EP0939786A2 - Colorant en pate - Google Patents

Colorant en pate

Info

Publication number
EP0939786A2
EP0939786A2 EP98954147A EP98954147A EP0939786A2 EP 0939786 A2 EP0939786 A2 EP 0939786A2 EP 98954147 A EP98954147 A EP 98954147A EP 98954147 A EP98954147 A EP 98954147A EP 0939786 A2 EP0939786 A2 EP 0939786A2
Authority
EP
European Patent Office
Prior art keywords
color paste
color
plastic
weight
paste 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.)
Withdrawn
Application number
EP98954147A
Other languages
German (de)
English (en)
Inventor
Matthias Sikorski
Werner Klockemann
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.)
Performance Chemicals Handels GmbH
Original Assignee
Performance Chemicals Handels GmbH
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Performance Chemicals Handels GmbH filed Critical Performance Chemicals Handels GmbH
Publication of EP0939786A2 publication Critical patent/EP0939786A2/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • 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
    • C08J3/22—Compounding polymers with additives, e.g. colouring using masterbatch techniques
    • C08J3/226—Compounding polymers with additives, e.g. colouring using masterbatch techniques using a polymer as a carrier
    • 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
    • C08J3/22—Compounding polymers with additives, e.g. colouring using masterbatch techniques
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
    • C08L75/02—Polyureas
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
    • C08L75/04—Polyurethanes
    • 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
    • C09B67/002—Influencing the physical properties by treatment with an amine
    • 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
    • C09B67/0065—Preparation of organic pigments of organic pigments with only non-macromolecular compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D17/00—Pigment pastes, e.g. for mixing in paints
    • C09D17/004—Pigment pastes, e.g. for mixing in paints containing an inorganic pigment
    • 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
    • C08J2471/00—Characterised by the use of polyethers obtained by reactions forming an ether link in the main chain; Derivatives of such polymers

Definitions

  • the invention relates to a color paste composition containing color pigments and their use for coloring polyurethane, polyurea or epoxy plastics
  • color pigments contribute through light absorption and light scattering with light scattering predominates with inorganic color pigments, light absorption with organic pigments.
  • pigments are present in insoluble form in plastic and also go at the usual reaction temperatures or melting temperatures, e.g. B when processing plastics, not in solution
  • Colorants such as color paste compositions
  • raw dye pigments are always possible if the plastic is sufficiently agitated (miscibility) and heatable in this work step.
  • Raw dye pigments are preferably used when there is a high concentration of color pigment in the plastic.
  • the plastic is used for this mostly used in the form of granules
  • the direct introduction of the pigment powder harbors the risk of the color intensity being distributed unevenly. This process is mostly used only for white pigments and "carbon black"
  • color pigments are usually used in the form of dispersions of the pigments (color pastes) in neutral media that are compatible with the plastic.
  • color pastes in neutral media that are compatible with the plastic.
  • the agglomerates are broken up as extensively as possible and the air is displaced in order to To create the most perfect possible pigment-plastic matrix compound.
  • the drying step of the raw pigments can often be saved during the production of the color paste because the solvent wets the pigment particles and thus displaces the adhering water
  • Color pastes are added during the manufacture of the plastics or the processing of the plastic powder or granules. In the latter case, the color paste is mixed with the plastic powder or granulate and then processed further using extruders or injection molding machines
  • Known solvents (dispersants) for color pastes are, for example, di-octyl phthalate (DOP), trichlorethylene phosphate, polyols or paraffinols.
  • DOP di-octyl phthalate
  • trichlorethylene phosphate polyols or paraffinols.
  • the color pigment is always in dispersed, highly concentrated form. If the dye goes into solution, we speak in contrast to liquid dyes
  • the color pigments are thus in the form of aggregates. Large and large distribution of the aggregates determine the color properties of the dye additive
  • pigments are usually sold in predispersed form, for example as color paste, which makes it easier to distribute the colorants in the plastic to break up the agglomerates
  • Color pastes should be designed so that the color pigments in the plastics have the following properties
  • plastics whose glass transition temperature is below the storage temperature may tend to bloom.
  • the migration phenomenon is described as blooming, in which pigment particles from the plastic / pigment system migrate to the surface of the plastic at room temperature
  • Pigments can be classified on the basis of their color-forming properties. Some color pigments are listed in Table I.
  • Polyurethane plastics are usually colored directly during production, e.g. during reaction injection molding (RIM). Colored pigments are used almost exclusively for the production process of colored polyurethanes, which is not technically easy to handle. It is preferred to add the color pigments directly to the foamable mixture, if necessary, so that during the process Foam formation is present. The color additives are exposed to high thermal loads. Temperatures of 150 ° C and higher can be reached in the reaction mixture. Isocyanate, polyol and activator mixture are brought into contact for the reaction. The pigments are often added to the so-called activator mixture and with it led together to the mixing head, where the final mixing of all reactants takes place.
  • RIM reaction injection molding
  • the pigment can also be mixed with the polyol component, the prepolymer or the NCO component.
  • the pigment can be metered in by metering pumps, e.g. n take the form of gear pumps.
  • the activator mixture contains typical polyurethane catalysts such as tertiary amines and / or tin salts
  • a problem in the production of polyurethane plastics is the tendency of the pigments, especially the inorganic pigments, to flocculate.
  • the tendency of the pigments to agglomerate between the mixing of the reactants and the final curing of the polymer leads to a clearly inhomogeneous pigment distribution, especially white pigments tendency to flocculate
  • white pigments tendency to flocculate The resulting reduction in the white pigment content in some areas can lead to a significant decrease in color depth and color brightness.
  • a thin surface layer in particular has a higher color density. If the plastics are exposed to surface wear, the lower color density of the underlying layer occurs
  • the prior art is to counteract this tendency by the choice of the pigments, grain size and type of coating (eg aluminum silicate coated TiO 2 )
  • DE 3 1 51 753 discloses pigment preparations which contain high molecular weight reaction products of polyalkylamine compounds with ethylene oxide and propylene oxide. However, no reactive amine compounds are obtained which contain at least one primary and / or secondary amine group per molecule also do not receive any color pastes suitable for the "reactive coloring" of plastics, which ensure homogeneous coloring of the plastic and do not tend to migrate, bloom or flocculate after incorporation into the plastic
  • the object of the present invention is to provide color pastes which are suitable for sufficiently dispersing color pigments in the plastics, preferably in molded plastic parts, while at the same time ensuring a homogeneous coloring of the plastic and after incorporation into the plastic not for migration, for Bloom or tend to flocculate
  • the amine compounds are preferably at least in the range from 0 ° C to 50 ° C at normal pressure as liquids.
  • the amine compounds are reactive amine compounds with regard to the monomer components used and therefore preferably predominantly (per molecule) have secondary and / or primary amine groups, the primary amine groups are preferred. It is therefore particularly preferred that the amine compounds per molecule have at least 50% primary amine groups.
  • the diperging agent is advantageously a primary or secondary polyetheramine, which particularly preferably has polyethylene oxide and / or polypropylene oxide units and, independently thereof, preferably has terminal primary amine groups (for example a polyalkylene glycol reacted with an amine, preferably ammonia).
  • Amines are also also With several, for example, more than two amine groups, such as, for example, the reaction products of diethylene triamine, triethylene tetramine, tetraethylene pentamine and dipropylene triamine with polyalkylene ethers, suitable for the use according to the invention.
  • Pigments which can be used according to the invention are listed in Table I.
  • the pigment can be chemically uniform or chemically in combination different pigments are used. It is preferably an inorganic pigment or carbon pigment, particularly preferably an inorganic white pigment
  • the invention further relates to colored polyurethane, polyurea or epoxy plastics produced using the color paste according to the invention, the pigment preferably being added in an amount of 0.3 to 10% by weight, based on the components used to produce the plastic
  • plastics are preferably colored during production, the color paste being admixed during the reaction of the starting materials or being contained in a reaction component or the reaction medium.
  • the color pastes according to the invention can be used particularly advantageously in the production process for colored polyurethanes described above
  • the product according to the invention has at least one group which is reactive with the isocyanate groups present
  • the color pigments which are / were wetted by the dispersant, are apparently incorporated and fixed in the plastic matrix. This procedure surprisingly prevents migration or blooming of the color pigments, and thus also agglomeration of the pigments, and leads to a uniform color depth after curing Color brightness
  • the color pastes can also be used in dilution.
  • Conventional unreactive dispersants such as dioctyl phthalate or dispersants with a reactive hydrogen group such as polyether or polyester polyols are suitable
  • Polyurethanes are generally not chemically uniform plastics.
  • Polyurethanes in the sense of the invention are the reaction products of compounds with at least one isocyanate group with hydrogen-active compounds such as polyols, amines or carboxylic acids or also epoxides, urethane, urea and allophanate -, Biuret, amide, carbodiimide, uretonimine, uretdione, isocyanurate or oxazolidone groups are formed.
  • the polyurethanes are usually produced by the "one-shot process” or the "prepolymer process” Color paste according to the invention introduced only in the last manufacturing stage of the plastic
  • polyureas are also used.
  • Polyurethanes are primarily known as foams, elastomers and solid molded parts. They also play a role as PUR lacquers, paints, adhesives, coating materials, elastifiers and fibers.
  • Polyureas are characterized by a higher heat resistance than that Polyurethanes made of them are used either as pure polyureas or as copolymers that contain both polyurea and polyurethane bonds
  • Dyed polyureas according to the invention are particularly advantageously produced in which the color paste according to the invention or a dilution of this color paste in a ratio of 1 1 to 1 100, in particular 1 10 to 1 100, preferred essentially with an amine compound of the above-mentioned type (B), via a high-pressure mixing head at 10 to 500 bar, in particular 30 to 300 bar, is added during the production of the polyurea -Connection introduced
  • the color pastes according to the invention it is possible to use the color pastes according to the invention to prepare dilutions from 1 1 to 1 100, which have a settling stability of more than one week and can therefore be used as a premix in production reachable there
  • epoxy plastics are the reaction products of epoxides with amines, acids or alcohols (phenols).
  • the reaction of epichlorohydrin with bisphenol-A in particular has become important for the synthesis of polymers.
  • the use of color pastes for so-called 2K systems is preferred, such as those used for coatings
  • the color paste can furthermore contain conventional dispersing aids such as surfactants, emulsifiers, foam inhibitors, such as, for example, polysiloxane-polyether copolymers, plasticizers, internal release agents, such as, for example, zinc stearates, or antioxidants
  • conventional dispersing aids such as surfactants, emulsifiers, foam inhibitors, such as, for example, polysiloxane-polyether copolymers, plasticizers, internal release agents, such as, for example, zinc stearates, or antioxidants
  • Titanium dioxide Zinc white (ZnO) Zinc sulfide (ZnS) Barium sulfate (BaSO4)
  • Iron oxide black (Fe 3 O)
  • Chromium oxide green (Cr 2 O 3 )
  • Cobalt green (Co, Ti, Al, Ni, Zn mixed oxide)
  • Cobalt blue (Co, Al, Cr mixed oxide)
  • Iron oxide brown FeO Fe 2 O 3
  • Molybdate Red Pb (Cr, Mo, S) O 4
  • Iron oxide yellow (Fe 2 O 3 x H 2 O)

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Processes Of Treating Macromolecular Substances (AREA)
  • Pigments, Carbon Blacks, Or Wood Stains (AREA)
  • Coloring (AREA)

Abstract

L'invention concerne un colorant en pâte renfermant des pigments colorés et un composé aminé comme agent de dispersion, ainsi que l'utilisation de ce colorant en pâte pour colorer notamment des matières plastiques en polyuréthane, polycarbamide et époxyde.
EP98954147A 1997-09-09 1998-09-08 Colorant en pate Withdrawn EP0939786A2 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE1997139601 DE19739601A1 (de) 1997-09-09 1997-09-09 Farbpasten zum Einfärben von Kunststoffen
DE19739601 1997-09-09
PCT/DE1998/002658 WO1999013002A2 (fr) 1997-09-09 1998-09-08 Colorant en pâte

Publications (1)

Publication Number Publication Date
EP0939786A2 true EP0939786A2 (fr) 1999-09-08

Family

ID=7841790

Family Applications (1)

Application Number Title Priority Date Filing Date
EP98954147A Withdrawn EP0939786A2 (fr) 1997-09-09 1998-09-08 Colorant en pate

Country Status (3)

Country Link
EP (1) EP0939786A2 (fr)
DE (1) DE19739601A1 (fr)
WO (1) WO1999013002A2 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10047838B4 (de) * 2000-09-27 2016-07-21 Chemicon GmbH Verfahren und Vorrichtung zur Applikation von Reaktionsharzbeschichtungen
US7060750B2 (en) * 2004-04-28 2006-06-13 Bayer Materialscience Llc Moisture-curable, polyether urethanes and their use in sealant, adhesive and coating compositions
US20090069467A1 (en) * 2005-04-21 2009-03-12 Gloria Ruiz Gomez Pigment formulations

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3151753A1 (de) * 1981-12-29 1983-07-07 Basf Ag, 6700 Ludwigshafen Hochkonzentrierte, nichtstaubende, feste und leicht verteilbare pigmentpraeparation und deren verwendung
DE3622710A1 (de) * 1986-07-05 1988-01-07 Basf Lacke & Farben Verfahren zur herstellung von waessrigen, epoxid-aminaddukte enthaltenden pigmentdispersionen
US5059249A (en) * 1989-02-21 1991-10-22 Basf Corp. Process for dispersing organic pigments with ultrasonic radiation
JPH0815519A (ja) * 1994-06-27 1996-01-19 Toray Ind Inc カラーペーストおよびその製造方法
DE19620989A1 (de) * 1996-05-24 1997-11-27 Bayer Ag Pigmentpräparationen

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9913002A3 *

Also Published As

Publication number Publication date
WO1999013002A3 (fr) 1999-05-06
DE19739601A1 (de) 1999-03-11
WO1999013002A2 (fr) 1999-03-18

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