CN101173114A - Solid formaldehyde-free pigment preparations - Google Patents

Solid formaldehyde-free pigment preparations Download PDF

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Publication number
CN101173114A
CN101173114A CNA2007101692300A CN200710169230A CN101173114A CN 101173114 A CN101173114 A CN 101173114A CN A2007101692300 A CNA2007101692300 A CN A2007101692300A CN 200710169230 A CN200710169230 A CN 200710169230A CN 101173114 A CN101173114 A CN 101173114A
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Prior art keywords
ketone
pigment
formaldehyde
pigment preparation
weight
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Chinese (zh)
Inventor
A·温宁
P·邓金杰
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Evonik Operations GmbH
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Degussa GmbH
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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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/20—Compounding polymers with additives, e.g. colouring
    • C08J3/205—Compounding polymers with additives, e.g. colouring in the presence of a continuous liquid phase
    • 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
    • C09B67/0001—Post-treatment of organic pigments or dyes
    • C09B67/0004—Coated particulate pigments or dyes
    • C09B67/0008—Coated particulate pigments or dyes with organic coatings
    • C09B67/0013—Coated particulate pigments or dyes with organic coatings with polymeric coatings
    • 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
    • C09B67/006—Preparation of organic pigments
    • C09B67/0063—Preparation of organic pigments of organic pigments with only macromolecular substances
    • 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
    • C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
    • C09C1/0003—Compounds of molybdenum
    • 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
    • C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
    • C09C1/0006—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black containing bismuth and vanadium
    • 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
    • C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
    • C09C1/0096—Compounds of antimony
    • 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
    • C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
    • C09C1/04—Compounds of zinc
    • C09C1/043—Zinc oxide
    • 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
    • C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
    • C09C1/10—Compounds of cadmium
    • C09C1/12—Cadmium sulfoselenide
    • 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
    • C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
    • C09C1/14—Compounds of lead
    • 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
    • C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
    • C09C1/14—Compounds of lead
    • C09C1/20—Lead chromate
    • 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
    • C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
    • C09C1/34—Compounds of chromium
    • C09C1/346—Chromium oxides
    • 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
    • C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
    • C09C1/44—Carbon
    • C09C1/48—Carbon black

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Paints Or Removers (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Phenolic Resins Or Amino Resins (AREA)

Abstract

The invention relates to a solid paint preparation almost without formaldehyde which consists of at least one paint and a resin, relating the production method and the application in a paint, a japanning, a blinder, an ink or a printing ink.

Description

The solid pigment preparation that does not contain formaldehyde
Technical field
The present invention relates to that form and solid pigment preparation that contain formaldehyde hardly, its preparation method and the purposes in coating, japanning, binding agent, ink or printing-ink thereof by at least a pigment and resin.
Background technology
This class solid pigment preparation is used for the coating material such as coating, japanning, binding agent, ink or printing-ink, is used to apply the article that for example are made of metal and plastics.These application compositions are suitable for all and can be applicable to modern metal and plastic coat and printing-ink conventional coating method in the industry, for example spraying, electrostatic spraying and the printing that utilizes various printing processes to carry out.
Usually, colored coating material is to make by the pigment preparation of at first preparation liquid state and the method that then applies up with underlying coating layer.
Preparation during pigment preparation with filler and colo(u)rant dispersion in liquid medium.For this reason, use the dispersion agent mechanical shear stress required and will realize high as far as possible compactedness simultaneously usually to be reduced to effective dispersible solid.Dispersion agent helps the pulverizing of agglomerate, the wetting and/or surface that covers the dispersed particles of wanting as surface active cpd with stablize them in case unfavorable agglomeration once more.
Wetting agent and dispersion agent can be simplified the process of sneaking into of pigment and filler when preparation coating and japanning, these pigment and filler are determining the outward appearance and the physicochemical property of coating significantly as important preparation composition.In order to utilize best, these solids must be distributed in japanning and the coating, in case also must stablize the dispersion state of this acquisition on the other hand equably on the one hand.Also to become to assign to bear the effect of stabilizing component in many cases by binding agent.Therefore, this binding agent also is the important component of coating material, because they help hardness dry quickly and raising gained film.
For solvent-laden coating material, to prepare solvent-laden pigment preparation usually, and it be applied with different solvent-laden priming paint based on different wetting agent and dispersion agent.Then usually to prepare aqueous pigment preparations equally for aqueous coating material, and it be applied with different moisture priming paint based on different wetting agent and dispersion agent.
For fear of having general consistency and dissolved pigment preparation in organic solvent owing to preparing and deposit expensive that a large amount of pigment preparations causes, also just need developing with binding agent.This class for example is documented among the DE4404809 based on the pigment preparation of ketone resin.Put down in writing among the EP1078946 polyalkylene oxide of block copolymerization water typely also can be modulated to the dispersion agent that contains solvent type universal pigment preparation as being modulated to.In O.Z.6490 (DE102005012316) record based on block copolymerization and contain the polyalkylene oxide of Styrene oxide 98min. and the universal pigment preparation of the combination of ketone resin has wide consistency and the solvability in used organic solvent and water with used binding agent equally.In addition, also suppressed foamy formation in the aqueous pigment preparations.
All these liquid pigment preparations also contain organic solvent and dispersion agent and also have some other auxiliary agent usually except water, as anti-drying dose, auxiliary rheological agents, anti-skinning agent, biocide or be used to improve the preparation of winter hardiness.For avoiding these auxiliary agents and avoid pigment is consumed energy and scatter operation consuming time, just need develop by the simple agitation solid pigment preparation in the water-soluble or organic solvent of energy just.Put down in writing among the EP0702055 colo(u)rant dispersion in having the high-molecular weight organic binder bond, the promptly so-called formula pigment of admixing is in order to prepare coloured and solvent-laden coating.But these pigment are for reagglomeration and unstable, thereby feasible can not the elimination reliably may be owing to forming the defective that projection causes.
Pigment preparation described in the EP0702062 is modulated.But the inorganic salt of Gum Rosin have wherein been used for the structure of improving pigment, this material can remain in the pigment preparation on the one hand and may cause defective in organic coating, dispersion process can not reach best on the other hand, thereby makes must repeatedly carry out wet grinding when for example using phthalocyanine pigments.
In EP0902061, described and be used to prepare vinyl pyrrolidone homopolymer or the multipolymer of admixing the formula pigment preparation.These pigment preparations are specially adapted to the industry japanning or the solvent-free plastics of dyeing watersoluble.
Described a kind of solid pigment preparation among the DE10256416, it is by pigment dyestuff, functionalized pigment derivative and be selected from nonionic polyoxyalkylene or the water-soluble surface-active additives of its special derivative is formed.But used those are different in the pigment preparation of these additives and invention.
Described a kind of by hybrid pigment and urea-formaldehyde resin or urea ketone resin and then extrude the method for preparing color compositions among the US6734231.This resin does not contain formaldehyde.
The masterbatch of being made up of the mixture of three kinds of key components has been described: a) acrylate resin, ketone resin or urea formaldehyde, b) citrate, acetyl citrate or tartrate and c among the EP0432480) dyestuff and/or pigment and additive.But citrate, acetyl citrate or tartaric use can bring some problems when ground pigment.In addition, ketone resin or urea formaldehyde contain formaldehyde.
Described a kind of pigment preparation among the WO2004/078852, wherein will have organic pigment particle in small, broken bits and inorganic pigment granules combined, and these particles also have organic macromole coating.
Summary of the invention
Task of the present invention is to look for a kind of solid pigment preparation, it does not contain formaldehyde and its composition is simple as far as possible, so and it is because the dispersed first-selection of answering is arranged in various working mediums very easily is to go by simple the stirring in the working medium that (companion goes into) be distributed to liquid state.By in containing solvent or not solvent-laden application scenario, using this solid-state pigment preparation that does not contain formaldehyde, should be able to obtain higher colour strength and flocculation stability.
Surprisingly, task of the present invention can be by using at least a resin B) and solve with at least a pigment is combined.
Now be surprised to find, this solid pigment preparation that does not contain formaldehyde can be blended into like a dream and contain in solvent or the not solvent-laden coating.They can be dissolved in organic solvent or the binding agent melt easily.They have been endowed the consistency with many binding agents.Resulting coating has very good distribution.
Content of the present invention is not contain the solid pigment preparation of formaldehyde, and it contains basically
A) at least a pigment of 40 to 99 weight %,
B) 1 to 60 weight % is at least a based on aromatic ketone or itself and at least a aromatics, aliphatic series and/or alicyclic two and/or the carbonyl hydrogenated ketone resin of the reaction product of polyisocyanates and/or carbonyl hydrogenated ketone/urea formaldehyde and/or carbonyl hydrogenated and hydrogenated ketone/urea formaldehyde
C) at least a mineral filler of 0 to 50 weight %,
Composition A wherein), B) and weight summation C) be 100 weight %.
As composition A) can use the pigment and the carbon black of organic or inorganic.
Admissible pigment dyestuff is an azo pigment for example, azo azomethine pigment, metal complex pigment, Anthrachinoide pigment, phthalocyanine pigment, many ring pigment, particularly thioindigo series, quinacridone series, two  piperazine series, pyrroles's series, naphthalene tetracarboxylic acid series, perylene series, indanthrone series, Isoamidolin (on) series, those pigment that isoindolinone is serial, flavanthrene is serial, pyranthrone is serial or isoviolanthrone is serial.The mixture of this class pigment or sosoloid equally also are feasible.Specially suitable is the pigment that is selected from azo pigment, two  piperazine pigment, pyrrole pigment (preferred especially diketopyrrolo-pyrrole pigment), quinacridone pigment, phthalocyanine pigment, indanthrone or isoindolinone pigment.Important pigment dyestuff is those that put down in writing in color index (Color Index) lining.What belong to this type of for example has C.I. Pigment red 202, C.I. pigment red 122, a C.I. Pigment red 144, C.I. Pigment red 170, C.I. Pigment red 177, C.I. Pigment red 179, C.I. Pigment red 254, C.I. Pigment red 255, C.I. Pigment red 264, C.I. pigment brown 23, C.I. pigment yellow 13, C.I. Pigment Yellow 73 74, C.I. pigment yellow 83, C.I. Pigment Yellow 73 109, C.I. Pigment Yellow 73 110, C.I. pigment yellow 147, C.I. Pigment Yellow 73 191.1, C.I. pigment orange 48, C.I. pigment orange 49, C.I. pigment orange 61, C.I. pigment orange 71, C.I. pigment Blue 15, C.I. pigment blue 60, C.I. pigment violet 19, C.I. pigment Violet 23, C.I. pigment violet 37, C.I. pigment Green 7, C.I. pigment green 36.
Suitable mineral dye is for example independent or mixed metal oxide that uses, mixed metal oxide, merimee's yellow, lead chromate, chromium sulphate lead plumbate, lead molybdate, ultramarine, cobalt blue, manganese indigo plant, chromoxide green, transparent vert emeraude, cobalt green, metallic sulfide, cadmium sulfoselenide, zinc ferrite or pucherite.
Can be separately or mixedly use channel black, dim or furnace black as carbon black.These carbon blacks can also be through rear oxidation and/or granulation.
Can also use organic and inorganic pigment or sooty any mixture.
In principle, all carbonyl hydrogenated ketone resins based on aromatic ketone, carbonyl hydrogenated ketone/urea formaldehyde and carbonyl hydrogenated and hydrogenated ketone/urea formaldehyde all are suitable.According to the present invention, reduce resin B greatly) in the content of the formaldehyde that is harmful to health.Do not contain formaldehyde and mean, carbonyl hydrogenated ketone resin of the present invention have be lower than 3ppm, preferably be lower than 2.5ppm, especially preferably be lower than the free formaldehyde content of 2.0ppm.This resin B) for example is disclosed among DE102006026758.3, DE102006026760.5, DE102006009079.9, the DE102006009080.2 and preferably in category of the present invention, uses.Equally, they and at least a aromatics, aliphatic series and/or alicyclic two or the reaction product of polyisocyanates also be suitable as composition B in the solid pigment preparation).
All ketone all is suitable as the ketone that is used to prepare carbonyl hydrogenated ketone resin and carbonyl hydrogenated ketone/urea formaldehyde, particularly independent or mixed form uses acetone, methyl phenyl ketone, methylethylketone, tertiary butyl methyl ketone, 2-heptanone, propione, methyl iso-butyl ketone (MIBK), cyclopentanone, cyclododecanone, 2,2,4-and 2,4, the mixture of mixture, suberone and the cyclooctanone of 4-trimethylammonium cyclopentanone, pimelinketone and all have the mixture that one or more carbonatomss are total up to the pimelinketone that the alkyl of 1 to 8 alkyl replaces.The example of the alkyl substituted ring heptanone of being worth mentioning is 4-tert-pentyl pimelinketone, 2-sec.-butylcyclohexanone, 2-tertiary butyl pimelinketone, 4-tertiary butyl pimelinketone, 2-methylcyclohexanone and 3,3, the 5-trimethylcyclohexanone.
But that can use usually that all mention in the literature is suitable for ketone resin and ketone/urea formaldehyde synthetic ketone, generally is all C-H-acid ketone.Preferably be used alone or as a mixture carbonyl hydrogenated ketone resin and ketone/urea formaldehyde, i.e. methyl phenyl ketone, pimelinketone, 4-tertiary butyl pimelinketone, 3,3,5-trimethylcyclohexanone and heptanone based on following these ketone.
The aldehyde composition that is suitable as carbonyl hydrogenated ketone/urea formaldehyde is the aldehyde of non-side chain or side chain in principle, as formaldehyde, acetaldehyde, butyraldehyde-n, isobutyric aldehyde, valeral and lauric aldehyde.That can use usually that all mention in the literature is suitable for ketone resin synthetic aldehyde.But separately preferred or mixing ground uses formaldehyde.
Required formaldehyde uses with the form of about 20 to 40 weight % aqueous solution or alcoholic solution (for example methyl alcohol or butanols) usually.Other types of service of formaldehyde equally also are fine, and for example can also use paraformaldehyde or three  alkane.The aldehyde of aromatics can be contained in the mixture with formaldehyde equally such as phenyl aldehyde.
As composition B) precursor compound, preferred especially separately or mix ground and use by methyl phenyl ketone, pimelinketone, 4-tertiary butyl hexanone, 3,3 carbonyl hydrogenated resin and formaldehyde that 5-trimethylcyclohexanone and heptanone form.A bit weaker ground can use unhydrided ketone/urea formaldehyde, but its photostabilization is less.
The resin that ketone and aldehyde form carries out hydrogenation under the pressure that is being no more than 300bar under the catalyzer existence condition with hydrogen.At this moment, the carbonyl of ketone resin can change secondary hydroxyl into.According to the difference of reaction conditions, a part of hydroxyl can decompose, thereby obtains methylene radical.Following formula has promptly been illustrated this process:
Figure S2007101692300D00051
All ketone that also have aromatic group except C-H acid proton all are suitable as in order to prepare the ketone of carbonyl hydrogenated and hydrogenated ketone resin (composition B), particularly aralkyl ketone such as methyl naphthyl ketone, methyl phenyl ketone and/or its derivative such as cyclosubstituted acetophenone derivs are as hydroxy acetophenone, methyl acetophenone, ethylbenzene ethyl ketone, tert.-butylbenzene ethyl ketone phenylcyclohexane ethyl ketone methyl phenyl ketone.
By selection component B) hydrogenation conditions also can the hydrogenation hydroxyl, thereby form alicyclic ring.Hydrogenated resin has the OH number of 50 to 450mg KOH/g, and preferred 100 to 350mgKOH/g, preferred especially 150 to 300mg KOH/g.Aryl content be lower than 50 weight %, preferably be lower than 30 weight %, especially preferably be lower than 10 weight %.Put down in writing a kind of method among the DE3334631.
Still the formaldehyde that exists in ketone resin and the ketone/urea formaldehyde can be methyl alcohol by this hydrogenation process hydrogenation, and it is removed from product.Therefore, carbonyl hydrogenated ketone/urea formaldehyde almost is not contain formaldehyde.
The process practice that carbonyl is converted into secondary alcohol by the hydrogenation ketone resin is (for example DE870022, DE3241735, JP11012338) for a long time.The synthetic resins SK that typical and known product is Degussa AG.Equally also can use based on the carbonyl of the ketone that contains aryl and hydrogenated ketone/urea formaldehyde.Such resin is documented among the DE3334631.The OH number of this product is very high, surpasses 200mg KOH/g.
Be suitable as in order to preparation hydrogenation ketone resin, the aromatics of the derivative of carbonyl hydrogenated ketone/urea formaldehyde or carbonyl hydrogenated and hydrogenated ketone resin, aliphatic and/or alicyclic two and/or polyisocyanates be for example following two or the polyisocyanates that is used alone or as a mixture: cyclohexyl diisocyanate, methylcyclohexane diisocyanate, the ethylcyclohexane vulcabond, phenylene diisocyanate, the propyl cyclohexane vulcabond, methyl diethyl cyclohexane vulcabond, tolylene diisocyanate, two (isocyanate group phenyl) methane, the propane vulcabond, the butane vulcabond, the pentane vulcabond, hexane diisocyanate is as 1, hexamethylene-diisocyanate (HDI) or 1,5-two isocyanic acids-2-methylpentane (MPDI), the heptane vulcabond, the octane vulcabond, the nonane vulcabond is as 1,6-two isocyanic acids-2,4,4-trimethyl cyclohexane or 1,6-two isocyanic acids-2,2,4-trimethyl cyclohexane (TMDI), nonane triisocyanate such as 4-isocyanic acid methyl isophthalic acid, 8-octane vulcabond (TIN), decane vulcabond and triisocyanate, undecane two and triisocyanate, dodecane two and triisocyanate, isophorone diisocyanate (IPDI), two (isocyanic acid methylcyclohexyl) methane (H 12MDI), the isocyanic acid isocyanatomethyl, 2,5 (2,6)-two (isocyanic acid methyl), two ring [2.2.1] heptane (NBDI), 1,3-two (isocyanate group) hexanaphthene (1,3-H 6-XDI) or 1, and 4-two (isocyanic acid methyl) hexanaphthene (1,4-H 6-XDI).
The preferred polyisocyanates that another group is used to prepare hydrogenation ketone resin, carbonyl hydrogenated ketone/urea formaldehyde or carbonyl hydrogenated and hydrogenated ketone/urea formaldehyde derivative is that those have the compound more than two isocyanate groups by dimerization, trimerization, allophanic acid esterification, per molecule biuretized and/or that the simple vulcabond of urethane makes, these simple vulcabond for example, as IPDI, TMDI, HDI and/or H 12The reaction product of MDI and polyvalent alcohol (for example glycerine, TriMethylolPropane(TMP), tetramethylolmethane) or polynary polyamines, or by simple vulcabond such as IPDI, HDI and H 12The trimerization of MDI and three isocyanuric acid esters that obtain.
Also can replace the carbonyl hydrogenated ketone resin of a part, carbonyl hydrogenated ketone/urea formaldehyde or carbonyl hydrogenated and hydrogenated ketone resin by other hydroxy-functional polymers such as the polyester of hydroxy-functional and/or polyacrylic ester.Adjusting function more targetedly thus is as toughness or hardness (claim 2).
Be accelerated reaction, can use appropriate catalyst with by preparing resin based on the hydrogenation ketone resin of aromatic ketone and at least a aromatics, aliphatic series and/or alicyclic diisocyanate and/or polyisocyanates and/or carbonyl hydrogenated ketone/urea formaldehyde and/or carbonyl hydrogenated and hydrogenated ketone resin.Need so for economic reasons.All not stanniferous compounds all are suitable for quickening the OH-NCO-reaction in principle.
Organotin is known good catalyzer as dibutyl alkene dilaurate (DBTL) or dibutyl tin diacetate (DBTA).Catalyzer based on bismuth metal, zirconium, iron or aluminium is very suitable equally, as carboxylate salt, inner complex and complex compound.
Pure organic catalyst is fit to too, as tertiary amine for example 1,4-diazabicylo [2.2.2] octane (DABCO), 1,8-diazabicylo [5.4.0] 11-7-alkene (DBU), N, N-dimethylcyclohexylamine (DMCA) or 1,5-diazabicylo [2.3.0] ninth of the ten Heavenly Stems-5-alkene (DBN).
Prepared based on aromatic ketone and at least a aromatics, aliphatic series and/or alicyclic diisocyanate and/or polyisocyanates the hydrogenation ketone resin and/or the melting range of the reaction product of carbonyl hydrogenated ketone/urea formaldehyde and/or carbonyl hydrogenated and hydrogenated ketone resin for being higher than 140 ℃, preferably be higher than 145 ℃, especially preferably be higher than 150 ℃.
These products are for a long time known.Typical product is the Kunstharz 1201 of Degussa AG.
As composition C) also can use filler simultaneously.They in most cases be powdered and in working medium insoluble,practically material.They are mainly obtained by decomposing, purify, grinding and then sieve into particle fraction by the mineral of natural origin.But also can use sintetics such as vitriol or carbonate as filler, if consider for example purity (brightness) or special fineness.Different with pigment, filler generally has less covering power.Except extended volume (making cheaper), they have also shown very special effect in film, for example reflection, surface tissue, wear-resisting or anti-building stones impact.Its granularity, size-grade distribution, particle shape, grain pattern, hardness, density, color, wettability, wear resistance, surface adsorption, refractive index, chemical constitution, purity, stability and price are depended in their use.
Be applicable to that filler in the solid pigment preparation of the present invention is for example based on those of kaolin, talcum, mica, other silicate, quartz, cristobalite, wollastonite, perlite, diatomite, fibrous packing, aluminium hydroxide, barium sulfate or lime carbonate.
Content of the present invention also is a kind of method for preparing formaldehydeless solid pigment preparation, and described preparation comprises basically:
A) at least a pigment of 40 to 99 weight %,
B) 1 to 60 weight %'s is at least a based on aromatic ketone or itself and at least a aromatics, aliphatic series and/or alicyclic two and/or the carbonyl hydrogenated ketone resin of the reaction product of polyisocyanates and/or carbonyl hydrogenated ketone/urea formaldehyde and/or carbonyl hydrogenated and hydrogenated ketone resin
C) at least a mineral filler of 0 to 50 weight %,
Composition A wherein), B) and weight summation C) be 100 weight %,
It is characterized in that, preparation in organic solvent and/or water by pigment A), based on aromatic ketone or itself and at least a aromatics, aliphatic series and/or alicyclic two and/or the carbonyl hydrogenated ketone resin of the reaction product of polyisocyanates and/or carbonyl hydrogenated ketone/urea formaldehyde and/or carbonyl hydrogenated and hydrogenated ketone resin B) and optional mineral filler C) suspension formed, this suspension of dispersion and separate solid pigment preparation in suitable device.
Can consider ball mill especially, have the agitating ball mill or the radiation agitator mill of level or vertical stratification as dispersing apparatus.But, also can use for example Dispermat, Skandex mixing machine, Red Devil, single-wheel mill, three disc sharpeners or bead mill.The separation of solid pigment preparation can be carried out with the drying installation of routine, for example in fluidized-bed, spray-dryer, belt dryer or vacuum drier.The depolymerization for preparing contained agglomerate of going in the pigment preparation process of the present invention for example can utilize hammer mill, needle mill, impact mill or screen separator mill to carry out, but also can be nested in the drying process, for example carries out with the form of mill-drying.
The solid pigment preparation that does not contain formaldehyde of the present invention can be blended into and go all well-known to those skilled in the art containing in solvent and not solvent-laden coating system such as japanning, coating, binding agent, ink or the printing-ink.These systems can be for example physical dryness, oxidation drying or in the japanning of 1 component or 2 compositions, have reactive.
The resin that many physical drynesses are arranged, for example Nitrocellulose, polyvinyl butyral acetal, VC-multipolymer, acrylate, methacrylic acid, cellulose ester, ether of cellulose, hydrocarbon resin, phenol resins, Gum Rosin, maleic ester resin, polystyrene resin, silicone resin, rubber-based is coated with coating resins such as thermoprene, chlorinated rubber, chlorinatedpolyolefins or low polyhutadiene, polyolefine, polyvinyl ester, polyvinyl alcohol, polyvinyl acetal, epoxide, aminoresin, acyl ammonia resin and vibrin.The coated material of oxidation drying is a Synolac for example.1 component coating material is based on for example (methyl) acrylate resin, Resins, epoxy, polyvinyl acetate resins, vibrin or urethane resin.These resins also can be undersaturated, promptly contain acrylate or methacrylic ester two key, for example (methyl) acrylate resin of (methyl) acrylated, epoxidation (methyl) acrylate resin, polyester (methyl) acrylate resin, polyethers (methyl) acrylate resin or urethane (methyl) acrylate resins.That the coating material of 1 component also can be based on hydroxyl and contain melamine resin or blocked polyisocyanate resin as those of the polyacrylate resin of linking agent or vibrin.2 component coating materials be for example based on polyepoxide system or hydroxyl and contain non-blocked polyisocyanate resin as those of the polyacrylate resin of linking agent or vibrin.
In coating system, can use all auxiliary agent well-known to those skilled in the art and additives.What belong to this type of is defoamer for example, air release agent, and auxiliary rheological agents can for example influence the surface additive of oilness, scratch resistance, adhesion inhibiting properties, distribution situation and glossiness, base material wetting additive, drying material, stablizer or biocide.
Therefore, content of the present invention also is not contain the purposes of solid pigment preparation in coating, japanning, binding agent, ink or printing-ink of formaldehyde, and wherein said preparation contains substantially:
A) at least a pigment of 40 to 99 weight %,
B) 1 to 60 weight %'s is at least a based on aromatic ketone or itself and at least a aromatics, aliphatic series and/or alicyclic two and/or the carbonyl hydrogenated ketone resin of polyisocyanates reaction product and/or carbonyl hydrogenated ketone/urea formaldehyde and/or carbonyl hydrogenated and hydrogenated ketone resin
C) at least a mineral filler of 0 to 50 weight %,
Composition A wherein), B) and weight summation C) be 100 weight %.
The solid pigment preparation that does not contain formaldehyde of the present invention is characterised in that utmost point dispersibility easily in used various working mediums, particularly be dissolved in the liquid working medium by simple stirring (admixing).By this solid pigment preparation being used for containing solvent or not solvent-laden occasion, powder painting for example just can obtain having very high colour strength, the coating system of high glossiness and good resistance flocculence very.
Embodiment
Following examples should be regarded further elaboration the present invention as, rather than its Application Areas is limited:
Embodiment
1) the carbonyl hydrogenated ketone/urea formaldehyde (non-of the present invention) of preparation
Preset 1200g methyl phenyl ketone, 220g methyl alcohol, 0.3g benzyl tributyl ammonium chloride and 360g 30% formalin and stir.Stir the 25% caustic soda aqueous solution that adds 32g then.Then stir 30% formalin that adds 655g through 90min down at 80 to 85 ℃.Reflux temperature stirs down closes agitator after the 5h and water is separated mutually from resin.Thick product washs with aqueous acetic acid, until the fusing sample clarification of resin.Then by the distillation dry resin.
Obtained the resin of the little Huang of 1270g.Resin is that clarification is brittle and have a fusing point of 72 ℃.It for example is dissolved in acetic ester such as N-BUTYL ACETATE and the vinyl acetic monomer, is dissolved in aromatics such as toluene and the dimethylbenzene, and is insoluble in the ethanol.
The resin that 400g is so made is dissolved in the 650g tetrahydrofuran (THF) (water-content about 7%).In autoclave (Parr company), under the condition of 260bar and 160 ℃, carry out hydrogenation then with the catalyst basket that is filled with the commercially available Ru catalyzer of 100mL (3% Ru is arranged on the aluminum oxide).Via strainer reaction mixture is discharged from reactor after the 20h.
Character: hydroxyl value 315mg KOH/g; 116 ℃ of fusing points; The colour that records (50% vinyl acetic monomer solution) according to Gardner is 0.2.
Hydrogenated resin is dissolved in ethanol, methylene dichloride, vinyl acetic monomer, N-BUTYL ACETATE, Virahol, acetone and the diethyl ether.It is insoluble in nonpolar solvent such as normal hexane or the test gasoline.
2) prepare solid pigment preparation of the present invention
The Spezialschwarz 4 (the C.I. Pigment black 7 of Degussa AG) that stirs 380g with the water of 520g forms aqueous cake of press.In an autonomous container with carbonyl hydrogenated ketone/urea formaldehyde 1 of 467g) be dissolved in the 467g ethanol and add 76.5g ULTRA Talc 609 (Barretts MineralsInc.).Talcum/resin compound joined in the pigment cake of press and in dissolver disperse.Pigment dispersion is dry and grind to form micro mist in drying cupboard.
3) prepare solvent-laden pigment preparation (non-of the present invention)
Mix the Spezialschwarz 4 of 280g and carbonyl hydrogenated aldehyde/ketone resin 1 of 520g) 50% solution that in acetic acid methoxyl group propyl ester, forms and the Disperbyk 163 of 187g (Byk-Chemie company) and add granulated glass sphere at 1: 1 into 1mm according to volume ratio.In Dispermat CV under 3000 commentaries on classics/min conditions dispersed mixture 80min.
4) prepare solvent-laden priming paint (non-of the present invention)
Utilize the granulated glass sphere of 2mm in Dispermat CV and under the condition of 2400 commentaries on classics/min and 25 ℃ of cover temperature, to stir listed materials 20min in the table.Then at room temperature dry white middle oily alkyd paint 24h.Binding agent (solid) is 1: 0.8 to the ratio of white pigment.
Table 1: the composition of priming paint
Materials Consumption (weight %)
Alkydal F 49(55％) 61.92
Kronos 2310 27.24
Ca Sikkativ(5％Ca) 0.77
Co-Sikkativ(10％Co) 0.53
Zr-Sikkativ(12％Zr) 0.18
Mn-Sikkativ(10％Mn) 0.10
Octa-Soligen VP 033 0.26
Dimethylbenzene 4.5
Acetic acid methoxyl group propyl ester 2.1
Test gasoline 2.1
Borchinox M2 0.3
Summation 100.0
5) prepare coating composition of the present invention
Prepare pigment preparation 2) and 3) priming paint (4) that adds white stirred with the preparation coating material and by part ground.Table 2 has provided coating composition and performance thereof.
Table 2: coating composition
Prescription Embodiment Comparative example
4) white paint 150.0g 150.0g
2) black solid pigment preparation 3.2g -
3) black pigment preparation - 4.2g
Butyl glycol 3.0g 3.0g
Hydropalat 535N 2.3g 2.3g
Black pigment % based on white pigment 3.2 3.2
The technical feature of the coating on the Standard Steel
Bed thickness (μ m) 23 23
Pendulum hardness after record according to K  nig 28 days 85 84
Crosscut value after 28 days 0 0
Erichsen deep-draw value (mm) after 28 days 6.5 6.5
20 °/60 ° of glossiness after 28 days 75/87 74/87
Mist degree after 28 days 50-53 51-55
The Δ E value of wiping 0.96 0.99
Do not contain the solid pigment preparation of formaldehyde and the coating composition of solvent-laden white alkyd paint has very high glossiness and favorable mechanical and color characteristics based on the present invention shown in the embodiment.These character are with suitable based on the coating composition of solvent-laden pigment preparation.

Claims (26)

1. do not contain the solid pigment preparation of formaldehyde, it comprises basically:
A) at least a pigment of 40 to 99 weight %,
B) 1 to 60 weight %'s is at least a based on aromatic ketone or itself and at least a aromatics, aliphatic series and/or alicyclic two and/or the carbonyl hydrogenated ketone resin of the reaction product of polyisocyanates and/or carbonyl hydrogenated ketone/urea formaldehyde and/or carbonyl hydrogenated and hydrogenated ketone/urea formaldehyde
C) at least a mineral filler of 0 to 50 weight %,
Composition A wherein), B) and weight summation C) be 100 weight %.
2. do not contain the solid pigment preparation of formaldehyde, it comprises basically:
A) at least a pigment of 40 to 99 weight %,
B) 1 to 60 weight %'s is at least a based on aromatic ketone or itself and at least a aromatics, aliphatic series and/or alicyclic two and/or the carbonyl hydrogenated ketone resin of the reaction product of polyisocyanates and/or carbonyl hydrogenated ketone/urea formaldehyde and/or carbonyl hydrogenated and hydrogenated ketone/urea formaldehyde, and use the polymkeric substance of another kind of at least hydroxy-functional simultaneously
C) at least a mineral filler of 0 to 50 weight %,
Composition A wherein), B) and weight summation C) be 100 weight %.
3. as at least one described solid-state pigment preparation that does not contain formaldehyde of above-mentioned claim, it is characterized in that, as composition A) be used alone or as a mixture the pigment or the carbon black of organic or inorganic.
4. as at least one described solid-state pigment preparation that does not contain formaldehyde of above-mentioned claim, it is characterized in that, be used alone or as a mixture and be selected from following pigment dyestuff: thioindigo series, quinacridone series, two  piperazine series, pyrroles's series, naphthalene tetracarboxylic acid series, perylene series, indanthrone series, Isoamidolin (on) series, isoindolinone is serial, flavanthrene is serial, pyranthrone is serial or isoviolanthrone is serial azo pigment, azo azomethine pigment, metal complex pigment, Anthrachinoide pigment, phthalocyanine pigment, encircle pigment more.
5. as at least one described solid-state pigment preparation that does not contain formaldehyde of above-mentioned claim, it is characterized in that independent or mixed form uses and is selected from following mineral dye: metal oxide, mixed metal oxide, merimee's yellow, lead chromate, chromium sulphate lead plumbate, lead molybdate, ultramarine, cobalt blue, manganese indigo plant, chromoxide green, transparent vert emeraude, cobalt green, metallic sulfide, cadmium sulfoselenide, zinc ferrite or pucherite.
6. as at least one described solid-state pigment preparation that does not contain formaldehyde of above-mentioned claim, it is characterized in that, use channel black, dim or furnace black as carbon black.
7. as at least one described solid-state pigment preparation that does not contain formaldehyde of above-mentioned claim, it is characterized in that, use C-H-acid ketone to come prepared composition B).
8. as at least one described solid-state pigment preparation that does not contain formaldehyde of above-mentioned claim, it is characterized in that, at composition B) carbonyl hydrogenated ketone resin and ketone/urea formaldehyde in separately or mix ground and use and be selected from ketone as described below as precursor compound: acetone, methyl phenyl ketone, methylethylketone, tertiary butyl methyl ketone, 2-heptanone, propione, methyl iso-butyl ketone (MIBK), cyclopentanone, cyclododecanone, 2,2,4-and 2,4,4-trimethylammonium cyclopentanone, suberone, cyclooctanone, pimelinketone, have one or more carbonatomss and be total up to the mixture of the pimelinketone that the alkyl of 1 to 8 alkyl replaces.
9. as at least one described solid-state pigment preparation that does not contain formaldehyde of above-mentioned claim, it is characterized in that, at composition B) carbonyl hydrogenated ketone resin and ketone/urea formaldehyde in use 4-tert-pentyl pimelinketone, 2-sec.-butylcyclohexanone, 2-tertiary butyl pimelinketone, 4-tertiary butyl pimelinketone, 2-methylcyclohexanone and 3,3, the 5-trimethylcyclohexanone.
10. as at least one described solid-state pigment preparation that does not contain formaldehyde of above-mentioned claim, it is characterized in that, in carbonyl hydrogenated ketone resin and ketone/urea formaldehyde, use methyl phenyl ketone, pimelinketone, 4-tertiary butyl pimelinketone, 3,3,5-trimethylcyclohexanone or heptanone separately or with mixing.
11. as at least one described solid-state pigment preparation that does not contain formaldehyde of above-mentioned claim, it is characterized in that, as composition B) in carbonyl hydrogenated ketone resin and the aldehyde composition in carbonyl and the hydrogenated ketone/urea formaldehyde, separately or mix ground and use formaldehyde, acetaldehyde, butyraldehyde-n and/or isobutyric aldehyde, valeral, lauric aldehyde.
12. as at least one described solid-state pigment preparation that does not contain formaldehyde of above-mentioned claim, it is characterized in that, use formaldehyde and/or paraformaldehyde and/or three  alkane.
13. as at least one described solid-state pigment preparation that does not contain formaldehyde of above-mentioned claim, it is characterized in that, as composition B) use by methyl phenyl ketone, 4-tertiary butyl methyl ketone, pimelinketone, 4-tertiary butyl pimelinketone, 3,3,5-trimethylcyclohexanone, heptanone are separately or mix the carbonyl hydrogenated product and the formaldehyde of the resin that forms.
14. as at least one described solid-state pigment preparation that does not contain formaldehyde of above-mentioned claim, it is characterized in that, at composition B) carbonyl and hydrogenated ketone/urea formaldehyde in use aryl alkyl ketone.
15. as at least one described solid-state pigment preparation that does not contain formaldehyde of above-mentioned claim, it is characterized in that, at composition A) carbonyl and hydrogenated ketone resin in contain the ketone that is selected from methyl phenyl ketone, cyclosubstituted acetophenone derivs such as hydroxy acetophenone, methyl acetophenone, ethylbenzene ethyl ketone, tert.-butylbenzene ethyl ketone, phenylcyclohexane ethyl ketone, methyl naphthyl ketone.
16. as at least one described solid-state pigment preparation that does not contain formaldehyde of above-mentioned claim, it is characterized in that, as composition B) separately or mix ground and use and be selected from following vulcabond: cyclohexyl diisocyanate, methylcyclohexane diisocyanate, the ethylcyclohexane vulcabond, phenylene diisocyanate, the propyl cyclohexane vulcabond, methyl diethyl cyclohexane vulcabond, tolylene diisocyanate, two (isocyanate group phenyl) methane, propane vulcabond, butane vulcabond, the pentane vulcabond, hexane diisocyanate such as hexamethylene diisocyanate (HDI) or 1,5-is diisocyanate based-2-methylpentane (MPDI), the heptane vulcabond, octane vulcabond, nonane vulcabond are as 1, and 6-diisocyanate based-2,4,4-trimethyl cyclohexane or 1,6-diisocyanate based-2,2,4-trimethyl cyclohexane (TMDI), nonane triisocyanate such as 4-isocyanic acid methyl isophthalic acid, 8-octane vulcabond (TIN), decane vulcabond and triisocyanate, undecane two and triisocyanate, dodecane two and triisocyanate, isophorone diisocyanate (IPDI), two (isocyanic acid methylcyclohexyl) methane (H 12MDI), isocyanic acid methyl cyclohexyl isocyanate, 2,5 (2,6)-two (isocyanic acid methyl), two ring [2.2.1] heptane (NBDI), 1,3-two (isocyanic acid methyl) hexanaphthene (1,3-H 6-XDI) or 1, and 4-two (isocyanic acid methyl) hexanaphthene (1,4-H 6-XDI).
17. as at least one described solid-state pigment preparation that does not contain formaldehyde of above-mentioned claim, it is characterized in that, as composition B) use by dimerization, trimerization, allophanic acid esterification, biuretized and/or polyisocyanates that the simple vulcabond of urethane makes.
18., it is characterized in that, as composition B as at least one described solid-state pigment preparation that does not contain formaldehyde of above-mentioned claim) use based on IPDI, TMDI, H 12The isocyanic ester of MDI and/or HDI.
19. as at least one described solid-state pigment preparation that does not contain formaldehyde of above-mentioned claim, it is characterized in that, based on the melting range of the reaction product of the hydrogenation ketone resin of aromatic ketone and at least a aromatics, aliphatic series and/or alicyclic diisocyanate and/or polyisocyanates and/or carbonyl hydrogenated ketone/urea formaldehyde and/or carbonyl hydrogenated and hydrogenated ketone resin for being higher than 140 ℃, preferably be higher than 145 ℃, especially preferably be higher than 150 ℃.
20. as at least one described solid-state pigment preparation that does not contain formaldehyde of above-mentioned claim, it is characterized in that, use hydroxy-functional polymers to come prepared composition B).
21. as at least one described solid-state pigment preparation that does not contain formaldehyde of above-mentioned claim, it is characterized in that, as composition C) use compound based on kaolin, talcum, mica, other silicate, quartz, cristobalite, wollastonite, perlite, diatomite, fibrous packing, aluminium hydroxide, barium sulfate or lime carbonate.
22. prepare the method for almost formaldehydeless solid pigment preparation, described preparation comprises basically:
A) at least a pigment of 40 to 99 weight %,
B) 1 to 60 weight %'s is at least a based on aromatic ketone or itself and at least a aromatics, aliphatic series and/or alicyclic two and/or the carbonyl hydrogenated ketone resin of the reaction product of polyisocyanates and/or carbonyl hydrogenated ketone/urea formaldehyde and/or carbonyl hydrogenated and hydrogenated ketone resin
C) at least a mineral filler of 0 to 50 weight %,
Composition A wherein), B) and weight summation C) be 100 weight %,
It is characterized in that, preparation in organic solvent and/or water, by pigment A), based on aromatic ketone or itself and at least a aromatics, aliphatic series and/or alicyclic two and/or the carbonyl hydrogenated ketone resin of the reaction product of polyisocyanates and/or carbonyl hydrogenated ketone/urea formaldehyde and/or carbonyl hydrogenated and hydrogenated ketone resin B) and mineral filler C randomly) suspension formed, in suitable device, disperse this suspension and separate solid pigment preparation.
23. the method for the solid pigment preparation that preparation as claimed in claim 28 is almost formaldehydeless, it is characterized in that, suspension is disperseed in ball mill, agitating ball mill, radiation agitator mill, Dispermat, Skandex mixing machine, Red Devil, single-wheel mill, three disc sharpeners or bead mill.
24. the method as the almost formaldehydeless solid pigment preparation of the described preparation of at least one item in the claim 28 to 29 is characterized in that separate solid pigment preparation in fluidized-bed, spray-dryer, belt dryer or vacuum drier.
25. the method as the almost formaldehydeless solid pigment preparation of the described preparation of at least one item in the claim 28 to 30 is characterized in that, at its after separating solid pigment preparation is carried out de-agglomerate in hammer mill, needle mill, impact mill or screen separator mill.
26. contain the purposes of solid pigment preparation in coating, japanning, binding agent, ink or printing-ink of formaldehyde hardly, described preparation contains basically:
A) at least a pigment of 40 to 99 weight %,
B) 1 to 60 weight %'s is at least a based on aromatic ketone or itself and at least a aromatics, aliphatic series and/or alicyclic two and/or the carbonyl hydrogenated ketone resin of the reaction product of polyisocyanates and/or carbonyl hydrogenated ketone/urea formaldehyde and/or carbonyl hydrogenated and hydrogenated ketone resin
C) at least a mineral filler of 0 to 50 weight %,
Composition A wherein), B) and weight summation C) be 100 weight %.
CNA2007101692300A 2006-11-03 2007-11-02 Solid formaldehyde-free pigment preparations Pending CN101173114A (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019155287A1 (en) * 2018-02-08 2019-08-15 Guangdong Huarun Paints Co., Ltd. Ketone-aldehyde modified resin and the preparation process thereof

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DE102004020740A1 (en) 2004-04-27 2005-11-24 Degussa Ag Polymer compositions of carbonyl-hydrogenated ketone-aldehyde resins and polyisocyanates in reactive solvents
DE102007047586A1 (en) * 2007-10-05 2009-04-09 Evonik Degussa Gmbh Coating compositions
DE102007047584A1 (en) * 2007-10-05 2009-04-09 Evonik Degussa Gmbh Ink compositions

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DE19643704A1 (en) * 1996-10-23 1998-04-30 Huels Chemische Werke Ag Aqueous resin dispersions
DE102004005207A1 (en) * 2004-02-03 2005-08-11 Degussa Ag Use of radiation-curable resins based on ketone and / or urea-aldehyde resins
DE102004039083A1 (en) * 2004-08-12 2006-02-23 Degussa Ag Tin-free, high-melting reaction products of carbonyl-hydrogenated ketone-aldehyde resins, hydrogenated ketone resins and carbonyl- and ring-hydrogenated ketone-aldehyde resins based on aromatic ketones and polyisocyanates

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019155287A1 (en) * 2018-02-08 2019-08-15 Guangdong Huarun Paints Co., Ltd. Ketone-aldehyde modified resin and the preparation process thereof
US11692059B2 (en) 2018-02-08 2023-07-04 Guangdong Huarun Paints Co., Ltd. Ketone-aldehyde modified resin and the preparation process thereof

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