CH670096A5 - - Google Patents

Description

DESCRIPTION The invention relates to new cationic naphtholactam compounds and processes for their preparation. The compounds are used as dyes for dyeing and / or printing textile fiber materials, especially those which consist of or contain polyacrylonitrile materials (PAC) or acid-modified polyamides or polyesters.

There are already, e.g. from DE-A 2 525 113 and EP-A 17 621, naphtholactam-1,8 compounds and their use for dyeing e.g. PAC materials are known whose naphthalene backbone is either unsubstituted or substituted with non-ionogenic substituents, especially with bromine.

We have now found new naphtholactam-1,8-compounds with a substituted vinyl group in the 4-position, which have valuable coloring properties. You excel e.g. when dyeing mixtures of PAC or similar fully synthetic fibers with wool from a very good wool reserve.

The invention therefore relates to naphtholactam compounds of the formula wherein R3 and R4 independently of one another each represent an optionally substituted Q-C6-alkyl radical, R5 is hydrogen, halogen, Q-C4-alkyl or C1-C4-alkoxy 35, R6, R7, R8 and R9 independently of one another each represent hydrogen, or an optionally substituted Q-C6-alkyl radical or one or two of these substituents R6-R9 are an optionally substituted aryl group, R10 is an optionally substituted QQ-alkyl group or a 40 C2-C4-alkenyl group means Z is -CHR11- or -O- and Ru is hydrogen or QQ-alkyl, and wherein Xe is an anion.

R is preferably hydrogen.

Y is e.g. a cyano, methoxycar-45 bonyl, ethoxycarbonyl, methylsulfonyl or ethylsulfonyl radical. Y particularly preferably represents cyano.

A preferred embodiment of the naphtholactam compounds according to the invention are compounds of the formula (1) in which R is hydrogen and Y is cyano. 50 R1 has the meaning of an optionally substituted Q-Q-alkyl radical, which generally includes in this application an unbranched or branched alkyl radical such as e.g. Methyl, ethyl, n- or iso-propyl, n-, sec- or tert-butyl, n- or iso-pentyl or n- or iso-hexyl, which is unsubstituted or e.g. substituted by hydroxy, Q-C4-alkoxy, phenoxy, QQ-alkoxycarbonyl, Q-C4-alkanoyloxy, cyano, halogen such as fluorine, chlorine or bromine, phenyl or phenyl substituted by nitro, halogen, Q-C4-alkyl or QQ-alkoxy is.

60 Examples of suitable substituted Q-C6-alkyl radicals are: hydroxyethyl, methoxymethyl, methoxyethyl, ethoxyethyl, ethoxypropyl, n-propoxymethyl, iso-propoxy-

670 096

methyl, butoxymethyl, butoxyethyl, butoxypropyl, ethoxypentyl, 2-hydroxyeth.oxypentyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, methoxycarbonylethyl, ethoxycarbonylethyl, acetoxyethyl, cyanoethyl, chloroethyl, benzyl, phenylethyl, 2-, 3- or 4-methylbenzyl or 2- , 3- or 4-methoxybenzyl.

In preferred naphtholactam compounds of the formula (1), R1 denotes an C 1 -C 4 -alkyl radical which is unsubstituted or substituted by hydroxyl, methoxy, ethoxy, cyano or chlorine.

Particularly preferred R1 radicals are methyl, ethyl, cyanoethyl or methoxyethyl.

One group of useful naphtholactam compounds includes compounds of formula (1) wherein R2 is a radical of the formula

. —V r3

W v (2)

represents. R3 and R4 each independently represent an optionally substituted Q-Q-alkyl radical, which is defined as described above.

R3 and R4 are each independently an C1-C4-alkyl radical which is unsubstituted or substituted by hydroxyl, methoxy, ethoxy, cyano, acetoxy or phenyl.

R3 and R4 independently of one another particularly preferably mean ethyl, hydroxyethyl, 2-hydroxypropyl, methoxyethyl or ethoxyethyl.

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

If R5 is a C1-C4-alkyl radical, this means, as is generally the case in this application, methyl, ethyl, n- or isopropyl or n-, sec- or tert-butyl; R5 is preferably methyl or ethyl.

If R5 is a C] -C4-alkoxy radical, it can be, as generally in this application, a methoxy, ethoxy, n- or iso-propoxy or n-, sec- or tert-butoxy radical . R5 as the C] -C4 alkoxy radical is preferably ethoxy and in particular methoxy.

R5 in the meaning halogen is e.g. fluorine, bromine and especially chlorine.

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

The radical R5 can be arranged ortho or meta to the nitrogen atom.

Another group of useful naphtholactam compounds are compounds of the formula (1) in which R2 is a radical of the formula r5

is. The meanings and preferences mentioned above apply to R5.

R6, R7, R8 and R9 can, as optionally substituted Q-Cg-alkyl radicals, independently of one another, each have the meaning as previously defined.

If one or two of these substituents R6 to R9 represent an optionally substituted aryl group, e.g. in question: the unsubstituted phenyl or a- or β-naphthyl group or the e.g. phenyl or naphthyl group substituted by halogen such as fluorine, chlorine or bromine or by C1-C4-alkyl or C1-C4-alkoxy.

R6 and R7 are preferably hydrogen and R8 and R9 are each independently hydrogen, methyl or ethyl.

R10 can be an optionally substituted Q-Q-alkyl radical, as defined above, or a C2-C4 alkenyl group, e.g. represent the -CH2-CH = CH2 group.

R10 is preferably an optionally substituted C 1 -C 6 -alkyl radical and particularly preferably an unsubstituted or substituted by hydroxy, Q-C4-alkoxy, cyano or phenyl C 1 -C 4 -alkyl radical. Particularly preferred meanings of R10 are methyl, ethyl, hydroxyethyl, methoxyethyl, ethoxyethyl and cyanoethyl.

Z stands for -O- or for -CHR1

As a C 1 -C 4 -alkyl radical, R11 can have the meanings defined above. R "is preferably hydrogen, methyl or ethyl. Z in particular denotes -O-, 2 ^ CH2 or -CH-CH3.

I.

Xe in the meaning of an anion represents both organic and inorganic ions, e.g. Halogen, such as chloride, bromide or iodide, rhodanide, sulfate, methyl sulfate, ethyl sulfate, aminosulfonate, perchlorate, carbonate, bicarbonate, phosphate, phosphoromolybdate, phosphorus wolf ramate, toluenesulfonate -, Phosphotungsten molybdate, benzene sulfonate, naphthalene sulfonate, 4-chlorobenzenesulfonate, oxalate, maleate, formate, acetate, propionate, lactate, succinate, chloroacetate, tartrate, methanesulfonate or ben- ions, or complex anions, such as that of double chlorine zinc.

Particularly preferred because of their good coloring properties are dyes of the formula (1) given above, in which R is hydrogen, Y is cyano, R1 is an C1-C4-alkyl radical which is unsubstituted or substituted by hydroxyl, methoxy, ethoxy, cyano or chlorine, R2 a radical of the formulas (2) or (3) given above, R3 and R4 independently of one another each represent an unsubstituted or substituted by hydroxyl, methoxy, ethoxy, cyano, acetoxy or phenyl C 1 -C 4 -alkyl radical, R5 is hydrogen, chlorine, methyl Is ethyl, methoxy or ethoxy, R6 and R7 are each hydrogen, R8 and R9 are each independently hydrogen or methyl or ethyl, R10 is an unsubstituted or substituted by hydroxy, C, -C4-alkoxy, cyano or phenyl-substituted CrC4-alkyl radical , Z represents -O- or -CHR11- and R "is hydrogen, methyl or ethyl, and wherein Xe represents an anion.

A particularly preferred embodiment of the naphtholactam compounds according to the invention are compounds of the formula (1) in which R is hydrogen and Y is cyano, R1 is methyl, ethyl, cyanoethyl or methoxyethyl, R2 is a radical of the formula (2) given above, R3 and R4 independently from each other are ethyl, hydroxyethyl, 2-hydroxypropyl, methoxyethyl or ethoxyethyl, R5 is hydrogen, methyl or methoxy and Xe is an anion.

Another particularly preferred embodiment relates to naphtholactam compounds of the formula (1) in which R is hydrogen and Y is cyano, R1 is methyl, ethyl, cyanoethyl or methoxyethyl, R5 is hydrogen, methyl or

4th

5

10th

15

20th

25th

30th

35

40

45

50

55

60

65

5

670 096

Methoxy is, Xe is an anion, R2 is a radical of the formula (3) given above, R6 and R7 are each hydrogen, R8 and R9 are each hydrogen, methyl or ethyl, R10 is methyl, ethyl, hydroxyethyl, methoxyethyl, ethoxyethyl or cyanoethyl, Z is -O- or -CHR "and Rn is hydrogen or methyl.

The naphtholactam compounds of the formula (1) according to the invention are prepared, for example, in such a way that a naphtholactam compound of the formula r1-îjj ç == 0

A A

I I! I.

\ A /

ìh = c-y

Condensation reaction to be saponified again in a known manner.

The compounds of formula (4) are new and also an object of the invention; they can be prepared, for example, by using a naphtholactam compound of the formula

10th

r1 — îjl ç = 0

A A

i n i • • •

V V

Ar

(5),

(4),

15

in the presence of a solvent and a catalyst with a compound of the formula in which R, Y and R1 has the meaning given above, with 20 H2C = C of a compound of the formula

• Y R

(6),

• r'w *

V

\ -u / • ar »

(2a)

25th

or a compound of the formula rA

30th

/ ~ Q '

\ ± S JlO

\

r9

(3a),

wherein R3, R4, R5, R6, R7, R8, R9, R10 and Z each have the meaning given above, in the presence of a condensing agent, wherein if a hydroxy group occurs in the meanings of the symbols of the formula (1), this in the starting compounds of the formulas (4), (2a) or (3a) must be present as an acyloxy group and is only converted to the hydroxyl group after the condensation by hydrolysis.

As condensing agents e.g. the following water-releasing reagents into consideration: phosphoric acid halides, such as phosphorus oxytrichloride, phosphorus oxytribromide, phosphorus pentachloride, and sulfuryl chloride, thionyl chloride, phosgene, zinc chloride, aluminum chloride etc. Mixtures of these compounds can also be used, such as e.g. a mixture of phosphorus oxytrichloride and zinc chloride or phosphorus oxytrichloride and phosphorus pentoxide.

The condensation reaction is carried out with heating, generally at 50 to 150 ° C, especially between 75 and 85 ° C. Solvents are not required, but the reaction mixture can, if desired, be mixed with an inert organic solvent, e.g. a chlorinated hydrocarbon such as dichloroethane, tetrachloroethane or chlorobenzene.

If the starting compounds of the formulas II and / or III contain hydroxyl groups, these are preceded by the condensation reaction by acylation, for example by means of acetic anhydride, at a temperature of about 70 ° to 85 ° C. to acyloxy groups in order to

35

40

45

50

55

60

65

wherein R and Y have the meaning given above, at a temperature of e.g. 70 to 200 ° C implemented. The naphtholactam 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 e.g. organic solvents and especially dipolar aprotic solvents such as e.g. Dimethylformamide.

Suitable catalysts are e.g. organometallic compounds and in particular compounds of precious metals, such as Platinum or palladium, with organic acid esters and / or organophosphorus residues; Examples are diacetato-bis-triphenylphosphine palladium (II) or diacetato-bis (tri-o-tolylphosphine) palladium (II). The reaction optionally takes place under a protective gas atmosphere.

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

The naphtholactam compounds of the formula (1) according to the invention are suitable as dyes for dyeing and, with the addition of binders and solvents, for printing a wide variety of textile fiber materials, e.g. of those made from polyvinyl chloride, polyamides, polyurethanes, polyesters of aromatic dicarboxylic acids such as e.g. Polyethylene terephthalate, acid-modified polyesters or polyamides, polymers of acrylonitrile or copolymers of acrylonitrile and asymmetric dicyanoethylene or vinyl acetate or contain them. The naphtholactam compounds of the formula (1) are particularly suitable for dyeing and / or printing textile fiber materials which consist of or contain polyacrylonitrile materials or acid-modified polyamides or polyesters. They are also suitable for spin dyeing and for dyeing the materials mentioned in the hydrated state, i.e. at a suitable location between the spinneret and dryer (gel staining).

The materials mentioned are preferably dyed from an aqueous, neutral or acidic medium by the exhaust process, if appropriate under pressure or by the continuous process. The textile material can be in a wide variety of forms, for example as fiber, thread, fabric, knitted fabric, piece goods and finished goods such as shirts and pullovers.

The new dyes on these materials result in

670 096

6

Lante, strong blue colorations, which are characterized by high light fastness and good wash, sweat, sublimation, decaturation, rubbing, carbonizing, water, sea water, chlorine water, over-dyeing and solvent fastness.

The dyes of the formula (1) have good stability in a wide pH range and can be easily combined with other cationic dyes.

The naphtholactam compounds of the formula (1) according to the invention are very particularly suitable for dyeing mixtures of the abovementioned materials with wool, since they have a very good wool reserve, i.e. the wool content of such blended fabrics is practically not dyed.

They can also be used for dyeing and printing paper and stained cotton, and for the production of inks and oil paints.

In the following examples, the parts (T) are parts by weight, the percentages are percentages by weight, and the temperatures are given in degrees Celsius.

example 1

62.5 parts of N-methyl-4-bromonaphtholactam-1, 8, 22.6 parts of anhydrous sodium acetate, 14.8 parts of acrylonitrile and 0.02 parts of diacetato-bis- (tri-o- tolylphosphine) palladium (II) entered. The suspension is heated to 130 ° C. within 30 minutes under constant nitrogen protection and then stirred at this temperature for 9 hours. The yellow reaction product which has precipitated after cooling to room temperature is filtered off, washed in succession with dimethylformamide, ethanol and water and dried. 42.5 T of the compound of the formula hac-tjl <p = 0 are obtained

/ \ A

! il I • • •

^ / \ ^

Ìh = ch-cn

Melting point after recrystallization 207-208 ° C. Further product can be obtained from the filtrate by precipitation with water, so that the yield becomes practically quantitative.

If the procedure is exactly as described in the example above and the substituted ethenes mentioned in the table below are used instead of acrylonitrile, further valuable naphtholactam compounds are obtained.

unsaturated compound Melting point of the corresponding naphtholactam compound

Example 2

4.7 parts of N-methyl-4-cyanovinylnaphtholactam-1.8 according to Example 1, 3.3 parts of N, diethylaniline and 0.3 parts of zinc chloride are mixed and 6.1 parts of phosphorus oxytri-5 chloride are added at 40 ° C. . Then allowed to stir for 24 hours at a temperature of 78-80 ° C.

When the condensation has ended, the mixture is poured onto ice, the pH is adjusted to 1.6 with sodium hydroxide solution and the mixture is stirred for a further 30 minutes. The crude dye is filtered off, dried and extracted with toluene. The dye of the formula ch3 i ch2 = c -cn ch, = ch-cooc2h5 is obtained

ch2 = ch-so, -c2h5

ch2 = ch-.

ch2 = ch-.

/

N

164-167 ° C 157-158 ° C 217-218 ° C

160-161 ° C

173-174 ° C

15

20th

©

Z2 "5

.A.A. -

i ii i ci

\ A /

t% r

Ìh = ch-cn

0

as a dark blue powder; it dyes polyacrylonitrile fibers in pure blue with excellent fastness properties.

25 Example 3

9.1 parts of N-ethyl, N- (2-hydroxyethyl) aniline are placed in a flask and 6.6 parts of acetic anhydride are added at 50 ° C. The mixture is left to stir at 70-75 ° C. until complete acetylation (about 30 minutes) and then 11.7 parts of 3 ° N-methyl-4-cyanovinylnaphtholactam-1, 8 according to Example 1 and 0.75 parts of zinc chloride are added added. Subsequently, 15.1 T of phosphorus oxytrichloride are added dropwise and this mixture is stirred for 24 hours at a temperature of 70-72 ° C. After the condensation has ended, an ice / water mixture is poured in and the mixture is stirred at 70-75 ° C. until the acetyl group has completely saponified (about 90 minutes). Then the pH of the mixture is adjusted to 1.6 with sodium hydroxide solution and stirring is continued for 1.5 hours at room temperature.

The crude dye which has precipitated completely with the addition of saline is filtered off, dried and purified by extraction with toluene.

The dye of the formula is obtained

40

45

50

K> - <A A * = * C2H * - ° h i n i • • •

^ / \ ^

Ìh = ch-cn

©

cl

©

55 as a dark blue powder; it dyes polyacrylonitrile fibers in pure blue with excellent fastness properties.

Examples 4-25

If one proceeds as described in Examples 2 or 3, 60 and, instead of the starting materials mentioned there, equivalent amounts of the naphtholactam and dialkylaniline or hydroquinoline or benzomorpholine compounds listed in Table 1 are used, valuable blue dyes with similarly good properties are obtained .

7

670 096

Example No.

Naphtholactam compound

Dialkylaniline or hydroquinoline or benzomorpholine compound

4th

H3C — Ijl <j! = 0

• r • •

ini.

% / \ / • •

£ h = ch — cn

/ "'WCaH5

n * = \ nc2h5 ch3

5

H 3 c — Ijl <j! = 0

/ \

1 II 1

\ / \ / • •

Ìh = ch-cn h3c

\ / \ • = • c2h5

6

h3c — tjl— <p = o

1 II 1 \ / \ /

ìh = ch-cn

/ ~ "WC2H5

N. =. (\ ZHs och3

7

h3c- ^ i — ç = o

/ \

l '•

1 II 1 «. •. #

^ \ ^

Ìh = ch-cn h3co

/-S.V-

\ / \

• = • c2h5

8th

h 3 c — ijt— ■ - <p = 0 / \

1 II 1

\ /

èH = CH-CN

/ ■ \ _ / 2Hb

\ / \ • = • c2h4—0-ch3

9

H3C-fjI Ç = 0

• r •

1 H I \ / \ /

% r

Ìh = ch-cn

^ cghit-0-CH3 nc2hi, -0-ch3

10th

H3C-ìjI <p = 0

/ \ / \% r%

1 II 1 \ / \ /

• •

Ah = ch-cn

/ \ / 'V

nc2h5

11

H3C-fjl <p = 0

/ \ / \ l '•

1 II 1 \ /

Ìh = ch-cn

0—

/ \

/ "W \ / \ • = • C2H5

670 096

8th

Example No.

Naphtholactam compound

Dialkylaniline or hydroquinoline or benzomorpholine compound

12

H 3 C-Ijl (p = 0

/ \ /%

1 II 1

\ /

•

d: H = CH-CN

/ - \ _ / 2Hs \ / \

C2Hi, -OH

ch3

13

H 3 C-Ijl <jl = 0

/ \ / \ • r •

1 II 1

vv

Ìh = ch-cn h3c

\ / \

• = • cah ^ -OH

14

H 3 C-Ijl <p = 0

/ \ / \ 1 II 1

\ / \ / • «

Ìh = ch-cn

N * = \ SC2Hi, -OH 0-CH3

15

H3C — Ijl— <p = o

/ \ / \

1 II 1 \ /

• •

Ìh = ch-cn

H3CO

/ ~ \ _ / 2H5

\ / \ • = • Cj-H ^ -OH

16

H 3 C-Ijl <p = 0

1 II 1 •. • •

V \ / Ìh = ch-cn

H3c y ^ • -N / \: H3 \ 2HAH

17th

h3c — ljr — cp = o / \ / \

• ê •

1 II 1

• • •

^ / \ ^ • •

Ìh = ch-cn

• -X- •

/ \ • - • 1

\ / \ • = • C2Hi, -OH

18th

H 5 C 2 -IjT <jj = 0

/ \ / \ • • •

1 II 1 \ / \ /

• •

<!: h = ch-cn

/ ~ \ _ / 2 "5

\ / \ • = • C2H5

19th

H 5 C 2 -Ijjl cp == 0

/ \ / \ • • •

1 II 1 \ / \ /

Ìh = ch-cn

/ ~ \ _ / 2Hs \ / \ • = • C2Hi, -OH

9

670 096

Example No.

Naphtholactam compound

Dialkylaniline or hydroquinoline or benzomorpholine compound

20th

H 5 C 2 -ijl <p = 0

A A

• r •

1 II 1 \ / \ / £ h = ch-cn

• - •

/ \

\ / \ • = • c2hu — oh

21st

nc-c2h4-ijf <p = 0

A A

1 11 1

\ A / • •

£ h = ch-cn

./"WC2Hs \ / \ \ =. C2h5

22

H 3 c-o-c 2 H 4-ljr-cp = o

A A

1 II 1

% A S

Ìh = ch-cn

\ / \

. = • nc2h5

23

H 3 c-o-c 2 H i »-ljr— <p = 0

A A

1 II 1

% A /

Ìh = ch-cn h3c

.-. A \ / CH3

y ^ • -N / \ H3 nC2HAH

24th

H3 C — îjî <p == 0

A A

1 II 1

\ A /

ìh = c-CN

ch3

/ V

\ / \ • = • C2hi, -OH

25th

H 3 C-Ijl <p = 0

A A

1 II 1 \ / \ /

<!: H = CH-S02-C2H5

\ / \ • = • C2HU-oh

Example 26

5 g of the dye prepared according to Example 3 are pasted with 2 g of 40% acetic acid and dissolved by adding 4000 g of hot water. 1 g of sodium acetate and 2 g of an adduct of 15 to 20 equivalents of ethylene oxide with N-octadecyldiethylenetriamine quaternized with dimethyl sulfate are added and 100 g of polyacrylonitrile fabric are added at 60.degree. The bath is heated to 100 ° C. within 30 minutes and then stained boiling for 90 minutes. The liquor is then allowed to cool to 60 ° C. over a period of 30 minutes. The material colored in this way is then removed and then rinsed with lukewarm and cold water.

A pure, blue polyacrylonitrile dye is obtained which has good fastness properties.

Example 27

60 A polyacrylonitrile copolymer consisting of 93% acrylonitrile and 7% vinyl acetate is dissolved in 15% in dimethylacetamide. The spinning liquid is extruded into a spinning bath which consists of 40% dimethylacetamide and 60% water. The resulting 65 spun tow is then stretched according to known methods and dimethylacetamide is removed by rinsing with hot and cold water.

This wet spun cord is made by diving in one

670 096

10th

Dyed bath at 42 ° C, which contains 9 g / 1 of the dye according to Example 1 and whose pH was adjusted to 4.5 with acetic acid.

The contact time fiber cable / dyeing liquor is 2 seconds. The excess liquor is then squeezed out and the spinning cable is fed to the dryer. The result is a blue colored fiber cable with good fastness properties.

Example 28

A printing paste consisting of:

25 T of the dye obtained in Example 2, 30 T of thiodiglycol,

20 T acetic acid (80%)

350 T boiling water, 500 T locust bean thickening,

30 T tartaric acid 1: 1.5 15 T di- (ß-cyanoethyl) formamide and

30 T of a naphthalenesulfonic acid formaldehyde condensation product.

A polyacrylonitrile fabric printed with this printing paste is then fixed on an HT suspension loop damper for 20 to 30 minutes at 101 ° C. to 103 ° C. and finished as usual. A blue print with good general fastness properties is obtained.

C.

Claims (15)

670 096 PATENT CLAIMS 1. Naphtholactam compounds of the formula r1 —ljî == ç — r2 / \ / \ I II I \ / \ / ÌH = ^ - Y © (1) 10th wherein R is hydrogen or methyl, Y is cyano, Q-Q-alkoxycarbonyl, C1-C4-alkylsulfonyl, phenyl or 15 pyridyl, R1 is an optionally substituted Q-Q-alkyl radical, R2 is a radical of the formula S \ w / \ r3 20th r1 * or a radical of the formula rA (2) 25th y \ z— • 'r8 / \ / H> (3) 30th represents, where R3 and R4 each independently represent an optionally substituted QQ-alkyl radical, R5 represents hydrogen, halogen, C 1 -C 4 -alkyl or C1-C4-alkoxy, R6, R7, R8 and R9 independently of one another each represent hydrogen, or one optionally substituted QQ-alkyl radical or one or two of these substituents R6-R9 are an optionally substituted aryl group, R10 is an optionally substituted QQ-alkyl group or a C2-C4-alkenyl group, Z is -CHR11- or -O- and R11 is hydrogen or Ci-C4-alkyl, and wherein Xe is an anion. 2. Naphtholactam compounds according to claim 1, characterized in that R1 is an unsubstituted or substituted by hydroxy, methoxy, ethoxy, cyano or chlorine Ci-C4-alkyl radical. 3. Naphtholactam compounds according to one of claims 1 or 2, characterized in that R is hydrogen and Y is cyano. 4. Naphtholactam compounds according to one of claims 1 to 3, characterized in that R2 is a radical of the formula (2), where R3 and R4 independently of one another each an unsubstituted or substituted by hydroxyl, methoxy, ethoxy, cyano, acetoxy or phenyl Represent C4 alkyl radical. 5. Naphtholactam compounds according to one of claims 1 to 3, characterized in that R2 is a radical of the formula (3), where R6 and R7 are hydrogen and R8 and R9 are each independently hydrogen, methyl or ethyl. 6. Naphtholactam compounds according to one of claims 1 to 3 or 5, characterized in that R10 is an unsubstituted or substituted by hydroxy, Q-Q-alkoxy, cyano or phenyl C, -C4-alkyl radical. 7. naphtholactam compounds according to any one of claims 1 to 3, 5 or 6, characterized in that Z for 35 40 45 -O- or -CHR1, where R11 is hydrogen, methyl or ethyl. 8. naphtholactam compounds according to any one of claims 1 to 7, characterized in that R5 is hydrogen, chlorine, methyl, ethyl, methoxy or ethoxy. 9. Naphtholactam compounds of the formula (1) according to claim 1, in which R is hydrogen, Y is cyano, R1 is an unsubstituted or substituted by hydroxy, methoxy, ethoxy, cyano or chlorine QQ alkyl radical, R2 is a radical of the formulas given above ( 2) or (3), R3 and R4 independently of one another each represent an unsubstituted or substituted by hydroxy, methoxy, ethoxy, cyano, acetoxy or phenyl QQ-alkyl radical, R5 is hydrogen, chlorine, methyl, ethyl, methoxy or ethoxy, R6 and R7 are each hydrogen, R8 and R9 are each independently hydrogen or methyl or ethyl, R10 is an unsubstituted or substituted by hydroxy, QQ-alkoxy, cyano or phenyl-substituted C 1 -C 4 -alkyl radical, Z is -O- or -CHR11- and R11 is hydrogen, methyl or ethyl, and wherein Xe represents an anion. 10. Naphtholactam compounds of formula (1) according to claim 1, wherein R is hydrogen and Y is cyano, R1 is methyl, ethyl, cyanoethyl or methoxyethyl, R2 is a radical of the above formula (2), R3 and R4 are independently ethyl, hydroxyethyl , 2-hydroxypropyl, methoxyethyl or ethoxyethyl, R5 is hydrogen, methyl or methoxy and Xe is an anion. 11. Naphtholactam compounds of formula (1) according to claim 1, wherein R is hydrogen and Y is cyano, R1, R5 and Xe have the meaning given in claim 9, R2 is a radical of formula (3) given in claim 1, R6 and R7 each represents hydrogen, Rs and R9 each represent hydrogen, methyl or ethyl, R10 represents methyl, ethyl, hydroxyethyl, methoxyethyl, ethoxyethyl or cyanoethyl, Z is -O- or -CHR11- and R11 is hydrogen or methyl. 12. Naphtholactam compounds of the formula "> c -? = 'r <) - <A A • = • ClH» 0H I II I • • • ^ \ / Ìh = ch-cn c-H5 © x , fc) (7) 50 wherein Xe is an anion, according to claim 1. 13. A process for the preparation of naphtholactam compounds of the formula (1) according to claim 1, characterized in that a naphtholactam compound of the formula 55 r1 -ijj (j) = 0 / \ / \ I II I W " £ h = c-y (4), 65 wherein R, Y and R1 has the meaning given in claim 1, with a compound of the formula 3rd 670 096 A / V \ ^ / or a compound of the formula (2a) Rl -] jj === (p — R2 / \ • • • I II I \ / \ / £ h = c-y © , 0 (1), io / \ / * ' y s.-Y 1 ° \ R9 where R is hydrogen or methyl, Y is cyano, Q-C4-alkoxycarbonyl, Q-C4-alkylsulfonyl, phenyl or (3a), pyridyl, R1 is an optionally substituted Q-C6-alkyl radical, R2 is a radical of the formula 15 in which R3, R4, R5, R6, R7, R8, R9, R10 and Z each have the meaning given in Claim 1, in the presence of a condensing agent, where if a hydroxy group occurs in the meanings of the symbols of the formula (1), this must be present as acyloxy group in the starting compounds of the formulas (4), (2a) or (3a) and is only converted into the hydroxyl group after the condensation by hydrolysis. 14. Compounds of the formula K1 -IjJ <^ = 0 .A / \. 20th • - • |? 3 Y v (2) or a residue of the formula 25th * -X - <s_ + H. \ r9 (3) I. 30th ■ • • V V 4 "Ty (4), wherein R, Y and R1 has the meaning given in claim 1, as a means for carrying out the method according to claim 13.