DE2703594A1 - DYE COMPOSITIONS - Google Patents

Abstract

Aqueous dispersions of a dispersion dye contain a dispersant mixture containing a) a fluorine-free surfactant and b) a surfactant with a terminal perfluoro group. Such dispersions, especially of hydrophobic dyes, are easily and uniformly dispersible in water and have little tendency to sediment and to form aggregates. They may be used for the preparation of dye baths and printing pastes for textile materials.

Description

The invention relates to dye compositions and in particular to aqueous dispersions, the disperse dyes contain.

Disperse dyes are defined by the Society of Dyers and Colourists as "substantially water-insoluble dyes that have a substantivity for one or more hydrophobic fibers, such as cellulose acetate fibers, and the common catfish from a fine

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aqueous dispersion are applied ". Usually they are also applied to cellulose triacetate, nylon and polyester fibers. You can also use the Surface coloring used by certain thermoplastics will. For all these purposes they are available as concentrated solid or liquid compositions that containing surfactants. A fine one Uniform distribution of the dye throughout the dyebath Is necessary to achieve a satisfactory leveled color. In addition, the commercially available Forms of the dye compositions be that a uniform dyebath can easily be made from them.

Those previously used in disperse dye compositions Surface-active agents have conical water structures, to which hydrophilic groups are bound. All of these surfactants are hereinafter referred to as "Hydrocarbon surfactants". Depending on the nature of the hydrophilic group, the surface-active hydrocarbons can be anionic, catiodic or have non-ionic character. As the hydrophilic groups, there can be used anionic surface active agents, for example Sulfate, sulfonate, phosphonate or carboxylate groups may contain cationic surfactants for example quaternary ammonium or phosphonium groups or contain tertiary sulfonium groups, and can include nonionic surfactants for example Polyoxyalkylene chains, such as polyoxyethylene or polyoxypropylene chains, or contain amine oxide groups.

According to the invention, an aqueous dispersion of a disperse dye is now proposed in which the Hydrocarbon surfactant dispersant according to the above definition and an over-surface-active Agent terminated with a perfluoro group.

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In order to promote the dispersibility in water, the dye ran in the composition; in a finely divided form, that is to say that the dimensions of the particles are as is customary in dye baths which are used for applying the disperse dyes to textile fibers. The dimensions of the particles can be, for example, less than 5> i and in particular 3 to 5 y .

The perfluoro terminated surfactant in the composition according to the invention the formula:

R _f - X - Y

have, wherein R_ is a perfluoroalkyl group C F-. where η is an integer greater than 2 X is either a direct bond or a divalent bridging group and Y is a hydrophilic one Group stands.

The perfluoroalkyl group R_ preferably contains 5 to 12 carbon atoms. Specific examples of perfluoroalkyl groups R_ are the straight-chain groups C ₇ F ₁ and CqF ₁ p. and particularly the branched-chain groups CGF j-, ^C io ^F i9 ^{and C} l2 ^F 2V ^{Dle Favor} R ^th branched-chain groups have the formula C "F ^, _ .., wherein m is an integer of more than the third Surfactants containing such perfluoro groups are available by methods described in British Patents 1,130,822 and 1,366,691.

The hydrophilic group Y can have any character. For example, you can be one of those groups be mentioned above in the case of the surface-active hydrocarbons

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substances were named.

The bridging group -X- can be a simple alkyl run, such as an alkylene rrupoe with 2 to 6 carbon atoms, or an arylene group, for example a phenylene group, be. However, it is preferably linked to the perfluoro group R-. via a heteroatom, in particular an oxygen atom that is present in bridge X. So the preferred Erilcker.rrurr er: -X-consist of Oxyalkylene groups, especially polyoxynalkylene groups, the belspielsv / eise has the formula - (OC ^ Hk) -, in which ρ is an integer from 3 to 40, preferably IC to 25, and from oxyarylene groups, for example of the formula -OCz-H ^ -, The attachment to R «can also be via a -CONH-alkylene or -SO_-alkylene group.

Specific examples of terminal surfactants Perfluoro groups in the erfindunrsgemäße Compositions can exist are the compounds

CH ₂ ) -OC ₁₀ F ₁₉ , wherein q _t .;: En has an average value of 11, 22 or 33

^C 10 ^F 19 ^OC 6 ^H 4 ^S0 3 ^Na

^ C ₇ P ₁₅ CONHC ₃ H ₆ N (CH ₃ ) ₃ 7 ₂ ⁺ SO ₄ ⁼

The preferred surface active agent having a terminal perfluoro group has the structure CGF ₁ (OCH ₂ CH ₀ J ₂₃ CCqF _15, wherein the 23 oxyethylene units in this formula, the throughput

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average value of a mixture of compounds with oxyethylene chains to denote different lengths.

In addition to the surface-active hydrocarbons, only small amounts of the surface-active agent with a perfluoro group are required to achieve water-repellent compositions. For example, the dye compositions contain surfactants rr.with a terminal perfluoro group in an amount of about 0.01 to about 2.0 wt. *, Based on the dye. Amounts less than about 0.1. "Generally range from, in order to draw the full benefits of the invention. Amounts of more than 1.0 wt.% Found no improvements associated with further amounts added in the ratio. Therefore, the preferred range is 0.1 to 1.0% by weight of perfluoro-terminated surfactant based on the dye.

The surface active hydrocarbon can be any surface active Be an agent which has a hydrocarbon structure with a hydrophilic group attached, as they are known from the art or as they are used in practice as dispersants for disperse dyes will. Examples of suitable dispersants are the alkali metal salts, especially sodium salts, of Naphthalene-2-sulfonic acid / formaldehyde condensates, the phenol / formaldehyde / sodium sulfite / sodium hydroxide reaction product, which is described in DT-OS 24 01 818 1st, alkali metal, in particular sodium and ammonium salts of lgnosulfonic acids and the cresol / formaldehyde / sodium sulfite reaction product, The FIAT Report No. 1013 of 11/25/46 and is known as "Dispersant SS".

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In the case where the alkali metal salt is a Naphthalene-2-sulfonic acid / formaldehyde condensate as surface active hydrocarbon is used, the aqueous dispersion can also be poly (vinylpyrrolidone) which is usually added as an aqueous solution. The poly (vinyl pyrrolidone) has a synergistic effect Effect on this special dispersant system.

The hydrocarbon surfactant can be used in amounts of 1 to 200 weight percent, preferably 10-100 weight percent the dye, be present. It has been found that the amount of hydrocarbon surfactant used for Achievement of a satisfactory dispersion is required due to the presence of the surfactant Agent with perfluoro group is smaller than it is otherwise would be the case. The cheapest amounts of each additive therefore compromise between what is achievable technical effect (improved dispersion) and the cost of additives.

The amount of that present in the dispersions according to the invention Dye can be from 5 to 60% by weight, based on the total dispersion, but is generally in the range Range from 15 to 30 wt. 2.

The aqueous dye dispersion must be sufficient in water Contain amount that a flowable composition is formed. So the water can be 25 to 90 wt.?, Preferably 25 to 50% by weight, based on the total dispersion.

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The invention is of particular value when the disperse dye in the composition a hydrophobic one Has character, that is, if it is of such a nature that its surface is not easily exposed to water is wetted. Disperse dyes which contain an alkyl chain of at least Ί carbon atoms a particularly hydrophobic character.

In particular, a disperse dye can be used in the invention Composition in one of its possible. tautomeric forms by the formula:

Λ - N = K

are represented, wherein A stands for a phenyl group which is substituted by a nitro, cyano or trifluoronethyl group or a group of the formula -SO ₀ R, -CONR R, -COR ^ or -SO-NR R and optionally further by a or two nitro, cyano, lower alkoxy, hydroxy-lower alkoxy, acyloxy, lower alkoxy, lower alkyl or phenoxy groups may be substituted, R is an alkyl, cycloalkyl, aryl or aralkyl group, R is hydrogen or a Is an alkyl, cycloalkyl, aryl or aralkyl group, R- * is hydrogen or an alkyl group and Z is an alkyl or cycloalkyl group, both of which may be optionally substituted, or an aryl group which may be substituted.

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The same dyes and their production are in the GB-PS 1 398 7M and the ΟΕ-ΡΛ 33718/73 described.

The alkyl groups R, R ur.d R are preferably alkyl groups with 1 to 10 carbon atoms, such as "ethyl-, Ethyl, n-propyl, n-eutyl, amyl, hexyl, octyl, dimethylhexyl and dodecyl fountain. The cycloalkyl groups R and R are preferably cyclohexyl groups. The aryl

3 k
groups R and R are preferably monocyclic aryl groups, viie, for example, phenyl, tolyl and xylyl groups. the

3 4
Aralkyl groups R and R are preferably phenyl-lower alkyl groups, such as, for example, benzyl and β-phenylethyl groups.

The term "lower" refers to groups with no more than 5 carbon atoms.

Examples of hydroxy-lower alkoxy groups are ß-hydroxyethoxy and 'Λ-hydroxypropoxy groups. The acyloxy-lower alkoxy groups are preferably lower alkyl-carbonyloxy-lower alkoxy groups such as β-acetoxy thoxy groups.

The alkyl groups preferably contain at least ¹ Z J carbon atoms and particularly 4 to 12 carbon atoms. Examples of these are butyl, amyl, hexyl, 2-ethyl-nhexyl, octyl, decyl, dodecyl and dimethylhexyl groups. Examples of cycloalkyl and aryl groups Z are the cyclohexyl and phenyl groups.

The invention is of particular value when the dye in the composition has the above formula, wherein the phenyl group A is _{substituted by a group -SO 2} NR R

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is ated, where R is a hydrogen atom or an alkyl,

2 is cycloalkyl or aralkyl group and R is an alkyl group having 5 or more carbon atoms, and wherein the phenyl group A is further represented by a nitro, cyano, Alkyl, alkoxy, phenyl or phenoxy group or a chlorine or eromator. can be substituted.

The alkyl groups R preferably contain 5 to 12 carbon atoms, as is the case with n-amyl, n-hexyl, n-octyl, n-decyl, n-dodecyl, 2-ethyl-n-hexyl and 1,1,3,3-tetramethyl-n-butyl groups the case is.

An example of a cycloalkyl group R is the cyclohexyl group. Examples of aralkyl groups R are phenyl lower alkyl groups, such as .B. Benzyl and ß-phenyl-ethyl groups. The aryl groups R are preferably nocyclic aryl groups, such as, for example, phenyl, tolyl and xylyl groups. The alkyl groups R preferably contain 1 to 12 carbon atoms, as is the case with the methyl, ethyl, propyl, butyl, amyl, n-hexyl, n-octyl, n-decyl and n-dodecyl groups is; but they are preferably lower alkyl groups. It will j
Is hydrogen atom.

ky! groups. It is most preferred that R is a

The invention is of very particular value when the pure dye in the composition has the formula:

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wherein R is hydrogen and R and Z have the meanings given above.

A particularly preferred dye is that in

2
Vielehen Π stands for the 2-ethylhexyl group, the sulfonamide group is in the p-position to the azo group and Z stands for the n-buty group.

The erfindungsgenäften aqueous dye dispersions can be prepared by ά <£> moving the dye, the surfactant with endsta'ndiger perfluoro group and the surface active hydrocarbon in the presence of particulate grinding elements, such as pebbles, hard balls or coarse sand, in water. Undried press pastes from the preparation of the dye can advantageously be used directly in this application process. When a dispersion of sufficient fineness has been formed, the grinding elements are removed. The liquid disoslon obtained can then be used as such or, if appropriate , dried by known techniques which prevent re-aggregation of dispersed particles , for example by spray-drying or freeze-drying.

The aqueous dye dispersions according to the invention are particularly suitable for producing dye baths or printing pastes from which the disperse dyes can be applied to textile materials in a known manner. They are also suitable for incorporating the dyes into aqueous printing inks.

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The aqueous dye dispersions can optionally an organic liquid that is immiscible with water, such as a polyhydric alcohol, as a humectant and / or to prevent the dispersion from freezing at low temperatures, such as during storage in the Outdoors in cold weather can occur. Suitable compounds for this purpose are, for example the Xthylenengiycol and Glycerin. Such additives can be used in amounts up to 50% by weight, based on the aqueous Phase, depending on the protection required.

The dispersions can also contain protective agents in order to protect them from attack by microorganisms. A suitable protective agent is, for example, the sodium salt of o-phenylphenol.

Protective agents can be obtained in quantities from 0.01 to 0.5% by weight on the entire dispersion.

Compared to similar compositions in which only surface-active carbons are present, the aqueous dispersions according to the invention, in particular those which contain hydrophobic dyes and very particularly the dyes indicated by the formulas above, are more easily and more uniformly dispersible in water. In addition, the compositions have a lower tendency to settle and form aggregates.

example 1

This example relates to the preparation of a liquid that contains a hydrophobic dye and a dispersant and is used for dyeing polyester fibers in conventional

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1?

union dye baths is provided.

53.40 parts of a yellow dye paste containing 29.00 parts of the dye obtained by diazotizing 4-aminobenzenesulfone-N- (2-ethylhexyl) amide and coupling with in-butyl-3-cyano-6-hydroxy- ⁱ -methylpyrid-2- _{one had} been obtained, v / urden with 17, ^ 0 parts of a hydrocarbon dispersant by heating phenol, formaldehyde, sodium sulfite and sodium hydroxide in an autoclave according to Example 1 of DT-OS 2k 01 818 2.0 parts of a liquid aqueous solution of a perfluoro-terminated surfactant of the formula, ^C 8 ^F 15 ^(OCH 2 ^CH 2 ⁾ 23 ^OC 8 ^F 15, as defined above, 1.75 parts of a 20% aqueous Solution of the sodium salt of o-phenylphenol and 12.96 parts of glycerine mixed.

The pH was adjusted to 10.9 to 7.8 by adding acetic acid. The mixture was mixed with 333-part particulate milling elements in a mill equipped with discs rotating at 3000 rpm. After 30 minutes, an amount of 20% aqueous glycarin was added to make the final composition 26%. Dye, 15.6? Medium and 0.31? Contained sodium salt of o-phenylphenol and the remainder consisted of 20% aqueous glycerin. After brief mixing, the batch was stripped of the grinding components, leaving approximately 71 parts of liquid .

Comparison game

A comparative product was prepared according to the procedure of Example 1 except that the perfluoro-terminated surfactant was omitted .

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The two products were separated by stirring in of 6 parts in 150 parts of water disnerrlert, and the apparently homogeneous dispersion was examined after dividing it into three equal portions. The first was quickly heated to 10 ° C and passed through two filter papers Whatman No. 4 filtered. The second and the third were made treated in a similar manner and in 10 minutes and 30 minutes respectively Heated to the boil for minutes. The precipitate remaining on the filter paper was then examined, whereby the the following results were obtained:

Comparative example

3eisDiel 1

track

track

Cook for 10 minutes

! Cook for 30 minutes

Trace + a lot of dark spots

track

small amount

Sour

The products were further tested by dyeing textured polyester yarn using a small laboratory wrap dyeing machine. At a depth of shade of 2Ϊ, which was achieved in Ί5 minutes at 130 ⁰ C and in a subsequent rinse with cold water (no reductive · tion purification treatment) gave the product of Example 1 is less Färbebadabscheidung than that of the comparative example and also had the coloration of Example 1 a better authenticity compared to rubbing.

Example 2

This example relates to the preparation of a flowable aqueous paste that approximates

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Contained dye and was suitable for milling to make a print paste component.

To 552 parts of water were added 21 parts of a 58% aqueous solution of the sodium salt of a condensate of naphthalene-β-sulfonic acid and formaldehyde, 27 parts of a 30% aqueous solution of polyvinylpyrrolidone and 0.5 part of a surface-active agent with an integral perfluoro group of the formula CgF ₁₅ (OCH ₂ CH ₂ J ₂ ^ OCpF _{1 r} which is a synergistic dispersant system, was added and then mixed using a Silverson mixer / homogenizer. ¹ JOO parts 1, ^ - dimethylamino-anthraquinone (a disperse dye with a hydrophobic character) were added Added uniformly to the stirred mixture over one hour, a flowable dispersion was obtained.

In a similar procedure, which was performed in the absence of a surfactant with perfluoro group, it was not possible to incorporate the dye even after a five-hour mixing, since the dye was not fully wetted by the Geraisch.

Example 3

The procedure of Example 2 was repeated, except that the Ί00 parts 1, ^ - dimethylaminoanthraquinone replaced by 400 parts of l-hydroxy - ^ - anilino-anthraquinone became. A similar result was obtained.

l-Hydroxy - ^ - anilino-anthraquinone is an extremely hydrophobic dye that, in the absence of the surfactant with perfluoro group, does not even work in 7 hours

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was wetted.
Example h

This example is for making a aqueous dispersion containing a hydrophobic dye and a dispersant and for coloring Polyester fiber is provided in conventional dye baths.

7 ^, 1 part of a yellow dye ^{paste containing 43.0 parts of the dye obtained by diazotizing 1} <-aminobenzenesulfon-N- (2-ethylhexyl) amide and coupling with in-butyl-3-cyano-6-hydroxy- ² <-methylpyrid-2-one was obtained with 19.2 parts of Reax 85 (a sodium lignosulfonate; "Reax" is a registered trademark), 3.2 parts of a 10% aqueous solution of a perfluoro-terminated surfactant of the formula CgF (OCH ₂ CH ₂ ) ₂₃ OCgF ₁₅ , 1.9 parts of a 2OX aqueous solution of the sodium salt of o-phenylphenol and 10 ^ parts of glycerol mixed.

The pH of the mixture was adjusted to 10.5 to 7.9 by the addition of 20% aqueous acetic acid, and the mixture was agitated with 333 parts of particulate grinding elements in a mill equipped with discs rotating at 3000 rpm turned. After 30 minutes, such an amount of 2055 aqueous glycerine was added that the final composition was k0% dye, \ 6% Reax, 0.27? surfactant with perfluoro group and 0.31? Containing sodium salt of o-phenylphenol and otherwise consisted of 20% aqueous glycerol.

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This product was for high temperature dyeing Polyester yarn example 1 suitable

Polyester yarn at 130 ⁰ C according to the specification of Bei-

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Claims (1)

PATENTA "ISPR Ü CHE 1.) Aqueous disintegration of a disperse dye, which as a dispersant has a surface-active Hydrocarbon, which has a hydrocarbon structure, to which a hydrophilic group is bound, contains, characterized in that the dispersion further comprises a perfluoro-terminated surfactant contains. 2.) Dispersion according to claim 1, characterized in that the particle dimensions of the disperse dye 3 to 5, u. X 3) dispersion according to claim 1 or 2, characterized in that the surface active agent having the formula R ^ er.dständiger perfluoro group -X-Y, wherein R ~ a perfluoroalkyl group of formula ^C _n ^F? Nl ^{is "wob} ei is an integer η is greater than 2, X is either a direct bond or a divalent bridging group, and Y is a hydrophilic group. 1.) Dispersion according to claim 3, characterized in that that the group R- contains 5 to 12 carbon atoms. 5.) Dispersion according to claim 3, characterized in that the group R- is a branched-chain group of Formula C «Mr. stands where m is an integer greater than 3 is. 6.) Dispersion according to one of claims 3 to 5, characterized in that X represents a polyoxyethylene group with 3 to OO oxyethylene units or an oxyphenylene group 0 0 0 3 1/10 4 1 ORIGINAL INSPECTED 2 7 O 3 b 9 4 where the group 1 'is attached to a terminal oxygen atom same is bound. 7 jDipnersior. r. according to claim 6, characterized in that -ekenr., that the number of OxvSthyler units in the PcIyoxyäthylengruppe 10 to 25. 8.) Dispersion according to claim 1 or 2, characterized in that the surface-active agent rr.it er.cständiger perfluoro group has the formula C ₃ F ₁₅ (OCH ₂ CH ₂ J ₂₃ OCp? ^, Wherein the 23 oxyethylene units are on one. Get the average of a mixture of compounds with oxyethylene chains of different lengths. 9.) Dispersion according to one of claims 1 to S, characterized in that it is 0.1 to l, CHew- £ of the surfactant with a terminal perfluoro group, based on the disperse dye. 10.) Dispersion according to one of claims 1 to 9, characterized in that it contains 1 to 200 Cev% surface-active hydrocarbon, based on the disperse dye. 11 ·) dispersion according to claim 10, characterized in that it 10 to ICO Cew-2 surface-active carbon, based on the disperse dye. 12.) Dispersion according to one of claims 1 to 11, characterized in that it contains 25 to 90 Oew-2 water, based on the total dispersion. 13 ·) Dispersion according to claim 12, characterized in that it contains 25 to 50% by weight of water, based on the total Dispersion, contains. 7 09831/1041 l ^.) Dispersion according to one of claims 1 to 13, characterized in that the disperse dye has a hydrophobic character. 15.) Dispersion according to Ar.soruch 1 * 1, characterized in that that the dispersant has an alkyl chain has at least ^ carbon atoms. 16.) Dispersion according to one of claims 1 to 15, characterized in that the disperse dye has the formula in one of its possible tautomeric forms AK = V, has, wherein A is a phenyl group through a nitro, cyano or trifluoromethyl group or a Group of the formula, -SO-R ⁵ , -CONR ^ R ⁵ , -COR ³ or SO ₀ KR ^ R ⁵ 3
is substituted, where R is an alkyl, cycloalkyl, ü is aryl or aralkylpruDpe, R is a hydrogen atom or is an alkyl, cycloalkyl, aryl or aralkyl group and R is a hydrogen atom or an alkyl group, and Z represents an unsubstituted or substituted alkyl, cycloalkyl or aryl group. 17.) Dispersion according to claim 16, characterized in that the group A is substituted by one or two nitro, cyano, lower alkoxy, hydroxy- lower alkoxy, aryloxy, lower alkyl or phenoxy groups. 7 0 9 8 3 1/1 0 - * r- 270359A S. 18.) Dispersion according to Ancnruch l6, characterized in that that the alkyl groups P.- ', R and R ^ alkyl groups with Are 1 to 10 carbon atoms. 19.) Dispersion according to Ansori.ch l6 or 17, characterized in that
are hexyl groups. 20.) Dispersion according to claim l6 or 17, characterized in that
Are aryl groups. indicates that the cycloalkyl groups R and R ^s cyclo- 3 H indicates that the aryl groups R and R are nonocyclic 21.) Dispersion according to one of claims l6 or 17> characterized in that the aralkyl groups R ^ and R Are phenyl-lower alkyl groups. 22) Dispersion according to one of claims l6 to 21, characterized in that the alkyl groups Z at least Contains 4 carbon atoms. 23 ·) Dispersion according to claim 22, characterized in that the alkyl groups Z ¹ J contain up to 12 carbon atoms. 24.) Dispersion according to one of claims l6 and 18 to 23, characterized in that the phenyl group A passes through 12 1 a group -SO-KR R is substituted, wherein R is a Hydrogen atom or an alkyl, cycloalkyl or aralkyl 2
group and R represents an alkyl group having 5 or more carbon atoms. 25.) Dispersion according to claim 2k, characterized in that the phenyl group A is further substituted by a nitro, cyano, alkyl, alkoxy, phenyl or phenoxy group or a chlorine or bromine atom. 709831/1041 26.) Dispersion according to one of claims 24 or 25, characterized in that the alkyl group R ⁴ "contains 5 to 12 carbon atoms. characterized in that the aryl group R is a monocyc- 27.) Dispersion according to one of claims 24 to 26, characterized by <
Lische aryl group is. 28.) Dispersion according to one of claims 2Ί to 27, each characterized in that
Contains carbon atoms. characterized in that the alkyl group R 1 to 12 29.) Dispersion according to claim 28, characterized in that that the alkyl group R is a lower alkyl group. 30.) Dispersion according to one of claims 2 ¹ I to 26, characterized in that R stands for a hydrogen atom. 31.) Dispersion according to claim 24, characterized in that that the disperse dyes have the formula: in which R ^{1 represents} hydrogen and R and Z have the meanings given above. 32.) Dispersion according to claim 31, characterized in that Z stands for an n-butyl group and the group of the formula -SO ₃ NR ¹ R consists of the sulfone (2-ethylhexyl) amide group, which is in p- Position to the azo grouping is located. 709831/1041 33.) Dispersion according to one of claims 1 to 32, characterized in that it is also one with V.'asser Miscible organic liquid in a r-! er.r * e up to 50 wt%, based on the active phase as humectant and to prevent the dispersion from freezing. 3 ¹ ^.) Dispersion according to claim 33, characterized in that the organic liquid which is miscible with water consists of a higher value alcohol. 35 ·) Dispersion according to claim 3 ^, characterized in that that the polyhydric alcohol from Xthyler.glycol or Consists of glycerin. 36.) Dispersion according to one of claims 1 to 35, characterized in that it also has a protective agent to protect the dispersion against attack by microorganisms. 37.) Dispersion according to claim 36, characterized in that the amount of the protective agent is 0.01 to 0.5 % by weight, based on the entire dispersion. 38.) Process for the preparation of a dispersion according to Claim 1, characterized in that one of the. Oisnerion dye, the surface-active agent with acidity Perfluoro group and the surface-active hydrocarbon in the presence of particulate grinding elements moved in water and that after formation of a dispersion of sufficient fineness, the particulate Xahlelemente away from the dispersion. 709831/1 CK 1