EP1769034A1 - Nouvelles modifications cristallines du c.i. pigment yellow 181 et procedes de realisation associes - Google Patents

Nouvelles modifications cristallines du c.i. pigment yellow 181 et procedes de realisation associes

Info

Publication number
EP1769034A1
EP1769034A1 EP05757161A EP05757161A EP1769034A1 EP 1769034 A1 EP1769034 A1 EP 1769034A1 EP 05757161 A EP05757161 A EP 05757161A EP 05757161 A EP05757161 A EP 05757161A EP 1769034 A1 EP1769034 A1 EP 1769034A1
Authority
EP
European Patent Office
Prior art keywords
shoulder
modification
rel
intensity
pigment yellow
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP05757161A
Other languages
German (de)
English (en)
Inventor
Martin U. Schmidt
Gerald Mehltretter
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Clariant Produkte Deutschland GmbH
Original Assignee
Clariant Produkte Deutschland GmbH
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Clariant Produkte Deutschland GmbH filed Critical Clariant Produkte Deutschland GmbH
Publication of EP1769034A1 publication Critical patent/EP1769034A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0025—Crystal modifications; Special X-ray patterns
    • C09B67/0028—Crystal modifications; Special X-ray patterns of azo compounds
    • C09B67/0029—Crystal modifications; Special X-ray patterns of azo compounds of monoazo compounds

Definitions

  • the present invention relates to four new crystal modifications (eta, theta, jota, kappa) of Cl.
  • Pigment Yellow 181 of the formula (1) their preparation and
  • AIs CI. Pigment Yellow 181 (hereinafter: P.Y. 181) becomes the compound of
  • the compound (1) may also be present in another tautomeric and / or cis-trans isomeric form and optionally also contain water molecules, usually up to 10 wt .-%.
  • Crystal modifications have the same chemical composition, but a different arrangement of the building blocks (molecules or ions) in the crystal.
  • the crystal structure determines the chemical and physical properties, therefore, the individual crystal modifications often differ in rheology, color and other coloristic properties.
  • the different crystal modifications can be identified by X-ray powder diffractometry. From PY 181 so far six crystal modifications are known. They are referred to below as alpha, beta, gamma, delta, epsilon and zeta modification. They are characterized by the following characteristic lines in the X-ray powder diagram (Cu-K ⁇ 1 radiation, double diffraction angles 2 ⁇ in degrees, d values in A "1 in degrees, interplanar spacings d in A '1 ):
  • P.Y. 181 in the alpha phase is obtained when the diazonium salt of 4- (4'-amino-benzoylamino) benzamide with 5-Acetoacetylaminobenzimidazolon
  • the beta phase is obtained by treating the P.Y.181 obtained from the coupling with dimethylformamide as described in Example 1 in EP-A-0 010 273.
  • the gamma phase is obtained by carrying out the coupling in pyridine and then heating the reaction mixture to reflux.
  • the delta phase is obtained by treatment of P.Y. 181 in the
  • the epsilon phase is obtained in an analogous manner by treatment with
  • N-methylpyrrolidone N-methylpyrrolidone.
  • the zeta phase is obtained by carrying out the coupling in a mixture of water and N-methylpyrrolidone and then heating the reaction mixture to reflux.
  • PY 181 can be prepared in four new crystal modifications by heating the pigment after synthesis in certain solvents, wherein the pigment dissolves partially or completely, and then precipitates again.
  • the new crystal modifications are called eta, theta, iota and kappa modification. They are characterized by the following characteristic lines (Cu K ⁇ -i radiation, 2 ⁇ values in degrees, d values in A "1 , measured at room temperature in transmission):
  • the number of observable peaks of an X-ray powder diagram particularly depends on the crystallite size distribution Anisotropy of the particle shape, the anisotropic crystal quality (in particular with respect to stress, strain and crystal defects), on the amount of sample, the diffractometer used and on the measurement geometry.
  • the intensities in all cases additionally depend on texture effects, especially in the case of anisotropic crystallite form, as well as on the method used to extract the intensities. Under favorable conditions, the following lines can be observed (Cu K ⁇ -i radiation, 2 ⁇ values in degrees, d values in A "1 , measured at room temperature in transmission):
  • Solvent molecules contained in the crystal lattice usually up to 10 wt .-%, based on the total weight. All four new modifications are sparingly soluble and are characterized by yellow shades and good coloristic properties.
  • the present invention therefore provides a process for the phase transformation of Cl. Pigment Yellow 181, characterized in that the compound of the formula (1)
  • a solvent from the group consisting of water, dimethylacetamide, mixture of dimethyl sulfoxide and N-methylpyrrolidone, and mixture of 1, 2-dichlorobenzene and N-methylpyrrolidone at a temperature of 40 to 250 0 C, preferably 110 to 210 0 C, act.
  • the starting material for the preparation of the new crystal phases is preferably PY 181 in one of the known modifications, particularly preferably in the alpha or in the beta modification, but it is also possible in each case one or more of the new crystal modifications with the described measures in one of the other to transform new crystal modifications.
  • the isolated PY 181, for example in the ⁇ - or in the ⁇ -phase expediently completely or partially dissolved in the solvent according to the invention and then precipitated again by addition of water, lowering the temperature and / or evaporation of the solvent.
  • the heating of the pigment can be carried out both under normal pressure and under elevated pressure, wherein the pressure between 1 bar and 200 bar, preferably between 1 bar and 50 may be bar.
  • the duration of the solvent treatment may suitably be 1 minute to 10 hours, preferably 30 minutes to 5 hours.
  • the theta phase is obtained by recrystallization in a mixture of dimethyl sulfoxide and N-methylpyrrolidone. It is PY 181, z. B. the beta phase, dissolved in a mixture of dimethyl sulfoxide and N-methylpyrrolidone in the mixing range of 25 to 75 volume percent to 75 to 25 volume percent, preferably in a mixing range of 40 to 60 to 60 to 40 volume percent, preferably at a temperature between 150 0 C and 200 0 C, and precipitated by subsequent lowering of temperature and / or addition of water.
  • the eta phase is formed in an analogous manner, if a mixture of N-methylpyrrolidone and 1, 2-dichlorobenzene in the mixing range of 25 to 75 volume percent to 75 to 25 volume percent, preferably in a mixing range of 40 to 60 to 60 to 40 volume percent Solvent begins.
  • the iota phase is obtained when PY 181, z. B. the beta phase, preferably in dimethylacetamide heated to a temperature between 120 and 18O 0 C, the suspension is filtered off and the filtrate is cooled to room temperature. The pigment crystallizes out of the solution.
  • the kappa phase is obtained when PY 181, for example, the alpha phase, in water, preferably to a temperature of 110 0 C to 15O 0 C, in particular from 120 ° C to 14O 0 C, heated in a pressure reactor, conveniently for 1 minute to 6 hours, preferably for 10 minutes to 2 hours. A longer heating is possible, but brings no technical advantages. Subsequently, the pigment is filtered off.
  • the new ones can be used Crystal modifications in pure form or as mixtures of the new phases with each other and / or with the known phases arise.
  • a pure or predominantly pure crystal modification arises preferentially when starting from a solution or suspension in which seed crystals or seed crystals of this modification are already present, and when the precipitation is carried out so slowly that the supersaturation is kept within a range in which the Crystal growth rate is relatively high, the nucleation rate, however, is relatively low, so that the existing crystal nuclei grow while maintaining the modification.
  • the use of a mechanical stirrer can be advantageous because it smashes existing crystals of the desired modification into many smaller fragments, which then serve as nuclei for this modification (so-called secondary nucleation). If the supersaturation is higher, e.g. because the solution is cooled more rapidly, the nucleation rate is much higher, so that many nuclei of this modification and other modifications can spontaneously form; In this case, it is preferable to obtain modification mixtures which consist only in part of the desired modification.
  • the preparation of a blend of several of the modifications of the present invention, or of one or more of the modifications of the invention having the known modifications, may be of interest if certain coloristic and rheological properties are desired, especially if properties are desired that are in between the properties of the pure modifications.
  • the present invention therefore also relates to a PY 181 mixture which is at least 10%, preferably at least 25%, in particular at least 50%, more preferably at least 75%, most preferably at least 90% of the eta-modification, the theta-modification, the iota-modification, the kappa-modification or a mixture of said modifications.
  • the fine distribution can be done by wet or dry grinding or kneading.
  • the grinding or kneading may be followed by a treatment with a solvent, with water, or with a solvent / water mixture in order to convert the pigment into a usable form.
  • pigment dispersants can be added at any point in the process. It is also possible to use mixtures of these additives. The addition of the additives can be done all at once or in several portions. The additives can be used at any point in the synthesis or the various
  • Post-treatment, or after the post-treatment can be added.
  • the most appropriate time must first be determined by preliminary experiments.
  • the PY 181 in the modifications according to the invention or in mixtures containing the modifications according to the invention are suitable for pigmenting high molecular weight organic materials of natural or synthetic origin, for example of paints, plastics, resins, paints, printing inks, pigment preparations, in particular aqueous or solvent-containing pigment preparations, electrophotographic toners and developers, inks, ink-jet inks, color filters and electronic inks, and for coloring seeds.
  • the modifications according to the invention are particularly suitable for coloring plastic films.
  • Electrophotographic toners and developers are understood as meaning one- or two-component powder toners (also referred to as one- or two-component developers), magnetic toners, liquid toners, latex toners, polymerization toners and special toners which are generally known to the person skilled in the art.
  • Typical toner binders are Polymerisati ⁇ ns-, polyaddition and
  • Polycondensation resins such as styrene, styrene acrylate, styrene butadiene, acrylate, polyester, phenolic epoxy resins, polysulfones, polyurethanes, individually or in combination, as well as polyethylene and polypropylene, which may contain other ingredients, such as charge control agents, waxes or flow aids or be modified afterwards with these additions.
  • Ink-jet inks are understood as meaning those aqueous or non-aqueous based, microemulsion inks and inks which operate according to the hot-melt process, which are generally known to the person skilled in the art.
  • Example 2 Preparation of the theta phase by recrystallization in DMSO and NMP The procedure is as in Example 1, but using dimethyl sulfoxide instead of 1, 2-dichlorobenzene. PY 181 is obtained in the theta phase.
  • P.Y. 181 in the beta phase 30 parts are heated to boiling with 160 parts of dimethylacetamide, it dissolves in a small part. The suspension is filtered off. Upon cooling to room temperature, the dissolved portion of the pigment slowly re-crystallizes from the filtrate. One receives P.Y. 181 in the iota phase.
  • Example 4 Production of the kappa phase by pressure treatment with water
  • PY 181 in the alpha phase 25 parts are heated with 500 parts of water in an autoclave to 140 0 C for 120 minutes. The suspension is allowed to cool and the pigment is filtered off. The press cake is washed salt-free and dried. PY 181 is obtained in the kappa phase.
  • PY 181 in the alpha phase 25 parts are heated with 500 parts of water in an autoclave to 140 0 C for 120 minutes. The suspension is allowed to cool and the pigment is filtered off. The presscake is washed salt-free and heated to 11O 0 C with 1400 parts of glacial acetic acid for 30 minutes. The pigment is filtered off and the presscake is washed with water and acetone. PY 181 is obtained in the kappa phase.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Developing Agents For Electrophotography (AREA)
  • Paints Or Removers (AREA)

Abstract

L'invention concerne le C.I. Pigment Yellow 181 obtenu avec de nouvelles modifications cristallines (eta, theta, jota, kappa) en traitant avec certains solvants une des phases connues ou une autre phase selon l'invention de ce pigment. Les nouvelles phases cristallines se caractérisent par des nuances de couleur jaune et par de bonnes propriétés chromatiques.
EP05757161A 2004-07-09 2005-06-15 Nouvelles modifications cristallines du c.i. pigment yellow 181 et procedes de realisation associes Withdrawn EP1769034A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102004033287A DE102004033287A1 (de) 2004-07-09 2004-07-09 Neue Kristallmodifikationen von C.I. Pigment Yellow 181 und Verfahren zu ihrer Herstellung
PCT/EP2005/006405 WO2006005408A1 (fr) 2004-07-09 2005-06-15 Nouvelles modifications cristallines du c.i. pigment yellow 181 et procedes de realisation associes

Publications (1)

Publication Number Publication Date
EP1769034A1 true EP1769034A1 (fr) 2007-04-04

Family

ID=34971774

Family Applications (1)

Application Number Title Priority Date Filing Date
EP05757161A Withdrawn EP1769034A1 (fr) 2004-07-09 2005-06-15 Nouvelles modifications cristallines du c.i. pigment yellow 181 et procedes de realisation associes

Country Status (5)

Country Link
US (1) US7709614B2 (fr)
EP (1) EP1769034A1 (fr)
JP (1) JP2008505229A (fr)
DE (1) DE102004033287A1 (fr)
WO (1) WO2006005408A1 (fr)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102007005991A1 (de) 2007-02-07 2008-08-14 Clariant International Ltd. Feinteiliges C.I. Pigment Yellow 181
DE102007008218A1 (de) * 2007-02-20 2008-08-21 Clariant International Ltd. Pigmentzusammensetzung auf Basis von C.I. Pigment Yellow 191
US20090062312A1 (en) * 2007-08-29 2009-03-05 Protia, Llc Deuterium-enriched indiplon
JP5292039B2 (ja) * 2008-03-07 2013-09-18 富士フイルム株式会社 アゾ顔料組成物、アゾ顔料組成物の製造方法、アゾ顔料組成物を含む分散物、着色組成物及びインクジェット記録用インク
JP5331468B2 (ja) * 2008-03-07 2013-10-30 富士フイルム株式会社 アゾ顔料組成物、アゾ顔料組成物の製造方法、アゾ顔料組成物を含む分散物、着色組成物及びインクジェット記録用インク
CN102165019B (zh) 2008-09-29 2014-04-16 富士胶片株式会社 偶氮颜料，用于制备偶氮颜料的方法及含有偶氮颜料的分散体和着色组合物
JP4968226B2 (ja) 2008-09-30 2012-07-04 富士通株式会社 アンテナ、及びリーダライタ装置
JP5481177B2 (ja) 2008-12-09 2014-04-23 富士フイルム株式会社 アゾ顔料、アゾ顔料の製造方法、アゾ顔料を含む分散物、及び着色組成物
JP5608482B2 (ja) 2009-09-04 2014-10-15 富士フイルム株式会社 水系顔料分散物及びインクジェット記録用水性インク
AU2010290459B2 (en) 2009-09-04 2014-06-12 Fujifilm Corporation Aqueous pigment dispersion, and aqueous ink for inkjet recording
DE102009048542A1 (de) 2009-10-07 2011-04-21 Clariant International Ltd. Leicht dispergierbare Pigmentzubereitung auf Basis von C.I. Pigment Yellow 155
EP2390283A1 (fr) 2010-05-31 2011-11-30 FUJIFILM Corporation Pigment azoïque ou son tautomère, son procédé de fabrication, dispersion de pigments, composition de coloration, encre d'enregistrement par jet d'encre, composition de coloration pour filtre couleur et filtre couleur
JP5712166B2 (ja) 2011-07-29 2015-05-07 富士フイルム株式会社 アゾ顔料を含む分散物、着色組成物及びインクジェット記録用インク並びに分散物の製造方法
EP2738223B1 (fr) 2011-07-29 2017-11-08 Fujifilm Corporation Pigment azoïque, dispersion contenant un pigment azoïque, composition de teinture et encre pour impression à jet d'encre

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BE786775A (fr) * 1971-07-26 1973-01-26 Hoechst Ag Pigment monoazoique, sa preparation et ses utilisations
DE2845947A1 (de) * 1978-10-21 1980-04-30 Hoechst Ag Azoverbindungen, verfahren zu ihrer herstellung und ihre verwendung
US6274728B1 (en) * 1997-01-27 2001-08-14 Ciba Specialty Chemicals Corp. Soluble chromophores having improved solubilizing groups
DE10031558A1 (de) 2000-06-28 2002-01-10 Clariant Gmbh Verfahren zur Konditionierung von organischen Pigmenten
DE10032315A1 (de) * 2000-07-04 2002-01-17 Clariant Gmbh Neue Kristallmodifikationen von C.I. Pigment Yellow 191 und Verfahren zu ihrer Herstellung
DE10045790A1 (de) 2000-09-15 2002-03-28 Clariant Gmbh Neue kristalline Modifikationen eines gelben Disazo -Farbmittels und Verfahren zu ihrer Herstellung

Non-Patent Citations (1)

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Title
See references of WO2006005408A1 *

Also Published As

Publication number Publication date
US7709614B2 (en) 2010-05-04
WO2006005408A1 (fr) 2006-01-19
DE102004033287A1 (de) 2006-02-02
JP2008505229A (ja) 2008-02-21
US20080058531A1 (en) 2008-03-06

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