EP0261220A1 - Dispersions de solides dans des liquides organiques - Google Patents

Dispersions de solides dans des liquides organiques

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Publication number
EP0261220A1
EP0261220A1 EP87902576A EP87902576A EP0261220A1 EP 0261220 A1 EP0261220 A1 EP 0261220A1 EP 87902576 A EP87902576 A EP 87902576A EP 87902576 A EP87902576 A EP 87902576A EP 0261220 A1 EP0261220 A1 EP 0261220A1
Authority
EP
European Patent Office
Prior art keywords
pigment
dispersing agent
xylene
formula
dispersant
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Withdrawn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
EP87902576A
Other languages
German (de)
English (en)
Inventor
Peter John Ansell
Alan John Bignold
Alan Richard Luxton
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.)
Revertex Ltd
Original Assignee
Revertex Ltd
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 Revertex Ltd filed Critical Revertex Ltd
Publication of EP0261220A1 publication Critical patent/EP0261220A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/006—Preparation of organic pigments
    • C09B67/0069—Non aqueous dispersions of pigments containing only a solvent and a dispersing agent
    • C09B67/007—Non aqueous dispersions of phthalocyanines containing only a solvent and a dispersing agent
    • 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
    • C09C3/10—Treatment with macromolecular organic 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
    • C09D17/002—Pigment pastes, e.g. for mixing in paints in organic medium
    • 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
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/45—Anti-settling agents
    • C—CHEMISTRY; METALLURGY
    • 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
    • C01P2006/00—Physical properties of inorganic compounds
    • C01P2006/22—Rheological behaviour as dispersion, e.g. viscosity, sedimentation stability

Definitions

  • the present invention relates to pigment dispersions which comprise particular pigment dispersants which promote the dispersion in liquid organic media of solids, in particular, inorganic and organic pigments or dyestuffs, and to paints, enamels, printing inks and other surface coatings, and to articles made of plastics or rubbers, and other compositions which contain the dispersions of the invention.
  • the present invention provides a pigment dispersion which comprises from 5 to 90% by weight of at least one pigment and/or extender, from 0.01 to 50% by weight of a pigment dispersant which contains in its molecule at least one polar segment and at least one polymeric, non-polar, solvent compatible segment having a molecular weight in the range of from 500 to 10,000, preferably 500 to 3,000, and is derived from repeating monomer units of an unsaturated hydrocarbon; and an organic liquid dispersing medium which comprises at least a major proportion of a hydrocarbon or chlorinated hydrocarbon.
  • the molecular structure of the dispersants used in the present invention is distinguished by comprising at least one segment (A) which is polymeric, non-polar and essentially hydrocarbyl in composition, the segment (A) being covalently linked to segment (B) which is polar.
  • segment (A) which is polymeric, non-polar and essentially hydrocarbyl in composition
  • segment (B) which is polar.
  • the structure of the dispersing agents may be represented by the diagrams:
  • each segment comprises repeating units corresponding to one or more parent unsaturated hydrocarbon monomers such as ethylene (ethene), propylene, 1,3- butadiene or isobutylene (2-methyl-l-propene), which repeat to the extent that the average degree of polymerisation of the hydrocarbyl segment lies within the range from 10 to about 350, and preferably within the range 10 to 200, most preferably 10 to 70.
  • the polar segment B this may, on the one hand, consist of a group exhibiting a relatively low formula weight, not exceeding say about 400, such as carboxyl, ester, amide etc.
  • a preferred class of groups to be present in segment B are the half esters and substituted half esters of 1,2-dicarboxylic acids, or the amides and
  • segment B may be represented by a polymeric sequence of repeating polar groups or units which may be linked to segment A through one of the same type of polar groups or through a different polar group.
  • Such repeating groups or units comprise ether groups, amides, esters, urethanes etc. while the polar unit through which segment A may be linked to the polymeric polar segment may be one of the same aforesaid types or may be different, such as a carboxyl, sulphonyl, hydrazo or ureido groups.
  • a preferred polymeric sequence contains a plurality of urethane groups linked to segment A through a urethane, ester, amide or urea group.
  • the degree of polymerisation of the polar segment (B) corresponds to the range from 2 to about 50, preferably from 2 to about 5.
  • the polar group or groups become adsorbed onto the surface of the pigment, while the polymeric non-polar group extends into the organic liquid and sterically prevents agglomeration of the pigment particles.
  • surfactants Compounds having a combination of polar sections and non-polar sections in the molecule are known as surfactants, but such surfactants have hydrophobic sections of relatively low molecular weight (typically up to 250) and as such, do not function as effectively as materials of the present invention.
  • hydrophobic sections of relatively low molecular weight typically up to 250
  • dispersants One preferred class (A) of dispersants is represented by formula I:
  • C or D is a hydrophobic straight or branched polymeric chain, the other being hydrogen; preferred are polyethylene, butadiene or polyisobutylene; M is hydrogen or a metal ion or an ammonium or substituted ammonium ion; suitable ions are Na + , K + , NHj, HN + (Me) 3 and HN + (Et) 3 ;
  • X is 0 or NR where R is hydrogen, alkyl (such as methyl, ethyl) cycloalkyl (such as cyclohexyl), aryl (such as phenyl) or aralkyl (such as benzyl); Q is hydrogen or TZ where T is alkylene, arylene, poly(alkylene oxide), poly(alkylene imine), polyurethane, polyurea, polyester or polyamide; and Z is hydrogen, hydroxyl, N(R) 2 or the group:
  • the compounds represented by formula I are most conveniently prepared by a two-stage reaction procedure, the first of which is the maleinisation of unsaturated compounds having one carbon - carbon double bond located near to the end of the molecule to give the compounds of formula II.
  • Preferred unsaturated compounds are polyisobutylene and long chain - olefins such as those produced by the oligomerisation of ethylene.
  • Maleinisation may be carried out by heating the compound with maleic anhydride at temperatures of up to 220°. Such reactions are well known.
  • the reaction of the compounds of formula II with alcohols or amines gives the compounds of formula I.
  • the reaction of one mole of the compound of formula II with one mole of a mon functional alcohol or amine produces a product of the AB type.
  • the reaction of 2 moles of the compound of formula II with one mole of a difunctional alcohol or amine produces a material of the ABA type.
  • Suitable alcohols include methanol, ethanol, propanol; diols such as ethylene glycol; and polyalkylene oxides such as polyethylene glycol.
  • di-hydroxy-ter inated low molecular weight polyesters and polyurethanes may be used.
  • the polyesters may be prepared by the reaction of a diacid (such as terephthalic acid or adipic acid), a diacid chloride (such as isophthaloyl chloride) or a diester (such as dimethyl phthalate or dimethyl adipate), with a stoichiometric excess of a diol (such as hexamethylene diol, butanediol or hydroquinone).
  • the polyurethanes may be prepared by reaction of a di-isocyanate (such as toluene di-isocyanate, particularly the commercially available mixture of 2,4- and 2,6-toluene di-isocyanates, 4,4-di(isocyanato phenyl) methane or hexamethylene di-isocyanate with an excess of a diol as previously described.
  • a di-isocyanate such as toluene di-isocyanate, particularly the commercially available mixture of 2,4- and 2,6-toluene di-isocyanates, 4,4-di(isocyanato phenyl) methane or hexamethylene di-isocyanate
  • the anhydrides of formula II may be reacted with amines to give half amides.
  • Suitable amines include n-butylamine, hexadecylamine, ammonia, diamines (such as 1, 2-diaminoethane) and amino alcohols (such as ethanolamine).
  • diamines such as 1, 2-diaminoethane
  • amino alcohols such as ethanolamine
  • Long-chain amines (such as hexadecyl amine) and amino alcohols (such as ethanol amine) are particularly preferred as giving very effective dispersants for inorganic pigments.
  • Other amines which may be used are diamino-terminated polyamides and polyureas.
  • the polyamides may be prepared by well-known procedures such as by the reaction of a dicarboxylic acid, diacid chloride or diester (as previously described) with an excess of a diamine (such as ethylene diamine, hexamethylene diamine or p-phenylene diamine).
  • a diamine such as ethylene diamine, hexamethylene diamine or p-phenylene diamine
  • the polyureas may be made by reaction of a di-isocyanate (as previously described) with an excess of a diamine (as previously described) or by any other well-known procedure.
  • a further class (B) of dispersants for use in the present invention is represented by formula III.
  • E may be sulphate, bisulphate, monoalkyl or monoaryl sulphate, chloride, bromide or iodide or other such inorganic or organic ion, and x is 1, 2 or 3.
  • polyisobutylene with maleic anhydride to give polyisobutenyl succinic anhydride (PIBSA) and subsequent reaction with a polyamine (eg tetraethylene pentamine) gives a complex mixture of products containing such compounds as V.
  • PIBSA polyisobutenyl succinic anhydride
  • a polyamine eg tetraethylene pentamine
  • additives are known as additives for lubricating oils) e.g. U.S. 3,252,908, 3,762,873, 3,632,510, Ger Offen DE 3,246,123 and 2,232,028).
  • Such additives are used as corrosion inhibitors, oxidation inhibitors, emulsifying agents and suspending agents. In their latter role, they are able to disperse and suspend small particles of metal, carbon and other foreign matter in the oil and prevent sludge formation. In fulfilling this role, they are sometimes referred to as dispersants, but this application is quite different from the present invention.
  • the materials are able to disperse high levels (up to 90% parts by weight of total) of pigment, and in doing so must wet out the original pigment surface and any new surface produced during the milling stage, to prevent flocculation of the dispersed pigment and to reduce the viscosity of the dispersion so that it is fluid even at high pigment loadings.
  • M is as above defined.
  • These compounds may be prepared from a hydroxy-terminated polybutadiene (itself made by reaction of a polybutadienyl lithium with an alkylene oxide, such as propylene oxide or ethylene oxide) with a cyclic carboxylic anhydride. Phthalic anhydride, maleic anhydride and particularly succinic anhydride are preferred.
  • a dispersant which gives good dispersing efficiency for one pigment may not be as efficient for another pigment. It is an advantage of the present invention that a wide range of different dispersant types can be made and a particular product chosen for use with a particular pigment.
  • the half-esters and half-amides are effective for inorganic pigments, whereas for organic pigments, a more complex polar group such as a polyurethane group is required.
  • the pigment dispersants used in the present invention are included in the dispersions in an amount of from 0.01 to 50% by weight based on the weight of the dispersion, preferably 0.1 to 20% by weight. These levels are lower than those normally used in such dispersions in the prior art. It is highly desirable to use the lowest level of dispersing agent necessary to achieve good dispersion both on economic grounds and to minimise any undesirable side-effects which the dispersing agent may have on the properties of the final paint, ink or the like.
  • the pigment dispersions of the present invention contain from 5 to 90% by weight of at least one pigment based on the weight of dispersion, preferably 15 to 60% in the case of organic pigments and 40 to 90% in the case of inorganic pigments. It is highly desirable to achieve the highest possible level of solid material in the dispersion, whilst maintaining fluidity, both on economic grounds and in order to give the paint or ink manufacturer greater flexibility in product formulation.
  • the levels of solid material in the dispersions of the present invention are in general higher than those found in the prior art.
  • Organic liquids which are suitable as dispersing media for the pigments include aliphatic and aromatic hydrocarbons and mixtures thereof and chlorinated hydrocarbons.
  • Preferred solvents are xylene, toluene, chlorobenzene, carbon tetrachloride, chloroform, white spirit and perchlor ethylene.
  • the organic liquid may contain a minor proportion of a polar solvent, such as an ester, ketone or alcohol, A mixture such as xylene/butanol is suitable for use in the invention.
  • the solvent selected depends upon the final use for the dispersion and on the solubility of the other components such as resin binders used in the final paint or ink.
  • the dispersing agent should be soluble, partially soluble or dispersible in the organic liquid.
  • a wide range of pigments may be used in the dispersions of the present invention. Suitable materials are listed in "Encyclopedia of Chemical Technology", Third Edition, Vol 17, P. 788-870 (Wiley).
  • Examples of typical inorganic pigments are titanium dioxide, zinc oxide, iron oxides, carbon black, the chromates, molybdates and sulphate/chromates of lead, barium and calcium, cadmium sulphide, chromium oxide, cobalt blue, lithopone, mercury-cadmium oranges and reds, ultramarine, zirconium oxide, zinc chromate and molybdate, zinc sulphide, Prussian blue and vermillion.
  • Extenders and fillers such as calcium carbonate, talc, mica, kaolin, and barytes may also be included in the composition.
  • organic pigments examples are those based on the azo and diazo compounds, phthalocyanines, especially copper phthalocyanines, quinacridones, dioxazines, thioindigos, indanthrones, isoindanthrones, anthraquinones, triphendioxazines, lakes and toners.
  • phthalocyanines especially copper phthalocyanines, quinacridones, dioxazines, thioindigos, indanthrones, isoindanthrones, anthraquinones, triphendioxazines, lakes and toners.
  • the dispersing agents of the invention may be used alone, or in the case of organic pigments, may be used advantageously in conjunction with auxiliary dispersing agents based on modified pigments, such as Solsperse 22000 and Solsperse 25000, which are commercially available.
  • the dispersions may also contain other additives such as resins, rheology-modifying agents, wetting agents, anti-settling agents, other dispersants, and preservatives, etc.
  • the pigment dispersions of the present invention may be used in a variety of end applications, including paints, inks and other resinous coatings containing resins such as alkyd, acrylics, melamine/formaldehyde or chlorinated rubbers as the binders therefor.
  • the dispersions may be made by conventional techniques which are well known in the art and described in "Surface Coatings - Vol 2" p 439-444 Oil and Colour Chemists Assn, Australia (Chapman ⁇ Hall).
  • the methods which may be used include ball-milling, sand-milling, high-speed dispersing, cavitation mixing, etc.
  • the pigment and any other solids, the organic liquid and the dispersing agent may be mixed together all at once or separately in any order. Mixing and/or grinding is continued until a stable dispersion is obtained with the mean particle size of the solid reduced to the required size, usually below 10 microns and preferably below 5 microns.
  • the solid or aqueous slurry of the solid may be treated with a solution of the dispersing agent in a solvent or with an aqueous emulsion of such a solution.
  • the solvent and water may subsequently be removed to give a dry pigment which can then be easily redispersed at a later stage.
  • the present invention includes within its scope a pigment which is coated with a pigment dispersant which contains in its molecule at least one polar segment and at least one polymeric, non-polar, solvent compatible segment having a molecular weight in the range of from 500 to 10,000, preferably 500 to 3,000, and is derived from repeating monomer units of an unsaturated hydrocarbon.
  • the coated pigments may be used in a variety of end applications. These include paints, inks, and other coatings containing resins such as alkyds, acrylics, melamine/formaldehyde or chlorinated rubbers as binders for such coatings. They may also be incorporated directly as pigments in the manufacture of plastic materials. For this end use they are incorporated into the plastic during manufacture and for processing.
  • the coated pigments are preferably in particulate form.
  • toluene di-isocyanate refers to the commercially available 80:20 mixture of the 2:4- and 2:6- isomers.
  • Example l Polyiaobutenyl Succinic Anhydride.
  • Dispersing Agent 1 was removed under reduced pressure to give Dispersing Agent 1 as a viscous brown liquid.
  • Dispersing Agent 1 To a 50% w/w solution (50 g) of Dispersing Agent 1 in xylene was added methanol (5 g) and one drop of triethylamine as catalyst. The mixture was heated under reflux under nitrogen for 3 hours using an oil bath at a maximum temperature of 10 100°. Disappearance of the anhydride absorption band in the infra-red spectrum indicated complete reaction. The product was a brown solution (Dispersing Agent 2) , an approximately 50% w/w solution of the half ester in xylene.
  • Dispersing Agent 2 One equivalent of triethylamine per equivalent.of acid was added to Dispersing Agent 2 to give Dispersing Agent 3.
  • Dispersing Agent 4 To a 50% solution of Dispersing Agent 1 in xylene was added slowly and with stirring one mole equivalent of ethanolamine per mole of total anhydride. The total mixture became warm 25 and external cooling was used to maintain the temperature below 50° to avoid cyclisation to the imide.
  • the product (Dispersing Agent 4) was a brown liquid, an approximately 50% w/w solution of the half-amide in xylene.
  • Dispersing Agent 5 was prepared as an 35 approximately 50% w/w solution of the half-amide in xylene.
  • Example 6 Imide from PIBSA and
  • Dispersing Agent 5 was heated to reflux temperature under nitrogen and the water produced was removed from the distillate using a Dean-Stark trap. Heating was continued - 15 -
  • Dispersing Agent 6 (30 g) was heated to 40° under nitrogen. Dimethyl sulphate (2.2 g) was added with stirring. The temperature of the mixture rose to 64°. When the exotherm had finished, the mixture was heated at 90° for 1 hour and then cooled to give Dispersing Agent 7 an approximately 50% w/w solution of the quaternary salt in xylene.
  • Example 10 Half-Ester from PIBSA and Polyethylene Glycol.
  • Dispersing Agent 1 10 g
  • polyethylene glycol monomethyl ether 4.8 g, average molecular weight 350, Aldrich Chemical Company Limited
  • octane (DABCO 0.1 g) was heated with stirring under nitrogen at 165-170° for 6 hours to give a half-ester as a viscous brown liquid.
  • Dispersing Agent 10 Example 11. Carbory-terminated Polybutadiene.
  • Hydroxy-functional polybutadiene (100 g, average molecular weight 1500 by g.p.c. analysis) prepared by end-capping living polybutadienyl lithium with propylene oxide, was heated a five molar excess of succinic anhydride, xylene (10 g) , triethylamine (0.2 g) as catalyst and N,N'-diphenyl-p-phenylendiamine (0.1 g) as antioxidant, under nitrogen for 6 hours at 150°. The mixture was cooled, filtered and the solvent removed under reduced pressure from the filtrate to give Dispersing Agent 11.
  • Example 12 Di-half-amide from PIBSA and 1,2-Diaminoethane.
  • Example 4 In a similar manner to that of Example 4, an approximately 50% w/w solution (Dispersing Agent 12) of the diamide in xylene was prepared from 2 moles of Dispersing Agent 1 per mole of 1,2-diaminoethane.
  • Example 14 Polyisobutylene-Polyamide-Polyisobutylene Triblock Polymer.
  • 1,6-Hexanediol (11.8 g) was heated to 70° under nitrogen on an oil bath and isophthaloyl chloride (15.2 g) was added in small portions over about 30 minutes. Hydrogen chloride was evolved as the reaction proceeded. When the addition was complete, the temperature was raised to 135° and held for 30 minutes to give a dihydroxy-terminated polyester oligomer (Intermediate 5) as a viscous colourless liquid which solidified on cooling.
  • Example 16 Polyisobutylene-Polyurea-Polyisobutylene Triblock Polymer.
  • Example 18 Dispersant Containing Polyethylene As The Hydrophobe.
  • a mixture of Gulftene 30+ (84 g, an alpha olefin fraction containing about 78% of olefins of carbon number 30 and above, produced by polymerisation of ethylene. Gulf Oil Chemicals Company) , maleic anhydride (20 g) and phenothiazine (0.2 g) as polymerisation inhibitor was heated to 185-220° under nitrogen with stirring for 12 hours to give a brown liquid which cooled to a pale brown wax Intermediate 7.
  • Dispersing Agent 1 was reacted with 3-aminopropyltrimethoxy silane (silane A-1100, Union Carbide) to give Dispersing Agent 19 as an approximately 50% w/w solution of the silane-functional half-amide in xylene.
  • Triethylammonium salt of stearic acid Comparative Material 3.
  • Lithene PM25MA (a maleinised polybutadiene prepared from 100 parts by weight of polybutadiene of average molecular weight 1300 and 25 parts by weight of maleic anhydride, Revertex Limited) .
  • Triethylammonium salt of methyl half-ester of Lithene PM25MA One equivalent of triethyl amine per equivalent of acid was added to Comparative Material 7 to give Comparative Material 8.
  • Comparative Material 9 was produced by adding one mole of 3-(N,N-dimethylamino)propylamine per mole of anhydride to Lithene PM25MA.
  • Pigment dispersions were made up as follows using titanium dioxide RHD-2 (Tioxide UK Limited) as the pigment. They were dispersed by stirring and the dispersion assessed qualitatively for fluidity on a scale where:
  • Comparative Materials 1 and 2 show the need for the dispersing agent to contain a long polymeri hydrophobic chain.
  • dispersions were made up using titanium dioxide RCR-2 (Tioxide UK Limited) as the pigment.
  • Dispersions were made up using red iron oxide (Bayferrox 1120-Z, Bayer) .
  • Dispersions were made up using Barytes (E-Weiss) as the pigment.
  • Dispersions were made up using Dinitraniline Orange (Pigment Orange 5) .
  • Dispersions were made by ball-milling the ingredients for 6 hours. The resulting dispersions were fluid and the pigment deflocculated.
  • One method of assessing the efficiency of dispersing agents is to measure the amount of dispersing agent required to produce a fluid dispersion of pigment.
  • the dispersing agents were diluted with xylene to give a 25% w/v solution (i.e. 100 ml of solution contained 25 g of non-volatile material as measured by placing the sample irra vacuum oven at 120° for 1 hour) .
  • the dispersant solution wa added dropwise from a burette to a mixture of the pigment an xylene.
  • the mixture was stirred with a spatula and addition of dispersant solution continued until a fluid dispersion, which would flow from a spatula in an almost continuous stream, was obtained.
  • the volume of dispersant solution added was recorded.
  • Dispersing Agent 1 0.92 0.69 >1.0 >1.5 0.30
  • Dispersing Agent 4 0.90 0.82 0.32 0.74 0.16
  • Dispersing Agent 5 0.81 0.75 0.24 0.76 0.18 Dispersing Agent 7 0.39
  • Dispersing Agent 9 0.97 0.95 0.33 1.00 0.16
  • Dispersing Agent 11 1.13 Dispersing Agent 12 1.04 0.79 0.28 0.82 0.21
  • pigments dispersions were made up into air-drying paints and compared with paints made using pigment dispersions of the present invention in the following manner.
  • a stock solution of alkyd resin and drying agents was made up:
  • Dispersing agent 13 1.6 g 2 g
  • the resulting dispersions were fluid with the pigment well dispersed.
  • a pigment is treated with a dispersing agent of the invention to give a modified pigment which can be easily dispersed without additional dispersing agents.
  • Toluidine Red pigment 25 g was added to a solution of Dispersing Agent 13 (2.5 g) in cy ⁇ ohexane (600 ml). The mixture was heated to reflux temperature for 30 minutes with stirring and then cooled. After filtration, the modified pigment was dried under vacuum to give a red powder.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Dispersion Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
  • Pigments, Carbon Blacks, Or Wood Stains (AREA)
  • Paints Or Removers (AREA)

Abstract

Une dispersion de pigments comprend entre 5 et 90% en poids d'au moins un pigment et/ou diluant, entre 0,01 et 50% en poids d'un agent de dispersion de pigment contenant dans sa molécule au moins un segment polaire et au moins un segment polymère non polaire qui est compatible aux solvants et dont le poids moléculaire se situe entre 500 et 10000, de préférence entre 500 et 3000, ledit agent de dispersion de pigments étant dérivé d'unités monomères de répétition d'un hydrocarbure non saturé. Un milieu de dispersion de liquides organiques comprend au moins une majeure partie d'un hydrocarbure ou d'un hydrocarbure chloré.
EP87902576A 1986-04-04 1987-03-31 Dispersions de solides dans des liquides organiques Withdrawn EP0261220A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB8608213 1986-04-04
GB868608213A GB8608213D0 (en) 1986-04-04 1986-04-04 Dispersions of solids in organic liquids

Publications (1)

Publication Number Publication Date
EP0261220A1 true EP0261220A1 (fr) 1988-03-30

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Family Applications (1)

Application Number Title Priority Date Filing Date
EP87902576A Withdrawn EP0261220A1 (fr) 1986-04-04 1987-03-31 Dispersions de solides dans des liquides organiques

Country Status (4)

Country Link
EP (1) EP0261220A1 (fr)
AU (1) AU7210087A (fr)
GB (1) GB8608213D0 (fr)
WO (1) WO1987005924A1 (fr)

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US4859247A (en) * 1987-11-02 1989-08-22 Basf Corporation Low viscosity, highly concentrated pigment dispersions and method of making same
ATE81139T1 (de) * 1988-02-23 1992-10-15 Du Pont Blockmischpolymerisat-dispergiermittel.
GB9200519D0 (en) * 1992-01-10 1992-02-26 Ici Plc Composition of matter
AU689421B3 (en) * 1996-06-24 1998-03-26 Zone Properties Pty Ltd Ink composition
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GB8608213D0 (en) 1986-05-08
AU7210087A (en) 1987-10-20

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