US20010012559A1 - Pigmented porous material - Google Patents

Pigmented porous material Download PDF

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Publication number
US20010012559A1
US20010012559A1 US09/096,439 US9643998A US2001012559A1 US 20010012559 A1 US20010012559 A1 US 20010012559A1 US 9643998 A US9643998 A US 9643998A US 2001012559 A1 US2001012559 A1 US 2001012559A1
Authority
US
United States
Prior art keywords
alkyl
porous material
pigment
hydrogen
material according
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.)
Abandoned
Application number
US09/096,439
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English (en)
Inventor
John Zambounis
Patrick Verhoustraeten
Henri Dubas
Zhimin Hao
Patrice Bujard
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.)
BASF Performance Products LLC
Original Assignee
Ciba Specialty Chemicals Corp
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 Ciba Specialty Chemicals Corp filed Critical Ciba Specialty Chemicals Corp
Assigned to CIBA SPECIALTY CHEMICALS CORP reassignment CIBA SPECIALTY CHEMICALS CORP ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: BUJARD, PATRICE, DUBAS, HENRI, HAO, ZHIMIN, VERHOUSTRAETEN, PATRICK, ZAMBOUNIS, JOHN
Publication of US20010012559A1 publication Critical patent/US20010012559A1/en
Priority to US10/201,014 priority Critical patent/US6767620B2/en
Abandoned legal-status Critical Current

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    • 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
    • C09B68/00—Organic pigments surface-modified by grafting, e.g. by establishing covalent or complex bonds, in order to improve the pigment properties, e.g. dispersibility or rheology
    • C09B68/40—Organic pigments surface-modified by grafting, e.g. by establishing covalent or complex bonds, in order to improve the pigment properties, e.g. dispersibility or rheology characterised by the chemical nature of the attached groups
    • C09B68/44—Non-ionic groups, e.g. halogen, OH or SH
    • C09B68/443—Carboxylic acid derivatives, e.g. carboxylic acid amides, carboxylic acid esters or CN groups
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
    • B27K—PROCESSES, APPARATUS OR SELECTION OF SUBSTANCES FOR IMPREGNATING, STAINING, DYEING, BLEACHING OF WOOD OR SIMILAR MATERIALS, OR TREATING OF WOOD OR SIMILAR MATERIALS WITH PERMEANT LIQUIDS, NOT OTHERWISE PROVIDED FOR; CHEMICAL OR PHYSICAL TREATMENT OF CORK, CANE, REED, STRAW OR SIMILAR MATERIALS
    • B27K5/00—Treating of wood not provided for in groups B27K1/00, B27K3/00
    • B27K5/02—Staining or dyeing wood; Bleaching wood
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K9/00—Use of pretreated ingredients
    • C08K9/12—Adsorbed ingredients, e.g. ingredients on carriers
    • 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
    • C09B63/00—Lakes
    • 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
    • C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
    • C09B67/0077—Preparations with possibly reduced vat, sulfur or indigo dyes
    • 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
    • C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
    • C09B67/0092—Dyes in solid form
    • C09B67/0095—Process features in the making of granulates
    • 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
    • C09B67/0097—Dye preparations of special physical nature; Tablets, films, extrusion, microcapsules, sheets, pads, bags with dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK  ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
    • C09C3/00—Treatment in general of inorganic materials, other than fibrous fillers, to enhance their pigmenting or filling properties
    • C09C3/08—Treatment with low-molecular-weight non-polymer organic compounds
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H21/00—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties
    • D21H21/14—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties characterised by function or properties in or on the paper
    • D21H21/28—Colorants ; Pigments or opacifying agents
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2002/00—Crystal-structural characteristics
    • C01P2002/50—Solid solutions
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    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2004/00—Particle morphology
    • C01P2004/60—Particles characterised by their size
    • C01P2004/61—Micrometer sized, i.e. from 1-100 micrometer
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
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    • C01P2004/60—Particles characterised by their size
    • C01P2004/62—Submicrometer sized, i.e. from 0.1-1 micrometer
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
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    • C01P2006/12—Surface area
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    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
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    • C01P2006/14—Pore volume
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
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    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
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    • C01P2006/62—L* (lightness axis)
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
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    • C01P2006/63—Optical properties, e.g. expressed in CIELAB-values a* (red-green axis)
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    • C01P2006/64—Optical properties, e.g. expressed in CIELAB-values b* (yellow-blue axis)
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
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    • C01P2006/80—Compositional purity
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Definitions

  • the present application relates to porous materials given coloured pigmentation with organic pigments localized in their pores and to a process for their preparation.
  • Porous materials are commonly coloured with dyes that are applied, for example, as stains.
  • a requirement is that the porous material to be coloured has a high and uniform affinity for the dye; this requirement, however, is seldom met.
  • Porous materials coloured with dyes possess, moreover, an undesirably low light stability, and in contact with water or organic liquids (beverages, for example) marks may be formed on articles that are in contact with the materials, since the dyes are in some cases leached out again.
  • Another method of imparting a coloured appearance to porous materials is to provide them with a pigmented coating.
  • This method has the disadvantage that the pores become sealed by the pigmented coating material, with the result that it becomes difficult if not impossible to perceive visually the nature of the porous material.
  • This is a great disadvantage, especially with natural porous materials, since it is their properties, especially their natural appearance and their permeability, that are the most prized.
  • the properties of the porous material are impaired by a pigmented coating.
  • EP 648 770 and EP 648 817 disclose carbamate-functional, soluble chromophors which can be converted to the corresponding pigments by heating them to relatively high temperatures, with the ensuing elimination of the carbamate radicals. These compounds are suitable for the mass colouring of polymers and, according to EP 654 711, for the colouring of resists and of polymer coats to which they are applied. Compounds of the same type but with improved properties are known from EP 742 556 and U.S. application Ser. No. 09/013,659.
  • U.S. Pat. No. 5,243,052 discloses carbonates of quinophthalones, which are of limited solubility and can be used in heat-sensitive recording systems.
  • the leuco dye is embedded within a polymer, preferably in polyethyloxazoline.
  • Soluble derivatives of triphenylmethane dyes are known from U.S. Pat. No. 4,828,976. They are likewise used in heat-sensitive recording systems, together with a binder such as cellulose acetate-butyrate, polyvinylpyrrolidone or copolymerized ethylene/maleic anhydride.
  • EP 742 556 furthermore, describes textured pigmentary coatings which are prepared from soluble or meltable precursors and which cover all or part of a substrate surface.
  • the substrates mentioned include fibres and fabrics. It has been found, however, that these pigmentary coatings fail to meet high requirements in terms, in particular, of their rub fastness.
  • porous materials can be coloured without impairing their properties, and especially without clogging the pores, if fragmentable pigment precursors in melted or dissolved form are introduced into the pores and then converted to their pigmentary form.
  • a particularly advantageous result of this is an increase in production flexibility, and possibilities for making savings, when producing articles from coloured porous materials.
  • the resulting colorations are surprisingly strong in colour, fast to weathering, light and heat, rubbing, water and solvent, and are also highly uniform optically provided the material itself is uniform in its porosity.
  • this permits the use of materials whose quality would not enable any satisfactory results to be obtained on conventional colouring, a feature which, especially in the case of naturally occurring organic porous materials of complex structure, such as wood, leather or hair, for example, paves the way for ecologically significant, improved utilization of natural resources.
  • a further great advantage is that following the colouring of the porous material its nature is, surprisingly, still apparent to the eye.
  • the present invention accordingly provides a coloured porous material comprising in its pores an effectively colouring amount of an organic pigment which is obtainable by fragmenting a meltable or solvent-soluble pigment precursor.
  • Porous materials can be mineral or organic, natural, refined or synthetic.
  • the material may, for example, be chalk, pumice, fired clay, unglazed porcelain, gypsum, concrete, kieselguhr, silica gel, zeolites, wood, paper, leather, imitation leather or hair, in whatever form, or products derived from these.
  • It is preferably a material composed of refined or unrefined organic components of natural origin or, with particular preference, is a refined or unrefined natural organic material. In particular, it can be either hard wood or soft wood.
  • the material consists of fine particles, most preferably inorganic particles, such as chalk, pumice, fired clay, unglazed porcelain, gypsum, kieselguhr, silica gel or zeolite powders.
  • the particle size is preferably from 0.1 to 10 ⁇ m, most preferably from 1 to 3 ⁇ m.
  • the organic pigment's concentration may be low or high, depending of the desired colour saturation. A low concentration of the organic pigment in the powdered inorganic material leads to pastel tints, while a high concentration of the organic pigment in the powdered inorganic material leads to higher saturations.
  • Examples of high molecular mass organic materials which can be coloured or pigmented with the instant pigmented porous material powders are cellulose ethers, cellulose esters, such as ethylcellulose, nitrocellulose, cellulose acetate and cellulose butyrate, natural resins or synthetic resins, such as addition polymerization resins or condensation polymerization resins, such as amino resins, especially urea-formaldehyde and melamine-formaldehyde resins, alkyd resins, phenolic resins, polycarbonates, polyolefins, polystyrene, polyvinyl chloride, polyamides, polyurethanes, polyesters, ABS, polyphenylene oxides, rubber, casein, silicone and silicone resins, individually or in mixtures.
  • cellulose ethers such as ethylcellulose, nitrocellulose, cellulose acetate and cellulose butyrate
  • natural resins or synthetic resins such as addition polymerization resins or condensation polymerization resins, such
  • the abovementioned high molecular mass organic compounds can be present, individually or in mixtures, as plastic masses, as melts or in the form of spinning solutions, varnishes, coating materials or printing inks.
  • Organic high molecular mass materials coloured with the instant pigmented porous material powders possess outstanding colour properties.
  • This invention therefore also provides a composition comprising a high molecular mass organic material and an effective pigmenting amount of an instant pigmented porous material powder.
  • the instant pigmented porous material powders are preferably employed in an amount of from 0.1 to 50% by weight, most preferably from 1 to 30% by weight, based on the high molecular mass organic material to be pigmented.
  • the pigmenting of the high molecular mass organic substances with the instant pigmented porous material powders is carried out, for example, by mixing such solid solutions, in the form of masterbatches if desired, into these substrates using roller assemblies, mixers or milling apparatus.
  • the pigmented material is subsequently brought into the desired final form by methods known per se, such as calandering, compression moulding, extrusion, coating, casting or injection moulding. So as to produce non-rigid mouldings, or to reduce their brittleness, it is often desirable to incorporate plasticizers into the high molecular mass compounds prior to their forming. Examples of compounds which can be used as such plasticizers are esters of phosphoric acid, phthalic acid or sebacic acid.
  • the plasticizers can be incorporated into the polymers before or after the incorporation of the instant pigmented porous material powders.
  • the high molecular mass organic materials and the instant pigmented porous material powders together if desired with additives such as fillers, other pigments, siccatives or plasticizers, are finely dispersed or dissolved in an organic solvent or solvent mixture for them both.
  • additives such as fillers, other pigments, siccatives or plasticizers
  • the instant pigmented porous material powders are particularly suitable for colouring plastics, especially polyvinyl chloride and polyolefins, and for colouring paints, preferably automotive or metallic finishes, for example those containing metal particles or mica particles.
  • a feature of porous materials is the presence of pores, by which are meant cavities within the physical shell of the material, which may be partly or totally filled with a gas, for example air, or with a liquid, for example water.
  • the pores extend at least in part to the surface of the material.
  • the volume of the pores is preferably at least 5% relative to the volume of the geometric shell of the material.
  • the volume of the pores is from 20 to 90% relative to the volume of the geometric shell of the material.
  • the cross-section of the pores is so fine that by virtue of capillary force an aqueous liquid does not flow out under gravity.
  • the average cross-section of the pores is from 1.10 ⁇ 16 to 10 ⁇ m 2 , determined at a transverse section through the material, by dividing the total pore area by the number of pores.
  • Introducing the pigment precursor into the pores of the porous material is effected by applying a solution or melt of the pigment precursor to the porous material using any desired, known method, for example by spraying or impregnation in a bath.
  • a solution or melt of the pigment precursor for example by spraying or impregnation in a bath.
  • the methods of and conditions for treatment of certain materials are known in the technical literature, to which express reference is hereby made.
  • the methods of and conditions for treating wood and wood products with solutions are described in detail in Ullmann's Encyclopaedia of Industrial Chemistry, Vol. A28, 305-393 (5th Edition 1996) and Kirk-Othmer Encyclopaedia of Chemical Technology, Vol. 24, 579-611 (3rd Edition 1978).
  • the application temperature can be an elevated temperature but is judiciously kept low enough for the dissolved or melted pigment precursor not to undergo any, or any significant, decomposition during the minimum time required for the application.
  • the solution or melt of the pigment precursor may be augmented with further substances known for treating the material, examples being fungicides, antibiotics, flame retardants or moisture repellents.
  • Suitable solvents are water or, preferably, any desired protic or aprotic solvents, examples being hydrocarbons, alcohols, amides, nitrites, nitro compounds, N-heterocycles, ethers, ketones and esters which may also be either mono- or polyunsaturated or chlorinated: examples are methanol, ethanol, isopropanol, diethyl ether, acetone, methyl ethyl ketone, 1,2-dimethoxyethane, 1,2-diethoxyethane, 2-methoxyethanol, ethyl acetate, tetrahydrofuran, dioxane, acetonitrile, benzonitrile, nitrobenzene, N,N-dimethylformamide, N,N-dimethylacet-amide, dimethyl sulfoxide, N-methylpyrrolidone, pyridine, picoline, quinoline, trichloroethane, benzene
  • solvents which do not corrode the substrate that is to be coloured, or do so only very slowly and which have a boiling point of between 40° C. and 170° C., especially to aromatic hydrocarbons, alcohols, ethers, ketones and esters.
  • Particular preference is given to toluene, methanol, ethanol, isopropanol, 1,2-dimethoxyethane, 1,2-diethoxyethane, 1-methoxy-2-propanol, acetone, methyl ethyl ketone, ethyl acetate, tetrahydrofuran and dioxane, and mixtures thereof.
  • the concentration of the pigment precursor in water or a solvent is usually from 0.01% by weight, based on the weight of the solution, to approximately 99% by weight of the saturation concentration, it also being possible in certain cases to employ supersaturated solutions without premature precipitation of the solvate.
  • the optimum concentration is around ⁇ 0.1-50% by weight, often around 1-20% by weight, based on the weight of the solution.
  • Conversion of the pigment precursor into the pigmentary form takes place by fragmentation under known conditions, for example thermally in the presence or absence of a catalyst, such as an acid or a cationic photoinitiator which can be introduced into the pores of the porous material before, at the same time as or after the pigment precursor.
  • a catalyst such as an acid or a cationic photoinitiator which can be introduced into the pores of the porous material before, at the same time as or after the pigment precursor.
  • Fragmentation can be carried out individually, or simultaneously with any further known, subsequent treatment; for example, in the course of curing an additional transparent coating film.
  • an effectively colouring amount is meant that amount which is sufficient to bring about a colour difference ⁇ E* (CIE-L*a*b*) of ⁇ 2 when the coloured material is compared with the uncoloured material under the standard illuminant D 65 and at a viewing angle of 10°.
  • This amount is preferably from 0.01 to 30% by weight, most preferably from 0.1 to 15% by weight, based on the weight of the coloured material.
  • Judicious fragmentable pigment precursors are those whose structure includes a complete pigment framework substituted on at least one heteroatom N, O or S.
  • the substituent involved is preferably an oxycarbonyl radical.
  • the heteroatom is part of the chromophor or bonded directly to the chromophor, in the course of fragmentation the oxycarbonyl radical is generally eliminated and replaced by a hydrogen atom, so that the structure of the resulting pigment corresponds to that of the unsubstituted pigment framework.
  • the heteroatom is bonded to a substituent of the chromophor, then the fragmentation process is sometimes more complex, and the precise structure of the resulting pigment cannot always be clearly ascertained.
  • the pigment precursors can be employed individually or else in mixtures with other pigment precursors or with colorants—for example, dyes customary for the corresponding application.
  • the components of the mixture are preferably those whose colour in the pigmentary form is red, yellow, blue, brown or black. From these it is possible to produce brown shades having a particularly natural occurrence. Any dyes added are likewise preferably red, yellow, blue, brown or black.
  • Preferred pigment precursors are, for example, compounds of the formula (I)
  • A is the radical of a chromophor of the quinacridone, anthraquinone, perylene, indigo, quinophthalone, indanthrone, isoindolinone, isoindoline, dioxazine, azo, phthalocyanine or diketopyrrolopyrrole series which is attached to x groups B via one or more heteroatoms selected from the group consisting of N, O and S and forming part of the radical A, B is hydrogen or a group of the formula
  • At least one group B is not hydrogen and, if x is from 2 to 8, the groups B can be identical or different, and
  • L is any suitable solubilizing group, for example tert.-butyl or tert.-amyl. Many other groups suitable for solubilizing pigments are known, for example, from the publications referred to above.
  • A preferably contains at least one directly adjacent or conjugated carbonyl group at each heteroatom attached to x groups B.
  • A is the radical of known chromophores having the basic structure
  • D is hydrogen, C 1 -C 6 alkyl, unsubstituted or halo- or C 1 -C 6 alkyl-substituted phenyl, benzyl or phenethyl or B,
  • R 1 and R 2 independently of one another are hydrogen, halogen, C 1 -C 24 alkyl, C 1 -C 6 alkoxy or phenyl,
  • R 3 is hydrogen, halogen or C 1 -C 24 alkyl
  • R 4 , R 5 and R 6 independently of one another are hydrogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, NECOC 1 -C 4 alkyl, NECOphenyl or N(E) 2 where at least one of the radicals R 4 , R 5 and R 6 is NECOC 1 -C 4 alkyl, NECOphenyl or N(E) 2 ,
  • R 7 is a group
  • R 8 is hydrogen, C 1 -C 24 alkyl, benzyl or a group
  • R 9 is hydrogen, E or R 7 ,
  • R 10 , R 11 , R 12 and R 13 independently of one another are hydrogen, C 1 -C 24 alkyl, C 1 -C 6 alkoxy, halogen or trifluoromethyl,
  • R 14 and R 15 independently of one another are hydrogen, halogen or C 1 -C 4 alkyl
  • R 16 is hydrogen or halogen
  • M is H 2 , a divalent metal selected from the group consisting of Cu(II), Zn(II), Fe(II), Ni(II), Ru(II), Rh(II), Pd(II), Pt(II), Mn(II), Mg(II), Be(II), Ca(II), Ba(II), Cd(II), Hg(II), Sn(II), Co(II) and Pb(II), preferably Cu(II), Zn(II), Fe(II), Ni(II) or Pd(II), or a divalent oxo metal selected from the group consisting of V(O), Mn(O) and TiO, T 1 is —CHR 8 —, —CO— or —SO 2 —,
  • R 17 is hydrogen, C 1 -C 6 alkyl, —N(E)R 18 , N(E) 2 , —NECOR 19 , —COR 19 or
  • R 18 is hydrogen or C 1 -C 6 alkyl
  • R 19 is C 1 -C 6 alkyl
  • R 20 is hydrogen, halogen, C 1 -C 6 alkyl or C 1 -C 6 alkoxy
  • z is zero or 1 and y is a number from 1 to 8,
  • G 1 and G 2 independently of one another are a group of the formula
  • R 21 and R 22 independently of one another are hydrogen, halogen, C 1 -C 24 alkyl, C 1 -C 6 alkoxy, C 1 -C 8 alkylthio, C 1 -C, 8 alkylamino, —CN, —NO 2 , -phenyl, trifluoromethyl, C 5 -C 6 cycloalkyl, —C ⁇ N—(C 1 -C 24 alkyl),
  • T 2 is —CH 2 —, —CH(CH 3 )—, —C(CH 3 ) 2 —, —CH ⁇ N—, —N ⁇ N—, —O—, —S—, —SO—, —SO 2 — or —NR 27 —,
  • R 23 and R 24 independently of one another are hydrogen, halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy or —CN
  • R 25 and R 26 independently of one another are hydrogen, halogen or C 1 -C 6 alkyl
  • R 27 is hydrogen or C 1 -C 6 -alkyl
  • R 27 is H or O—E
  • R 28 to R 31 independently of one another are hydrogen, halogen, —COO—C 1 -C 6 alkyl or —CONE—C 1 -C 6 alkyl
  • R 32 to R 36 independently of one another are hydrogen, halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, nitro, acetyl or SO 2 NEC 1 -C 6 alkyl, and R 37 is hydrogen, halogen, C 1 -C 6 alkyl or Cl-C 6 alkoxy,
  • R 38 and R 39 independently of one another are hydrogen, C 1 -C 12 alkyl, or C 6 -C 12 aryl which is unsubstituted or substituted by halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, nitro, acetyl, SO 2 NEC 1 -C 6 alkyl or SO 2 NE 2
  • R 40 and R 41 independently of one another are hydrogen, halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, nitro, cyano, CONE 2 , SO 2 NEC 1 -C 6 alkyl, SO 2 NE 2 , SO 3 E, SO 3 Na or C 6 -C 12 aryl which is unsubstituted or substituted by halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, nitro, acetyl, SO 2 NEC 1 -C 6 alkyl or SO 2 NE 2
  • R 40 and R 41 independently of
  • R 42 is hydrogen, halogen, nitro, cyano, hydroxyl or C 1 -C 6 alkoxy, and
  • R 43 is hydrogen, CN, C 1 -C 6 alkyl, C 1 -C 6 alkoxy or halogen
  • each E independently of the others is hydrogen or B, with the proviso that in each formula E is B on at least one occasion, and B is as defined above.
  • Preferred quinacridones are those in which in formula III R 1 and R 2 independently of one another are hydrogen, chlorine or methyl.
  • Preferred pyrrolo[3,4-c]pyrroles are those in which in formula XIII G 1 and G 2 are the same and are a group of the formula
  • R 21 and R 22 independently of one another are hydrogen, chlorine, bromine, C 1 -C 4 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 alkylamino, CN or phenyl,
  • T 2 is —O—, —NR 27 —, —N ⁇ N— or —SO 2 —, and
  • R 27 is hydrogen, methyl or ethyl.
  • Preferred azo compounds are those in which in the formulae XVa to XVf R 32 to R 36 independently of one another are hydrogen, halogen, methyl, methoxy, nitro, acetyl or SO 2 NECH 3 , and R 37 is halogen or methoxy.
  • E is hy drogen or B 1 with the proviso that in each formula E is B on at least one occasion, and B is as defined above,
  • R 44 and R 45 independently of one another are C 1 -C4alkyl, and E is hydrogen or B. with the proviso that E is B on at least one occasion, and B is as defined above,
  • R 46 and R 47 independently of one another are hydrogen, methyl, tert-butyl, chlorine, bromine, CN or phenyl, and E is hydrogen or B, with the proviso that E is B on at least one occasion, and B is as defined above,
  • R 48 is hydrogen or C 1 -C 4 alkyl
  • E is hydrogen or B, with the proviso that E is B on at least one occasion, and B is as defined above,
  • E is hydrogen or B, with the proviso that E is B on at least one occasion, and B is as defined above, and
  • azo compounds of the formula XVa, XVb, XVe or XVf in which R 32 to R 36 independently of one another are hydrogen, chlorine, methoxy, nitro, acetyl or SO 2 NECH 3 , and R 37 is halogen or methoxy, with the proviso that in each formula E is B on at least one occasion, and B is as defined above.
  • Particularly noteworthy soluble chromophores are those which can be prepared from Colour Index Pigment Yellow 73, Pigment Yellow 74, Pigment Yellow 83, Pigment Yellow 109, Pigment Yellow 139, Pigment Orange 71, Pigment Orange 73, Pigment Red 122, Pigment Red 185, Pigment Red 202, Pigment Red 254, Pigment Red 255, Pigment Red 264, Pigment Blue 25, Pigment Blue 26, Pigment Blue 60, Pigment Blue 64, Pigment Violet 19, Pigment Violet 29 and Pigment Violet 37.
  • —L is a group of the formula
  • R 49 , R 50 and R 51 independently of one another are C 1 -C 6 alkyl
  • R 52 and R 53 independently of one another are C 1 -C 6 alkyl, O, S or N(R 60 ) 2 -interrupted C 1 -C 6 alkyl, unsubstituted or C 1 -C 6 alkyl-, C 1 -C 6 alkoxy-, halo-, cyano- or nitro-substituted phenyl or biphenylyl,
  • R 54, R 55 and R 56 independently of one another are hydrogen or C 1 -C 6 alkyl
  • R 57 is hydrogen, C 1 -C 6 alkyl or a group of the formula
  • R 58 and R 59 independently of one another are hydrogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, halogen, cyano, nitro, N(R 60 ) 2 , unsubstituted or halo-, cyano-, nitro-, C 1 -C 6 alkyl- or C 1 -C 6 alkoxy-substituted phenyl,
  • R 60 and R 6 are C 1 -C 6 alkyl
  • R 62 is hydrogen or C 1 -C 6 alkyl
  • R 63 is hydrogen, C 1 -C 6 alkyl, unsubstituted or C 1 -C 6 alkyl-substituted phenyl
  • Q is p,q-C 2 -C 6 alkylene which is unsubstituted or substituted one or more times by C 1 -C 6 alkoxy, C 1 -C 6 alkylthio or C 2 -C 12 dialkylamino, p and q being different numeric locants,
  • X is a heteroatom selected from the group consisting of N, O and S, where m is 0 if X is O or S and is 1 if X is N, and
  • L 1 and L 2 independently of one another are unsubstituted or mono- or poly-C 1 -C 12 alkoxy-, —C 1 -C 2 alkylthio-, —C 2 -C 24 dialkylamino-, —C 6 -C 12 aryloxy-, —C 6 -C 12 arylthio-, —C 7 -C 24 alkylarylamino- or —C 12 -C 24 diarylamino-substituted C 1 -C 6 alkyl or [-(p′,q′-C 2 -C 6 alkylene)-Z-] n -C 1 -C 6 alkyl, where n is a number from 1 to 1000, p′ and q′ are different numeric locants, each Z independently of the others is a heteroatom O, S or C 1 -C 12 alkyl-substituted N, and C 2 -C 6 alkylene in the repeating units [—C 2
  • L 1 and L 2 can be saturated or mono- to deca-unsaturated, uninterrupted or interrupted in any desired points by from 1 to 10 groups selected from the group consisting of —(C ⁇ O)— and —C 6 H 4 —, and may carry no or 1 to 10 further substituents selected from the group consisting of halogen, cyano and nitro.
  • Q is C 2 -C 4 alkylene and L 1 and L 2 are [—C 2 -C 12 alkylene-Z- ] n — C 1 -C 12 alkyl or are C 1 -C 12 alkyl which is substituted one or more times by C 1 -C 12 alkoxy, C 1 -C 12 alkylthio or C 2 -C 24 dialkylamino, and m and n are as defined above.
  • Q is C 2 -C 4 alkylene
  • X is O and m is zero
  • L 2 is [—C 2 -C 12 alkylene—O—] n —C 1 -C 12 alkyl or is C 1 -C 12 alkyl which is substituted one or more times by C 1 -C 12 alkoxy, especially those in which -Q-X- is a group of the formula —C(CH 3 ) 2 —CH—O—.
  • Alkyl or alkylene can be straight-chain, branched, monocyclic or polycyclic.
  • C 1 -C 12 alkyl is, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, cyclobutyl, n-pentyl, 2-pentyl, 3-pentyl, 2,2-dimethylpropyl, cyclopentyl, cyclohexyl, n-hexyl, n-octyl, 1,1,3,3-tetramethylbutyl, 2-ethylhexyl, nonyl, trimethylcyclohexyl, decyl, menthyl, thujyl, bornyl, 1 -adamantyl, 2-adamantyl or dodecyl.
  • C 2 -C 12 alkyl is mono- or polyunsaturated it is C 2 -C 12 alkenyl, C 2 -C 12 alkynyl, C 2 -C 12 alkapolyenyl or C 2 -C 12 alkapolyynyl in which two or more double bonds may if appropriate be isolated or conjugated, examples being vinyl, allyl, 2-propen-2-yl, 2-buten-1-yl, 3-buten-1 -yl, 1,3-butadien-2-yl, 2-cyclobuten-1 -yl, 2-penten-1 -yl, 3-penten-2-yl, 2-methyl-1 -buten-3-yl, 2-methyl-3-buten-2-yl, 3-methyl-2-buten-1 -yl, 1,4-pentadien-3-yl, 2-cyclopenten-1 -yl, 2-cyclohexen-1 -yl, 3-cyclohexen-1 -yl, 2,4-cyclohex
  • C 2 -C 4 alkylene is, for example, 1,2-ethylene, 1,2-propylene, 1,3-propylene, 1,2-butylene, 1,3-butylene, 2,3-butylene, 1,4-butylene or 2-methyl-1,2-propylene.
  • C 5 -C 12 alkylene is, for example, an isomer of pentylene, hexylene, octylene, decylene or dodecylene.
  • C 1 -C 12 alkoxy is O—C 1 -C 12 alkyl, preferably O—C 1 -C 14 alkyl.
  • C 6 -C 12 aryloxy is O—C 6 -C 12 aryl, for example phenoxy or naphthoxy, preferably phenoxy.
  • C 1 -C 12 alkylthio is S—C 1 -C 12 alkyl, preferably S—C 1 -C 4 alkyl.
  • C 6 -C 12 arylthio is S—C 6 -C 12 aryl, for example phenylthio or naphthylthio, preferably phenylthio.
  • C 2 -C 24 dialkylamino is N(alkyl 1 )(alkyl 2 ), where the sum of the carbon atoms in the two groups alkyl 1 and alkyl 2 is from 2 to 24, preferably N(C 1 -C 4 alkyl)C 1 -C 4 alkyl.
  • C 7 -C 24 alkylarylamino is N(alkyl 1 )(aryl 2 ), where the sum of the carbon atoms in the two groups alkyll 1 and aryl 2 is from 7 to 24, for example methylphenylamino, ethylnaphthylamino or butylphenanthrylamino, preferably methylphenylamino or ethylphenylamino.
  • C 12 -C 24 diarylamino is N(aryl 1 )(aryl 2 ), where the sum of the carbon atoms in the two groups aryl 1 and aryl 2 is from 12 to 24, for example diphenylamino or phenylnaphthylamino, preferably diphenylamino.
  • Halogen is chlorine, bromine, fluorine or iodine, preferably fluorine or chlorine.
  • n is preferably a number from 1 to 100, with particular preference a number from 2 to 12.
  • the porous material may also contain other compounds in its pores, for example binders or surfactants known in the art to improve the pigment's dispersibility. It has however surprisingly been found, that improved results are obtained when the porous material is treated with a silane or siloxane compound, particularly when the porous material is inorganic, for example silica gel.
  • the amount of silane or siloxane compound is preferably from 1 to 100% by weight, most preferably from 5 to 20% by weight, based on the weight of the organic pigment.
  • silane or siloxane compound is preferably of structure
  • R 64 to R 67 are independently OH
  • silane or siloxane compounds are diphenylsilanediol, diphenylmethoxysilane, glycidoxypropyltrimethoxysilane and 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane.
  • the invention also provides a process for preparing a coloured porous material of the invention whose pores comprise an effectively colouring amount of an organic pigment, comprising
  • Heating or irradiation step be carried out by any desired means; for example, by treatment in a thermal oven or by electromagnetic radiation, for example visible light, UV or IR radiation, or microwaves, in the presence or absence of a catalyst.
  • electromagnetic radiation for example visible light, UV or IR radiation, or microwaves
  • the conditions required for fragmentation are known per se for each class of pigment precursors.
  • step (b) is usually accomplished by heating to a temperature of from 100 to 250° C., preferably from 150 to 200° C., particularly preferably from 160 to 200° C., or by irradiating with an amount of energy sufficient for said pigment precursor to be heated to said temperature.
  • the fragmentation temperature may be lowered by using a catalyst, for example an acid.
  • the heating time is not critical, as long as care is taken that it is sufficiently long for the fragmentation to be completed. Typically, it ranges from several seconds to several hours, preferably from about 1 to about 30 minutes. The required heating time can be decreased by elevating the temperature.
  • the process may of course comprise additional steps which are known per se, for example a prior bleaching and/or a subsequent overcoating with, for example, a colourless nitrocellulose lacquer.
  • porous material also contains other compounds in its pores, it is preferred to add the latter at the latest before step (b), most preferred before step (a).
  • a 100 ⁇ 252 ⁇ 1 mm piece of obeche wood stored at 40% residual moisture content is treated with a solution of 3 g of pigment precursor of the formula
  • a wooden sheet coloured red with good fastness properties is obtained whose structure corresponds completely, both optically and to the touch, to that of natural wood.
  • a 100 ⁇ 252 ⁇ 1 mm piece of ash wood stored at 40% residual moisture content is treated with a solution of 3 g of pigment precursor of the formula
  • a wooden sheet coloured red with good fastness properties is obtained whose structure corresponds completely, both optically and to the touch, to that of natural wood.
  • [0155] are dissolved in 881 g of tetrahydrofuran.
  • 75 g of porous silica powder having a particle size of 1.4 ⁇ m, a porosity of 21 nm, a pore volume of 1.6 ml/g and a BET surface of 300 m 2 /g (silica grade 310P / Fuji Silysia) are then added to the solution and the whole is stirred at room temperature for 24 hours.
  • the slurry is then filtrated; the residue is dried at 400° C./100 mbar and then heated at 1800° C. to regenerate the pigment.
  • a red powder containing 10.6% by weight of C.I. Pigment Red 254 is obtained.
  • Example 3 The procedure of Example 3 is used, with the difference that 4.4 g of glycidoxy-propyltrimethoxysilane is added to the solution before the silica powder. A red powder containing 12.5% by weight of C.l. Pigment Red 254 is obtained.
  • Example 3 The procedure of Example 3 is used, with the difference that porous silica powder having a particle size of ⁇ 2.7 ⁇ m, a porosity of 24 nm, a pore volume of 1.8 mVg and a BET surface of 300 m 2 /g (silica grade 250/ Fuji Silysia) is used. A red powder containing 16.7% by weight of C.I. Pigment Red 254 is obtained.
  • Example 5 The procedure of Example 5 is used, with the difference that 4.4 g of diphenylsilanediol are added to the solution before the silica powder. A red powder containing 4.73% by weight of C.I. Pigment Red 254 is obtained.
  • Example 6 The procedure of Example 6 is used, with the difference that 2-(3,4-epoxy-cyclohexyl) ethyltrimethoxysilane is used instead of diphenylsilanediol. A red powder containing 4.54% by weight of C.I. Pigment Red 254 is obtained.
  • Example 6 The procedure of Example 6 is used, with the difference that diphenylmethoxy-silane is used instead of diphenylsilandiol. A red powder containing 5.04% by weight of C.I. Pigment Red 254 is obtained.
  • Example 8 The procedure of Example 8 is used, with the difference that porous silica powder having a particle size of 1.8 ⁇ m, a porosity of 7 nm, a pore volume of 0.8 ml/g and a BET surface of 500 m 2 /g (silica grade 530/Fuji Silysia) is used. A red powder containing 3.12% by weight of C.I. Pigment Red 254 is obtained.
  • Example 7 The procedure of Example 7 is used, with the difference that the porous silica powder of Example 9 is used. A red powder containing 2.03% by weight of C.I. Pigment Red 254 is obtained.
  • Example 6 The procedure of Example 6 is used, with the difference that the porous silica powder of Example 9 is used. A red powder containing 1.54% by weight of C.I. Pigment Red 254 is obtained.
  • Example 11 The procedure of Example 11 is used, with the difference that porous silica powder having a particle size of 2.5 ⁇ m, a porosity of 17 nm, a pore volume of 1.25 ml/g and a BET surface of 300 m 2 /g (silica grade 430/Fuji Silysia) is used.
  • 17 g of the product from Example 3 are mixed with 67 g of polyvinyl chloride, 33 g of dioctyl phthalate, 2 g of dibutyltin dilaurate and 2 g of titanium dioxide and processed on a roller bed at 160° C. for 15 minutes to form a thin film.
  • the red PVC film thus produced has a high chroma and a high transparency.
  • thermosetting acrylic varnish consisting of
  • topcoat (wet film about 50 ⁇ m). After a further 30 minutes of evaporation at room temperature, the coating is baked at 130° C. for 30 minutes.

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US09/096,439 1997-06-17 1998-06-11 Pigmented porous material Abandoned US20010012559A1 (en)

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US20070033747A1 (en) * 2005-06-17 2007-02-15 The Board Of Regents Of The University Of Texas System Organic/Inorganic Lewis Acid Composite Materials

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ID24721A (id) 2000-08-03
AU726461B2 (en) 2000-11-09
US6767620B2 (en) 2004-07-27
CN1134514C (zh) 2004-01-14
CN1264408A (zh) 2000-08-23
DE69801503D1 (de) 2001-10-04
JP2002506470A (ja) 2002-02-26
EP0990014B1 (en) 2001-08-29
KR20010013949A (ko) 2001-02-26
AU8537498A (en) 1999-01-04
DE69801503T2 (de) 2002-04-11
CA2286677A1 (en) 1998-12-23
EP0990014A1 (en) 2000-04-05
NZ500140A (en) 2000-10-27
WO1998058027A1 (en) 1998-12-23
US20030012943A1 (en) 2003-01-16

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