or benzyloxy, C -alkyl-carbonyl, benzoyl, hydroxyethyl.oderC ralkoxycarbonyl, in particular hydrogen or C alkyl, especially hydrogen,

R and R 'are hydrogen or methyl or when K is 1,4-phenylene, independently one another hydrogen or methyl or together cyclohexylene, especially hydrogen or methyl, especially hydrogen,

R, a group of the formula -C = C-R or, when K is 1,4-naphthylene, also a group of the formula R ^ R '

ι »ι ⁶

- C = C - R ₇ ,

in particular a group of the formula -C = OR or, if K is 1,4-naphthylene, also vinyl, especially a group of the formula -C = CR ₅ ,

R is hydrogen, C -alkoxy-C-alkyl, methoxyathoxymethyl, acetoxymethyl or chloropropionyloxymethyl, especially hydrogen, methoxyathoxymethyl or acetoxymethyl, especially hydrogen,

one of R ^ and R 'is hydrogen, the other is hydrogen, chlorine or bromine ο b

and R is hydrogen or methyl.

In many cases, the coupling components of the benzene series are also preferred (Formula II).

The preparation of the new compounds of the formula I is characterized in that that a diazotized amine of the formula IV

D-NH ₂ (IV)

with a compound of the formula V.

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/ \ OR R _R. H- KN ^ T _t ^{2 3} \ / 3 (V)

'CH-CH-CH-O - C R,

2 2 4

clutch.

The coupling components of the formula V are produced, for example, according to an known method by adding one mole of a compound of formula VI

H-K- NHR (VI)

with 1 mole of a compound of formula VII

ClCH ₀ -CH-CH _0-0 -C-R, 2 2 4

condensed in the presence of an acid-binding agent, e.g. potassium hydroxide, or 1 mole of a compound of the formula VI to 1 mole of a compound of

Formula VIII

^R 3 ^R 3

CH-CH-CH - 0 - C R (VIII)

at 70 to 90 ⁰ C deposits.

The compounds of formula VII can be prepared analogously to known methods, e.g. by adding the corresponding alcohol to epichlorohydrin, in the presence of boron trifluoride etherate. The connections of the Formula VIII can be prepared from the compounds of formula VII by treatment with a base such as potassium hydroxide.

The processing of the novel compounds of formula I for dyeing preparations is effected in a generally known manner _s for example by grinding in the presence of dis- pergier- and / or fillers. The preparations, optionally dried in vacuo or by atomization, can, after the addition of more or less water, be used for dyeing, padding or printing in what is known as a long or short liquor.

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The dyes are excellent on textile material from an aqueous suspension made of fully synthetic or semi-synthetic, hydrophobic, high-molecular organic substances. They are particularly suitable for Dyeing, padding or printing of textile material made of linear, aromatic polyesters, as well as cellulose-2 l / 2-acetate, cellulose triacetate and synthetic Polyamides.

They are colored, padded or printed according to known methods, e.g. the one in the French patent 1,445,371.

The dyeings obtained have good all-round fastness properties. To be highlighted are the color strength and the drawability of the new dyes on polyester fiber material.

It is often possible to use the dyes by a heat, solvent and / or Mill treatment or by recrystallization into another, stable modification convict. Suitable methods and the advantages that can be achieved thereby are known to the person skilled in the art.

In the following examples, parts mean parts by weight and percentages Percentages by weight, the temperatures are given in degrees Celsius.

example 1

To a mixture of 14.3 parts of a-naphthylamine and 14.85 parts of 2-hydroxy -3-chloropropyl-prop-2'-ynyl ether is added in portions to 5.6 parts of pulverized Potassium hydroxide, the temperature rising from an initial 25 ° to 50 °. The mixture is stirred for 10 hours at 85 °, cooled to room temperature, approx. 100 parts of dilute hydrochloric acid and separates after ten minutes of intense Stir, the organic phase, N- [3- (Prop-2'-ynoxy) -2-hydroxypropyl] -anaphthylamine in oily form.

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Example 2

To 147 parts of concentrated sulfuric acid are slowly added at 60 ° with stirring 8 parts of crystallized sodium nitrite are added. The solution is cooled to 10-20 °, 10 parts of glacial acetic acid are added and, after further cooling to 0-5 °, 26.2 parts 2-bromo-4,6-dinitroaniline too. A further 10 parts of glacial acetic acid are added, the mixture is heated at 0-5 ° for 3 hours and the excess nitrosylsulfuric acid is destroyed with little urea.

The diazonium salt solution thus obtained is then slowly added with stirring a solution of 25.5 parts of that obtained in Example 1, cooled to 0-5 ° Compound given in 400 parts of methanol. After the coupling is complete, the resulting dye is precipitated by adding 36% sodium hydroxide solution, Stirred for 1 hour, filtered off and washed acid-free with water.

To improve the dyeing properties and the dispersion stability the dye is redistributed in 100 parts of water, stirred for 3 hours at 90 °, filtered off, washed with water and dried. The so obtained dye of the formula

N = N -U J) - NHCH CH-CH -O-CH OH

dyes polyester fiber material in blue tones with excellent fastness properties.

example

a) 14.3 parts of a-naphthylamine and 11.4 parts of allyl glycidyl ether are 10 Stirred at 80 ° for hours. The mixture is allowed to cool to room temperature, 50 parts of dilute hydrochloric acid are added, and the mixture is stirred for about 10 minutes separates the organic phase, N- (3-allyloxy-2-hydroxypropyl) -a-naphthylamine in oily form.

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b) To a (below 20 °) mixture of 122 parts more concentrated Sulfuric acid and 35 parts of 40% nitrosulfuric acid without to exceed, added 26.2 parts of 2-bromo-4,6-dinitroaniline and stirred for 3 hours. This solution is then slowly stirred and cooled to -5 ° up to 0 ° to 25.7 parts of the compound prepared according to a), dissolved in 100 parts of methanol, added dropwise. After the coupling has ended, the resulting dye is precipitated by adding 30% strength sodium hydroxide solution for 1 hour stirred, filtered off and washed acid-free with water. To improve the dyeing properties and the dispersion stability, the Dye redistributed in 100 parts of water, stirred for 2 hours at 90 °, filtered off, washed with water and dried. The thus obtained Dye of the formula

dyes polyester fiber material in blue tones with excellent fastness properties.

APPLICATION EXAMPLE

7 parts of the dye prepared according to Example 2 are mixed with 4 parts dinaphthylmethandisulfonsaurem sodium, 4 parts of sodium cetyl sulfate and 5 parts of anhydrous sodium sulfate in a ball mill for 48 hours to one fine powder ground.

2 parts of the dye preparation thus obtained are made into a paste with a little water and the suspension obtained through a sieve a 3 parts sodium lauryl sulfate added in dyebath containing 4000 parts of water- The liquor ratio is 1:40. 100 parts of cleaned polyester fiber material are now added to _ 40-50 ° in the bath, are 20 parts of a chlorinated benzene emulsified in water to, slowly heats the bath to 100 ° and stains for 1-2 hours at 95-100 °.

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The navy blue colored fibers are washed, soaped, washed again and dried. The level dyeing meets high fastness requirements.

Analogously to the working instructions of Examples 1 to 4, the procedures according to the invention can also be used Dyes of the following tables can be prepared.

909811/0772

Tabel

150-4105

The dyes in this table correspond to the formula

N = N

CH-CH-CH-O - C - C I t ^

s C - R _r

CO CJ CO OO

E.g.
No. ^R i ^R 3 ^R 3 ^R 5 ^R 2 ^R 12 ^R 14 ^R 13 do. ^R io ^R n Nuance on
Eolyester.
rasermateri 4th -C ₂ H ₅ H H H H H H -NO ₂ -NO ₂ H -CH ₃ Red 5 -C ₂ H ₄ CN -CH H -CHCH ₃ OCH ₃ -COCH Cl H do. -C ^ HN = N-
6 5 H -NHCOCH ₃ do. 6th do. H H H -CH ₃ do. H -SO ₂ CH ₃ -CONH ₂ H H orange 7th H H H -CH ₂ -OCH ₃ H -NO ₂ Cl -NO ₂ -SO ₂ CH ₃ -OC ₂ H ₅ -NHCOCH blue δ H H H H H do. Br do. -CON (C ₂ H ₅ ) ₂ -OCH ₃ do. do. 9 H -CH ₃ -CH ₃ -C (CHJ "OC H H -NO ₂ -CN do. -OC ₂ H ₅ -NHCOC H do. 10 ~ ^C 4 ^H 9 H H -CH ₂ -OCH ₃ -COC _C H_ do. -SO CH do. -OCH ₃ -CH ₃ do. 11 H H H H H -CN H do. do. violet 12th -C ₂ H ₄ OCOCH ₃ H H -CH ₂ -OC ₂ H ₅ H Cl Cl H Cl Brown 13th ~ ^C 2 ^H 5 H H H -COOC H H H H H Scarlet fever 14th -CH ₂ -CH ₂ -OCH ₃ -CH ₃ -C ₂ H ₅ H -CH ₂ -CH ₂ -OCH ₃ Br Br H -C ₂ H ₅ Brown 15th -C ₂ H OCOOCH ₃ H H -CH ₂ -OCOCH ₃ -CH ₂ -CH-OCH Cl H H -NHCOCH Red 16 H H H -CH -OCOC H Cl H
ι Cl H -OCH ₃ H orange

5SD CO

he- a CM 4Y r-1 CN • st • • co * IN THE CU cn in 4-1 CO CM CNl co 4Y CM CU CN CN - • 20th CN CNl (U CM -U CO cn 4Y • CO co « CNl • ] I Xi co
CD CD Ed
O O 5 Ed ο Ed O O EC O Ed CiO S. Ed O Ed Ed S. Ed O td on Ed S. O EC 8th OO B. ω Ed 8th O O EC Ed O te O O I-I r-l I. U ■ -I CJ TJ CN TJ TJ CJ
O TJ CJ C. cn VO U O CJ I. CJ U CJ C. O I. TJ U I. Ö I. i-l CJ cn M. TJ CJ CJ
I. Ό CJ TJ ! -i CU SM I. CJ
O I. I. CD S. CJ O ι O I. ce I. I. CU O O
I. S. O I. to CB CL) -I I. U I. O O CM 4Y U • ri I. U 4-t Cu O st
td O Ed t-l O O O I. a) cn-t-i ] te Ed CM I. U O Ed i-l EC OO te CJ CUi-J t-l CJ O
I. I. st CM CM in cdi-14 ^ te te co Ed l-i Ed td EC CM Ed EC 3 Ocd Ed O EC CM O CM ! 3P- (p CtN CO O O CM CO α 8th [? *; CJ
I. ι — Ι cn • O EC • 3 U CM CM Ed 1 CJ Ed EC I. U Ed EC U EC EC O O CJ EC O υ Ed I. co P3 Ed CJ T) I. I. ' CO I. m
Ed EC CO EC st in t-l I. I. I. Ed CM EC EC U Ed EC t-l ErP Ed CJ CJ CN I. CNl
CJ VO pi CO CJ O I. S. I. ■ CJ Ed O U EC st EC I. O O CJ
I. I - *. te O Ed td Ed EC EC EC CJ te EC te Ed
CsI CM EC O Ed O O EC co " O
I. EC σ » st
Ed t-l O
I - I-l EC EC O CM Ed CN pi Ed CM CJ CJ CN Ed EC co CJ
I. st CO " O st EC cn VO [ CN CN cn CN • • CJ S. td Ed CJ CN ■ O • * O Ed O O O σι O Ed 1-1 p- { CRF CM st CJ EC te Ed O ! 3 O CM O ! 3 O Ϊ3 T) TJ τ-Ι CJ CNl I. CJ
I. O CM * - ' O 23 Ό I. Ed TJ cn TJ I. O cn I. O CO O Ό CM Ed O I-l CJ I. O BJ * CJ EC O ο td pi 1 CJ CN! I. VO CO st I. O CJ I. ■ η Ed EC CO I. I. Ed CJ CN CN! VD I. CJ m CJ co O Ed EC CM ιοί [V ₁ I. VO EC U EC in U m O 1 EC CM Ed O EC O Ed EC st CN EC Ed co O CM CJ Ed t-l O td
O U 1 pi co
I. CN) U EC O I. O I-I td CM , —Ι U 1-1 O td ! 3 Ed t-l t-l CJ / - ^ EC CJ PQ CJ I. CJ O CO Ed CN td M.
M. t-l Ed t-l CN I. ι — 4 O CJ i-l pi Ed O en CJ-O U CN CM Ed I. Ed σ> Ed te te td Ed CJ CJ Ed EC te CNl VO
td α st CM Cj in O EC pi ι te co O in Ed 8th CJ co td O co O 8th CNl CO co Ed st
te O CJ EC Ed Ed CJ CM CN O O O CM O O
I. I. O O • CJ I. cn CO I. O O EC Ed Ed CN T) Ed O CJ CJ • S. te Ed CM CM O O I. te CJ I. TJ O
I. I. pi EC td EC Ed Ed Ed EC EC td td CO Cslhrj Ed EC Ed S. Ed G EC «Cn
pi cj-o EC EC CJ cn
pi CJ UJ cn Τ— I OHD ¹ CJ CM 8th Ed ⁰ "" ¹ O CM Ed Ed p ~ { G st S. CJ yyy ^ H Ed O O O I. S. CNl CM m CM CJ / —S I. O EC EC Ed O EC I. CJ
te VO CJ
Ed I. O ^ O O O st
td te S. I. 8th CM CJ i-l cm CM CJ
I. CN pi S. te
O EC co VO I.
O CJ
I. i-l CM cn CO st cn cn in cn ft
Ul O

90981 1/0772

F-I St "

he- F-r
al in O Cj O O 0 O 0 0 cn B. cn
SJ O 0 -21 - X a O O 0 cn 0 0 0 O O cn cn
PS X O O cn CJ O «Η CJ CJ 0 0 O ! M Oil j_ 01 OI α to Oil
CJ "LS -Q "O • a -a • a • 0 Ό 0
0 O CJ -a "O * a -a • a "53 "O - PS
O
O CJ • ο • 0 closely
X 0 "Hi 0 O
I. ■ οι -a CJ X PH X SjTS «A ¹ CJ "O 0
I. O O
O CJ O
I. CJ f fas I. CJ CJ
■ C5 JEJ CJ SS «N
se
CM - st I. Pn I. I. ecJ- «Η ¹ S. 0 55 O I. Yo «0
■ 0 0 co cn
W.
O ta O -a O
I. 0 O 0 O 0 PS X OSi cn CJ * CJ
0 ■ O "O -0 O • a ■ a "Ö "HJ 0
SS
CJ O -a CTt I W! JUj! υ CJ 0 0 "O O 0 O Ό -CN do. CM
G ND- I. cn
Pm
CJ
I. CJ CJ I. "Ö SS • 0 "O FI
CJ "Ö -a Ό CJ I. I O = CJ
I. X X I. x ¹⁰ ! 3 0 O X , -I OI ■ de. «Ο * de. -CN do. • op ! M
ph T- * HOD- ■ - ■ 1 O
O
I. O O ό O do. 0 de. O X OT OC
X pi X X Ό Ό O "55 X X ■ «N ""1 O I. O SS (M U • ep de. X
Ot O O O I » O
IS O 0 "O O O 0 O 0 SJf I. 0
CJ
I. C. B-t "Et "O • a "O X de. O * X χ X X -CN O OK
X
sr
0 "-J CJ SS «0 OI Oil m O I. 0 X F-I O
I. CM
O
55 -CN I. ω . O • op do. do. do. X • ep X 0 art I. F-I X O X O CM I. X X X X χ X X X X X X X X X X X M. SS X X OI X X X X X X X X X P « X X X X X X X SS SS X X X SS X SS O I. X X X Oil
S. Wt-M
Ir * - * X SS χ X X X (***** OT W. X sr
sr OK
sr n-l
»0 Oil OT
Vt sr «N a
I. X X X X X X sr X O
«I. pi I. X X X X % PS! sr OO
sr "ST SS X SS X SS of * «E»
sr is « t »β Ol
PTI PTi OT O <r *
sr sr OI
sr IN.
sr (& .-

909811/0772

150-4105

. So. H S. H M. H H H H St. ^R w ^E 13 do. ^R 10 η nuance on poly
^Λ ιι esteirt'aser-
material 0 Brown '"do. H '\ do. 17th -GH ₂ -eH »GHGi -GH ₃ -GH ₃ H -GtL-GH ₀ -Q-GOG ₀ Hp H - ^Q 2 ^H 5 -BQgH ₃ -SO ₂ CH ₃ -HO ₂ do. -CH ₃ -CN blue
t -NHC-OC ₄ H ₉ Red 18th -GH _? -GGi «GH ₂ H H H H -GH ₂ -CH ₉ -OGOG ₃ H ₇ -GQGH ₃ -SQ ₂ C ₂ H ₅ do. -SO ₂ NH-C ₂ H ₅ -C ₂ H ₅ -NHCOC.H. do.
R. -NHCO-C ₂ H ₄ -OCH -NH-CO-NH-C "H, \ do.
Λ η ι Sf) -GH ₀ -GiL-GJi 'H H H H H H H J J -CN ' -NHC-C H CHCH -OC ₂ H ₅ Red C ₄ H ₉ O-CO 60 -CH ₂ -GH ₂ -GH ₂ - H H H H -GH ₂ OGH ₃ -CH ₃ Br H -SO ₂ NH ₂ -OC ₀ H, -OHl -NHC-OCH ₀
2 4 - ^ 3 Red -NH-CO-CH ₀ -C, "GH ₂ -OGOH GH ^ H H
ί -NO ₂ Red 61 H do. H -CH ₂ OCH ^ H H J H do. H -NHGQ-GH ₀ -CJy do. 62 H H H -COOC ₂ H ₅ H CH - CH.-NN-
6 5 6 4 H -NHGO-C _n H, C Ai . · ■ do. ^
2 4 6 5 63 -G ^ H ₈ -OG ₂ H ₉ H H H H -COOGH ₃ H 4-NO ₂ -C ₆ J ₄ -NN- H -NH-CO-CJi-OClD do,
2 4 ,, "3 64 • = »6 Jig ° QGQQUH" H II H H H 2, A-Di-NO ₂ -C ₆ H ₃ - H -M-CO-O ₃ H ₆ OC ^ dO. 6 3 = G _? H ₄ -0G00GqH _s "GH H H Eq H 4-NO ₂ ^ -CN-C ₆ Hg- H -NH-CO-NH-CH ₂ 66 H H Br H 3-CH ₂ -C ₆ H ₄ -NN- H gh o-eo 67 -GHq-GBi-GH ,, H H H H 68 -GH H H H H 2,3,5-Tri-Cl- ^CH 3 -C ₆ H ₂ -NN- 69 -C H H H H 3,5-Di-Br-C ₆ H ₃ - H 70 H H H H

150-4105

E.g
No. ^R i ^R 3 ^R 3 ^R 4 ^R 2 ^R 12 ^R 13l ^R 14 3,5-Di-OCH -C, H-
-N = N- ^R io R! Nuance on
11! Polyester 71 -C ₂ H ₄ CN H TT H H H H 2-Br-C ^ HN = N-
6 4 H -NH-CO-C ₀ HC ^ H ₁ . Red
2 4 6 5 ^ 72 -C ₂ H ₄ OCOCH ₃ H H H H H H -CN H -NH-CO-C ₀ H.Br do.
2 4 73 H H H H H H H H -NHCOCH do.
i

Tabel

150-4105

The dyes in this table correspond to the formula

N = N

CH-CH-CH L , L

3 O

CC = C- R _r

E.g.
No. -C ₂ H ₅ ^R 3 ^R 3 ^R 5 h I Cl ■ ρ Τ
^R 14 ^R 13 ^R io H Nuance on
^ H polyester Red 74 H H · H H H Cl Cl H H -NHCOCH do. 75 -C ₂ H ₄ OCOC ₆ H ₅ H H -CH ₂ -OCH ₃ H -NO ₂ Cl -SO ₂ N (CH ₃ ) ₂ H -OCH ₃ -CH ₃ blue 76. -C ₀ H.OCOOCH ₀
2 4 3 H H do. H -CH ₃ -NHCOCH -NO ₂ , -OC ₂ H ₅ H -NHCOCH red _N 77 H H H H ~ COC, H _C
DJ -OCH ₃ -CH ₃ do. " ^CH 3 4:
do. 1 78 " ^C 4 ^H 9 -CH ₃ ■ -CH ₃ H -COCH Cl -OCH ₃ do. Cl violet: 79 -C ₃ H ₇ H H -CH ₂ -OCH ₃ do. -OCH ₃ Cl do. -CH ₃ do. i red
I.
I.
I. 80 H H H do. -CH ₃ do.

Tabel

150-4105

The dyes in this table correspond to the formula

14th

CH CH-CH- O-CC = CR Z ₁ I j

E.g.
No. ^R i ^R 3 :
^{1 r} ; ^R 2 ^R 5 * _l2 Cl ^R 13 Nuance on
polyester 81 H H H -COCH ₃ H -NO ₂ -CN blue 82 H H H H -CH ₂ -OCH ₃ Br -NO ₂ do. do. 83 H -CH -CH ₃ H H J Br do. do. 1 84 . " ^C 2 ^H 5 H H H -CH ₂ -OCH ₃ -NO ₂ -SO ₂ CH ₃ do. do. L. 85 H H H do. -CN -CN do. do. 86 do. H H H H do. Br do. do. 87 H -CH ₃ -COCH -NO ₂ do. do.

150-4105

Tabel

The dyes in this table correspond to the formula

■ ρ π |

^R 3 \ A -0-CC = C- R _r

E.g.
No. ^R i ^R 3 ^K 3 ^R 2 ^R 5 ^R 15 ^E ! 6 j t H -NHCOCH Nuance on
polyester P 88 -C ₂ H ₄ CN H H H H H -CN H -CH ₃ Red S ^g 9 -C ₂ H ₄ OCOCH ₃ H H H -CH ₂ OCH ₃ H -SO ₂ CH ₃ -OC ₂ H ₅ -NHCOCH do. H H H -COCH H -NO ₂ -NO ₂ H do. blue ^ 91
ο H H H -COC ₄ H ₉ -CH ₂ -OCH ₃ Cl -CN -OCH ₃ -CH ₃
do. violet
NJ ^ l 92
Ni 93 -CH ₃
H -CH ₃
H " ^C 2 ^H 5 H
-CH-OCOCH H
H Cl H
-OC ₂ H ₅ -NHCOCH
do. do.
Red 94
95 -C ₂ H ₄ CN
H H -CH ₃
H H
H -C (CH ₃ ) ₂ OCH ₃
H H -SCN H Cl do.
blue 96 H H H H H Cl Cl -OCH ₃ -CH Red 97 -C ₂ H ₅ H H H -CH ₂ -OCH ₃ H -SO ₂ C ₂ H ₅ H H do. 98 H H H H H Br Cl H H do. 99 -C ₂ H ₅ H H -COOC-H _n
H 9 -CH ₂ -OC ₂ H ₅ Br Br H Cl do. C ₀ 100 H -CH ₃ -CH ₃ H -C (CH ₃ ) ₂ OCH ₃ -CH ₃ -CN H -NHCOCH do. <3 101 -C ₂ H ₄ OH H H H -CH ₀ -OCOCH ₀
ZJ j-CN
ί -CN do. - *
ro

Tabel

150-4105

The dyes in this table correspond to the formula

R-

CH ₀ -CH-CH. - 0-CC = CR. 2 t 2

OR ₂

E.g.
No. ^R i H H ^R 2 ^R 5 ^R 17 - ^{:; 0} 2 H ^R ll Nuance on
polyester 102 H H H H H H do. -OC, H. -NHCOCH blue 103 H H H -COCH -CH ₂ -OCH -CH c: H do. do. 104 -C ₂ H ₅ H H do. H Cl He -OC ₂ H ₅ Cn ₃ do. 105 H -CH ₃ -CH ₃ do. -CH ₉ -OCOCH ₃ 3r -NO ₂ -OCH ₃ -NHCOCH blue 106 H H H H -CH ₂ -OCH ₃ Cl -CN H -CH ₃ do. 107 H H H H H Br -SO ₂ C ₂ H ₅ H Cl do. 108 - ^C 2 ^H 5 H H H H H -CN -OCH ₃ -CH ₃ do. 109 -C, K, OCOCH-
2 <* 3 H H -CN co. do.

in

0Λ

U Hl

► pi

pci O I

U I

W Pi U-O

O/

CM'

CN

ω Φ B. φ ο Λ ti U Φ
cn H Φ Φ • rl ¹ Cf τ) Φ οι Century Yyy α 0 φ 4Y M. U) 4Y C. U φ φ • Η D.

Ή "1 • n CO Ll I. ri m CM U in £ N Lf co CM η ro J-J CO η _t I) O CM D ίι n) eat te η (rt «3 33 a CC 31 a) U O CC O CJ ■ υ O O • d ce
Γ , —T CJ 8th U l "l a υ U vO U σ CJ U M. U -J U O O -O O CJ a I. ¹ U QJ '/) I. U
I. CC I. .. .-. 33 .., Ti cc 33 rM co ro
31 ... - ro
rti co H), -1 33 31 U ρ O 33 ro H t-4 31 rs ο CJ
O I. 33 CJ CJ
O i I-I 1 j I. U CJ U
I. CJ Ä I. O cc Ό 31 CM 31 ( rc in 33 31 in CJ CC I. CC J I. 1 33 I. CJ CM CtJ "' ¹ CJ υ cc CM co Tl 33 t_j I. CC 31 33 I. Pooh 31 CJ 33 31 33 'C ■ r! I. in I. CJ σ 33 ro CI CJ CM CM
CJ
O CC 33 cn
il
r I I. CM
ri O I. cn
t-l V 33 O τ — ϊ CC I. • ■ -t O ro 31 erf 33 -O 33 r-J . — I U 33 V CJ υ I - 4 ra I. PI ο 33 ro in
tl in Si CM OCH t — I O t-l CC Ki 33 ι T υ _u CM
CJ O CC CQ O U cc * CJ CTi el O
tl CJ 33 CC U 33 cc PI co 33 CO DODO r-1
t-l cc 33
H I. 31 CM in 33 a cc 33 33 -cn 33 31 33 t-l CO U 33 - ^ 33 33 r-J I-l CJ rH I. i-l OO
il Bl O αϊ Ρϊ

909811/0772

St.

(D ■ H
Q) r-i
_m .i G ^ "1
Q) M. X)
BS
r ■ O M. Cm (U Ul H O) (U •H Tl Ό β α) (U XJ <N
Il j υ O α » -P M. Ul Oj XJ to H -U ΠΙ β Cm Q) •H P.

CJ

CJ 3ί 85

ro

33 CJ

ro 33

CJ 33 O I

• ö

Ot

33

33 33 ro 33 ro CJ CJ 33 U 33 I. I. U I. CJ O O I. I. 33

DQ

U3 33

tr.

Π3 33 fq 33 33

CsI

υ υ 33

w " ¹

CsI

υ yes

CsI CJ O I

cn

egg

ta

T3

ro 33

CJ O Ό CJ I

Π3

U O 33 33

«N

ro

CsI 3J

I.

-CH 33 33 'HD- -CH, 33 a ⁰⁰ 33 33 33 33 f I Sd- 33 ro
Oi 33 33 33 ro
33
CJ

Tuesday

υ ο υ ο

33 "" ¹ r \ UI

33

CJ I.

33

33 O

Ch

-T 33

33 _a

cy

U I.

Oil

co O

O i-f cm ro <i- in CsI CsI csj CsI CsI CsI

909811/0772

Dyes of the formula

Tabel

150-4105

O.N

N-N-

CH ₂ -CH-CH ₂ -O-CH ₂

^R 6 ^R 6

t I

-C = C-R

O CD CXl

E.g.
lio. ^R l ^R 2 H H ^R 7 ^R 12 H ^R 14 Shade on polyester
iasermaterial 127 H H H Cl H Cl " ^S0 2 ^C 6 ^H 5 -NO ₂ blue 123 -C ₂ H ₅ H H Br H Br -SO ₂ C ₂ H ₅ do. do. 129 H - ^C 2 ^H 5 H Cl H J -SCN do. do. 1 130 H -COCH Br H -CH ₃ Br •H -CN do. c 131 - ^nC 4 ^H 9 -CHO H
H H
H H Br do. do. 132
133 H
-CH ₃ H
H H Cl H
H -SO ₂ CH ₃
-CN -NO ₂
-CN do.
do. 134 H -COC ₂ H ₅ ' H H H -SO ₂ CH ₃ do. do. 135 "UC ₃ H ₇ -CH ₂ C ₆ H ₅ - H H H 'J -NO ₂ do. 136 H H H H H -CN violet 137 H H H H H '-NO ₂ blue 138 -CH ₃ -COCH ₂ Cl H H H do. do. 139 H -CH ₂ CH ₂ OH H Cl H do. do. 140 - ^C 2 ^H 5 -COCH H ' Cl ruby

T a b e 1 1 e

150-4105

E.g.
No. ^R l ^R 2 H H H R ₁₂ -NO ₂ Shade on polyester
fiber material 141 H H H H H J do. blue 142 H -COCH H H H Cl do. do. 143 H do. H H H Br do. do. 144 H do. H J do.

Table 10

co

CD OO

Dyes of the formula

D-N

CH-CH-CH ₀ -O-CH,
t 2 Z

OR «

^R i
C.

C-R

E.g.
No. . ^R i ^R 2 V ^r ; ^R 7 O ₂ N ^ Nuance on polyesu ^ r-
fiber material 145 H H H "H H ^H 3 ^C ~ | T ~ -Nii blue 146 H -COOCH H H H Cl -. ^ ILI do. H
H -COCH
H
-COCH Cl H
Cl
H H
H
H www 0 ₂ N ^ ~ S - ³ ^
O ₂ N - ¹ ^ VX 147
148
149 -CH ₃ H H Br H Ne ^ ~ "S do.
do.
do. 150 H H H H H O ₂ J ^ T do. 151 do.

ro oo co

150-4105

Tabel

Example no. Shade on polyester

H-CH -CH-CH-ττ-C = CH
λ , I

OH

blue

NO

2 OC ₂ H ₅

O ₂ N- (O) -N ^

CH

NHCOCH do.

Cl

NH-CH ₂ -CH-CH ₂ -O-ς - C = 3CH OCOCH ₃ ' ^Π

Red

■ N

NH-CH-CH-CH-O-CH-C = CH

Z, Z Z

OH

blue

Red

NH-CH-Ch-CH-O-CH-C = C-CH-OCH
OH

N N

■ NH-CH ₂ -CH-CH ₂ -O-CH ₂ -C = C
OH

do.

Ψ

S ¹ OCOCH "

^{Ξ CH}

do.

do.

90981 1/0772

15C-4105

example
No. Cl
\ Cl
/ N = N- —Ν (O f 160 /
Cl Cl

Shade on polyester

-CH-CH-CH-O-CH-C = CH yellow 2, LL

OH

Br

Br

V ^

CH ₃ -CH-CH-CH ₂ -O-CH ₂ -C = CH yellow OH

37OO / HW / HB

909811/0772

Claims (14)

Claims • CH - CH - CH ₂ - O - C - R where D is the remainder of one in disperse dye chemistry common diazo component,
K is the remainder of a coupling component of the 1,4-phenylene or 1,4-naphthylene series,
R is hydrogen, alkyl or alkenyl or, when K is a radical of 1,4-phenylene series, also through halogen, hydroxy, alkoxy, Acyloxy, phenyl, phenoxy, cyano, alkenyloxy, alkinyloxy or Alkoxyalkinyloxy substituted alkyl or optionally halogen-substituted alkenyl, R hydrogen, acyl or optionally a halogen, alkoxy, hydroxy, Phenyl, phenoxy, benzyloxy or acyloxy as substituents .bearing alkyl,
R and R 'independently of one another are hydrogen or alkyl or if R 909811/0772 - 2 - 150-4105 283712 Hydrogen denotes, together and with the carbon atom bonded to it, also cyclohexylene, R denotes a group of the formula -C ³ CR or, if K, 1,4-naphthylene means also a group of the formula * 6 ^ g - C = C - R ₇ , R is hydrogen or a group of the formula ■ * Rr ¹ - C - 0 - R ₉ , R and R ¹ one hydrogen, the other hydrogen 6 6 or halogen, R hydrogen or alkyl, R and R ¹ independently of one another are hydrogen or alkyl 8 8 and R is hydrogen, acyl or optionally alkoxy, alkoxyalkoxy or acyloxy denotes alkyl bearing substituents and the molecule only bears those substituents that are found in disperse dyes are common. 2. The azo compounds of the formula I according to claim 1, wherein D is phenyl which can have up to four substituents, including up to four chlorine or bromine, up to two from the group cyano, iodine, trifluoromethyl, C -alkylsulfonyl and nitro and / or one from the group methyl, methoxy, formyl, C -alkyl- 1-4 carbonyl, C -alkoxy-carbonyl, amino carbonyl, C -alky 1-aminocarbonyl, Di- (C -alkyl) -aminocarbonyl, phenyl, benzoyl, Benzylcarbonyl, Pheny! Sulfonyl, Toluylsulfonyl, aminosulfonyl, C "-Elkylaminosulfonyl, C -Alkoxycarbonyl, Rhodan, Di- (C -alkyl) -aminosulfonyl and / or phenylazo, which is up to can carry three substituents, including up to three chlorine or bromine., up to two methyl, C -alkoxy, cyano and / or Nitro and a phenyl; Benzthiazolyl, can carry up to two substituents which namely up to two from the group of chlorine _s bromine, cyano and nitro and / or from from the group methyl, C1-4 -alkylsulfonyl, aminosulfonyl and rhodan; 1 ~ 2 90981 1/0772 - 3 - 150-4105 Benzisothiazolyl, which can carry up to two substituents, namely up to two from the group consisting of chlorine, bromine and cyano and / or one from the group consisting of nitro and C -alkylsulfonyl; Thienyl, which can have up to three substituents, including up to two from the group consisting of chlorine, bromine, cyano and nitro and / or one from the group consisting of methyl, phenyl, C -alkyl-carbonyl, methoxycarbonyl and hydroxyl; Thiazolyl, which can carry up to two substituents, up to two from the group chlorine, bromine and cyano and / or one from the group methyl, nitro and C -alkylsulfonyl, 3-phenyl-l, 2,4-thiadiazolyl (5) or 2-phenyl-1,3,4-thiadiazolyl (5); K unsubstituted 1,4-naphthylene or a radical of the formula II (II) R hydrogen, chlorine, bromine, C alkyl, C alkoxy, hydroxyethoxy, Methoxyethoxy or cyano-C-alkoxy; R hydrogen, chlorine, bromine, C alkyl, C alkoxy, C alkyl carbonylamino, Bromo- or Chloräthylcarbonylamino, cyano, Formy lamino, C -alkoxy-C -alkyl-carbonylamino, C -alkoxycarbonylamino, PhBnOXy-C ₁ "-alkyl-carbonylamino, C ~alkoxy-C" _ -alkoxy-carbonylamino, C., -alkoxy-carbony1-C -alkylamino-carbonylamino, benzoylamino or phenyl-C-alkyl-carbonylamino;
R, if K is 1,4-naphthylene, hydrogen or C -alkyl, otherwise also once by chlorine, bromine, hydroxy, C -alkoxy, 1 — ζ Formyloxy, C -alkyl-carbonyloxy, C -alkoxycarbonyloxy, C "-alkylaminocarbonyloxy, phenoxy, phenyl, benzoyloxy or cyano-substituted C", -alkyl, β-hydroxy-5-chloropropyl, benzyl, allyl, 2- or 3-chloro or bromo-allyl or a group of the formula -CH CHOHCH OCH C ^S CH or 909811/0772 150-4105 R is hydrogen, C -alkyl, which may optionally be a chlorine, Bromine, C1-3 alkoxy, phenoxy, formyloxy, C1-4 alkyl-carbonyloxy or benzyloxy, C -alkyl-carbonyl, benzoyl, C -alkoxycarbonyl or hydroxyaryl, R and R 'hydrogen or methyl or when K is 1,4-phenylene, independently of one another hydrogen or methyl or together cyclohexylene, R. a group of the formula -C ^£ CR or, if K, 1,4-naphthylene RR 'also means a group of the formula 6,6 -C = C-R R_ hydrogen, C -alkoxy-C -alkyl, methoxyethoxymethyl Acetoxymethyl or chloropropionyloxymethyl, one of R and R 'is hydrogen, the other is hydrogen, chlorine or ο Bromine and R denote hydrogen or methyl. 3. The azo compounds of the formula I, according to the preceding claims, wherein D is a radical of the formula III (III), 14th where R "hydrogen, chlorine, bromine, iodine, nitro, cyano, methylsulfonyl, Ethy! Sulfonyl, methoxycarbonyl or ethoxycarbonyl, R nitro, aminosulfonyl or di- (C -alkyl) -aminosulfonyl, R is hydrogen, chlorine, bromine, iodine, cyano, methylsulfonyl or ethylsulfonyl and R ¹ , hydrogen or, if R, is hydrogen, also chlorine or 14 Mean bromine. 4. The azo compounds of the formula I, according to the preceding claims, wherein K is 1,4-naphthylene or, preferably a radical of the formula II 90981 1/0772 150-4105 where R
and R 10
11 (ID, Hydrogen, C -alkoxy or hydroxyethoxy Hydrogen, methyl, formylamino or C -Alley 1-carbonyl- mean amino. 5. The azo compounds of the formula I, according to the preceding claims, wherein R when K is 1,4-naphthylene, hydrogen or C -alkyl, _{otherwise C 9} -alkyl, in particular hydrogen, which is also substituted once by C -alkyl-carbonyloxy or cyano. 6. The azo compounds of the formula I, according to the preceding claims, where R " Is hydrogen or C1-4 alkyl, in particular hydrogen. 7. The azo compounds of the formula I, according to the preceding claims, wherein R and R 'are hydrogen or methyl, especially hydrogen. 8. The azo compounds of the formula I according to the preceding claims, wherein R is a group of the formula -C ^S CR or, if K, 1,4-naphthylene means, also vinyl, preferably a group -C = CR and R ₁ . Signify hydrogen, methoxyethoxymethyl or acetoxymethyl, preferably hydrogen. 9. The azo compounds of the formula I, according to the preceding claims, wherein D is a radical of the formula III a (III a) where R
and R ₁ , Nitro or. Cyan Mean chlorine, bromine, cyano or methylsulfonyl. 90981 1/0772 150-4105 10. The azo compounds of the formula I, according to the preceding claims, wherein K is 1,4-naphthylene or a radical of the formula II 11 (II), wherein Methoxy or ethoxy
1.0 and R C -alkyl-carbony! amino mean. 11. The azo compounds according to claim 1, of the formula 12th 14th CH-CH-CH-O-C-C = C-R, where R is hydrogen, chlorine, bromine, iodine, nitro, cyano, methylsulfonyl, Ethylsulfonyl, methoxycarbonyl or ethoxycarbonyl, R nitro, aminosulfonyl or di- (C -alkyl) -aminosulfonyl, U χ. Z. R. Hydrogen, chlorine, bromine, iodine, cyano, methylsulfonyl or Ethylsulfonyl and R ', hydrogen or, if R _{1 is} hydrogen, also chlorine or 14 14 Bromine, R is hydrogen, C -alkoxy or Ilydroxyäthoxy and R is hydrogen, methyl, formylamino or C -alkyl-carbonyl- amino,
R is hydrogen, C -alkyl or once through C -alkyl-carbonyl oxy or cyano substituted C -alkyl, R hydrogen or C ₁ -alkyl,
R and R 'are hydrogen or methyl
and R is hydrogen, methoxyethoxymethyl or acetoxymethyl. 90981 1/0772 150-4105 12. The azo compounds according to claim 11, of the formula wherein R is nitro or cyano and R is chlorine, bromine, cyano or methyl sulfonyl, R methoxy or ethoxy and R is C -alkyl-carbonylamino. 13. The azo compounds according to claim 1, of the formula wherein R is nitro or cyano and R chlorine, bromine, cyano or methylsulfonyl R, R ' 14 ι D, O and R is a group of the formula -C = C-R or -C = C-R, . R hydrogen, methoxyethoxymethyl or acetoxyraethyl, one of R ^ and R 'hydrogen, the other hydrogen, chlorine or D D bromine
and R is hydrogen or methyl. 14λ The azo compounds according to claim 13, wherein R. is a group of the formula -C = CH. l5. Means for dyeing or printing, characterized in that it is next to Dispersants and / or fillers or dispersants and thickeners contains a dye according to Claims 1 to 14. 90981 1/0772 (DOPV - 8 - 150-4105 16. Process for the preparation of the azo compounds of the formula I according to claim 1, characterized in that a diazotized amine of the formula IV D - NH ₂ (IV) with a compound of the formula V. HKN ^, 2 ^K 3 \ / ^K 3 _(v) "CH-CH-CH-O - C —R ₄ ^v ' clutch. Y]. Use of the azo compounds according to claim 1 as disperse dyes, for dyeing or printing fibers or threads or articles made therefrom made from fully or semi-synthetic, hydrophobic, high molecular weight organic substances. 18 · Processes for dyeing or printing fibers or threads or therefrom manufactured articles from fully or semi-synthetic, hydrophobic, high molecular weight organic substances using the azo compounds of formula I according to claim 1. . Those colored with the azo compounds of the formula I according to claim 1 or printed item. 90981 1/0772