MXPA98008516A - A method for conditioning organi pigments - Google Patents

Abstract

The present invention relates to a process for preparing pigment compositions comprising a) conditioning an organic pigment at a temperature of about 50 to about 200 ° C with 1) at least about 0.1% by weight, based on the organic pigment, of one or more surfactants, consisting of (i) an anionic surfactant of the formula: wherein R1 is C8-C30 aliphatic or modified C8-C30 aliphatic, wherein at least one carbon atom of the main chain is substituted with -O-, -S -, -CONH-, -NHCO-, -CH = CH, -OSi (C1-C4 alkyl) 2- or C5-C7 cycloalkylene, R2 is hydrogen, C1-C6 alkyl or Y-Z '; R3 is hydrogen or alkyl C1-C6, or R2 and R3 together are C4-C7 alkylene, X is a direct bond or -NHC (= NH) -, or X and R2 taken together with N + form a heterocyclic ring of five to seven members; (cycle) difunctional C1-C8 aliphatic, Z is -COO, -SO3, -PO3 = .1 / n Mn + (where Mn + is a hydrogen ion or an n-valent cation), or OH, with the proviso that, if Z is OH, then an anionic counterion must be present, and Z'es -COO-.1 / n Mn +, -SO3.1 / nMn +, or -PO3 = .2 / n Mn + (where Mn + is a hydrogen ion and / or an n-valent cation) or OH, with the proviso that Z 'must be OH if z is OH, ii) a surfactant of formula (II): wherein R1 is C8-C30 aliphatic or modified C8-C30 aliphatic, where at least one carbon atom in the main chain is substituted with -O-, -S-, -CONH-, -NHCO-, -CH = CH-, -OSi (C1-C4 alkyl) 2-, or C5-C7 cycloalkylene optionally substituted, R2 is hydrogen, C1-C6 alkyl or -Y-Z ', X is a direct bond or -NHC (= NH) -, or X and R2 taken together with N form a heterocyclic ring of five to seven members; And it is difunctional C1-C8 aliphatic (cyclo) and Z'es -COO.1 / n Mn +, -SO3.1 / n Mn +, or -PO3 = .2 / n Mn + (where Mn + is a hydrogen ion and / or an n-valent cation) or OH, or iii) mixtures thereof, and 2) about 1 to about 100 parts by weight, per part by weight of the organic pigment, of a liquid in which the pig The organic substance is substantially insoluble, thus forming a suspension of the organic pigment conditioned in the liquid, b) eventually treating the conditioned organic pigment on the surface, and c) collecting the organic pigment.

Description

A METHOD FOR CONDITIONING ORGANIC PIGMENTS BACKGROUND OF THE INVENTION This invention relates to a process for the preparation of pigment compositions having better dispersibility in plastic and other macromolecular materials by conditioning organic pigments with non-solvents containing certain surfactants. Organic pigments in the form initially obtained after chemical synthesis, which are often referred to as crude pigments, are generally unsuitable for use as pigments and must be subjected to one or more additional finishing steps that modify the size of the pigments. the particles, the shape of the particles and / or the crystalline structure in such a way that a good pigment quality is obtained. See, for example, K. _ Merkle and H. Scháfer, "Surface Treatment of Organic Pigments", in Pigment Handbook, Vol. III (New York: John Wiley &Sons, Inc., 1973, page 157; RB McKay, "The Development of Organic Pigments with Private Reference to Physical form and Consequent Behavior in Use ", in Rev. Prog. Coloration, 10, 25-32 (1979), and RB McKay," Control of the application performance of classical organic pigments ", in JOCCA, 89-93 (1989) The most commonly used methods of conditioning involve the dissolution or suspension of the crude pigment in strong mineral acids, followed by precipitation, and / or milling of the crude pigment.The conditioning with a strong acid involves the treatment of the crude pigment with aqueous mineral acid. , such as sulfuric acid, in a process known as "acid filling" (where an acid solution containing protonated pigment is formed) or "acid swelling" (where a protonated pigment suspension forms.) After the treatment is completed. acid, the pigment is precipitated by adding the strongly acid solution to a liquid in which the pigments are completely or almost completely insoluble, such as water or methanol or others. lower aliphatic alcohols, as well as their mixtures. Sometimes a further treatment of the conditioned organic pigments is desirable or necessary, particularly when the pigments are to be dispersed in plastic. Surface treatment is a type of finish in which certain auxiliary agents, such as rosin or other resins, are applied to the pigments to influence their surface structure and, thus, their physical and coloristic properties. For example, W. Herbst and K. Hunger, Industrial Organic Pigments (New York: VCH Publishers, Inc., 1993), pages 205-207. For example, the treatment of organic pigments with emulsions of certain dispersing agents, such as sulfonated dicarboxylic acids, in non-aqueous volatile oils, such as naphtha, can improve the dispersibility of the pigments in non-aqueous vehicles used for inks, paints and varnishes. For example, US Pat. 2,268,144. Removal of said additional steps would be advantageous if desirable pigment properties could be maintained. U.S. Pat. 5,662,739 discloses a method for improving the dispersibility of quinacridone and dioxazine pigments using certain taurides of fatty acids. Fatty acid taurines, however, are amides more than ammonium or amine compounds such as those used in the present invention. European Patent Application 758,004 describes a method for improving the dispersibility for a specific pigment, Yellow Pigment 12, by carrying out the preparative coupling reaction in the presence of certain cationic surfactants and amine oxides. The European application, however, does not mention other types of pigment and does not suggest that the pigments could be conditioned in the presence of said surfactants. An object of the present invention was to reduce or eliminate the use of strong acids and eliminate the subsequent stages of surface treatment, while providing organic pigments that can be easily dispersed in plastic. These and other objects have been achieved by conditioning organic pigments with non-solvents containing specific types of surfactants containing nitrogen. SUMMARY OF THE INVENTION This invention relates to a process for preparing pigment compositions comprising (a) conditioning an organic pigment at a temperature of about 50 to about 200 ° C with (1) at least about 0.1% on weight (preferably 0.1 to 100% by weight, more preferably 2 to 15% by weight), relative to the organic pigment, of one or more surfactants, consisting of (i) an anionic surfactant of formula ( I) R2 I Rx-X-N + -YZ I where R1 is C8-C30 aliphatic or modified C8-C30 aliphatic, wherein at least one carbon atom of the main chain is substituted with -O-, -S- , -CONH-, -NHCO-, -CH = CH-, -OSi (C-C4 alkyl) 2- or C5-C7 cycloalkylene 10 optionally modified; R2 is hydrogen, C ^ C- or -Y-Z1 alkyl; R3 is hydrogen or C-C6 alkyl or R2 and R3 together are C4-C7 alkylene (thus forming a hetero cycle of five to eight members), - X is a direct bond or -NHC (= NH) -, or X and R2 taken together with the N + of formula (I) form a heterocyclic ring of five to seven members (preferably, where R2 and R3 together are not C4-C7 alkylene and, therefore, do not form another ring); Y is (cyclo) aliphatic C ^ Cg difunctional (preferably, C-C6 alkylene); 30 Z is -COO ", -S03", -P03 = -l / n M1 (where Mn + is a hydrogen ion or an n-valent cation), or OH, with the proviso that, if Z is OH, then it must be present a counterion, and Z 'is -COO ~ -l / n Mn +, -S03 ~ -l / n Mn +, o -P03 = -2 / n Mn + (where Mn + is a hydrogen ion and / or an n-valent cation), or OH, with the proviso that Z 'must be OH if Z is OH; 10 (ii) a surfactant of formula (II) R2 R ^ XNYZ '(II) wherein R1 is C8-C30 aliphatic or modified C8-C30 aliphatic, wherein at least one carbon atom in the main chain is substituted with -0-, -S-, -CONH-, -NHCO-, -CH = CH-, -OSi (C 1 -C 4 alkyl) 2-, or optionally substituted C 5 -C 7 cycloalkylene; R2 is hydrogen, alkyl or -Y-Z '; X is a direct bond or -NHC (= NH) -, or X and R2 taken together with the N of formula (II) form a heterocyclic ring of five to seven members; 30 Y is (cyclo) aliphatic Cj ^ C- difunctional (preferably, alkylene C ^ C, and Z 'is -COO "-l / n Mn +, -S03" -l / n Mn +, or -P03 = -2 / n Mn + (where Mn + is a hydrogen ion and / or an n-valent cation) or OH, or (iii) mixtures thereof, and (2) about 1 to about 100 parts by weight (preferably, 4 to 15 parts by weight) , by weight of the organic pigment, of a liquid in which the organic pigment is substantially insoluble, thus forming a suspension of the organic pigment conditioned in the liquid, (b) optionally treating the conditioned organic pigment on the surface, and ( c) collecting the conditioned organic pigment This invention is further related to pigment compositions prepared by the process of this invention and to the use of said pigment compositions in the pigmentation of macromolecular substances, coatings and inks DETAILED DESCRIPTION OF THE INVENTION organic pigments adec Those which can be conditioned according to the process of the present invention include perylene pigments, phthalocyanine, indantrone, isoindoline and quinacridone, as well as other known organic pigments. Mixtures, including solid solutions, of said pigments are also suitable. Perylenes, particularly the diimides and dianhydrides of perylene-3, 4, 9, 10-tetracarboxylic acid, are particularly suitable organic pigments. Suitable perylene pigments may be unsubstituted or substituted, for example, with one or more alkyl, alkoxy, halogens such as chlorine, or other typical perylene pigment substituents, including those substituted on the imide nitrogen atoms with groups chemically reasonable such as alkyl. Crude perylenes can be prepared by methods known in the art. For example, W. Herbst and K. Hunger, Industrial Organic Pigments (New York: VCH Publishers, Inc., 1993), pages 9 and 467-475; H. Zollinger, Color Chemistry (VCH Verlagsgessellschaft, 1991), pages 227-228 and 297-298, and M.A. Perkins, "Pyridines and Pyridones", in The Chemistry of Synthetic Dyes and Pigments, ed. HE HAS. Lubs (Malabar, Florida: Robert E. Krieger Publishing Company, 1955), pages 481-482. Phthalocyanine pigments, especially metal phthalocyanines, are also suitable organic pigments. Although copper phthalocyanines are preferred, phthalocyanine pigments containing other metals, such as those based on zinc, cobalt, iron, nickel or other such metals, can also be used. Metal-free phthalocyanines are also suitable, but, in general, are less preferred. The phthalocyanine pigments may be unsubstituted or partially substituted, for example with one or more alkyl, alkoxy, halogens such as chlorine or other typical phthalocyanine pigment substituents. Crude phthalocyanines can be prepared by any of several methods known in the art, but are preferably prepared by means of a reaction of phthalic anhydride, phthalonitrile or its derivatives with a metal donor, a nitrogen donor (such as urea or phthalonitrile itself). ) and an eventual catalyst, preferably in an organic solvent. For example, W. Herbst and K. Hunger, Industrial Organic Pigments (New York: VCH Publishers, Inc., 1993), pages 418-427.; H. Zollinger, Color Chemistry (VCH Verlagsgesellschaft, 1991), pages 101-104, and N.M. Bigelow and M.A. Perkins, "Phthalocyanine Pigments," in The Chemistry of Synthetic Dyes and Pigments, ed. HE HAS. Lubs (Malabar, Florida: Robert E. Krieger Publishing Company, 1955), pages 584-587; see also US Pat. 4,158,572, 4,257,951 and 5,175,282 and British Patent 1,502,884. Suitable pigments include indatrone pigments prepared by methods known in the art. For example, W. Herbst and K. Hunger, Industrial Organic Pigments (New York: VCH Publishers, Inc., 1993), pages 498-500; H. Zollinger, Color Chemistry (VCH Verlagsgesellschaft, 1991), pages 219-220 (see also page 237), and M.S. Whelen, "Ant raquinoneazines", in The Chemistry of Synthetic Dyes and Pigments, ed. HE HAS. Lubs (Malabar, Florida: Robert E. Krieger Publishing Company, 1955), pages 512-522. The indantrone pigments may be unsubstituted or partially substituted, for example with one or more alkyl, alkoxy, halogens such as chlorine or other typical substituents of indantrone pigments. In particular, non-derivatized indantrone (Blue Pigment 60 or, alternatively, Blue Vat 4) is preferred. The isoindoline pigments, which may optionally be symmetrically or asymmetrically substituted, are also suitable organic pigments and can be prepared by methods known in the art. For example, W.

Herbst and K. Hunger, Industrial Organic Pigments (New York: VCH Publishers, Inc., 1993), pages 398-415. A particularly preferred isoindoline pigment, Pigment Yellow 139, is a symmetrical adduct of iminoisoindoline and precursors of barbituric acid. The quinacridone pigments are also suitable organic pigments. Quinacridones (which, as used herein, include unsubstituted quinacridone, quinacridone derivatives and solid solutions thereof) can be prepared by any of several methods known in the art, but are preferably prepared by thermally closing the ring of several precursors of 2, 5-dynilinoterephthalic acid in the presence of phosphoric acid. For example, S.S. Labana and L.L. Labana, "Quinacridones", in Chemical Review, 61, 1-18 (1967), and US Patents, 3,157,659, 3,256,285, 3,257,405 and 3,317,539. Suitable quinacridone pigments may be unsubstituted or substituted (for example, with one or more alkyl, alkoxy, halogens such as chlorine or other substituents typical of quinacridone pigments). Other suitable organic pigments include dioxazines (ie triphenyloxazines), 1,4-diketopyrropyrroles, anthrapyrimidines, antantrones, flavantrones, indatrones, perinones, pyrantrones, thioindigos, 4,4'-diamino-1,1'-diantraquinonyl and compounds azo, as well as its substituted derivatives. The process of the present invention is suitable for conditioning raw organic pigments, but it is also possible to use this method to improve the dispersibility of pigments already conditioned using other conditioning methods. An organic pigment is first mixed in step (a) with surfactant (1) in the non-solvent liquid (2). Suitable surfactants are the ionic surfactants of formula (I) R2 R1-XN "-Y- Z (I) R rJ wherein R1, R2, R3, X, Y and Z are defined as above, and the non-ionic surfactants of formula (II) R2 I R'-X -? - YZ '(II) wherein R1, R2, R3, X, Y and Z' are defined as above The internal salts of formula (I) wherein at least one of R2 or R3 is hydrogen and Z is an anionic group and the compounds of formula (II) wherein Z 'represents -COOH, -S03H or -P03H-l / n Mn + (where Mn + is H + or an n-valent cation) may represent different ionic forms of the same compound. , the two forms may be in balance.) One skilled in the art would readily understand this aspect of representation and, if necessary, could determine which form would actually be present.For the purposes of this description, the distinction is not critical. "C8-C30 aliphatic" as used herein with respect to the descriptions of surfactants (1) refers to straight or branched chain aliphatic hydrocarbon groups having and 8 to 30 carbon atoms and which can be optionally modified by replacing one or more carbon atoms in the main chain with -O-, -S-, -CO? H-, -? HCO-, -CH = CH-, -OSi (alkyl) 2- or C5-C7 cycloalkylene in a chemically reasonable manner. When two or more such groups are present, they may also be present, of course, in chemically reasonable combinations. For example, heteroatoms are preferably not in an adjacent location with each other, or, when X is a direct bond, adjacent to the N + of formula (I) or N of formula (II). Even more, the groups -0-, -S-, -CONH- and -NHCO- can not be directly linked to the N + of formula (I) and are not directly linked to the N of formula (II). In addition to the eventual branching (which, in effect, corresponds to the alkyl substitution of a linear chain), the C8-C30 aliphatic groups (including any -CH = CH- and C5-C7 cycloalkylene) can be substituted with groups such as C-alkoxy - C6, halogen (especially fluorine in groups -CF2-), hydroxy, oxo (ie, as keto oxygen), (C-C6 alkoxy) -carbonyl, (C6-C10 aryloxy) carbonyl and cyano. Suitable C8-C30 aliphatic groups include alkyl groups, such as octyl, decyl, undecyl, lauryl (ie, dodecyl), myristyl (ie, tetradecyl), cetyl (ie, hexadecyl), stearyl (i.e., octadecyl) ), eicosanil and docosanil, as well as their isomeric forms; corresponding alkenyl, alkadienyl and alktrienyl groups, such as 8-heptadecenyl or 9-octadecenyl (such as its Z-isomer oleyl or E-elaidyl isomer); amidoalkyl groups, such as cocamidoalkyl (i.e., coconut fatty acid amides of aminoalkyl groups, particularly cocamidopropyl) and ricinoleamidoalkyl (particularly ricinoleamidopropyl), and polyethers, such as polyalkyleneoxyalkyl (particularly polyethyleneoxyethyl or polypropyleneoxypropyl). Particularly preferred C8-C30 aliphatic groups include cocamidopropyl, lauryl, stearyl, 8-heptadecenyl and oleyl. It is also possible, although not preferred, to replace some or all of the carbon atoms of the main chain of the R1 group with -OSi (C1-C4 alkyl) 2- groups, which means that the term "C8 aliphatic" C30"as used herein also includes polysiloxane groups in which the silicon and oxygen atoms are not directly attached to the nitrogen atom of the compounds of formulas (I) and (II), but are instead attached to through one or more intermediate carbon atoms. The term "(cyclo) aliphatic C-C8 difunctional" as used herein with respect to the definition of Y in the surfactants of component (1) refers to straight or branched chain difunctional aliphatic hydrocarbon groups having from 1 to 8 carbon atoms and cyclic hydrocarbon groups having from 5 to 8 ring carbon atoms, as well as difunctional C3-C7 cycloaliphatic groups which can be any of the group Z and the nitrogen atom of the compounds of the formulas (I) Y (II), or both, through methylene, ethylene or propylene groups, provided that the total number of carbon atoms of the main chain and the ring does not exceed eight. Examples of difunctional alkylene (cyclo) aliphatic groups such as propylene, butylene, pentylene, hexylene, heptylene and octylene (and alkyl-substituted derivatives up to a total of eight carbon atoms), and C5-C8 cycloalkylene, such as 1,2 and 1, 3-cyclopentylene, 1,2-, 1,3- and 1,4-cyclohexylene and 1,2-, 1,3- and 1,4-cyclohep-tylene. Carbon-carbon double bonds in the chain may also be present, provided they are not adjacent to N + and N of formulas (I) and (II), respectively, or to OH. Although not generally preferred, it is also possible to replace one or more carbon atoms in the aliphatic chain and / or in the cycloaliphatic ring with heteroatoms, such as N (for example, as NH or N-alkyl), O or S, provided that said heteroatoms are not located adjacent to each other or to N + and Z (and Z 'eventual) of the formula (I) or to N and Z' of the formula (II). Preferred difunctional (cyclo) aliphatic groups are C-C6 alkylene groups, especially methylene and ethylene groups. The term "alkyl as used herein refers to straight or branched chain aliphatic hydrocarbon groups having from 1 to 6 carbon atoms, also referred to as lower alkyl, are examples of C-C alkyl. methyl, ethyl, propyl, butyl, pentyl, hexyl and their isomeric forms The term "alkoxy" refers to straight or branched chain alkyloxy groups having from 1 to 6 carbon atoms. Examples of alkoxy methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy and its isomeric forms are examples. The term "C7-C16 aralkyl" refers to C1-C6 alkyl substituted with C3-C10 aryl, such that the total number of carbon atoms is from 7 to 16. Examples of C7-C16 aralkyl are benzyl, phenethyl and naphthylmethyl. The term "(C-C6 alkoxy) carbonyl" refers to straight or branched chain alkoxycarbonyl groups having from 1 to 6 carbon atoms in the alkoxy moiety. Examples of (C-C6 alkoxy) carbonyl methoxycarbonyl are, ethoxycarbonyl, propoxycarbonyl, butoxycarbonyl, pentyloxycarbonyl, hexyloxycarbonyl and its isomeric forms. The term "(C6-C10 aryloxy) carbonyl" refers to phenoxycarbonyl and 1-or 2-naphthoxycarbonyl, where the axyl portion may also be optionally substituted with halogen, alkyl, alkoxy, alkoxycarbonyl or nitro. Examples of halogen are fluorine, chlorine, bromine and iodine. The surfactants of formulas (I) and (II) containing cations include compounds of formula (I) wherein Z is -P03 = -l / n Mn + and / or where R2 is -Y-COO "-l / n Mn +, -Y- S03"-l / n Mn + or -Y-P03 = -2 / n Mn + and compounds of formula (II) where Z is -C00" -l / n Mn +, -S03 ~ -l / n Mn +, or -P03 = -2 / n Mn + and / or where R2 is -Y-COC-l / n Mn +, -Y-S03 ~ -l / n Mn + or -Y-P03 = -2 / n Mn + where Mn + in each case is a hydrogen ion and / or an n-valent cation, and suitable cations include metal ions, such as alkali metal ions (eg, lithium, sodium or potassium ions), alkaline earth ions (e.g. , magnesium or calcium ions), aluminum ions and ammonium ions, such as RaRbRcRdN + (wherein Ra, Rb, Rc and Rd are independently hydrogen, alkylCg, C7-C16 hydroxy alkyl aralkyl and the like, such as NH4 +). formula (I) and formula (II) which do not contain heterocyclic rings formed by X and R2, taken together, are generally more preferred than those containing heterocyclic rings. Preferred non-cyclic ionic surfactants of formula (I) are those in which R1 is C8-C30 aliphatic or modified C8-C30 aliphatic, wherein at least one carbon atom of the main chain is substituted by -O-, -CONH- , -NHCO- or -CH = CH-; R2 and R3 are independently hydrogen or C-C6 alkyl (preferably, an alkyl group such as methyl); X is a direct bond or -NHC (= NH) -; Y is C-C6 alkylene (preferably, methylene or ethylene), and Z is -COO ", -S03" or OH, with the proviso that, if Z is OH, then a stoichiometric amount of an anionic counter ion must be present. (for example, a halide such as chlorine, sulfate, bisulfate, phosphate, hydrogen phosphate or an ester thereof, dihydrogen phosphate or an ester thereof, nitrate, carbonate or bicarbonate). Particularly preferred surfactants of formula (I) are amphoteric compounds wherein Z is an anionic group -COO "or -S03". Especially preferred surfactants of formula (I) cocamidopropylbetaine, an amphoteric compound in which R1 is cocamidopropyl, R2 and R3 are methyl, X is a direct bond, Y is methylene and Z is -COO "), and N- [3- (cocamido) propyl-N- (2-hydroxy-3-sulfopropyl) -N, N-dimethylbetaine, an amphoteric compound in which R1 is cocamidopro-pyl, R2 and R3 are methyl, X is a direct bond, and is 2-hydroxypropyl and Z is -S03". Preferred non-cyclic surfactants of formula (II) are those in which R1 is C8-C30 aliphatic or modified C8-C30 aliphatic wherein at least one carbon atom of the main chain is substituted with -O-, -CONH-, -NHCO- or -CH = CH-; R 2 is hydrogen, C 1 Cg alkyl or carboxyalkyl (preferably, hydrogen, methyl or carboxyethyl); X is a direct bond or -NHC (= NH) -; Y is C- ^ Cg alkylene (preferably methylene or ethylene), and Z 'is -COO "M + or -S03" M + (where M + is a hydrogen ion or an alkali metal ion) or OH. Particularly preferred surfactants of formula (II) are compounds wherein Z 'is -COO "M + or -S03" M + (where M + is a hydrogen ion and / or an alkali metal ion). An especially preferred surfactant of formula (II) is the sodium salt of N-lauryl-β-iminodipropionic acid, a compound wherein R 1 is lauryl, R 2 is carboxyethyl, X is a direct bond, Y is ethylene and Z is -C00"Na +. Also suitable are octadecylguanidine polyoxyethanol mixtures (a compound of formula (II) in which R1 is octadecyl, R2 is hydrogen, X is -NHC (= NH) -, - YZ is - (CH2CH20) xH (ie, hydroxy-terminated alkylene containing oxygen heteroatoms)) and its by-product octadecylamine polyoxyethanol (a compound of formula (II) in which R1 is octadecyl, R2 is hydrogen, X is a direct bond, -YZ is - (CH2CH20) XH) The cyclic surfactants of the formulas (I) and (II), wherein X and R2, together with the N + (ie in the formula (I)) or the N (ie in the formula (II)), form rings of five to seven members, are heterocyclic compounds containing at least the ring nitrogen atom shown in the The X groups of said heterocyclic compounds are not direct bonds, but must always contain at least one atom such that the group R1 is not directly connected to the nitrogen atom shown in formulas (I) and (II), respectively. The group X may contain more than one such atom, provided that the resulting heterocyclic ring contains no more than seven ring atoms. For example, the group X can be groups having the formulas II -CH-, -C ~, -N-, -CHCH2-, -CHCH2CH2, and the like, thus forming heterocyclic rings which can be represented by the following formulas for surfactants of formula (I) R < R1-CHCH2- N + -? - z, R1-CHCH2CH- N + -? _ Z, RR and the like (where R1, R3, Y and Z are defined as above and R2 completes a ring of five to seven members) and the following formulas for surfactants of formula (II) R2 R2- ^ R1-CHCH- N-Y-Z f R1-CHCH2CH2-N-Y-Z, and similar (where R1, Y and Z 'are defined as before and R2 completes a ring of five to seven members). The heterocyclic moiety may be unsaturated, including that which is an aromatic ring, provided that the group Y is not bonded to an aromatic quaternary ring nitrogen. The heterocyclic moiety may also contain additional heteroatoms such as N, O or S in place of one or more ring carbon atoms, preferably in such a way that no two heteroatoms are directly linked together. The heterocyclic ring systems which can be incorporated into surfactants of the formulas (I) and (II) include imidazolines, imidazoles, oxazolidines, oxazolines and oxazoles. The preferred heterocyclic ring systems are imidazolines in which the R1 group is attached to the carbon atom of the C-2 ring and Y is attached to one of the ring nitrogen atoms. Particularly preferred surfactants containing said heterocyclic moieties are 2- (8-heptadecenyl) -2-imidazoline-1-ethanol, a compound of formula (II) wherein X and R2 together form an imidazoline moiety, R 1 is 8-heptadecenyl, And it is ethylene and Z is OH and it is represented by the following formula and 4,5-dihydro-1- (hydroxyethyl) -1 (or 3) - (2-hydroxy-3-sulfopropyl) -2-norcocoalkylimidazolinium salt, an amphoteric compound within the scope of formula (I) and represented by one of the following formulas or by both I where R represents norcocoalkyl. Of course, the mixtures of surfactants described above are also suitable. It is also possible to include as additional components in * stage (a) surfactants outside the definition of formulas (I) and (II), as well as other conventional additives. Examples of such suitable additives include long chain fatty acids, such as stearic acid or behenic acid, or amides, esters or corresponding salts, such as magnesium stearate, zinc stearate, aluminum stearate or magnesium behenate; resin acids, such as abietic acid, rosin soap, hydrogenated or dimerized rosin; C12-C? a-disulfonic paraffin acids; sulfonated dicarboxylic acids or corresponding esters or amides thereof, such as sulfosuccinates, sulfosuccinamates and their derivatives; alkyl phosphates and phosphonates; amines, such as laurylamine or stearylamine; polyamines, such as polyethyleneimines; quaternary ammonium compounds, such as tri [(alkylC-benzyl) ammonium salts; alkylphenols; alcohols and diols, such as stearyl alcohol and dodecane-1,2-diol; fatty acids and alkoxylated amides, alkoxylated alcohols, alkoxylated alkylphenols and glycol esters, waxes, such as polyethylene wax, and plasticizers, such as epoxidized soybean oil, said additives can be incorporated in amounts ranging from about 0.1 to 20% by weight (preferably, from 0, 1 to 5% by weight), based on the amount of the surfactants according to the invention Conventional additives can in themselves sometimes improve the dispersibility of the pigment, however, even when such additives are included, the pigments prepared with The surfactants of formula (I) and (II) according to the invention exhibit better dispersibilities in relation to pigments not treated with surfactants according to the invention. a) is carried out in a liquid (2) in which the organic pigment is substantially insoluble, preferably water, a water-soluble organic liquid (including partially water-soluble) or mixtures of these. Suitable liquids include water and mixtures of water and lower aliphatic alcohols, such as methanol; ketones and ketoalcohols, such as acetone, methyl ethyl ketone and diacetone alcohol; amides, such as dimethylformamide and dimethylacetamide ethers, such as tetrahydrofuran and dioxane; alkylene glycols and triols, such as ethylene glycol and glycerol, and other organic liquids of this type known in the art. Other organic liquids can be used, but are generally less preferred. In general, at least 0.1% by weight is used (preferably 0.1 to 100% by weight (ie, one weight ratio of one to one) and, more preferably, 2 to 15% by weight) of the surfactant, relative to the organic pigment. The temperature for step (a) should be maintained between about 50 ° C and about 200 ° C, preferably between 70 ° C and 150 ° C. The conditioned organic pigment can optionally be surface treated in step (b), either in situ or after being isolated, by mixing the conditioned organic pigment with a suitable surface treatment additive in a liquid (such as those described above). wherein the organic pigment is substantially insoluble. Suitable additives include the additives described above for use in conjunction with the surfactants of the invention. The organic pigment conditioned and optionally treated on the surface is collected in step (c) by methods known in the art, but is preferably collected by filtration, followed by washing to remove residual salts and solvent. Other collection methods known in the art are suitable, such as centrifugation or even simple decanting, but are generally less preferred. The pigment is then dried for use or for further handling before use.

The pigments of this invention give a very good dyeing performance and are easily dispersible (for example, in plastic materials). Due to their light stability and migratory properties, the pigments according to the present invention are suitable for many different pigment applications. The pigments of the present invention are particularly suitable for use with macromolecular materials, especially macromolecular synthetically produced substances. Examples of synthetic macromolecular substances include plastic materials, such as polyvinyl chloride, polyvinyl acetate and polyvinyl propionate; polyolefins, such as polyethylene and polypropylene; high molecular weight polyamides; polymers and copolymers of acrylates, methacrylates, acrylonitrile, acrylamide, butadiene or styrene; polyurethanes, and polycarbonates. Other suitable macromolecular substances include those of natural origin, such as rubber; those obtained by chemical modification, such as acetylcellulose, cellulose butyrate or viscose; or those produced synthetically, such as polymers, polyaddition products and polycondensates. The materials pigmented with the pigments of the invention can have any desired shape, including molded articles, films and fibers. The pigments of the present invention are also suitable for blends pigmented with other materials, pigment formulations, coating compositions and paints, printing ink and colored paper. It is understood that the term "mixtures with other materials" includes, for example, mixtures with inorganic white pigments, such as titanium dioxide (rutile) or cement, or other inorganic pigments. Examples of pigment formulations include pastes washed with organic liquids or pastes and dispersions with water, dispersants and, if appropriate, preservatives. Examples of coating compositions and paints in which the pigments of this invention may be used include, for example, physical or oxidative drying lacquers, hot enamels, reactive paints, two-component paints, solvent-based paints or water, emulsion paints for watertight and tempered coatings. Printing inks include those known for use in printing on paper, fabrics and tinplate. The following examples illustrate details for the process of this invention. The invention, set forth in the foregoing description, should not be limited in spirit or scope by these examples. Those skilled in the art will readily understand that known variations of the conditions of the following procedures can be used. Unless otherwise indicated, all temperatures are degrees Celsius and all percentages and parts are percentages by weight and parts by weight, respectively. EXAMPLES Dispersibilities of the pigments in polyvinyl chloride ("PVC") were evaluated by comparing the development of hot ground and cold ground color according to the following procedure. For each sample studied, a mixture of 48.95 g of flexible PVC and 1.0 g of a 50% titanium dioxide paste was added to a hot two-roll mill (155 ° C) having a contact thickness of 25 mils (about 0.6 mm) and washed until uniform. A 0.050 g portion of the test pigment or comparative pigment was sprayed into the contact line over a period of about ten seconds, after which the washed material was cut and rotated in the mill for five minutes. . The pigmented sheet was then removed from the mill and placed on a clean flat surface to cool it. A piece cut from the resulting sheet was used and left to cool down to room temperature as a "hot mill" sample for evaluation. A sample cut from the same sheet was placed while it was still hot in a cold two-roll mill (24 ° C) having a contact thickness of 21 mils (about 0.5 mm), then folded and passed through the mill seven times. The cold-rolled sheet was again washed in the hot mill until smooth. A sample cut from the resulting sheet was used as a "cold-milled" sample for evaluation. The reflectances of corresponding hot-ground and cold-milled samples were determined using a Datacolor CS-5 spectrophotometer and converted to K / S values according to the Kubelka-Munk equation. Dispersibilities were calculated by comparing the K / S value of each hot-milled sample with the K / S value of the corresponding cold-milled samples (assumed to have reached 100% dispersion and maximum K / S values). In general, the dispersibilities were considered excellent for values of 80 to 100%, good for values of 60 to less than 80%, regular if they were 40 to less than 60%, poor if they were 20 to less than 40% and very poor if they were less than 20%. EXAMPLES 1-11 Treatment of dimethylperile dye not Examples 1-5 and 9 describe the conditioning of a crude dimethylperylene-diimide filter cake press (Pigment Red 179) according to the invention. Examples 1-5 (but not Example 9) also included sodium dioctylsulfosuccinate and aliphatic naphtha during conditioning. Comparative Example 6 was carried out by the same general method as that used for Example 2, except for the omission of cocamido-propylbetaine surfactant. Comparative Examples 7, 8, 10 and 11 were carried out by the same general method as that used in Example 1, except for the use of surfactants that are not according to the invention. Example 1 Crude dimethylperylenediimide filter press cake (86.1 g, corresponding to 26.0 g of pigment of 100% strength) was suspended in a mixture of 111 g of methanol, 192.9 g of water, 2.6 g of 50% sodium hydroxide and 7.4 g of 35% cocamidopropylbetaln. The resulting suspension was heated at 135 ° C for four hours in a laboratory Parr reactor, then cooled to 45 ° C and diluted to 700 ml with water. An aqueous emulsion containing 0.08 g of sodium dioctylsulfosuccinate and 0.8 g of aliphatic naphtha was added and the suspension was maintained at 45 ° C for three hours. The solid component was collected by filtration, washed, dried and pulverized to a powder having excellent dispersibility in PVC. The results of the test are shown in Table 1. Example 2 Crude dimethylperylenediimide filter press cake (86.1 g, corresponding to 26.0 g of 100% strength pigment) was suspended in a mixture of 303.9 g of water, 2.6 g of 50% sodium hydroxide and 7, 4 g of 35% cocamidopropyl betaine. The resulting suspension was heated at 145 ° C for four hours, then cooled and diluted to 700 ml with water. An aqueous emulsion containing 0.08 g of sodium dioctylsulfosuccinate and 0.8 g of aliphatic naphtha was added and the suspension was heated at 45 ° C for three hours. The solid component was collected by filtration, washed with water, dried and pulverized to a powder having excellent dispersibility in PVC. The results of the test are shown in Table 1. Example 3 A pigment was prepared in the same way as in the Example 1, except for the use of N- [3- (cocamido) -propyl-N- (2-hydroxy-3-sulfopropyl) -N, N-dimethylbetaine in place of cocamidopropylbetaine. The resulting pigment exhibited excellent dispersibility in PVC. The results of the test are shown in Table 1. Example 4 A pigment was prepared in the same manner as in Example 1, except for the use of 2- (8-heptadecenyl) -2-imidazoline-1-ethanol in place of cocamidopropylbetaine. The resulting pigment exhibited excellent dispersibility in PVC. The results of the test are shown in Table 1. Example 5 A pigment was prepared in the same manner as in Example 1, except for the use of the internal salt of 4,5-dihydro-1- (hydroxyethyl) -1 (or 3) - (2-hydroxy-3-sulfopropyl) ) -2-norcocoalkylimidazolinium instead of cocamidopropylbetaine. The resulting pigment exhibited excellent dispersibility in PVC. The results of the test are shown in Table 1. EXAMPLE 6 (Comparative) Crude dimethylperylenediimide (86.1 g, corresponding to 26.0 g of pigment of a strength of 100%) was suspended in a mixture of 296.1 g of methanol, 15.2 g of water and 2, 6 g of 50% sodium hydroxide. The resulting suspension was heated at 120 ° C for four hours, then cooled and diluted to 700 ml with water. An aqueous emulsion containing 0.8 g of sodium dioctylsulfosuccinate and 13.0 g of aliphatic naphtha was added and the suspension was heated at 45 ° C for three hours. The solid component was collected by filtration, washed, dried and pulverized to a powder having poor dispersibility in PVC. The results of the test are shown in Table 1. Example 7 (Comparative) A comparative pigment was prepared in the same manner as in Example 1, except for the use of the non-ionic surfactant Tergitol 15-5-9 (which is not according to the invention) instead of cocamidopropylbetaine. The resulting pigment exhibited good dispersibility in PVC, but was inferior to the pigment of Example 1 of the invention. The results of the test are shown in Table 1. Example 8 (Comparative) A comparative pigment was prepared in the same manner as in Example 1, except for the use of the anionic surfactant Dyasulf C-70 (which is not according to the invention) in place of cocamidopropylbetaine. The resulting pigment exhibited good dispersibility in PVC, but was inferior to the pigment of Example 1 of the invention. The results of the test are shown in Table 1. Example 9 Crude dimethylperylene dimiimide (86.1 g, corresponding to 26.0 g of pigment of a strength of 100%) in a mixture of 111.0 g of methanol, 192.9 g of water and 2.6 g of 50% sodium hydroxide containing 7.4 g of 35% cocamidopropyl betaine. The resulting suspension was heated at 135 ° C for four hours, then cooled and diluted to 700 ml with water. The solid component was collected by filtration, washed with water, dried and pulverized to a powder having good dispersibility in PVC. The results of the test are shown in Table 1. Example 10 (Comparative) A comparative pigment was prepared in the same manner as in Example 9, except for the use of the nonionic surfactant employed in Comparative Example 7 instead of cocamidopropylbetaine. The resulting pigment exhibited a regular dispersibility in PVC, but was inferior to the pigment of Example 9 of the invention. The results of the test are shown in Table 1. Example 11 (Comparative) A comparative pigment was prepared in the same manner as in Example 9, except for the use of the anionic surfactant employed in Comparative Example 8 instead of cocamidopropylbetaine. The resulting pigment exhibited a regular dispersibility in PVC, but was inferior to the pigment of Example 9 of the invention. The results of the test are shown in Table 1.

Table 1 PVC Dispersibilities for Examples 1-11 Dispersibility in PVC * Dioctyl sulfosuccinate sodium and aliphatic naphtha included during conditioning. Examples 1-11 show that the conditioning of perylene pigments in the presence of surfactants according to the invention (ie, Examples 1-5 and 9) provides more highly dispersible pigments than untreated pigments (ie, Example 6) or pigments conditioned with nonionic and anionic surfactants that are not according to the invention (ie, Examples 7, 8 , 10 and 11). Although the conditioning in the presence of sodium dioctylsulfosuccinate and aliphatic naphtha provided pigments having a better dispersibility in relation to the untreated pigments, the corresponding pigments prepared according to the invention were always superior. EXAMPLES 12-14 Perylene Pigment Treatment Example 12 describes the packaging of crude perylene-diimide filter press cake (Pigment Violet 29) according to the invention. Comparative Example 13 was carried out by the same method as that employed in the Example 12, except for the omission of the sodium salt of N-lauryl-β-iminodipropionic acid. The Comparative Example 14 was carried out by the same method as that employed in Example 12, except for the omission of the sodium salt of N-lauryl-β-iminodipropionic acid and the mixture of sodium dioctylsulfosuccinate and aliphatic naphtha during conditioning. Example 12 Crude perylenediimide filter presscake (83.9 g, corresponding to 26.0 g of 100% strength pigment) was suspended in a mixture of 185.1 g of methanol, 119.7 g of water , 2.6 g of 50% sodium hydroxide and 8.7 g of sodium salt of 30% N-lauryl-β-iminodipropionic acid. The resulting mixture was heated at 125 ° C for six hours in a laboratory Parr reactor, then cooled and diluted to 700 ml with water. An aqueous emulsion containing 0.9 g of sodium dioctylsulfosuccinate and 13.0 g of aliphatic naphtha was added to the suspension heated at 45 ° C for three hours. The solid component was collected by filtration, washed with water, dried in the oven and pulverized to a powder having good dispersibility in PVC The results of the test are shown in Table 2.

Example 13 (Comparative) A comparative pigment was prepared in the same manner as in Example 12, except for the omission of the sodium salt of N-lauryl-β-iminodipropionic acid. The resulting pigment exhibited a very poor dispersibility in PVC. The results of the test are shown in Table 2. Example 14 (Comparative) A comparative pigment was prepared in the same manner as in Example 12, except for the omission of the sodium salt of N-lauryl-β-iminodipropionic acid and the mixture of sodium dioctylsulfosuccinate and aliphatic naphtha. The resulting pigment exhibited a very poor dispersibility in PVC. The results of the test are shown in Table 2. Table 2 PVC Dispersibilities for Examples 12-14 PVC Dispersibility * Dioctyl sulfosuccinate sodium and aliphatic naphtha included during conditioning. Examples 12-14 show that the conditioning of perylene pigments in the presence of the sodium salt of N-lauryl-β-iminodipropionic acid according to the invention provides a highly dispersible pigment in comparison with the untreated pigment or with the pigment treated only with a mixture of sodium dioctyl sulfosuccinate and aliphatic naphtha. EXAMPLES 15-16 Treatment of indantrone pigment Example 15 describes the conditioning of crude indantrone (Blue Pigment 60 or Blue Vat 4, obtained as Blue Indantrene RSN (CDP) from Sunbelt Corporation) according to the invention. Comparative Example 16 was carried out by the same method, except for the omission of the codamidopropylbetaine surfactant. Example 15 100 parts of indantrone were introduced into a ball mill containing 3000 parts of steel balls as milling elements. The capacity of the ball mill was such that it was 60% full when fully loaded. The mill was rotated for 48 hours, after which the powder was discharged through a sieve that retained the grinding elements. The ground powder was added to water (four times the weight of the pigment) and stirred until completely wet. The powder moistened with methyl benzoate (80% by weight of pigment powder) was treated and then heated at 140 ° C for eight hours. After cooling the mixture, the methyl benzoate was hydrolyzed using 50% aqueous sodium hydroxide at 90 ° C for 2 hours. After cooling the hydrolysed mixture, cocamidopropylbetaine (10% by weight pigment) was added and the mixture was heated at 140 ° C for four hours. After cooling, the solid component was collected by filtration, filtered, washed with water and dried to give a conditioned pigment having excellent dispersibility in PVC. The results of the test are shown in Table 3. Example 16 (Comparative) A comparative pigment was prepared in the same manner as in Example 15, except for the omission of cocamidopropylbetaine. The resulting pigment exhibited good dispersibility in PVC. The test results are shown in Table 3.

Table 3 PVC Dispersibilities for Examples 15 and 16 Dispersibility in PVC Examples 15 and 16 show that the dispersibility of indantrone was improved by conditioning in the presence of cocamidopropylbetaine according to the invention. EXAMPLES 17-18 Treatment of a Copper Phthalocyanine Pigment Example 17 describes the conditioning of a mixture of cupric phthalocyanines containing 70% by weight of chlorine-free copper phthalocyanine and 30% by weight of monocyclic copper phthalocyanine according to the invention . Comparative Example 18 was carried out by the same method, except for the omission of the surfactant. Example 17 Example 15 was repeated, except for the substitution of indantrone with a mixture of 70% by weight of chlorine-free copper phthalocyanine (obtained from Toyo Ink Inc.) and 30% by weight of monochlorinated copper phthalocyanine (obtained of Sanyo Color Works). The resulting pigment had good dispersibility in PVC. The results are shown in Table 4. Example 18 (Comparative) A comparative pigment was prepared in the same manner as in Example 17, except for the omission of cocamidopropylbetaine. The resulting pigment exhibited a regular dispersibility in PVC. The results of the test are shown in Table 4.

Table 4 PVC Dispersibilities for Examples 17 and 18 Dispersibility in PVC Examples 17 and 18 show that the dispersibility of the pigments of chlorinated cupric phthalocyanines was improved by conditioning in the presence of cocamidopropylbetaine according to the invention. EXAMPLES 19-22 Treatment of isoindoline pigment Examples 19 and 21 describe the condition Pigment Yellow 139 (a isoindoline pigment) crude according to the invention. Example 21 also included sodium dioctyl sulfosuccinate and aliphatic naphtha during conditioning. Comparative Examples 20 and 22 were carried out by the same general method as that used in Examples 19 and 21, respectively, except for the omission of the cocamidopropylbetaine surfactant. Example 19 Crude Pigment Yellow 139 filter press cake (55.75 g, corresponding to 20 g of 100% strength pigment) was suspended in 300 g of water. When the mixture remained uniform, 5.7 g of cocamidopropyl betaine was added and the pH adjusted to 6.0. The mixture was heated at 130 ° C for two hours in a laboratory Parr reactor and then cooled to room temperature. The solid component was collected by filtration and washed with water. The cake of the wet filter press was dried in the oven at 60 ° C overnight to obtain 20.0 g of a yellow pigment exhibiting a smooth texture and regular dispersibility in PVC. The results of the test are shown in Table 5. Example 20 (Comparative) A comparative pigment was prepared in the same manner as in Example 19, except for the omission of cocamidopropylbetaine. The resulting pigment exhibited poor dispersibility in PVC. The results of the test are shown in Table 5. Example 21 Example 19 was repeated, except for the fact that the cooled mixture of the Parr reactor was treated with an aqueous emulsion of 0.6 g of sodium dioctyl sulfosuccinate, 10.0 g of aliphatic naphtha and 40.0 g of water and the resulting mixture was stirred at 45 ° C for 3 hours, after which the resulting suspension was filtered and washed with water. The wet cake was dried from the filter press in an oven at 60 ° C overnight to obtain 20.0 g of a yellow pigment exhibiting a smooth texture with excellent dispersibility in PVC. The results of the test are shown in Table 5. Example 22 (Comparative) A comparative pigment was prepared in the same manner as in Example 21, except for the omission of cocamidopropylbetaine. The resulting pigment exhibited good dispersibility in PVC. The results of the test are shown in Table 5.

Table 5 PVC Dispersibilities for Examples 19-22 Dispersibility in PVC * Dioctyl sulfosuccinate sodium and aliphatic naphtha included during conditioning.

Examples 19-22 show that the conditioning of isoindoline pigments in the presence of cocamidopropylbetaine according to the invention provides more highly dispersible pigments than untreated pigments. Although the conditioning in the presence of a mixture of sodium dioctylsulfosuccinate and aliphatic naphtha gave pigments with a better dispersibility in relation to the untreated pigments, the pigments prepared according to the invention were always superior to the corresponding pigments not conditioned according to the invention. For example, although the pigment of Example 19 exhibited only a regular dispersibility, the corresponding comparative pigment of Example 20 was inferior.

Claims (19)

1. CLAIMS 1. A process for preparing pigment compositions consisting of (a) conditioning an organic pigment at a temperature of about 50 to about 200 ° C with (1) at least about 0.1% by weight, based on the pigment organic, of one or more surfactants, consisting of (i) an anionic surfactant of formula R2 Rx-X-N + -YZ I R3 where R1 is C8-C30 aliphatic or modified C8-C30 aliphatic, wherein at least one carbon atom of the main chain is substituted with -O-, -S-, -CONH- , -NHCO-, -CH = CH-, -OSi (C 1 -C 4) alkyl 2- or C 5 -C 7 cycloalkylene; R2 is hydrogen, C-C6 alkyl or -Y-Z '; R3 is hydrogen or alkyl or R2 and R3 together are alkylene V-_ ^ -7 X is a direct bond or -NHC (= NH) -, or X and R2 taken together with N + form a heterocyclic ring of five to seven members; And it is (cyclo) aliphatic C ^ CQ difunctional; Z is -COO ", -S03", -P03 = -l / n Mn + (where Mn + is a hydrogen ion or an n-valent cation), or OH, with the proviso that, if Z is OH, then it must be present an anionic counter ion, and 10 Z 'is -COO "-l / n Mn +, -S03" -l / n Mn +, or -P03 = -2 / n Mn + (where Mn + is a hydrogen ion and / or a cation n - valent) or OH, with the proviso that Z 'must be OH if Z is 15 OH; (ü) a surfactant of formula R ^ R -X-N-Y-Z1 (II) wherein R1 is aliphatic C "-C, n or modified C8-C30 aliphatic, where at least one carbon atom in the main chain is substi 25 with -O-, -S-, -CONH-, -NHCO-, -CH = CH-, -OSi (C 1 -C 4) alkyl 2-, or optionally substituted C-C 7 cycloalkylene; R2 is hydrogen, C-C6 alkyl or 30 -. 30 -Y-Z '; X is a direct bond or -NHC (= NH) -, or X and R2 taken together with N form a heterocyclic ring of five to seven members; Y is (cyclo) aliphatic C ^ g difunctional and Z 'is -COO "-l / n Mn +, -S03" -l / n Mn +, or -P03 = -2 / n Mn + (where Mn + is a hydrogen ion and / or an n-valent cation) or OH, or (iii) mixtures thereof, and (2) about 1 to about 100 parts by weight, per part by weight of the organic pigment, of a liquid in which the organic pigment is substantial. essentially insoluble, thus forming a suspension of the organic pigment conditioned in the liquid; (b) optionally, treating the conditioned organic pigment on the surface, and (c) collecting the conditioned organic pigment.
2. 2. A process according to Claim 1, wherein the organic pigment is a perylene, a phthalocyanine, an indantrone, an isoindoline or a quinacridone.
3. 3. A process according to Claim 1, wherein the surfactant (1) is a non-cyclic ionic surfactant of formula R2 R ^ X-N'-YZ I R3 where R1 is C8-C30 aliphatic or modified C8-C30 aliphatic, wherein at least one carbon atom of the main chain is substituted with -0-, -CONH-, -NHC0 - or -CH = CH-; R2 and R3 are independently hydrogen or Cx-C6 alkyl; X is a direct bond or -NHC (= NH) -; Y is C-C3 alkylene, and Z is -COO ", -S03" or OH, with the proviso that, if Z is OH, then a stoichiometric amount of an anionic counterion must be present.
4. 4. A process according to Claim 1, wherein the surfactant (1) is cocamidopropylbetaine or N- [3- (cocamido) propyl-N- (2-hydroxy-3-sulfopropyl) -N, N-dimethylbetaine.
5. 5. A process according to claim 1, wherein the surfactant (1) is a non-cyclic surfactant of formula wherein R1 is the aliphatic aliphatic C8-C30 or aliphatic C8-C30, wherein at least one carbon atom of the main chain is substituted with -O-, - CONH-, -NHCO- or CH = CH-; R is hydrogen, alkyl or carboxyalkyl; X is a direct bond or -NHC (= NH) -, - Y is alkylene and Z 'is -C00"M + or -S03" M + (where M + is hydrogen or an alkali metal ion) or OH.
6. 6. A process according to Claim 1, wherein the surfactant (1) is the sodium salt of N-lauryl-β-iminodipropionic acid.
7. 7. A process according to Claim 1, wherein the surfactant (1) is a cyclic surfactant of formula R ^ Rx-X-N + -YZ R3 where R1 is C8-C30 aliphatic or modified C8-C30 aliphatic, wherein at least one carbon atom of the main chain is substituted with -0-, -CONH-, -NHCO- or -CH = CH-; X and R2 together with the N + form a ring of five to seven members; And it is alkylene and is -COO "-SO" or OH.
8. 8. A process according to Claim 1, wherein the surfactant (1) is an internal salt of 4,5-dihydro-1- (hydroxyethyl) -1 (or 3) - (2-hydroxy-3-sulfopropyl) -2-norcocoal -quimimidazolinium.
9. 9. A process according to Claim 1, wherein the surfactant (1) is a cyclic surfactant of formula R2 Rx-XNYZ 'where R1 is aliphatic C8-C30 or aliphatic Ca-C30 modified where at least one carbon atom of the main chain is substituted with -O-, -CONH-, -NHCO- or -CH = CH-; X and R¿ together with the N form a ring of five to seven members; Y is alkylene and Z1 is -COO "M + or -S03" M + (where M + is hydrogen or an alkali metal ion) or OH.
10. 10. A process according to Claim 1, wherein the surfactant (1) is 2- (8-heptadecenyl) -2-imidazoli-na-1-ethanol.
11. 11. A process according to Claim 1, wherein from 0.1 to 100% by weight, based on the organic pigment, of surfactant (1) is used.
12. 12. A process according to Claim 1, wherein from 6 to 12 parts by weight per part by weight of the liquid organic pigment (2) is used in step (a).
13. 13. A process according to Claim 1, wherein the liquid (2), in which the organic pigment is substantially insoluble, is water, a water-soluble organic liquid or a mixture thereof.
14. 14. A process according to Claim 1, wherein the conditioned pigment is treated with a surface treatment additive.
15. 15. A process according to Claim 1, wherein the conditioned pigment is collected by filtration.
16. 16. A pigment composition prepared according to the method of Claim 1.
17. 17. A pigmented macromolecular substance containing, as a pigment, a pigment composition prepared according to the method of Claim 1.
18. 18. A pigmented coating composition containing, as pigment, a pigment composition prepared according to Claim 1.
19. 19. A pigmented printing ink containing, as a pigment, a pigment composition prepared according to Claim 1.