GB2197334A

GB2197334A - Naphtholactam dyes and intermediates

Info

Publication number: GB2197334A
Application number: GB08726112A
Authority: GB
Inventors: Hansrudolf Schwander; Kurt Burdeska
Original assignee: Ciba Geigy AG
Current assignee: Novartis AG
Priority date: 1986-11-11
Filing date: 1987-11-06
Publication date: 1988-05-18
Anticipated expiration: 2007-11-06
Also published as: CH670096A5; GB2197334B; GB8726112D0; DE3738027A1; FR2606406A1; JPS63135458A

Description

1 GB2197334A 1

SPECIFICATION

Naphtholactam compounds, processes for their preparation and their use as dyes The invention relates to novel cationic naphtholactarn compounds, processes for their preparation and their use as dyes for dyeing and/or printing textile fibre materials, in particular those which consist of or contain polyacrylonitrile (PAC) materials or acid-modified polyamides or polyesters.

In the existing 1,8-naphtholactam compounds, disclosed for example in DEA-2,525,113 and EP-A-17,621, where their use for dyeing, for example, PAC materials is also disclosed, the naphthalene structure is either unsubstituted or substituted by nonionic substituents, in particular 10 by bromine.

There have now been found novel 1,8-naphtholactam compounds having a substituted vinyl group in the 4-position and having useful dyeing properties. They are distinguished, for example in the dyeing of mixtures of PAC or similar synthetic fibres with wool, by a very good reservation of the wool.

The invention accordingly provides naphtholactarn compounds of the formula R-NC -R 2 CH=C-Y 1 R 0 X in which R is hydrogen or methyl, Y is cyano, C,-C,-alkoxycarbony], C,_C4- alkylsulfortyl, phenyl or pyridyl, R' is a substituted or unsubstituted Cl-C6-alkyl radical, R 2 is a radical of the formula (1) 25 R3 35 'R4 (2) 40 R 5 or a radical of the formula R6 7 45 z ' R8 /F \\ A I R9 (3) 50 where R3 and R 4 are each, independently of the other, a substituted or unsubstituted C,_C6-alkyl radical, R5 is hydrogen, halogen, Cl-C4-alkyl or Cl-C4-alkoxy, R 6, R 7, W and R9 are each, independently of the others, hydrogen or a substituted or unsubstituted Cl-C,-alkyl radical or one or two of these substituents R 6 -R9 are a substituted or unsubstituted aryl group, RIO is a substituted or unsubstituted Cl-C,-alkyl group or a C,-C,-alkenyl group, Z is -CHRII- or -0- and W' is hydrogen or Cl-C4-alkyl, and in which X" is an anion.

R is here preferably hydrogen.

Y is for example a cyano, methoxycarbonyl, ethoxycarbonyl, methyisuifonyl or ethyisulfonyl radical. Y is particularly preferably cyano.

A preferred embodiment of the naphtholactarn compounds according to the invention corn 65 1 10 R5 R 2 GB2197334A 2 prises compounds of the formula (1) in which R is a hydrogen and Y is cyano.

R' is defined as a substituted or unsubstituted Cl-C6-alkyl radical, which in this application is in general to be understood as meaning an unbranched or branched alkyl radical, for example methyl, ethyl, n- or iso-propyl, n-, sec.- or tert.-buty], n- or iso- pentyl or n- or iso-hexy], which is unsubstituted or substituted, for example by hydroxyl, C,-C,-alkoxy, phenoxy, Cl-C,-alkoxycarbo- 5 nyi, Cl-C4-alkanoyloxy, cyano, halogen such as fluorine, chlorine or bromine, phenyl or nitro-, halogen-, C,-C,-alky]- or Cl-C,-alkoxy-substituted phenyl.

Examples of suitable substituted Cl-C6-alkyl radicals are: hydroxyethyl, methoxymethyl, me thoxyethyl, ethoxyethyl, ethoxypropyl, n-propoxymethyl, iso-propoxymethyl, butoxymethyl, bu tyoxyethy], butoxypropyl, ethoxypentyl, 2-hydroxyethoxypentyi, methoxyca rbonyl methyl, ethoxycarbonyimethyl, methoxycarbonylethyl, ethoxycarbonylethyl, acetoxyethyl, cyanoethyl, chloroethyl, benzy], phenylethy], 2-, 3- or 4-methylbenzyl and 2-, 3- or 4- methoxybenzyi.

In preferred naphtholactam compounds of the formula (1), R' is an unsubstituted or hydroxyl-, methoxy-, ethoxy-, cyano- or chlorine-substituted C,-C,-alkyl radical.

Particularly preferred radicals R' are methyl, ethyl, cyanoethyl or methoxyethyl.

A group of useful naphtholactarn compounds comprises compounds of the formula (1) in which R 2 is a radical of the formula R3 20 -N "'R4 (2) 25 In this formula R 3 and R4 are each, independently of the other, a substituted or unsubstituted Cl-C,-alkyl radical which is defined as above.

Preferably, R 3 and R4 are each, independently of the other, an unsubstituted or hydroxyl-, 30 methoxy-, ethoxy- cyano-, acetoxy- or phenyl-substituted C,-C,-alkyl radical.

Particularly preferably, R3 and R4 are independently of each other ethyl, hydroxyethyl, 2 hydroxypropyl, methoxyethyl or ethoxyethyl.

Preferred embodiments of the naphtholactams according to the invention concern compounds of the formula (1) in which R2 is a radical of the formula (2) and either R3 is ethyl and R4 35 hydroxyethyl or methoxyethyl or R3 and R4 are each ethyl, hydroxyethyl or methoxyethyl.

A C,-C,-alkyl radical R5 is in general, for the purposes of this application, to be understood as meaning methyl, ethyl, n- or iso-propyl or n-, sec.- or tert.-butyi; in this meaning, preferably R5 is methyl or ethyl.

A C,-C,-alkoxy radical R5 can be, in conformity with the general rule in this application, a methoxy, ethoxy, n-or iso-propoxy or n-, sec.- or tertAutoxy radical. A Cl-C4-alkoxy radical R5 is preferably ethoxy and in particular methoxy.

A halogen R5 is for example fluorine, bromine and in particular chlorine.

Particularly preferred meanings of R5 are methyl, ethyl, methoxy, ethoxy, chlorine and in particular hydrogen.

The radical R5 can be arranged in the ortho- or meta-position relative to the nitrogen atom.

A further group of useful naphtholactam compounds comprises compounds of the formula (1) in which R2 is a radical of the formula R6 R7 50 -0 z U 5 N<R9 1 10 R Rio In this formula, R5 is subject to the aforementioned definitions and preferences.

(3) Substituted or unsubstituted C,-C,-alkyl radicals R6, R7, W' and R9 can each, independently of the others, be as defined above.

A substituted or unsubstituted aryl group from one or two of these substituents R6 and R9 can be for example: unsubstituted phenyl, a- or fl-naphthyl or a phenyl or naphthyl group substituted for example by halogen such as fluorine, chlorine or bromine or by C,-C,- alkyl or C,-C,-alkoxy.65 3 GB2197334A 3 Preferably, R6 and R7 are each hydrogen and R8 and R9 are each, independently of the other, hydrogen, methyl, ethyl or methoxy.

RIO can be a substituted or unsubstituted C,-C6-alkyl radical which is defined as described above or a C2-C4-alkenyl group, for example a -CH27CH=CH2 group.

RIO is preferably a substituted or unsubstituted C,-C,-alkyl radical and particularly preferably an 5 unsubstituted or hydroxyi-, Cl-C4-alkoxy-, cyano- or phenyl-substituted C, -C,-alkyl radical. Parti cularly preferred meanings of RIO are methyl, ethyl, hydroxyethyl, methoxyethyl, ethoxyethyl and cyanoethyl.

Z is -0- or -CHRI I-.

A C,-C4-alkyl radical W' can be defined as above. Preferably, W' is hydrogen, methyl or ethyl. 10 Z is in particular -0-, "CH 2 or CH-CH3.

1 An anion XO can be not only an organic but also an inorganic ion, for example halogen, such 20 as chloride, bromide or iodide, thiocyanate, sulfate, methyisulfate, ethyisulfate, aminosulfonate, perchlorate, carbonate, bicarbonate, phosphate, phosphoromolybdate, phosphorotungstenate, toluene-sulfonate, phosphorotungstenomolybdate, benzenesulfonate, naphthalenesulfonate, 4-chlo robenzenesulfonate, oxalate, maleate, formate, acetate, propionate, lactate, succinate, chloroace- tate, tartrate, methanesulfonate or benzoate, or a complex anion, such as that of zinc chloride 25 double salts.

Particular preference is given on account of their good dyeing properties, to dyes of the aforementioned formula (1) in which R is hydrogen, Y is cyano, R' is an unsubstituted or hydroxyi-, methoxy-, ethoxy-, cyano-, or chlorine-substituted Cl-C4-alkyl radical, R 2 is a radical of the aforementioned formula (2) or (3), R 3 amd R4 are each, independently of the other, an unsubstituted or hydroxyl-, methoxy-, ethoxy-, cyano-, acetoxy- or phenyl- substituted Cl-C4-alkyi radical, R5 is hydrogen, chlorine, methyl, ethyl, methoxy or ethoxy R6 and R' are each hydrogen, W' and R9 are each, independently of the other, hydrogen, methyl, ethyl or methoxy, RIO is an unsubstituted or hydroxyl-, Cl-C4-alkoxy-, cyano- or phenyl-substituted Cl-C4-alkyl radical, Z is -0- or -CHR"-, W' is hydrogen or methyl or ethyl, and XO is an anion.

A particularly preferred embodiment of the naphtholactam compounds according to the inven tion comprises compounds of the formula (1) in which R is hydrogen, Y is cyano, R' is methyl, ethyl, cyanoethyl or methoxyethyl, R2 is a radical of the aforementioned formula (2), R3 and R4 are each, independently of the other, ethyl, hydroxyethyl, 2hydroxypropyl, methoxyethyl or ethoxyethyl, R5 is hydrogen, methyl or methoxy, and XO is an anion.

A further particularly preferred embodiment concerns naphtholactam compounds of the formula (1) in which R is hydrogen, Y is cyano, R' is methyl, ethyl, cyanoethyl or methoxyethyl, R5 is hydrogen, methyl or methoxy, XO is an anion, R 2 is a radical of the aforementioned formula (3), R6 and R7 are each hydrogen, W and R9 are each hydrogen, methyl or ethyl, RIO is methyl, ethyl, hydroxyethy], methoxy-ethy], ethoxyethyl or cyanoethyl, Z is -0- or - CHR11- and W' is hydro- 45 gen or methyl.

The naphtholactam compounds according to the invention and of the formula (1) are prepared for example by reacting a naphtholactam compound of the formula Rl-N-CO CH=C-Y (4), 55 1 R in which R, Y and R' are as defined above, with a compound of the formula 4 GB2197334A 4 R3 R4 R5 (2a) or a compound of the formula R6 R7 Z R8 N R 9 1 10 R5 (3a) in which R 3, R4, R5, R6, R7, R", R9, RIO and Z are each as defined above, in the presence of a condensing agent, provided that, if in the definitions of the symbols of the formula (1) a hydroxyl group occurs, this hydroxyl group must be present in the starting compounds of the formulae (4), (2a) or (3a) as an acyloxy group and is converted, only after the condensation, into the hydroxyl group by hydrolysis.

Suitable condensing agents are for example the following watereliminating reagents: phos phoric halides, such as phosphorus oxytrichloride, phosphorus oxytribromide, phosphorus penta- 30 chloride, and also sulfuryl chloride, thionyl chloride, phosgene, zinc chloride, aluminiurn chloride and the like. It is also possible to use mixtures of these compounds, for example a mixture of phosphorus oxytrichloride and zinc chloride or phosphorus oxytrichloride and phosphorus pentox ide.

The condensation reaction is carried out by heating, in general at 50 to 150'C, in particular 35 between 75 and 85'C. Solvents are not necessary, although, if desired, the reaction mixture can be diluted with an inert organic solvent, for example a chlorinated hydrocarbon, such as dichloro ethane, tetrachloroethane or chlorobenzene.

If the starting compounds of the formulae (4), (2a) and/or (3a) contain hydroxyl groups, these hydroxyl groups are converted before the condensation reaction by acylation, for example by 40 means of acetic anhydride, into acyloxy groups at a temperature of about 70' to 85'C, to be hydrolyzed back in a conventional manner after the condensation reaction.

The compounds of the formula (4) are novel and likewise form part of the subject-matter of the invention; they can be prepared for example by reacting a naphtholactarn compound of the formula R'-N-C==0 (5), Br in the presence of a solvent and of a catalyst with a compound of the formula H2C C.

Y (6), R in which R', R and Y are as defined above, at a temperature of, for example, 70 to 200T. The 65 GB2197334A 5 naphthplactam compounds of the formula (5), and the compounds of the formula (6) are known or can be prepared in a manner known per se. Suitable solvents for the reaction are for example organic solvents, in particular dipolar aprotic solvents such as dimethy1formamide.

Suitable catalysts are for example organometallic compounds, in particular compounds of noble metals, e.g. platinum or palladium, with organic acid esters and/or organophosphorus radicals; examples are diacetatobistriphenylphosphinepalladium(II) or diacetatobis(tri-o-tolylphosphine)-palla- dium(II). The reaction may be carried out under a protective gas atmosphere.

The aniline derivatives of the formula (2a) and the hydroquinoline or benzomorpholine deriva tives of the formula (3a) are known or can be prepared in a manner known per se.

The naphtholactarn compounds according to the invention and of the formula (1) are suitable 10 for use as dyes for dyeing and, in the presence of binders and solvents, for printing a wide range of textile fibre materials, for example those which consist of or contain polyvinyl chloride, polyamides, polyurethanes, polyesters of aromatic dicarboxylic acids, e.g. polyethylene terephtha late, acid-modified polyesters or polyamides, polymers from acrylonitrile of copolymers of acryl onitrile and asymmetrical dicyanoethylene or vinyl acetate. The naphtholactam compounds of the 15 formula (1) are suitable in particular for dyeing and/or printing textile fibre materials which consist of or contain polyacrylonitrile materials or acid-modified polyamides or polyesters. They are also suitable for spin-dyeing and for dyeing said materials in the hydrated state, i.e. at a suitable point between spinneret and dryer (gel dyeing).

The materials mentioned are preferably dyed from an aqueous, neutral or acid medium by the 20 exhaust method, if desired under superatmospheric pressure, or by a continuous method. In dyeing, the textile material can be present in a very wide range of forms, for example as fibre, filament, woven fabric, knitted fabric, piece goods and made-up goods, such as shirts and sweaters.

The novel dyes produce, on these materials, brilliant, deep blue dyeings which are distin- 25 guished by their high light fastness and a good wash, perspiration, sublimation, decatizing, rub, carbonization, water, seawater, chlorinated water, cross-dyeing and solvent fastness.

The dyes of the formula (1) have high stability within a relatively wide pH range and are highly compatible with other cationic dyes.

The naphtholactarn compounds according to the invention and of the formula (1) are very 30 particularly suitable for dyeing mixed blends of the abovementioned materials with wool, since they have a very good reservation of the wool, i.e. the wool portion of such blend fabrics is left virtually undyed.

Furthermore, they can be used for dyeing and printing paper and mordanted cotton and for producing inks and oil paints.

In the Examples which follow, parts and percentages are by weight, and the temperatures are given in degrees Celsius.

Example 1: 62.5 parts of N-methyl-4-bromonaphtho-1,8-lactam, 22.6 parts of anhydrous sodium acetate, 14.8 parts of acrylonitrile and 0.02 part of diacetatobis-(tri-o- -tolylphosphine)-palladium(li) are added in succession under nitrogen to 113 parts of dimethy1formamide. The suspension is 40 heated to 130'C in the course of 30 minutes under constant nitroben protection and is then stirred at that temperature for 9 hours. After cooling down to room temperature, the precipi tated yellow reaction product is filtered off, washed in succession with dimethy1formamide, ethanol and water and dried. This gives 42.5 parts of the compound of the formula H3C-N-CO CH=CH-CM Melting point after recrystallization 207-208"C. By precipitating with, water it is possible to obtain further product out of the filtrate, so that the yield becomes virtually quantitative.

The above Example is repeated, replacing the acrylonitrile by the substituted ethenes mentioned in the table which follows. This affords further useful naphtholactam compounds.

6 GB 2 197 334A 6 Substituted ethene Melting point of 5 corresponding naphtho lactam compound YH3 CH2=C-CN 164-167'C CH2=CH-CO0C2Hs 157158,c 10 CH2=CH-50,-C2Els 21721VC CH 2=CH- 160-161'C 15 CH2=CH- N 173-1740C 20 Example 2: 4.7 parts of N-methyf-4-cyanovinyinaphtho-1,8-lactam prepared as described in Example 1, 3.3 parts of KN-cliethylaniline and 0.3 part of zinc chloride are mixed, and 6.1 parts of phosphorus oxytrichloride are added at 4WC. This is followed by stirring at a temperature of 25 78-80'C for 24 hours.

The ending of the condensation is followed by pouring onto ice, adjusting the pH to 1.6 with sodium hydroxide solution and further stirring for 30 minutes. The crude dye is filtered off, dried and extracted with toluene. The dye of the formula H3C-N===C N CH 2 5 G:H==CH-CN - 9 9 C/ is obtained in the form of a dark blue powder; it dyes polyacrylonitrile fibres in sky blue shades having excellent fastness properties.

Example 3: 9.1 parts of N-ethyl,N-(2-hydroxyethyl)-aniline are charged to a flask, and 6.6 parts of acetic anhydride are added at 50'C. Stirring is continued at 70-75'C until the acetylation has ended (about 30 minutes), and 11.7 parts of N-methyl-4-cyanovinylnaphtho- 1,8-lactam as pre pared in Example 1 are then added, followed by 0.75 part of zinc chloride. 15.1 parts of phosphorus oxytrichloricle are then added dropwise, and this mixture is stirred at a temperature 50 of 70-72'C for 24 hours. After the condensation has ended, 60 parts of an ice/water mixture are added, and stirring is continued at 70-75'C until hydrolysis of the acetyl group is complete (about 90 minutes). The mixture is then brought to pH 1.6 with sodium hydroxide solution and is stirred at room temperature for a further 1.5 hours.

The crude dye precipitated completely by adding sodium chloride solution is filtered off, dried 55 and purified by extraction with toluene.

The dye of the formula 7 GB2197334A 7 H C-NC N 1_---'C2H5 C2 H4 - OH CH=CH-M G cl is obtained as a dark blue powder; it dyes polyacrylonitrile fibres in sky blue shades having 15 excellent fastness properties. Examples 4-25: Example 2 or 3 is repeated using, in place of the educts mentioned therein, equivalent amounts of the naphtholactam and dialkylaniline, hydroquinoline or benzomorpholine compounds listed in Table 1. This affords useful blue dyes having similarly good properties.

Example NaphthoLactam Dialkylaniline, hydro No. compound quinoline or benzomorpholine compound 4 H3 C--O C.,H5 C,-Hs H=CH-CN CH3 H3 CV-=0 H3C -\ C2115 \-NI \\./ \.,// \. =. /. \ C21-1s H=CH-CN 6 H 3 C- Y----=0 //. \ /. \\ --- C2Hs 1 \\ -NI \ C2Hs H=CH-CN OCH3 8 GB2197334A 8 Example Naphtholactam DialkylaniLine, hydro- No. compound quinoLine or benzomorpholine ompound 7 H3C-N-y=0 HiCO 1 5 1. / \\. C_H5 -NI G2H5 H=CH-CN 8 H3C- V-Y-O C'115 C,,H4-0-CH3 &=CH-CN 9 H3C-7-y=0 C2H14---0-CH3 N C2HN-O-CH3 H=CH-CN H3 C-'---=0 1;1 i. -NI C2Hs &=CH-CN H3 C--=0 1;1 1 ---NI C2Hs H=CH-CN 12 H 3 C-V---=0 C,Hs NI\ / \ \ / C2Ht,-OH /-.=.

\ H=CH-CN CH3 13 H 3 C-Y-=0 H3C 1 11 1. C2Hs -NI C2H4-CH H=CH-CN 9 GB2197334A 9 Example Naphtholactam Dialkylaniline, hydro- No. compound quinoline or benzomorpholine compound 14 H3C-T-=0 1 11 1. // \-NI C"1i4-OH H=CH-CN O-CH3 H3C- V-----0 H3C0 :,/ \ / \, 1\ C2Hs -NI CzH4-OH H=CH-CN 16 H 3 C-NI -=0 H3C CH 3 // \-NI \CH3 H=Cli-CN C2H4-011 17 H 3 C-V-=0 C2H4-OH H=CH-CN 18 CPHs CzHs &=CH-CN 19 H5C2---==0 C2H5 C2H4-011 &=CH-CN \\ /\ //. //. -ti/ \ H=CH-CN \.=./ C2H4-0H GB2197334A 10 ExampLe NaphthoLactam DiaLkylaniline, hydro No. compound quinoLine or benzomorphoLine compound 21 NC-C,ll CH5 --NI/ C,,Hs 11=CH-CN 22 H3C-O-C'Zli-y-=0 C2H5 -NI C,HS li=CH-CN 23 H3C-O-C2H4-,-=0 H3C CH3 \CH3 CzH4-OH fi=CH-CN 24 C2Hs ---NI/ C2HL,-OH H= _CN H3 H 3 C--Y=0 C, H C2H4-0H H=CH-SO2-CpHs Example 26: 5 9 of the dye prepared as described in Example 3 are pasted up with 2 g of 40% 50 acetic acid and made to dissolve by adding 4,000 g of hot water. After adding 1 g of sodium acetate and 2 g of an adduct, quaternized with dimethyl sulfate, of 15 to 20 equivalents of ethylene oxide with N-octadecyidiethylenetriamine, the resulting dyebath is entered with 100 g of polyacrylenetriamine, the resulting dyebath is entered with 100 g of polyacrylonitrile fabric at WC. The bath is heated to 1OWC in the course of 30 minutes and then held at the boil for 90 55 minutes. The liquor is then allowed to cool down to WC in the course of 30 minutes. The material thus dyed is then removed and subsequently rinsed with lukewarm and cold water.

The result obtained is a sky blue polyacrylonitrile dyeing having good fastness properties.

Example 27: A polyacrylonitrile copolymer consisting of 93% of acrylonitrile and 7% of vinyl acetate is dissolved in sufficient dimethylacetamide to produce a 15% solution. The spinning dope is extruded into a spinbath consisting 40% of dimethylacetamide and 60% of water. The resulting spun tow is then drawn in a conventional manner and freed from dimethylacetamide by rinsing with hot and cold water.

This wet tow is dyed by dipping into a bath at 42'C containing per litre 9 g of the dye prepared as described in Example 1 and adjusted to pH 4.5 with acetic acid.

11 GB2197334A 11 The contact time between two and dyeing liquor is 2 seconds. Excess dyeing liquor is then squeezed off, and the tow is guided to the dryer. The result obtained is a tow dyed in a blue having good fastness properties. Example 28: A print paste is prepared from:

parts of the dye obtained as described in Example 2, 30 parts of thiodiglycol, 20 parts of 80% acetic acid, 350 parts of boiling water, 500 parts of locust bean thickening, 30 parts of 1:1 tartaric acid, 15 parts of di-(fl-cyanoethyl)-formamide and 30 parts of a naphthalene sulfonic acid/formaldehyde condensation product.

A polyacrylonitrile fabric printed with this print paste is then fixed at 1010C to 1030C in an HT festoon ager in the course of 20 to 30 minutes and finished in a conventional manner. The 15 result obtained is a blue print having good all-round fastness properties.

Claims

CLAIMS 1. A naphtholactam compound of the formula

R'-N==C -R2 CH=C_y 1 R - 0 1 X (1) in which R is hydrogen or methyl, Y is cyano, Cl-C4-alkoxy-carbonyl, Cl- C4-alkylsulfonyl, phenyl or pyridy], R' is a substituted or unsubstituted Cl-C,-alkyl radical, R2 is a radical of the formula R3 "-R4 R5 or a radical of the formula (2) R6 R7 Z R8 N 9 1 R 10 R5 (3) where R3 and R 4 are each, independently of the other, a substituted or unsubstituted Cl-C6-alkyl radical, R' is hydrogen, halogen, C,-C,-alkyl or C,-C,-alkoxy, R 6, R7, R' and R9 are each, independently of the others, hydrogen or a substituted or unsubstituted Cl-C6-alkyl radical or one or two of these substituents R 6 -R9 are a substituted or unsubstituted aryl group, W) is a substituted or unsubstituted Cl-C,-alkyl group or a C2-C,-alkenyl group, Z is -CHR11- or -0and W' is hydrogen or C,-C,-alkyl, and in which X0 is an anion.
2. A naphtholactam compound according to claim 1, wherein R' is an unsubstituted or 65 12 GB 2 197 334A 12 hydroxyi-, methoxy-, ethoxy-, cyano-, or chlorine-substituted C,-C,-alkyl radical.
3. A naphtholactarn compound according to claim 1 or 2, wherein R' is methyl, ethyl, cyanoethyl or methoxyethyl.
4. A naphtholactam compound according to any one of claims 1 to 3, wherein R is hydrogen 5 and Y is cyano.
5. A naphtholactam compound according to any one of claims 1 to 4, wherein R2 is a radical of the formula (2).
6. A naphtholactam compound according to any one of claims 1 to 5, wherein R3 and R4 are each, independently of the other, an unsubstituted or hydroxyl-, methoxy-, ethoxy-, cyano-, acetoxy- or phenyl-substituted Cl-C4-alkyl radical.
7. A naphtholactam compound according to any one of claims 1 to 6, wherein R3 and R 4 are independently of each other ethyl, hydroxyethyl, 2hydroxypropyl, methoxyethyl or ethoxyethyl.
8. A naphtholactarn compound according to any one of claims 1 to 4, wherein R 2 is a radical of the formula (3).
9. A naphtholactarn compound according to any one of claims 1 to 4 or 8, wherein R6 or R7 are hydrogen and R8 and R9 are each, independently of the other, hydrogen, methyl, ethyl or methoxy.
10. A naphtholactarn compound according to any one of claims 1 to 4, 8 or 9, wherein RIO is an unsubstituted or hydroxyi-, Cl-C4-alkoxy-, cyano- or phenyl-substituted C,-C,-alkyl radical.
11. A naphtholactarn compound according to any one of claims 1 to 4 or 8 to 10, wherein RIO is methyl, ethyl, hydroxyethyl, methoxyethyl, ethoxyethyl or cyanoethyl.
12. A naphtholactarn compound according to any one of claims 1 to 4 or 8 to 11, wherein Z is -0-.
13. A naphtholactarn compound according to any one of claims 1 to 4 or 8 to 11, wherein Z is -CHR11- and W' is hydrogen, methyl or ethyl.
14. A naphtholactam compound according to any one of claims 1 to 13, wherein R5 iS hydrogen, chlorine, methyl, ethyl, methoxy or ethoxy.
15. A naphtholactam compound of the formula (1) according to claim 1, in which R is hydrogen, Y is cyano, R' is an unsubstituted or hydroxyi-, methoxy-, ethoxy-, cyano- or chlorine substituted Cl-C,-alkyl radical, R2 is a radical of the aforementioned formula (2) or (3), R3 and R4 30 are each, independently of the other, an unsubstituted or hydroxyi-, methoxy-, ethoxy-, cyano-, acetoxy- or phenyl-substituted Cl-C,-alkyl radical, R5 is hydrogen, chlorine, methyl, ethyl, me thoxy or ethoxy, R6 and R' are each hydrogen, R8 and R9 are each, independently of the other, hydrogen, methyl, ethyl or methoxy, RIO is an unsubstituted or hydroxyl-, Cl-C,-alkoxy-, cyano-or phenyl-substituted C,-C,-alkyl radical, Z is -0or -CHR"-, W' is hydrogen or methyl or ethyl, and X' is an anion.
16. A naphtholactam compound of the formula (1) according to claim 1, in which R is hydrogen, Y is cyano, R' is methyl, ethyl, cyanoethyl or methoxyethy], R2 is a radical of the aforementioned formula (2), R3 and R4 are each, independently of the other, ethyl, hydroxyethyl, 2-hydroxypropyl, methoxyethyl or ethoxyethy], R5 is hydrogen, methyl or methoxy, and X" is an 40 anion.
17. A naphtholactam compound of the formula (1) according to claim 1, in which R is hydrogen, Y is cyano, R', R5 and X" are as defined in claim 15, R2 is a radical of the aforementioned formula (3) in claim 1, R6 and R 7 are each hydrogen, R8 and R9 are each hydrogen, methyl or ethyl, RIO is methyl, ethyl, hydroxyethyl, methoxyethyl, ethoxy-ethyl or cyanoethyl, Z is -0- or -CHR11- and W' is hydrogen or methyl.
18. A naphtholactam compound of the formula C2Hs H,3C- H=CH-CN in which X is an anion.

0 j X (D (7)
19. A process for preparing a naphtholactam compound of the formula (1) according to claim 65 1, which comprises reacting a naphtholactam compound of the formula 0 13 GB2197334A 13 R'-N-C-0 CH=C-Y 1 (4) H 1 15 in which R, Y and R' are as defined in claim 1, with a compound of the formula -N - R5 R3 (2a) or a compound of the formula R6 R7 z R8 9 N R R 5_ R (3a) 30 in which R 3, R 4, R5, R6, R7, 8R, R9, RIO and Z are each as defined in claim 1, in the presence of a condensing agent, provided that, if in the definitions of the symbols of the formula (1) a hydroxyl group occurs, this hydroxyl group must be present in the starting compounds of the formulae (4), (2a) or (3a) as an acyloxy group and is converted, only after the condensation, into 40 the hydroxyl group by hydrolysis.
20. Use of the naphtholactam compound of the formula (1) according to claim 1, as a dye for dyeing and/or printing textile fibre materials which consist of or contain polyacrylonitrile materials or acid-modified polyamides or polyesters.
21. A compound of the formula R'-N-C=-0 CH=C-Y 1 H (4) in which R, Y and R' are as defined in claim 1.
22. A compound of the formula (4) according to claim 2 1, in which R is hydrogen and Y is 60 cyano.

Published 1988 at The Patent Office, State House, 66/71 High Holborn, London WC 1 R 4TP. Further copies may be obtained from The Patent Office, Sales Branch, St Mary Cray, Orpington, Kent BF15 3RD. Printed by Burgess & Son (Abingdon) Ltd. Con. 1/87.