EP1240257A4 - Traitements de surface pour pigments ameliorant la dispersibilite et presentant une activite biocide - Google Patents

Traitements de surface pour pigments ameliorant la dispersibilite et presentant une activite biocide

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Publication number
EP1240257A4
EP1240257A4 EP00988477A EP00988477A EP1240257A4 EP 1240257 A4 EP1240257 A4 EP 1240257A4 EP 00988477 A EP00988477 A EP 00988477A EP 00988477 A EP00988477 A EP 00988477A EP 1240257 A4 EP1240257 A4 EP 1240257A4
Authority
EP
European Patent Office
Prior art keywords
acid
composition
amine
equivalents
pigment
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Withdrawn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
EP00988477A
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German (de)
English (en)
Other versions
EP1240257A2 (fr
Inventor
George K Atkinson
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.)
Individual
Original Assignee
Individual
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Filing date
Publication date
Priority claimed from US09/426,709 external-priority patent/US6348092B1/en
Priority claimed from US09/427,129 external-priority patent/US6231662B1/en
Application filed by Individual filed Critical Individual
Publication of EP1240257A2 publication Critical patent/EP1240257A2/fr
Publication of EP1240257A4 publication Critical patent/EP1240257A4/fr
Withdrawn legal-status Critical Current

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Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y30/00—Nanotechnology for materials or surface science, e.g. nanocomposites
    • 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
    • C09C1/36—Compounds of titanium
    • C09C1/3607—Titanium dioxide
    • C09C1/3669—Treatment with low-molecular organic compounds
    • 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
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2004/00—Particle morphology
    • C01P2004/10—Particle morphology extending in one dimension, e.g. needle-like
    • C01P2004/12—Particle morphology extending in one dimension, e.g. needle-like with a cylindrical shape
    • 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
    • C01P2004/62—Submicrometer sized, i.e. from 0.1-1 micrometer
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2004/00—Particle morphology
    • C01P2004/60—Particles characterised by their size
    • C01P2004/64—Nanometer sized, i.e. from 1-100 nanometer
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2004/00—Particle morphology
    • C01P2004/80—Particles consisting of a mixture of two or more inorganic phases
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2004/00—Particle morphology
    • C01P2004/80—Particles consisting of a mixture of two or more inorganic phases
    • C01P2004/82—Particles consisting of a mixture of two or more inorganic phases two phases having the same anion, e.g. both oxidic phases

Definitions

  • This invention relates to surfactant treated particulate titanium dioxide and other pigments. More particularly, this invention is concerned with surfactant treated titanium dioxide and other particulate materials readily employable in coating compositions, plastic molding compositions, reinforced plastic composite compositions, and paper making compositions.
  • Industrial pigment particles agglomerate or cake together into hard packed clusters during the drying operation near the end of the manufacturing process. Forces holding pigment clusters together are not large in many cases but are yet large enough that the pigment user, those who incorporate industrial pigments into their products such as paints and plastics and the like, are required to subject industrial pigments to a milling operation in which the agglomerates are sheared under stress into particles of suitable smallness and homogenized into the matrix or product which incorporates them.
  • the process is dispersion.
  • Pigment dispersion is a bottleneck, a limiting requirement, and the most expensive operation in terms of energy and time in manufacturing processes which employ pigments.
  • This present invention is concerned with the employment of surfactants for the surface treatment of pigments during the pigment manufacturing process in order to provide pigments of improved dispersibility in subsequent manufacturing processes and in some cases, to provide improvements in certain important aspects of products incorporating these surface treated pigments.
  • Titanium dioxide pigments present a special case. Uncoated titania pigments are extremely difficult to disperse. In addition, their employment in pigmented plastics, coatings, papers, and fiber compositions induces a photoactivity which results in oxidative degradation which is destructive of the materials of which they are a part. As a consequence, most titanium dioxide pigments are provided with some form of surface coating during manufacture to promote dispersibility and to reduce photoactivity. Two materials in widespread use at present are silica and alumina. These materials are coated onto the surfaces of pigment particles in the range of three to ten percent by weight of TiO 2 .
  • Pigment particle wettability is improved due to a lowering of the interfacial tension between the pigment surface and the application medium.
  • German Pat. Nos. 889,042 and 930, 998 teach the use of surface-active substances as emulsif ⁇ ers together with oils in the manufacture of water-insoluble azo-dyestuffs having a soft grain.
  • U.S. Pat. No. 3,120,508 discloses that water-insoluble azo-dyestuffs having a particularly high tinctorial strength can be prepared by adding during the coupling cationic surface-active compounds without simultaneously using oils.
  • U.S. Pat. No. 3,437,502 teaches improvement of opacity and dispersibility of titanium dioxide through surface treatment with silica and alumina.
  • U.S. Pat. No. 3,658,566 teaches the production of titanium dioxide of improved properties by treatment with oxides of silicon and aluminum.
  • U.S. Pat. No.4,599,114 discloses improvement of pigmentary properties for a variety of pigments through surface treatment of pigment filter cakes.
  • Cationic surface-active compounds are described in the book "Surface- Active Agents and Detergents" by A. M. Schwartz, J. W. Perry and J. Berch, vol. II (1958), pages 103 to 119.
  • U.S. Pat. Nos. 4,599,114, 4,471,780, and 4,909,852 disclose compositions having surfactants consisting of the reaction product of a diamine, a carboxylic acid and a fatty acid.
  • U.S. Pat. No. 5,808, 118 discloses a composition which is the reaction product of a diamine, a sulfonic acid and a fatty acid.
  • British Patent No. 1,080,115 discloses the use of primary long chain alkyl amines for treating pigments improving their dispersibility.
  • Suitable cationic surface-active substances are, for example, long-chained aliphatic amino compounds that contain about 10 to 18 carbon atoms, or the salts of such nitrogen compounds with carboxylic acids, such as for example, formic acid, acetic acid, oleic acid, tallow fatty acid, lactic acid or mineral acids, for example, hydrochloric acid.
  • Fatty amines are for example, coconut oil amine, oleyl amine, stearyl amine, and tallow fat amine, as well as the secondary and tertiary amines or quaternary ammonium compounds derived therefrom that may carry as substituents aliphatic, aromatic or oxethylated radicals, for example, alkyldimethyloxyethyl ammonium chloride.
  • Oxethylated fatty amines in their secondary, tertiary or quaternary form are also suitable.
  • condensation products of long-chained, in some cases also unsaturated, carboxylic acids with amines in particular alkylenediamines, alkylenetriamines, or alkylenepolyamines containing alkylene radicals of low molecular weight, for example, ethylene diamine, diethylene triamine, etc., as well as the secondary, tertiary or quaternary amines formed by alkylation of the condensation products, especially in the form of their water-soluble salts with the above-mentioned acids.
  • fatty acid amides and esters of long-chained carboxylic acids with alkylol amines for example, triethanolaminoleate, stearate, and the like, further also cyclical, nitrogen-containing compounds, for example, long-chained derivatives of morpholine, imidazoline, piperidine, piperazine or pyridine.
  • alkylol amines for example, triethanolaminoleate, stearate, and the like
  • nitrogen-containing compounds for example, long-chained derivatives of morpholine, imidazoline, piperidine, piperazine or pyridine.
  • the above-mentioned amino compounds are used preferably in the form of their carboxylic or hydrochloric salts.
  • surfactants which have the capability of increasing the dispersibility of titanium dioxide and other pigments to which they are applied.
  • Titanium dioxide is an established pigmentary material which can also be employed as a reinforcing filler, albeit an expensive one. It is commonly made by two processes, the chloride process and the sulfate process.
  • the chloride process is dry process wherein TiCl is oxidized to TiO 2 particles.
  • titanium sulfate in solution, is converted by a metathesis reaction to insoluble and particulate titanium dioxide.
  • particle formation can be seeded by aluminum compounds. Thereafter, the processes are essentially the same.
  • the TiO 2 particles in a water slurry are put through multiple hydroseparations to separate out the large particles and the further refined pigment in slurry form is passed to a treating tank where the particles may be treated with an aluminum compound and/or silicon compound, such as aluminum triethoxide, sodium aluminate, aluminum trichloride, aluminum sulfate, ethyl silicate, sodium silicate, silicon tetrachloride, trichlorosilane, and the like.
  • the pigment is flocculated and precipitated with its coating of alumina and/or silica, or without any coating. It is then made into a filter cake by a vacuum drying and further dried in an oven, generally of a vibrating type.
  • the optimum average particle size can range from about 0.05 to about 0.35 microns with a range of about 0.1 to about 0.25 more preferable.
  • dispersion promoters of this invention alter the surface characteristics of the titanium dioxide or other pigments so that it is more readily and more thoroughly dispersed within the resin or plastic in which it is incorporated, and this serves to enhance the appearance of the resulting composite and increase the overall strength of the composite when the particulate material employed is one which serves to reinforce the plastic or resin.
  • the amount of dispersion promoter provided upon the titanium dioxide particles is that amount which alters the surface characteristics of the particles so that they are more readily dispersed within the resin, plastic, paper making composition or other medium in which they are incorporated.
  • the amount of the dispersion promoter which is supplied to the titanium dioxide may be from as little as about 0.25 weight percent to about 5 weight percent, based upon the weight of the titanium dioxide particles.
  • about 0.5 to about 3 weight percent of the dispersion promoter and/or its derivatives is adequate for the purposes of appropriately alterating the surface characteristic of the particles. Preferred is 2%.
  • the amount of dispersion promoter may be from about 1.00 to about 15.0 percent or higher.
  • the amount of dispersion promoter provided when used with carbon black particles is that amount which alters the surface characteristics of the particles so that they are more readily dispersed within the resin, plastic, paper making composition or other medium in which they are incorporated.
  • the amount of the dispersion promoter which is supplied to the carbon black may be from as little as about 1.00 weight percent to about 15.0 weight percent, based upon the weight of the carbon black particles.
  • about 4.0 to about 10.0 weight percent of the dispersion promoter and/or its derivatives is adequate for the purposes of appropriately alterating the surface characteristic of the particles. Most preferred is about 8.0 percent.
  • the amount of dispersion promoter provided when an organic pigment is used is that amount which alters the surface characteristics of the pigment so that it is more readily dispersed within the resin, plastic, paper making composition or other medium in which it is incorporate.
  • the amount of the dispersion promoter which is supplied to the organic pigment may be from as little as about 1.00 weight percent to about 15.0 weight percent, based upon the weight of the organic pigment.
  • about 4.0 to about 10.0 weight percent of the dispersion promoter and/or its derivatives is adequate for the purposes of appropriately alterating the surface characteristic of the pigment. Most preferred is about 4.0 percent.
  • the amount of dispersion promoter provided when inert pigments are used, as characterized herein, is that amount which alters the surface characteristics of the pigment so that it is more readily dispersed within the resin, plastic, paper making composition or other medium in which it is incorporated.
  • the amount of the dispersion promoter which is supplied to the inert pigment may be from as little as about 0.25 weight percent to about 3 weight percent of the dispersion promoter and/or its derivatives which is adequate for the purposes of appropriately alterating the surface characteristic of the pigment. Most preferred is 1%.
  • the amount of dispersion promoter provided when inorganic color pigments are used, as characterized herein, is that amount which alters the surface characteristics of the pigment so that it is more readily dispersed within the resin, plastic, paper making composition or other medium in which it is incorporated.
  • the amount of the dispersion promoter which is supplied to the inorganic color pigments may be from as little as about 0.25 weight percent to about 5 weight percent of the dispersion promoter and/or its derivatives which is adequate for the purposes of appropriately alterating the surface characteristic of the pigment. Most preferred is 2%.
  • the surfactants of this invention perform the role of dispersants when added directly to conventional paint formulations.
  • the dispersion promoter and/or its derivatives may be provided on the titanium dioxide particles by any of the known methods by which dispersion promoters are similarly supplied to particulate surfaces.
  • adding the dispersion promoter to the particles while tumbling, mixing the particles in a dilute liquid composition containing the dispersion promoter, or forming a slurry of the particles and dispersion promoter and drying, spray drying or the like represent adequate treating procedures.
  • the plastics and/or resin in which the titanium dioxide particles treated with the dispersion promoter and/or its derivatives include essentially any plastic and/or resin. Included in the definition of plastic are rubber compounds.
  • the treated titanium dioxide particles may be supplied to the plastic and/or resin while the same is in any liquid or compoundable form such as a solution, suspension, latex, dispersion, and the like. It makes no difference from the standpoint of this invention whether the plastic contains solvent or nonsolvent, or the solvent is organic or inorganic except, of course, it would not be desirable for any plastic or resin or any of the treated titanium dioxide to employ a solvent or dispersing medium which deleteriously affects the components being blended.
  • Suitable plastics and resins include, by way of example, thermoplastic and thermosetting resins and rubber compounds (including thermoplastic elastomers).
  • the plastics and resins containing the treated particles of this invention may be employed, for example, for molding (including extrusion, injection, calendaring, casting, compression, lamination, and/or transfer molding), coating (including lacquers, film bonding coatings, powder coatings, coatings containing only pigment and resin, and painting,) inks, dyes, tints, impregnations, adhesives, caulks, sealants, rubber goods, and cellular products.
  • molding including extrusion, injection, calendaring, casting, compression, lamination, and/or transfer molding
  • coating including lacquers, film bonding coatings, powder coatings, coatings containing only pigment and resin, and painting,
  • inks dyes, tints, impregnations
  • adhesives caulks, sealants, rubber goods, and cellular products.
  • the plastics and resins may be alkyd resins, oil modified alkyd resins, unsaturated polyesters employed in GRP applications, natural oils, (e.g., linseed, tung, soybean), epoxides, nylons, thermoplastic polyester (e.g., polyethyleneterephthalate, polybutyleneterephthalate), polycarbonates, polyethylenes, polybutylenes, polystyrenes, styrene butadiene copolymers, polypropylenes, ethylene propylene co- and terpolymers, silicone resins and rubbers, EPDM rubbers, SBR rubbers, nitrile rubbers, natural rubbers, acrylics (homopolymer and copolymers of acrylic acid, acrylates, methacrylates, acrylamides, their salts, hydrohalides, etc.), phenolic resins, polyoxymethylene (homopolymers and copolymers), polyurethanes, polysulfones, polyurethanes
  • the agents of the present invention are produced from a combination of the following materials described in the general formula:
  • Advantageous amines which are used include 2-amino-2-methyl- 1 -propanol, monoethanolamine, diethanolamine, triethanolamine, n-butylamine, and ethylenediamine.
  • Advantageous fatty amines include coco amine, lauryl amine, soya amine, stearyl amine, tallow amine, ether amines, ether diamines, and ethoxylated amines.
  • Advantageous dibasic and polybasic acids include dimer and trimer C 18 fatty acids, glutaric acid, succinic acid, and adipic acid.
  • the advantages provided by the surface treating agents of this invention are enhanced if the pigment particles are first exposed to minute amounts of materials of high charge density which bind to pigment surfaces and then act to attract the surface treating agents and bind them more closely and with more complete coverage to the pigment particle surfaces. Strong acids and bases act in this manner.
  • Aluminum chloride (28% in water) added at the rate of one- tenth of one percent of dry weight of pigment enhanced the performance of Formula X when added to the pigment slurry and mixed prior to adding Formula X.
  • strong bases such as 2-amino-2 -methyl- 1 -propanol can be used advantageously.
  • the surfactant may also be added alone without any prior treatment.
  • the agents of the present invention also exhibit biocidal activity when employed solely as a composition, when used as an additive, or when combined with a pigment to be applied to a surface.
  • the present invention is directed to an agent having the general formulas:
  • the reaction may be carried out in the presence of a medium such as propylene glycol or isopropyl alcohol.
  • Advantageous halogenated carboxylic acids include chloroacetic acid, chloropropionic acid, trichloroacetic acid, chlorofluoroacetic acid, trifluoroacetic acid, bromopropionic acid, and iodobenzoic acid.
  • Advantageous fatty acids include,oleic acid, stearic acid, coconut fatty acid, soya fatty acid, ether acids or 3-(alkoxy-) propionic acids where the alkyl group is eight or more, and polymerized C 18 acids.
  • Advantageous polyamines include coco, tallow, and oleyl diamines, 3-diethylaminepropylamine, and ether amines having the formula where R is six or more. Many combinations of these components have been found to be useful.
  • Advantageous compositions include one equivalent of 2-chloropropionic acid and one equivalent of stearic acid combined with two equivalents of tallow diamine (Formula A, Example I).
  • 2-chloropropionic acid and three equivalents of coconut fatty acid combined with four equivalents of tallow diamine (Formula B, Example II).
  • compositions of this invention may be used as direct-add dispersants in conventional paint dispersion.
  • An example is one equivalent of 2-bromopropionic acid and one equivalent Of C 18 polymerized fatty acid combined with two equivalents of tallow diamine. The reaction was carried out inpropylene glycol equal to 25% by weight of the composition.
  • An effective direct-add dispersant can be produced by combining a halogenated carboxylic acid with an appropriate amine.
  • An example is one equivalent of 2-chloropropionic acid combined with one equivalent of tallow diamine, the reaction carried out in propylene glycol equal to 25% of the weight of the composition Formula D, Example IN).
  • compositions of this invention are also useful as biocides.
  • Formula E Example V
  • one equivalent of 2-chloropropionic acid and one equivalent of oleic acid were combined with two equivalents of ether diamine.
  • the composition functions as a mildewcide when added to a commercial paint formulation.
  • selected compositions may be used as antiseptic agents in toiletries and soaps and as disinfectants in cleansers.
  • Some compositions can be used in food processing, such as Formulas F and G, Examples NI and Nil, were used as antibacterial agents for poultry processing rinses.
  • Some compositions maybe used as surfactants in enhanced oil recovery.
  • Some compositions are useful as liquid crystals.
  • Two and one half percent based on dry weight of pigment) of Formula A were added to titanium dioxide slurry (ASTM 476-73, 1988. Type II, III, IN). The slurry was mixed for optimal pigment particle coverage and dried. The dry pigment was suitable for use in waterborne and solvent borne paint formulations.
  • Titanium Dioxide - Filter Cake (55% Solids)
  • Grind is 7-8 Hegman in two minutes.
  • compositions of this invention perform as dispersants when used in conventional paint formulations.
  • Substrate 3/8" x 4" x 20" Interior Masonite Panel.
  • Panel A Two brush coats paint with no addition.
  • Panel.B Two brush coats of paint with five grams Formula E added to one half pint.
  • Formula F (twenty percent chlorine by weight), two equivalents of trichloroacetic acid and one equivalent of ether acid combined with three equivalents of ether diamine was used at the rates of 1%, 0.5%, and 0.25% in water as an antibacterial poultry rinse. Birds were immersed for 15 seconds, allowed to drip, and immersed in slush ice for two hours. They were removed, drained and rinsed with a 400 ml sterile Butterfield Phosphate solution for one minute. Rinsate was then plated on Aerobic Count and E. coli count Petri Film. Controls immersed in plain water and non-treated controls were included. Results were as follows:
  • A 1% solution
  • B .5% solution
  • C .25% solution
  • D Control
  • E Non-treated control
  • Aluminum trihydroxide (median particle size 1.0 micron) was treated with 0.1 percent (based on dry pigment weight) hydrochloric acid (37.4%>).
  • One percent (based on dry pigment weight) of Formula H one equivalent of 2-chloropropionic acid and one equivalent of C 18 polymerized fatty acid combined with two equivalents of tallow diamine) (the reaction being carried out in 25%> by weight of propylene glycol based on the weight of the reactants) was added to the slurry and mixed for optimal particle coverage.
  • the resulting aluminum trihydroxide treated pigment was suitable for employment in alkyd resin or EPDM rubber formulations.
  • Grind is 7 - 8H in two minutes.
  • the surface treating agents of this invention perform as dispersants when used in conventional paint formulations.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Nanotechnology (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Composite Materials (AREA)
  • Condensed Matter Physics & Semiconductors (AREA)
  • General Physics & Mathematics (AREA)
  • Materials Engineering (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Pigments, Carbon Blacks, Or Wood Stains (AREA)
  • Paints Or Removers (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention concerne une composition constituée par le produit réactionnel d'un acide carboxylique, d'une amine et éventuellement d'un acide gras. Cette composition présente des propriétés biocides et permet d'augmenter la dispersibilité des pigments. L'invention concerne également un additif destiné à améliorer les caractéristiques des pigments industriels. Cet additif, qui améliore la dispersibilité des pigments, est le produit réactionnel d'une amine, d'une amine grasse et d'un acide polybasique.
EP00988477A 1999-10-25 2000-10-23 Traitements de surface pour pigments ameliorant la dispersibilite et presentant une activite biocide Withdrawn EP1240257A4 (fr)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US09/426,709 US6348092B1 (en) 1999-10-25 1999-10-25 Surface treatments for pigments providing improved dispersibility and exhibiting biocidal activity
US427129 1999-10-25
US09/427,129 US6231662B1 (en) 1999-10-25 1999-10-25 Surface treatments for titanium dioxide and other industrial pigments
US426709 1999-10-25
PCT/US2000/041430 WO2001030888A2 (fr) 1999-10-25 2000-10-23 Traitements de surface pour pigments ameliorant la dispersibilite et presentant une activite biocide

Publications (2)

Publication Number Publication Date
EP1240257A2 EP1240257A2 (fr) 2002-09-18
EP1240257A4 true EP1240257A4 (fr) 2007-10-24

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EP00988477A Withdrawn EP1240257A4 (fr) 1999-10-25 2000-10-23 Traitements de surface pour pigments ameliorant la dispersibilite et presentant une activite biocide

Country Status (5)

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EP (1) EP1240257A4 (fr)
AU (1) AU782961B2 (fr)
CA (1) CA2389040A1 (fr)
MX (1) MXPA02004146A (fr)
WO (1) WO2001030888A2 (fr)

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FR2825293B1 (fr) 2001-06-05 2004-05-07 Coletica Particules solides insolubles dans l'eau traitees, preparation et utilisation
CN114181406B (zh) * 2021-12-03 2023-07-21 杭州高斯博医疗用品有限公司 一种具有抗菌功效的改性低蛋白天然乳胶及其制备方法

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US4909852A (en) * 1985-02-11 1990-03-20 Atkinson George K Treatment of titanium dioxide and other pigments to improve dispersibility
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US4599114A (en) * 1985-02-11 1986-07-08 Atkinson George K Treatment of titanium dioxide and other pigments to improve dispersibility
US4909852A (en) * 1985-02-11 1990-03-20 Atkinson George K Treatment of titanium dioxide and other pigments to improve dispersibility
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Also Published As

Publication number Publication date
WO2001030888A3 (fr) 2001-12-20
AU782961B2 (en) 2005-09-15
AU2468301A (en) 2001-05-08
WO2001030888A2 (fr) 2001-05-03
MXPA02004146A (es) 2003-08-20
CA2389040A1 (fr) 2001-05-03
WO2001030888A9 (fr) 2002-08-01
EP1240257A2 (fr) 2002-09-18

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