DE2602173A1 - AZO DYES AND USE OF THE SAME - Google Patents

Description

Dr.-lng.Held Dipl.-Phys. Wolff

Tel. (089) 293297 Telex 0523325 (patwo d)

Reg.No. 124 845 Telegram address: wolffpatent, munich

Postal check account Stuttgart 7211

(BLZ 60010070)

Deutsche Bank AG, 14/28630

ZIP 60070070)

Office hours: 8 a.m. to 12 p.m., 1 p.m. to 4.30 p.m.

except saturdays

January 12, 1976 25/2

EASTMAN KODAK COMPANY, 343 State Street, Rochester, New York State, United States of America

Azo dyes and their use

609831/0977

ORIGINAL INSPECTED

Azo dyes and their use

The invention relates to new azo dyes with a benzothiazole radical.

Azo dyes with a benzothiazole radical are known, for example, from US Pat. Nos. 2,822,359, 2,832,761 and 2,857,371.

The invention was based on the knowledge that particularly advantageous azo dyes with a benzothiazole residue are obtained when the benzothiazole radical is substituted in a certain way by a trifluoromethyl radical.

The invention accordingly relates to new azo dyes having a trifluoromethyl-2-aminobenzothiazole diazo group.

The azo dyes according to the invention are characterized by the following general formula:

in which:

R is a hydrogen or halogen atom or a methyl, ethyl, Methoxy, ethoxy, nitro, acetyl, carbomethoxy, carboethoxy, cyano or thiocyanate and

A is an aniline, 1,2,3,4-tetrahydroquinoline or benzomorpholine radical as a coupling component.

The coupling component is attached to the azo group through an aromatic ring carbon atom in the para position to the nitrogen atom of the coupler core bound, dvh. the 4-position of the aniline, the 6-position of the tetrahydroquinoline and the 7-position of the benzo

609831/0977

morpholine coupler.

The trifluoromethyl radical is preferably in the 4-position of the benzothiazole nucleus.

The novel azo dyes according to the invention are particularly notable compared to comparable dyes without a trifluoromethyl radical characterized in that they provide stronger and brighter colors.

The coupler residue represented by A is a common one for azo dyes Coupler radical, free of ionic substituents, for example carboxylate, sulfonate and ammonium radicals, their presence complete water solubility of the new azo compounds in customary aqueous dye liquors in the customary concentrations would result, which are used in the usual known methods of dyeing with disperse dyes.

The radical A of the general formula (I) is thus the radical of a customary one known coupling component, which is usually used "for the production of azo dyes. A can thus for example be a residue of a coupling component, as described, for example, in the following US Pat. Nos. 2,249,749, 2,249,774, 2,251,947, 2,286,795, 2 309 129, 2 436 100, 2 683 708, 2 683 709, 2 726 237, 2 773 054,

2 785 157, 2 805 218, 3 148 180, 3 161 632, 3 206 452, 3 336 285,

3 349 075, 3 370 055, 3 379 711, 3 380 990, 3 386 988, 3 423 394, 3 424 741, 3 429 871, 3 442 886, 2 092 398, 3 359 256, 2 891 942, 3 268 507, 2-967 858, 2 971 953, 3 117 956, 3 122 410, 3 178 405, 3 206 454, 3 329 669, 3 342 800, 3 398 135, 3 406 165, 3 407 189 known is.

Accordingly, in the given formula (I) is more advantageous

Way for a remainder of one of the following formulas: R ³ r3 r8

ι I

or

609831/0977

COPY ΐ?

where mean:

R is a hydrogen or halogen atom or a short

chain alkyl, short-chain alkoxy or trifluoromethyl radical or a radical of the formula -NH-acyl;

.R is a hydrogen atom or a short-chain alkyl

or short-chain alkoxy radical;

R an optionally represented by a short-chain alkyl

radical substituted cyclohexyl radical or an alkyl radical, preferably a short-chain alkyl radical, the is optionally substituted by a short-chain alkoxy, aryl, aryloxy, cyclohexyl, alkylsulfonyl, Arylsulfonyl, cyano, hydroxy, short chain alkanoyloxy, methylsulfonyl, short chain alkoxy carbonyl, short-chain alkoxycarbonyloxy, aroyloxy, short-chain alkylcarbamoyloxy, arylcarbamoyloxy, Alkylcarbamoylamino or arylcarbamoylamino radical or a halogen atom or a radical of one of the following Formulas:

.R ⁸ / Acyl / COv ' /' Nil 1? *

-CON, -N, -N r "or -SR ^IZ

V ^X

where mean:

R is a hydrogen atom or a short-chain alkyl or aryl radical;

9
R is a hydrogen atom or a short-chain one

Alkyl radical or

8 9
R and R together are a remainder of the formulas:

- (CH ₂ ) ₅ - or -CH ₂ CH ₂ -O-CH ₂ CH ₂ -;

R is a hydrogen atom or a short-chain one

Alkyl radical or an aryl or cyclohexyl radical;

609831/0977

R is ethylene, propylene, o-cyclohexylene or o-arylene radical;

X is a remainder of the formulas:

-CH ₉ -, -CO- or -SO ₉ -; and

R ^{12 is} an aryl; Benzyl-; Cyclohexyl-; 1,2,4-triazol-3-yl or 2-benzothiazolyl radical;

R is a hydrogen atom or an aryl or short-chain

gen alkyl radical, which can optionally be substituted by a hydroxy, cyano, short-chain Alkoxy, aryl, aryloxyl, cyclohexyl, short-chain alkanoyloxy, short-chain alkoxycarbonyl or short-chain Alkoxycarbonyloxy radical or

R ⁴ and R ⁵ together represent a radical of the formula: -CH ₂ CH ₂ -Y-CH ₂ CH ₂ -, in which Y represents a radical of one of the following formulas:
-CH ₂ -, -0- or -SO ₂ -;

R is a methyl radical, or, if R and R are each a

Represent hydrogen atom, a short-chain alkyl radical and

8th
R and R each represent a hydrogen atom or a methyl radical.

The alkyl and alkoxy radicals and the corresponding alkyl and alkoxy groups in such radicals preferably have 1 to 8 carbon a tome on. Short-chain alkyl and short-chain alkoxy radicals are to be understood here as meaning those with 1 to 4 carbon atoms. This means that, for example, in the case of a short-chain Alkoxycarbonyloxy the alkoxy group preferably has 1 to 4 carbon atoms.

609831/0977

The aryl and arylene radicals preferably consist of phenyl or phenylene radicals, which may optionally be substituted, for example by short-chain alkyl radicals, short-chain alkoxy radicals, short-chain alkoxycarbonyl radicals and / or halogen atoms, e.g. chlorine or bromine atoms.

The acyl radicals preferably consist of formyl, short-chain alkanoyl, Aroyl, cyclohexoyl, short-chain alkoxycarbonyl, aryloxycarbonyl, short-chain alkylsulfonyl, cyclohexylsulfonyl, arylsulfonyl, Carbamoyl, short-chain alkylcarbamoyl or arylcarbamoyl radicals. The alkanoyl radicals can optionally be substituted, for example by halogen atoms, aryl, cyano, short-chain ones Alkoxy, aryloxy and / or benzyloxy radicals. The alkoxycarbonyl radicals can optionally be substituted by, for example, hydroxy, Alkoxy and cyano radicals. Particularly advantageous dyes are those with optionally substituted alkanoyl, aroyl and alkoxycarbonyl radicals.

The halogen atoms advantageously consist of chlorine, bromine or Fluorine atoms.

The new dyes according to the invention can be used as disperse dyes for dyeing, for example, threads and fibers or other textile structures made of polyesters, polyamides, acrylic polymers, triacetate and other synthetic polymers can be used. In a particularly advantageous manner, they are suitable for what is known as transfer printing on textile structures made of polyesters and Polyamides. The invention therefore also relates to the use of the new azo dyes for dyeing threads and Fibers and other textile structures made of polymers, for example polyesters, polyamides, acrylic polymers, cellulose acetates and like that.

If the new dyes are used for transfer printing, dyeing methods such as those used by D. Burtonshaw in the journal "International Dyer and Textil

609831/0977

Printer ", 1971, pages 335-340, Textile Business Press, Ltd., Dorset House, Stamford Street, London, England will.

According to a known and widespread method, a sublimable dye is applied to a non-textile carrier, for example a paper carrier, whereupon the dye is transferred to an adjacent material by the action of heat will.

The dyes according to the invention are therefore suitable, for example advantageously for the production of sheet-like products for transfer printing, consisting of a non-textile carrier and at least one dispersion dye according to the invention applied thereto.

Advantageously, the dye or dyes can be present in a binder, for example a synthetic, semi-synthetic or natural resinous binder, e.g. a cellulose ester or a cellulose ether.

The non-textile carrier can, for example, consist of a paper carrier consist, e.g. a paper of comparatively low porosity or a metal carrier, e.g. an aluminum foil or a Foil made from a plastic material. All of these carriers can be on the side that does not contain any dye on another Be arranged carrier.

The dyes can be applied in the form of a printing ink, for example by the screen printing process or by lithographic or flexographic processes, by gravure printing or the so-called ^M letterpress "process can be ^{applied imagewise 1. One} or more dyes can be applied to the carrier.

609831/0977

The invention thus also enables the transfer printing of a Woven or knitted fabric or a sheet or a film made of, for example, a polyester or a polyamide, the one or more According to the invention, side of a sheet-like material containing dyes for transfer printing in contact with the material to be colored Woven or knitted fabric or the film to be colored is brought, whereupon the sheet-shaped coloring material and the material to be colored exposed to the action of heat until at least part of the dye (s) on the dye to be dyed Material has been transferred.

The dye transfer can take place at temperatures of, for example 180 ° to 23O ° C. If necessary, it can also be increased

2 pressure can be worked, for example a pressure of 0.105 kg / cm (e.g. with a pressure of up to 1.5 Ib./sq. in.). For the coloring can conventional known devices can be used.

As already stated, the dyes according to the invention are suitable excellent for the production of printing inks of the type customary for disperse dyes.

The dyes according to the invention are suitable for dyeing threads and fibers and other textile structures, which are more commonly known Way to be colored with disperse dyes. The dyes are particularly suitable for dyeing textile structures Polyesters and polyamides. The polymers which can be dyed with the dyes according to the invention can, however, also be in the form of coatings are present on a wide variety of substrates, e.g. on metals, leather, cotton or wool.

In a particularly advantageous manner, the dyes are suitable., For Dyeing of woven and knitted goods, laminated fabrics and knitted fabrics, as well as tiles, so-called "bonded fabrics" and so-called "piles" fabrics ", e.g. carpets.

609831/0977

-Sf-

Those of the following have been found to be particularly advantageous dyes Formulas II to IV proved:

where mean:

R is a hydrogen atom or a methyl, short-chain alkanolamino, Benzamido or short-chain alkoxycarbonylamino radical;

R is a methyl or methoxy radical or a hydrogen atom or if R is a hydrogen atom, a methyl or methoxy radical;

R is a short chain alkyl; Cyclohexyl-; Benzyl-; Aryl methylene; Cyclohexylmethylene; 2-cyanoethyl; 2-carbamoylethyl radical or an N-alkyl-2-carbamoyläthylrest with a short chain Alkyl radical or an N, N-dialkyl-2-carbamoylethyl radical with short-chain alkyl radicals or a radical of the formula -Z-R

609831/0977

where Z is an ethyl or propylene radical and R is a hydroxy radical or a short-chain alkanoyloxy, short-chain Alkoxycarbonyl or short-chain alkoxycarbonyloxy, Succinimido, glutarimido, phthalimido, aroyloxy, short-chain alkoxy, alkanoylamino or short-chain alkylamineccarbonyloxy radical or a short-chain alkylaminocarbonylamino or a short-chain alkoxycarbonylamino radical;

R is a hydrogen atom or a short-chain alkyl radical, a Cyclohexyl, arylmethyl or a cyclohexylmethyl radical or

13 13

a radical of the formula -Z-R wherein Z and R are as indicated

Have meaning;

7 8
R and R each represent a hydrogen atom or a methyl radical,

where it applies that the aryl radicals are preferably selected from phenyl, tolyl, Anisyl, ethoxyphenyl or chlorophenyl radicals exist.

If R and R both represent radicals of the formula -Z-R, then preferably has Z has the same meaning in both cases.

The new azo dyes according to the invention can be prepared according to customary methods known methods by diazotizing a trifluoromethyl-2-aminobenzothiazole and coupling the obtained diazonium salt with an aniline, tetrahydroquinoline or benzomorpholine dispersion azo dye coupler of the formula H-A.

The trifluoromethyl-2-aminobenzothiazoles can be followed using the following procedure:

C .H ₁ -COCl + NH-SCN 6 5 4

C ₆ H ₅ CONCS

0 SC ₆ H ₅ C-NHC-N;

OH

CF.

609831/0977

HLN-

Br,

ClCH ₂ CH ₂ Cl

ti

H ₂ N-CNH

CF.

When coloring the new dispersion azo dyes according to the invention on threads and fibers made of e.g. polyesters, e.g. poly (ethylene terephthalate), Cellulose acetate and polyamides, e.g. of the nylon type, are more excellent in strong scarlet to purple shades Achieve fastness properties, in particular to the action of light and moisture.

The azo dyes of the specified formulas II, III and IV are particularly suitable for transfer printing of polyesters and polyamides, in particular when R and R in the given formulas are radicals with fewer than 6 carbon atoms. The dyes are characterized by excellent volatility and deliver strong scarlet to bluish-red shades on polyesters and polyamides with excellent fastness properties, especially to light and moisture treatments.

The dyes of the formulas II, III and IV according to the invention are suitable is also advantageous for the so-called Th'ermosol color process and exhaust dyeing of fabrics, Knitted and yarns based on polyester and polyester cellulose. The dyes according to the invention also have excellent properties Stability at pH values of 4 to 8 when applied to textured polyester fibers at elevated temperatures, e.g. 120 to 130 C. The dyes according to the invention have thus excellent coloring properties.

2 ^ dyes of the formula II in which R and R represent methyl radicals and wherein R is a hydrogen atom, are particularly advantageous Lightfastness properties marked when dyeing on polyamides.

609831/0977

2-Amino-4-trifluoromethylbenzothiazole can be followed, for example using the following procedure:

With stirring, 13.25 g (0.094 moles) of benzoyl chloride are added to a solution of 7.9 g (0.104 moles) of ammonium thiocyanate in 30 ml of acetone at 30 ⁰ C. The mixture is stirred for 10 minutes under reflux and then cooled to 50 ⁰ C, after which 15.1 g (0.094 moles) of 2-aminobenzotrifluoride be added in one portion. The mixture is then stirred under reflux conditions for another 20 minutes. A solution of 13.2 g of sodium hydroxide in 140 ml of water is now added. The resulting mixture is then boiled for 15 minutes, is cooled whereupon the resulting clear solution at 2O ⁰ C. The pH of the solution is then adjusted by the addition of 21 ml concentrated HCl to 5 and then made by adding 4 "ml 88ligem ammonia just alkaline. After 30 minutes the mixture to 10 ⁰ C is cooled, filtered, and then the precipitated product, is washed with water and dried. The yield of o-trifluoromethylphenylthiourea obtained in this way is about 18.8 g, corresponding to theory. The melting point of the compound is 165 to 166 ^° C.

While stirring, 31.5 g of o-trifluoromethylphenylthiourea are added in 135 ml of 1,2-dichloroethane at 30 ° C., a solution of 9 ml of bromine in 65 ml of 1,2-dichloroethane is added. The mixture is stirred under reflux conditions for 3.7 hours, after which it is cooled to 10 ° C. The resulting precipitate is filtered off, washed with 1,2-dichloroethane and dried. The dried material is then stirred into 400 ml of water, whereupon the mixture is made basic by adding ammonia will. The compound is then filtered off and dried. The yield of 2-amino-4-trifluoromethylbenzothiazole that can be achieved in this way is around 25.6 g, corresponding to 821 of theory.

The following examples are intended to illustrate the invention in more detail.

609831/0977

example 1

0.72 g (0.01 mol) of sodium nitrite were slowly added in portions to 5 ml of concentrated sulfuric acid ^{with stirring at a temperature below 70 ° C.} The mixture was then ^{heated to 70 °} C. for 5 minutes, after which the solution was cooled to room temperature.

14 ml of concentrated sulfuric acid was added with stirring to a suspension of 2.18 g (0.01 mole) of 2-amino-4-trifluoromethylbenzothiazole in 24 ml of water. The mixture was ^{cooled to 0} ° C., whereupon the solution of sodium nitrite in sulfuric acid was added, the temperature being kept below 3 ° C. The diazotization took place within 2 hours at 0 ° C. The diazo solution obtained was then slowly mixed with vigorous stirring to a mixture of 2.2 g (0.0125 moles) of 2,5-dimethyl-n-sec.-butylaniline and 12 g of anhydrous sodium acetate and 60 ml of ethanol at a temperature below 6 ⁰ C were added. The coupling took place within 30 minutes at 6 ^° C. The mixture was then poured into cold water and stirred therein for 5 minutes. The precipitated solid dye was filtered off, washed with water and dried.

Examples 2 to 9

According to the procedure described in Example 1, 8 further dyes, starting from 2-amino-4-trifluoromethylbenzothiazole and the couplers specified in the following table are manufactured:

Table 1

Example No. Coupler

2 N, N-diethylaniline

3 N, N-diethyl-m-toluidine

4 2,5-dimethyl-N-ethylaniline

5 "3,5-dimethyl-N, N-diethylaniline

6 N, N-diethyl-m-chloroaniline

7 N, N-dipropylaniline

609831/0977

Table 1 continued

8 N, N-ethyl-o-ethylaniline

9 N-methyl-ε-methylaniline

Example 10

Following the procedure described in Example 1, another dye was prepared from 2-amino-6-trifluoromethylbenzothiazole and N, N-diethylaniline manufactured.

Example 11

According to the method described in Example 1, another dye according to the invention was made from 2-amino-6-trifluoromethylbenzothiazole and 2,5-dimethyl-N-sec-butylaniline.

example ] 2

Following the procedure described in Example 1, a mixture was made of dyes according to the invention from Ν, Ν-diethylaniline and one Mixture of approximately equal proportions of 2-amino-5-trifluoromethylbenzothiazole and 2-amino-7-trifluoromethylbenzothiazole prepared.

In the following Table 2 are the X _mo (nm.) Values measured in

jTIcljC

Acetone of the dyes of Examples 1 to 12 listed.

Table 2 example

Max

1 ■ 520

2 522

3,532

4 516

5 520

6 522

609831/0977

-M-

Table 2 continued

8 510

9 506

10 520

11 518

12 516

The dyes of Examples 1 to 12 were used to make printing inks. The procedure was as follows:

A certain amount of each dye was put in a ball mill with a mixture of ethanol and ethylene glycol in a volume ratio of 9: 1 using ethyl cellulose as a thickener Marry for 48 hours.

The printing inks obtained in this way were applied to sections of flexographic paper by roller coating and dried. The color transfer papers thus obtained were then used for dyeing fabrics made of polyamide (nylon) and polyester. In the case of the polyamide ^{fabric, the mixture was heated to 200 ° C. for 30 seconds and to 210 °} C. for 30 seconds in the case of the polyester fabric. In this way, strong scarlet to bluish-red prints were obtained which were characterized by excellent depth of color and good fastness properties. The light fastness properties were determined by exposing the test specimens in an exposure device of the "Xenotest 150" type (Cassella system, Original Hanau). The exposure times were 40 hours. The degree of bleaching was assessed with grades from 1 to 5, with grade 1 meaning strong bleaching and grade 5 no bleaching. The wash fastness of the polyester fabric and the polyamide fabric (nylon 66) were determined by the wash fastness methods 1S0 3 and 1S0 2, according to "Standard Methods for the Determination of Color Fastness of Textiles", 3rd edition, 1962, and supplement (1966). published by the Society of Dyers and Colourists, 19 Piccadilly, Bradford, Yorkshire, England.

609831/0977

In the case of the dyes of Examples 3 and 10, the results listed in Table 3 below were obtained:

Table 3

Dye polyester polyamide

of lightfastness washfastness lightfastness washfastness

Example 3 4-5 5 4 3-4

Example 10 S 5 3 3-4

When using the dyes for transfer printing, the inventive dyes of Examples 1 to 12 were found to be compatible with other dyes suitable for transfer printing such as dispersion yellow 3 and dispersion blue

Examples 13-20

Following the procedure described in Example 1, additional dyes were made prepared from 2-amino-4-trifluoromethylbenzothiazole and the couplers listed below:

(a) N-ethyl-N-cyanoethylaniline;

(b) N-ethyl-N-hydroxyethylaniline;

(c) N-ethyl-N-succinimidoethylaniline;

(d) N-ethyl-N-succinimidoethyl-m-toluidine;

(e) N, N-diethyl-m-acetamidoaniline;

(f) N-hydroxyethyl-2,2,4-trimethyltetrahydroquinoline; (g) · N-ethyl-ö-acetamidobenzomorpholine and

(h) N, N- "bis (hydroxyethyl) ^ -methoxy-S-acetamidoaniline.

Examples 21 to 28

Following the procedure described in Example 1, further dyes were obtained from 2-amino-6-trifluoromethylbenzothiazole and the couplers (a) to (h) of Examples 13 to 20 were prepared.

609831/0977

Examples 29 to 36

Following the procedure described in Example 1, mixtures of dyes were made from mixtures of approximately equal parts of 2-amino-5-trifluoromethylbenzothiazole and 2-amino-7-trifluoromethyl-benzothiazole and the couplers (a) to (h) of Examples 13 to 13.

The colors of the dyes of Examples 13 to 36 result from the following table 4.

Table 4

Coupler

13-20

Examples 21-28

29-36

(a) scarlet (b) Red (C) Red CD) bluish-red (β) bluish-red Cf) bluish-red Cg) violet Ch) bluish-red

scarlet

Red

Red

bluish-red

bluish-red

bluish-red

violet

bluish-red

scarlet red

Red

bluish-red bluish-red bluish-red violet

bluish-red

The dyes of Examples 13 to 36 can be particularly advantageously by customary color methods, for example dye using the "exhaust dyeing" method.

Further azo dyes were produced according to the processes described, the structure of which can be seen from the following tables 5, 6 and.

609831/0977

(U • H

(U

PQ

to to to to to X X X X X O U U U U U C. U U CVi U U O O O O O O O O CsI CsT CM CsI

LO LO LO LOU LO LO LOU LOU UUU

XXXX CsJX X X CVlS CVl CVl CSJ CVl CVl CVI CVl CNt X N N CM JJ CVIp ^ XXX

uuuuuuuuuuuuuu

IiIIIIIIIIIIII

J5J to τ— to to O_ ■ 2: CsI U X T ™ X X U U X CM U X U U CM CM X U r— \ C U U X X σ U O t-U O O U U U CM O X CM O O (N CM CM X VOX CM CM X X X U X U U τ— Χ X U U U LO I. U I I r-U U O I. CM X CM X CM CVl U X CM LO X VOX X 2i ~ U U X U U U U I I I. I I LO U X CsI CM X U U I I CM X U LO CsI X X CM U U I.

to to

X X

to to

to

UU UU

OO O O

UU (OCJ U

χ χ χ χ χ

2 2 U 2: Z ι ι ι

XX to X

to to to to to to

XXXXXX UUUU

to to to to to

X U to U U U U U U U O X O O O O O O O U U U U U U U U U X I. X X X X X X X 21 to 2: 2; 2Γ I. I. I. I. I. I. i I. to to to to to to to to

609031/0 ^ 77

cn »
ο
co

Continuation from table

51 52 53 54 55 56 57 58 59 60 61 62 63 64 65 66 67 68

69 2-CH ₃ -5-NHCOCH ₃

70 2-CH ₃ -5-NHCO CH ₃

3-NHCOCH 3 3-NHCOCH 3 3-NHCOCH 3 -H -H -H 3-NHCOCH 3 H 3-NHCOCH 3 3-NHCOCH 3 3-NHCOCH 3 3-NHCOCH 3 3-NHCOCH 3 3-NHCOCH 3 3-NHCOCH 3 3-NHCOCH 3 2-CH ₃ -5-NHCO CH ₃ 2-CH ₃ -S-NHCOCH ₃

-CH ₂ CH ₂ OH
-CH ₂ CH ₂ S- C = NNHCH = N,

-CH ₀ C, H ₁ -.
Praise

-C ₂ H ₅

" ^C 2 ^H 5
-CH ₂ CH ₂ OOCCH ₃

-Ch ₂ CH ₂ OOCCH ₂ CH ₃
-CH ₂ CH ₂ CN

" ^C 2 ^H 5
-CH ₂ CH ₂ CONH ₂

- ^C 2 ^H 5
-CH ₂ CH ₂ NHCOCI-I ₃

-CH-CH ₀ NHCOC ^ h ₁ .

LL 0 3

-CH 2 CH ₂ NHCOO H 11 -CH 2 ^C 6 ^H 5 2 ^C 6 ^H 5 -CH 2 ^C 6 ^H 11 ■ ^C 2 H 5 -CH (CH ₃ ) C ₂ H ₅ - ^C 6 -CH

—CHoC, -H _n
I 0 5

-C ₂ H ₅
-CH ₂ CH ₂ OOCCH ₃ - ^C 2 ^H 5
-CH ₂ CH ₂ CH ₃ -CH ₂ CH ₂ OOCCH _3, -CH ₂ CH ₂ OOCCH _3, -CH ₂ CH ₂ OOCCH _3, -CH ₂ CH (CH ₃₎ OOCCh ₃ - ^C 2 ^H 5
-CH ₂ CH = CH ₂ ■ ^C 2 ^H S
" ^C 2 ^H 5

" ^C 2 ^H 5
-CH ₂ CH ₂ COOCH ₃ -CH ₂ CH ₂ OOCCH ₃

Continuation from table 5

O
CO
CD

71 2-CH ₃ -5-NHCOCH ₃ -CH ₂ CH ₂ CN H 72 2-CH ₃ -S-NHCOCH ₃ -CH ₂ CH ₂ OOCCH ₃ H 73 3-NHCOCH ₃ -C ₂ H ₄ Cl -CH ₂ CH ₂ OOCCH ₃ 74 3-CH ₃ -CH ₂ CH ₂ CN -CH ₂ CH ₂ OOCCH ₃ 75 H -CH ₂ CH ₂ CONH ₂ -CH ₂ CH ₂ OOCCH ₃ 76 3-NHCOCH ₃ -C ₂ H ₄ OH -CII ₂ CH ₂ CH ₃ 77 3-NHCOCH ₃ -C ₂ H ₄ OH -CH ₂ CH ₂ CN 78 3-NHCOCH ₃ - ^C 2 ^H 5 -CH ₂ CH ₂ OOCNHC ₆ H ₅ 79 3-NHCOCH ₃ - ^C 2 ^H 5 -CH ₂ CHoOOCNHC ₂ H ₅ 80 3-NHCOCH ₃ " ^C 6 ^H 11 -CH ₂ CH ₂ OH 81 3-NHCOCH ₃ -CH ₂ C ₆ H ₁₁ -C ₂ H ₄ OOCNHC ₂ H ₅ 82 3-NHCOCH ₃ -C ₂ H ₅ -C ₃ H ₆ NHCONHC ₂ H ₅ 83 3-NHCOCH ₃ -CHoCHoNCOCHoCH- CO -CoH.CN 84 3-NHCOCH ₃ -CH ₂ CH ₂ CH ₃ -C ₉ H ₄ CN 85 3-NHCOCH ₃ ~ ^C 6 ^H 11 "* CH 0 CH * CH γ 86 3-NHCOCH ₃ -C ₂ H ₅ -CH ₂ CH ₂ CH ₂ OH 87 3-NHCOCH ₃ -C ₂ H ₅ -CH ₂ CH ₂ Ch ₂ NHCOCH ₃ 88 3-CH ₃ " ^C 6 ^H 11 - ^C 2 ^H S 89 3-NHCOCH ₃ - ^C 2 ^H 5 -CH ₂ CH ₂ CH 90 3-CH ₃ - ^C 2 ^H 5 -CH ₂ CHoOOCCH,

CJ) CD

Continuation from table

O
CO OO

97

98

99 100 101 102 103 104 105 106 107 108 109

3-CH ₃

3-CH ₃

2-OCH ₃ -5-NH-COCH ₃

2-OCH ₃ -S-CH ₃

2,5-di-OCH ₃

2-CH ₃ -5-OCH ₃

3-NHCOCH ₃

3-CH ³ " ^CH

³ " ^CH 3 3-NHCOC ₂ H

3-NHCOH

3-NHCOC ₂ H ₅

- ^C 2 3 - ^C 2 3 -CH 3 -CH 3 -CH -CH " ^C 2 " ^C 2 " ^C 2 " ^C 2 " ^C 2 5 - ^C 2 " ^C 2 " ^C 2 " ^C 2 -CH H ^ NCOCH ₀ CH ₀ C
4, ZZi " ^C 3 ^H 5 " ^C 2 " ^C 2 ^H 5 ^H 5 ₂ CH ₂ OOCCH ₂ CH ₂ OOCCH ₂ CH ₂ OOCCH ₂ CH ₂ OOCCH ^H 5 ^H 5 ^H 4 ^C 6 ^H 5 ^H 4 ^C 6 ^H 11 H ₄ OH H ₄ CONH ₂ H ₄ CONHC ₅ H ^H 5 ^H 5 2 ^C 6 ^H 5 H ₆ NHCOCH ₃

-CH ₂ CH ₂ OOCNHC ₂ H ₅ -CH ₂ CH ₂ OC ₆ H ₅ -CH ₂ CH ₂ OOCCH ₃ -CH ₂ CH ₂ OOCCH ₃ -CH ₂ CH ₂ OOCCH ₃ -CH ₂ CH ₂ OOCCH ₃ -CH ₂ CH (CH ₃ ) OII

" ^C 2 ^H 5
" ^C 2 ^H 5

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609831/0377

Continuation from table

CO CX)

130 2-CH, -5-NHCOC _n H _c
3 6 5 131 3-NHCOCH ₂ OH 132 3-NHCOCH ₂ Cl 133 3-NHCOCH ₂ OCH ₃ 134 3-NHCOCH ₂ CH ₂ Cl 135 3-NHCOCH ₂ OC ₆ H ₅ 136 3-NHCOCH ο C .H ₁ .
L D 5 137 3-NHSO ₂ CH ₃ 138 3-NHCOCH ₂ CH ₂ CN 139 3-NHCONHC ₂ H ₅ 140 3-NHCONHC ₆ H ₅ 141 3-NHCOCH ₂ OOCCh ₃ 142 3-NHCOCH ₃ 143 H 144 3-NHCOCH ₃ 145 3-CH ₃ 146 3-NHCOCH ₃ 147 3-NHCOCH ₃ 148 3-NHCOCH 149 3-NHCOCH?

H
-C ₂ H ₅

- ^C 2 ^H 5 - ^C 2 ^H 5 ^"C 2 ^H 5 - ^C 2 ^H 5 ■ ^C 2 ^H 5 - ^C 2 ^H 5" ^C 2 ^H 5 - ^C 2 ^H 5 - ^C 2 ^H 5

-CoHr

-CHoCHo NCO-OC ₆ H ₄ C O -CHoCHoNCO-o-cIh'CO

LL D 4

-CH ₂ CH ₇ NCOCh ₂ NHC O -CH ₂ CH ₂ NCOCH ₂ NhSo -CH ₂ CH ₂ N (CH ₃ ) SO ₂ CH ₃ -CH ₂ CH ₂ N (C ₂ H ₅ ) SO ₂ C ₆ H ₅ - CHoCHoNCO-OC _n H.SO ₉

LL 0 4 /

-CH ₂ CH ₂ NH (C ₆ H ₅ ) SO ₂ CH ₃

-CH ₂ (CH ₃ ) C ₂ H ₅ ■ ^C 2 ^H 5 " ^C 2 ^H 5" ^C 2 ^H 5 • ^C 2 ^H 5 -C ₂ H ₅ ■ ^C 2 ^H 5 " ^C 2 ^H 5 ■ ^C 2 ^H 5 " ^C 2 ^H 5" ^C 2 ^H 5 ■ ^C 2 ^H 5 .C ₂ H ₅ -C ₂ H ₅ ■ ^C 2 ^H 5 " ^C 2 ^H 5

" ^C 2 ^H 5 • ^C 2 ^H 5 -C ₂ H ₅

CD CZ)

Continuation from table 5

O CO OO

150 3-NHCOCH ₃ 151 3-NHCOCH ₃ 152 3-NHCOCH ₃ 153 3-NHCOCH ₃ 154 3-NHCOCH ₃ 155 3-NHCOCH ₃ 156 3-NHCOCH ₃ 157 3-NHCOCH ₃ 158 3-NHCOCH ₃ 159 3-NHCOCH ₃ 160 3-NHCOCH ₃ 161 3-NHCOCH ₃ 162 3-NHCOCH ₃ 163 3-NHCOCH ₃ 164 3-NHCOCH ₃ 165 3-NHCOCH ₃ 166 3-NHCOCH ₃ 167 3-NHCOCH ₃ 168 3-NHCOCH ₃ 169 3-NHCOCH,

- (CH ₂ ) ₅ -

CHo-CH-P-COOCH ₇
L 0 4 ^κ ο
CH ₂ CH (00CH ₃ ) CH ₂ OOCH ₃ -C ₂ H ₅
" ^C 2 ^H 5 CH ₂ CH (OOCH) Ch ₂ CI - ^C 2 ^H 5 CH ₂ CH ₂ OC ₂ H ₅
CH ₂ CH ₂ OOCC ₆ H ₅ " ^C 2 ^H 5 CH ₂ Ch ₂ OOCCH ₂ OC ₆ H ₅
CH ₂ CH ₂ OOCCH ₂ C ₆ H ₅
CH ₂ CH ₂ OOCH ₂ COCh ₃ ■ ^C 2 ^2h 5 ⁵
- ^C 2 ^H 5 CH ₂ CH ₂ OOCCH ₂ Cn - ^C 2 ^H 5 CH ₂ CH ₂ OOCCh ₂ CH ₂ OCH ₃ - ^C 2 ^H 5 CH ₂ CH ₂ OOCCh ₂ CH ₂ -COOC ₂ H ₅ -C ₂ H ₅ ^CH 2 ^C 6 ^H 5
CH ₂ C ₆ H ₁₁
^CH 2 ^C 6 ^H 5
CH ₂ C ₆ H ₁ -CH ₂ C ₆ H ₄ -
-CH ₂ C ₆ H ₄ -
" ^C 6 ^H 11
-CH ₂ C ₆ H ₁

AO

Continuation from table

ο ω oo

170 171 172 173 174 175 176 177 178 179 180 181 182 183 184 185 186 187 188 189

3-NHCOCH ₃

3-NHCOCH ₃

3-NHNHCOCH ₃

3-NHCOCH3

3-CH ₃

3-NHCOCH ₃

3-CH ₃

2,5-di-CH ₃

2,5-di-CH ₃

3-NHCOCH ₃

2,5-di-CH ₃

2-CH ₃ -S-NHCOCH ₃

2-CH ₃ -S-NHCOCH ₃

2-CH ₃ -5-NHCOCIl ₃

3-NHCOCH ₃

3-NHCOCH ₃

3-NHCOCH ₃

3-NHCOCH,

■ ^C 6 ^H 11

-CH ₂ CH ₂ OOCOC ₂ H

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Continuation from table 5

- α * 210 2-OCH ₃ -5-NHCOCH ₃ -C ₂ H ₄ CN -C ₂ H ₄ SO ₂ C ₂ H ₄ - - ^C 2 ^H 5 H 2 -C ₂ H ₅ O
<£>' 211 2-OCH ₃ -S-NHCOCH ₃ -C ₂ H ₄ CN -C ₂ H ₄ CH ₂ C ₂ H ₄ - H -C ₂ H ₄ OOCCH ₃ - ^C 2 ^H 5 O>
till 212 2-OCH ₃ -5-NHCOCH ₃ H -C ₂ H ₄ OC ₂ H ₄ - H -CH ₂ C ₆ H ₅ 213 3-NHCOC ₆ H ₁₁ - ^C 2 ^H 5 -CH ₂ CH ₂ CN " ^C 2 ^H 5 O 214 2-OCH ₃ -5-NHCOCH ₃ H -CH ₂ CH ₂ CN " ^C 6 ^H 11 - co 215 3-NHCOC ₆ H ₄ -P-COOCh ₃ " ^C 2 ^H 5 -CH ₂ CH ₂ OOCCH ₃ - ^C 2 ^H 5 216 H -CH ₂ CH ₂ OOCCH ₃ 217 H -CH ₂ CH ₂ SO ₂ CH ₂ CH 218 H -CH ₂ CH ₂ OCH ₂ CH ₂ 219 3-NHCOCH ₂ CH ₂ OH -CH ₂ CH (OOCCH ₃ ) CH ₂ Ci " ^C 2 ^H 5 220 2,5-di-CH ₃ -CH CH ₂ CH ₅ - ^C 2 ^H 5 221 2,5-di-CHj, 111 3-NHCOCH ₃ - (CH ₂ ) ₃ OOCCH ₃ 223 H - (.Ln ₇ ) , UULLM- 224 3-NHCOCH ₃ -CH ₂ CH ₂ OOCCH ₃ 225 3-CH ₃ -CH ₂ CH ₂ OOCCH ₃ 226 3-CH ₃ 227 3-CH ₃ 228 3-NHCOCH ₃ 229 3-NHCOCH ₃

Continuation from table

230 2,5-di-CH ₃ -CH ₂ C ₆ H ₁ , H.

²³¹ 3-NHCOCH ₃ -CH C ₆ H _{5 -CH c H}

CHCH

3 "CH ₂ C ₆ H ₁ -CHCH ₂ CH ₃

3-NHCOCH ₃ -CH ₂ C ₆ H ₁₀ -P-CH ₃ -CH CH CH

Table 6

example
No. R ² , R ⁶ , R ⁷ , R ⁸ 234 2,2,4,7-tetra-CH ₃ 235 2,2,4-tri-CH ₃ -7-NHCOCH ₃ 236 2,2,4,7-tetra-CH ₃ 237 2,2,4,7-tetra-CH 238 2,2,4,7-tetra-CH ₃ 239 2,2,4,7-tetra-CH ₃ 240 2,4-di-CH ₃ 241 2,4-di-.CH 242 2,2,4,7-tetra-CH ₃ 243 2,2,4,7-tetra-CH ₃ 244 2,2,4,7-tetra-CH ₃ 245 2,4-di-CH ₃ 246 2,7-di-CH ₃ 247 2,7-di-CH ₃ 248 2,7-di-CH ₃ 249 2,2,4-tri-CH ₃ 250 2,2,4,7-tetra-CH ₃ 251 2,2,4, -ti-CH ₃ 252
253 2,2,4-tri-CH ₃ -7-Cl
2,2,4-tri-CH -5,8-di-OCH ₃ 254 2,2,4-tri-CH ₃ -5,8-di-CH ₃ 255 2,2,4,7-tetra-CH ₃ 256 2,2,4-tri-CH ₃ -7-NHCOCH ₃ 257 2,2,4-tri-CH ₃ -7-NHCOCH ₃ 258 2,2,4-tri-CH ₃ -7-NHCOOC ₂ H ₅

-CH ₂ CH ₂ OH -C ₂ H ₅ - (CH ₂ ) ^ -CH ₂ CH ₂ CONH ₂ - (CH ₂ ) ₃ NHCOCH ₃ -CH ₂ CH ₂ Cl - (CH.

₃ NHC0CH ₃

-CH ₂ CH ₂ CONH ₂ -CH ₂ CH ₂ SC = NNHCh = N · ^C 2 ^H 5 -CH ₂ CH ₂ CN -C ₂ H ₅ -CH ₂ CH ₂ CONH ₂ -C ₂ H ₅ -CH ₂ CH ₂ NHCOCH ₃ -CH ₂ CH ₂ OOCCH ₃ -CH ₂ CH (OH) CH ₃ -CH ₂ CH ₂ CONH ₂ -C ₂ H ₅ -CH ₂ CH ₂ OH -CH ₂ CH ₂ CN -CH ₂ CH ₂ OOCCH ₃ - CH ₂ CH ₂ OOCCH ₃ -C ₉ H ₇₁ CONH ₉

2 6

§09831 / 0 $ ??

Continuation of table

259 260 261 262 263 264 265 266 267 268 269 270 271 272 273 274 275 276 277 278 279 280 281 282 283 284 285 286 287 288 289 290

2.2.4 2.2.4 2.2.4 2.2.4 2.2.4 2-CH

-tri-CH ₃ -7-NHC0CH ₂ 0H -tri-CH ₃ -7-NHCOCH ₂ Cl -tri-CH,

, 7-tetra-CH ₃ -tri-CH ₃ -> -7-NHCOCH-

-tri-CH ₃ -7-NHCOC ₂ H ₅

^l 3 2.2.4

2,2,4 2,2,4 2-CH, -7-NHCOCH

-tri-CH ₃ -7-NHCOCH ₃ -tri-CH ₃ -7-NHCOCH ₃ -tri-CH ₃ -7-NHCOCH ₃

-tri-CH ₃ -7-NHCOCH ₃ -tri-CH ₃ -7-NHCOCH ₃

3 2.2.4

2.2.4

2,2,4-tri-CH ₃ -7-NHC0CH

2,2,4-tri-CH ₃

2,2,4-tri-CH ₃

2,2,4-tri-CH ₇

2.2.4

2.2.4

2,2,4-tri-CH

2-CH,

, 7-tetra-CH ₃ I- tri-CH,

2-CH ₃ 2.2.4 2.2.4 2.2.4 2.2.4 2.2.4 2.2.4 2-CH

, 7-tetra-CH ₃ -tri-CH ₃ -7-NHC0CH ₃ -tri-CH ₃ -7-NIICOCH ₃ -tri-CH ₃ -7-NHCOCH ₃ -tri-CH ₃ -7-NHCOCH ₃ -tri- CH ₃ - 7-xNHCOCH ₃ -7-NHCOCH,

^l 3 2.2.4

2,2,4 2,2,4 2-CH, -7-NHCOCH

-trX-CH ₃ -7-NHCOCH ₃ -tri-CH ₃ -7-NHCOCH ₃ -trX-CH ₃ -7-NHCOCH ₃ " ^C 2 ^H 5
-C ₂ H ₅

- (CH ₂ D ₃ CH ₃

-CH ₂ CH ₂ OOCCH ₃

-CH ₂ CH ₂ OOCOC ₂ H ₅ -CH ₂ CH ₂ C ₆ H ₅ -C ₂ H ₄ Cl -C ₂ H ₄ NCOCH ₂ CH ₂ CO

-C ₉ H, OCONHC, H _c 2 4 6

-CH ₂ CH ₂ OOCC ₆ H ₅

■ ^C 2 ^H 5
-CH ₂ CH ₂ CONHCH ₃ -CH ₂ CH ₂ CN CH ₂ CH ₂ NCOCH ₂ Ch ₂ CO

) ₃ NHCOCH ₃ CH ₂ CH ₂ OH

CH ₂ CH ₂ NHCOCH ₃ CH ₂ CH ₂ OOCCH ₃ Ch ₂ CH ₂ CH ₂ NHCOCH ₃ C ₂ II ₄ SC ₆ H ₅ CH ₂ CH ₂ CN CH ₀ C ^ -H, -

Z Ό D

r C

CH-XH ₉ C 1 H Z 2 6

CH-CH (OH) CH

CH CH ₂ N (CH ₃ ) SO ₂ CH ₃ CHCHOCH

- (CH ₂ )

§09831 / 0977

Continuation from table

- 20 -

291 292 293 294 295 296 297 298 299 300 301 302 303 304 305 306 308 ₃ O9 310

NHCOCH,

NHCOCH.

2,2,4-tri-CH ₃ -5,8- (Ii-OCH ₃

2,2,4-tri-CH ₃ -5,8-di-CH ₃

2,2,4-tri-CH ₃ -5-OCH ₃ -8-CH ₃

2,2-di-CH ₃ -7-I

2-CH ₃ -7-NHCOCH ₃

2,2,4-tri-CH ₃ -7-

2-CH ₃ -7-NHCOCH ₃

2,2,4-tri-CH ₃ -7-NHCO CH ₃

2-CH ₃ -7-NHCOCH ₃

2,2-CH ₃ -7-NHCOCH ₃

2,2,4-tri-CH ₃ -7-NHCO CH ₃

2,2,4-tri-CH ₃ -7-NHCOC ₆ H ₅

2,2,4-tri-CH ₃ -7-NHCOOC ₂ H ₅

2,2,4-tri-CH ₃ -7-NHCOC ₆ H ₅

2,2,4-tri-CH ₃ -7-NHCOCH ₃

2-CH (CH _{3) 2} -7-NHCOCH ₂ OH

2-CH (CH _{3) 2} -7-NHCOCH ₂ OOCCH ₃

2-CH (CH ₃ ) ₂ -7-NHCOCH ₂ Cl

2,2,4-tri-CH ₃ -7-

NHCOCH. CH ₂ CH ₂ OOCCH ₃ ^C 2 ^H 5 C ₂ H ₅ C ₂ H ₅

-CH ₂ CH (OH) CH ₂ OH -CH ₂ CH ₂ OOCOC ₂ H ₅ -CH ₂ CH ₂ OOCC ₂ II ₅ -CH ₂ CH ₂ OOCCH ₃ -CH ₂ CH ₂ OOCCH ₃ -CH ₂ CH ₂ OOCH ₃ ~ ^C 2 ^H 5 - ^C 2 ^H 5 -C ₂ H ₄ OH ^"C 2 ^H 5 -C ₂ H _5" ^C 2 ^H 5 ^"C 2 ^H 5 -C ₂ H ₄ NHCONHC ₆ H ₅

609831

Table 7 example

No.

311 312 313 314 315 316 317 318 319 320 321 322 323 324 325 326 327 328 329 .330 331 332 333 334 33.5

3,6-di-CH ₃

3,6-di-CH ₃

3,6-di-CH ₃

3-CH ₃ -6-NHCOCH ₃

3,6-di-CH ₃

3,6-di-CH ₃

6-NHCOCH ₃

6-NHCOCH ₃

3,6-di-CH ₃

6-NHCOCH ₃

3,6-di-CH ₃

3,6-di-CH ₃

3,6-di-CH ₃

3,6-di-CH ₃

3,6-di-CH ₃

6-NHCOCH ₃

3,6-di-CH ₃

3-CH ₃

3-CH ₃ -O-Cl

3-CH ₃ -5i8-di-OCH ₃

3-CH ₃ -5,8-di-CH ₃

3-CH ₃

3,6-di-CH ₃

3-CH ₃

3,6-di-CH ₃ -CH ₂ CH ₂ OH -CH ₉ CH ₉ CONH ₇ - (CH ₂ ) ₃ NHCOCH ₃ " ^C 2 ^H 5 - (CH ₂ ) ₃ NHCONHC ₂ H ₅ -CH ₂ -CH ₂ Cl - (CH ₂ ) ₃ NHCOCH ₃ -CH ₂ CH ₂ CONH ₂ • -CH ₂ CH ₂ Sc = NNHCH = N - ^C 2 ^H 5 -CH ₂ CH ₂ CN -C ₂ H ₅ -CH ₂ CH ₂ CONH ₂ -C ₂ H ₅ -CH ₂ CH ₂ NHCOCH _3, -CH ₂ CH ₂ OH -CH ₂ CH (OH) CH ₃ -CH ₂ CH ₂ CONH ₂ - ^C 2 ^H 5 -CH ₂ CH ₂ OH -CH ₂ CH ₂ CN- ^C 2 ^H 5 -CH ₂ CH ₂ CONHCH ₃ -CH ₂ CH ₂ CN -CH ₂ Ch ₂ NCOCH ₂ CH ₂ CO

609831 / om

Continuation from Table 7

336 3-CH ₃ -O-NHCOCH ₃ 337 3-CH 338 3,6-di-CH ₃ 339 3,6-di-CH ₃ 340 3,6-di-CH ₃ 341 3,6-di-CH ₃ 342 3,6-di-CH ₃ 343 3,6-di-CH ₃ 344 3,6-di-CH ₃ 345 3,6-di-CH ₃ 346 3-CH ₃ -O-NHCOCH ₃ 347 3-CH ₃ 348 6-NHCOCH,

₃ NHCOCH ₃

-CH ₂ CH ₂ OH

-CH ₂ CH (OH) CH ₂ OH -CH ₂ CH ₂ N (CH ₃ ) SO ₂ CH ₃ -CH ₂ CH ₂ OC ₂ H ₅

-C ₂ H ₄ C ₆ H ₅

-CH ₂ C ₆ H ₅

-CH ₂ CH ₂ OOCCH ₃ -CH ₂ CH ₂ OOCOC ₂ H ₅ -CH ₂ CH ₂ OOCC ₂ H ₅ -CH ₂ CH ₂ OOCCH ₃ -CH ₂ CH ₂ OOCCH ₃ -CH ₂ CH ₂ OOCCH ₃

609831/0977

Claims (9)

PATENT CLAIMS a hydrogen or halogen atom or a short-chain alkyl, short-chain alkoxy or Trifluoromethyl radical or a radical of the formula -NH-acyl-; a hydrogen atom or a short chain Alkyl or short-chain alkoxy radical; a cyclohexyl radical optionally substituted by a short-chain alkyl radical or an alkyl radical, which is optionally substituted by a short-chain alkoxy, aryl, Aryloxy, cyclohexyl, alkylsulfonyl, arylsulonyl, Cyano-, hydroxy-, short-chain alkanoyloJQy-, 609831/0977 short chain alkoxycarbonyl, short chain alkoxycarbonyloxy, aroyloxy, short chain Alkylcarbamoyloxy, arylcarbamoyloxy, Alkylcarbamoylamino or arylcarbamoylamino radical or a halogen atom or a radical of one of the following formulas: / R / acyl / ^ υ \ 11 ₁₂ -CON; _q ; -N « _Λ , -K R ¹ 'or -SR ¹ ^ \ R ^y where mean: R is a hydrogen atom or a short chain Alkyl or aryl radical; q
R is a hydrogen atom or a short-chain q gen alkyl radical or R and R together a remainder of the formulas: - (CH ₂ ) ₅ - or -CH ₂ -CH ₂ -O-CH ₂ -CH ₂ ; R is a hydrogen atom or a short-chain one Alkyl, aryl or cyclohexyl radical; R is an ethylene, propylene or o-cyclohexylene radical or an o-arylene radical; X is a remainder of the formulas: -CH ₂ -, -CO- or -SO ₂ - and ι ο
R is an aryl, benzyl, cyclohexyl, 1,2,4- Triazol-3-yl or a 2-benzothiazolyl radical; R is a hydrogen atom or an aryl or short-chain alkyl radical which can optionally be substituted by a hydroxy, cyano, short-chain alkoxy, aryl, aryloxy, cyclohexyl, short-chain alkanoyloxy, short-chain alkoxycarbonyl or short-chain alkoxycarbonyloxy radical or 609831/0977 -JT- R and R together are a remainder of the formulas: -CH ₂ -CH ₂ -Y-CH ₂ -CH ₂ -, in which Y represents a radical of one of the following formulas: -CH ₂ -, -0- or -SO ₂ -; 6 7 8 R is a methyl radical or if R and R are each a Represent hydrogen atom, a short-chain alkyl 7 8
rest and R and R each represent a hydrogen atom or a methyl radical. 2. Azo dyes according to claim. 1, characterized by the following formula: where mean: 2
R is a hydrogen atom, a methyl, short-chain alkanoyl ^ amino, benzamido, or trifluoromethyl radical; a hydrogen atom or, if R e is a “methyl or methoxy radical; R is a hydrogen atom or if R is a hydrogen atom R is a short-chain alkyl; Cyclohexyl-; Benzyl-; Aryl methylene .; Cyclohexylmethylene; 2-cyanoethyl; 2-carbamoylethyl-; N-alkyl-i-carbamoylethyl (alkyl = short-chain); N, N-dialkyl-2-carbamoylethyl- (alkyl = short-chain) or a radical of the formula -Z-R, where Z is an ethylene or Propylene radical and R represents a hydroxy, short-chain alkanoyloxy, short-chain alkoxycarbonyl, short-chain alkoxycarbonyloxy, succinimido, glutarimido, phthalimido, aroyloxy, short-chain alkoxy, Alkanoylamino, short chain alkylcarbamoyloxy, short chain Alkylcarbamoylamino or short chain alkoxycarbonyl amino rest and 609831/0977 - Λ - R is a hydrogen atom or a short-chain alkyl, Cyclohexyl, arylmethylene or cyclohexylmethylene radical or a radical of the formula -Z-R, in which Z and R have the meaning given. 3. Azo dyes according to one of claims 1 and 2, characterized in that that they correspond to one of the following formulas: S / N = N- V η N (C ₂ H ₅ ) CF, CF. CH. CH, NHCOCH, NHCHCH ₉ eh t CH ₃ O Il CH ₉ I. ^N c -
It CH ₂ O or CF. \ -N * N-A ^ NCH 2- CH ₉ CCH. O NHCOCH, ΘΟ9831 / 0977 - -if - 4. azo dyes according to claim 1, characterized by the following Formula: where mean: 2
R is a hydrogen atom or a methyl, short-chain alkanoylamino, benzamido or short-chain alkoxycarbonylamino radical; R is a short chain alkyl; Cyclohexyl-; Benzyl-; Aryl methylene; Cyclohexylmethylene; 2-cyanoethyl; 2-carbamoylethyl-; N-alkyl-Z-carbamoylethyl (alkyl = short-chain); NjN-Dialkyl-Z-carbamoyläthyl-CAlkyl = short-chain) or a radical of the formula -Z-R, where Z is an ethylene- 1 τ
or propylene radical and R represents a hydroxy; short chain alkanoyloxy; short chain alkoxycarbonyl; short chain alkoxycarbonyloxy; Succinimido-; Glutarimido-; Phthalimido-; Aroyloxy-; short chain alkoxy; Alkanoylamino-; short chain alkylcarbamoyloxy; short-chain alkylcarbamoylamino or a short-chain alkoxycarbonylamino radical and 7 8 R and R each represent a hydrogen atom or a methyl radical. 5. Azo dyes according to claim 1, characterized by one of the following formulas: 609831/097? 4t - or ^H 3 f CH ₂ CH ₂ CH ₂ NHCNHc ₂ H ₅ 6. Azo dyes according to Claim 1, characterized by the following structural formula: CF. 2 4 7
wherein R, R and R have the meaning given in claim 4. -jr- 7. Azo dye according to claim 1, characterized by the following structural formula: N = N C-H.OH L · Mr. 8. Use of azo dyes according to Claims 1 to 7 for dyeing threads and fibers made from synthetic polymers. 9. Use of azo dyes according to Claims 1 to 7 for dyeing threads and fibers made from polyesters, polyamides and Cellulose acetate. 609831/0977