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WO2018169397A1 - Diatomées comme supports naturels à des fins de libération contrôlée pour protection et revêtements métalliques - Google Patents

Diatomées comme supports naturels à des fins de libération contrôlée pour protection et revêtements métalliques Download PDF

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Publication number
WO2018169397A1
WO2018169397A1 PCT/NL2018/050161 NL2018050161W WO2018169397A1 WO 2018169397 A1 WO2018169397 A1 WO 2018169397A1 NL 2018050161 W NL2018050161 W NL 2018050161W WO 2018169397 A1 WO2018169397 A1 WO 2018169397A1
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Prior art keywords
coating
compound
coating according
exoskeleton
species
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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.)
Ceased
Application number
PCT/NL2018/050161
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English (en)
Inventor
Santiago Juan Garcia ESPALLARGAS
Paul Johan DENISSEN
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.)
Technische Universiteit Delft
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Technische Universiteit Delft
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Filing date
Publication date
Application filed by Technische Universiteit Delft filed Critical Technische Universiteit Delft
Publication of WO2018169397A1 publication Critical patent/WO2018169397A1/fr
Anticipated expiration legal-status Critical
Ceased 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
    • 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
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • 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
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/08—Anti-corrosive paints
    • 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
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/16—Antifouling paints; Underwater paints
    • C09D5/1687—Use of special additives
    • 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
    • C09D7/60—Additives non-macromolecular
    • C09D7/61—Additives non-macromolecular inorganic
    • C09D7/62—Additives non-macromolecular inorganic modified by treatment with other compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/34—Silicon-containing compounds
    • C08K3/36—Silica
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K9/00—Use of pretreated ingredients
    • C08K9/10—Encapsulated ingredients

Definitions

  • the present invention relates to a coating and coating application comprising a natural carrier for controlled release of a compound, such as for metal protection, a product comprising said coating or coating application, a method of modifying a natural carrier for controlled release, and methods of forming said coating or coating application, wherein the natural carrier is selected from exoskeletons of a Heteromonyphyta species.
  • the present invention is in the field of said coating or coating application.
  • inhibitor release by different mechanisms (e.g. diffusion, pH, redox, ion exchange) while at the same time prevent unwanted inhibitor reactions with e.g. a surrounding polymer matrix and too fast inhibitor release leading to blistering.
  • a surrounding polymer matrix e.g. a polymer matrix
  • too fast inhibitor release leading to blistering e.g. a polymer matrix
  • nanocarriers yielding protection of small damages ( ⁇ 100 ⁇ width scratches) for short periods of immersion time, their long-term protection of relatively large damages is still under question. Together with their limited versatility, often synthesis complexity, and insufficient local release capacity motivates the constant search for alternatives.
  • Diatoms are a major group of unicellular algae with the unique feature of forming highly ordered hollow nanoporous silica exoskeletons ⁇ named frustules) .
  • Each of the estimated 100.000 extant species as well as the species found as mineral (diatomaceous earth) has a distinctive frustule (typically two symmetric sides hold together) which varies in size (from 2 pm to 4 mm) , shape and nanopore distribution and size.
  • the diatom exoskeletons may be described as forming "pill-box" structures.
  • the availability, morphological characteristics and potential application of fragmented bio- based diatom exoskeletons as carriers has recently attracted significant attention in the biomedical field where their use as drug delivery systems in fluid media has been studied.
  • WO 2010/148158 Al recites a process for preparation of microencapsulated release biocidal actives and aqueous or solvent compositions thereof. Said document does not relate to a coating.
  • EP 1 024 181 Al recites an anti-corrosive coating an teaches to use large amounts of hollow filler, with therein inhibitors and anti-oxidants . Both documents relate to adsorption, i.e. only a surface is
  • the present invention therefore relates to and further aspects thereof, which overcomes one or more of the above disadvantages, without compromising functionality and
  • the present invention relates to a coating, and likewise a coating application, comprising a natural carrier for controlled release of a compound, such as for metal protection, comprising 1-20 wt.%, preferably 2-19 wt.%, more preferably 3-18 wt.%, even more preferably 4-15 wt.%, such as 5-10 wt.%, of hollow structures, which may also be a halve structure, each structure enclosing an internal space thereof, wherein the hollow structures are selected from exoskeletons of a Hetero sparklephyta species, wherein the walls of the structure are mainly (e.g.
  • the term “active” may refer to "biologically active”, “chemically active”, “physically active”, and combinations thereof, i.e. capable of acting or reacting as such or providing such activity.
  • the amount of active compound may also be calculated on a weight/weight basis, and is typically in a range of 0.1- 1000 g active compound/kg carrier, preferably 1/100 g/kg, such as 2-50 g/kg, typically also depending on a molar weight of the active compound. Contrary to the prior art both the internal space and the surface of the hollow structure may be provided with active compound.
  • the natural carrier is formed by diatom species.
  • the carrier is a hollow structure which is formed by the exoskeleton of said diatom species.
  • the walls of the exoskeleton, and likewise if applicable the top and bottom (caps) are mainly of natural porous silica, and may contain further oxides, such as titanate.
  • the hollow structures have an internal space, which internal space is provided (such as filled, doped) with an active compound, such as a corrosion inhibitor.
  • the internal space may be largely or fully filled with said active compound (up to about 100 vol.%) or may be partly filled or even only slightly filled, depending on an application and/or intended use.
  • the active compound may be organic and inorganic. Also combinations of active compounds are envisaged.
  • the active compound may be present as such, or in a suitable solvent.
  • the present coating or application therewith overcomes prior art and provides a controlled release of the active compound, especially in engineering applications, corrosion inhibition of underlying surfaces, such as in pipelines, aerospace coatings, coatings for bridge structures, in concrete applications, etc.
  • the present diatoms can be used as carriers for the release of single or multiple chemical species to be released from the particles themselves or for the particles embedded in bigger matrices such as coatings or concrete.
  • the chemical species to be used can be broad in nature and can have different uses such as corrosion inhibition, self-healing, hydrophobicity, anti-biofouling, fire-retardant, anti-bacteria, anti-insects, colour
  • the present coatings give fast and adequate protection that can be sustained long; in
  • exoskeletons comprising an active compound can be produced with ease, can comprise high amounts of active compound, can have complex architectures at a microscale, and relates to naturally formed products (including those grown in a
  • the present coatings offer sufficient and constant supply of active compound, if applicable, and good release kinetics.
  • the present nanoporous diatom algae exoskeletons allow for local inhibitor loading.
  • Cerium loaded exoskeletons show a fast diffusion controlled release.
  • the Cerium loaded exoskeletons show long-term corrosion protection at damaged coatings.
  • the Cerium loaded exoskeletons have comparable protection to the chromium based primer.
  • the present invention has been proven for a cerium salt-epoxy-aluminium alloy system and a lithium salt-epoxy-aluminium alloy it is applicable to other inhibitor-coating-metal systems. It is possible to follow degradation processes of a damaged coating any electrochemical or optical technique designed to monitor corrosion processes such as scanning vibrating electrode technique or electrochemical impedance spectroscopy as well as other tools more common in industrial settings such as salt- fog spray.
  • the active compound is at least one of a corrosion inhibitor, a self-healing compound, a compound for modifying surface tension (e.g. hydrophobicity or
  • hydrophilicity a precursor for a coating, an anti-bio fouling compound, a fire-retardant, a bactericide, an
  • insecticide a colour restoration compound, an anti-icing agent, a de-icing agent, an anti-oxidant, a UV-protector, a lubricant, and an electrical conductor.
  • coating is intended also to include “coating application”, in so far as applicable.
  • the present invention relates to a product comprising the present coating or coating application, such as a pipeline, a platform, such as an off-shore platform, an oil platform, a rocket/shuttle platform, an aerospace carrier, a vehicle, an automotive, an airplane, a train, a bridge, a bridge structure, and concrete.
  • a platform such as an off-shore platform, an oil platform, a rocket/shuttle platform, an aerospace carrier, a vehicle, an automotive, an airplane, a train, a bridge, a bridge structure, and concrete.
  • the present invention relates to a method of modifying a natural carrier for controlled release, such as for metal protection, comprising providing natural porous silica exoskeletons structures of a Heteromonyphyta species, wherein the structures have an average height of 1 ⁇ -5000 urn, an empty inner space with a cross section of 80 nm-49 urn, and pores in the exoskeleton with an average size of 5-100 nm, wherein the inner space and pores of the structures is provided with 0.1-100 vol.%, preferably 0.2-80 vol.%, more preferably 0.5-50 vol.%, even more preferably 1-40 vol.%, such as 5-30 vol.%, of at least one of an organic or inorganic active compound, such as an inhibitor selected from rare earth salts, Li salts, etc., wherein the active compound is
  • the present invention relates to a method of forming a coating or coating application according to the invention.
  • the coating may comprise a thermoset and/or a thermoplast.
  • the present invention provides a solution to one or more of the above mentioned problems and overcomes drawbacks of the prior art.
  • the present invention is also topic of a scientific article by S.J. Garcia et al . , entitled "Cerium-loaded algae exoskeletons for active corrosion protection of coated AA2024- T3", which is submitted for publication, and which paper and contents and details thereof are incorporated by reference. Some of the paragraphs below relate closely to said article.
  • the paper provides various experimental results and characterizations of the present invention.
  • the Heteromonyphyta species may be an autotroph species, in particular a Bacillariophyceae, and more particular a
  • diatomophyceae diatomophyceae .
  • the species can be readily grown in a
  • the exoskeleton may be naturally grown, obtained from diatomaceous earth, or produced in a bioreactor with extant diatom species.
  • diatomaceous earth When obtained from diatomaceous earth smaller particles typically need to be separated from the intact or largely intact exoskeletons; such may also be the case for naturally grown exoskeletons or those produced in a bioreactor, though to a lesser extent typically.
  • the naturally grown exoskeleton or the exoskeleton obtained from diatomaceous earth may be obtained by removing non-intact skeletons, such as by filtering, by mass-separation, or by settling, whereby a part or most, or even all, non-intact skeletons are removed, or wherein the exoskeleton produced in the bioreactor may be obtained by removing organic matter from the diatom species, such as by heating. Therewith good control over and selection of e.g. a size distribution of exoskeletons is obtained.
  • the active compound may be at least one of phosphates, benzoates, silicates, vanadates, tungstates, zirconates, borates, molybdates, carbonic acids, amines, ketones, aldehydes, and heterocyclic compounds.
  • active compounds may be applied, alone and in combination, amongst others showing the versatility of the present coating.
  • a salt such as an organic or inorganic salt, such as a rare earth salt, such as wherein the cation is Ce, Nd, La, Sc, or Dy
  • a carboxylate such as diethyl dithiocarbamate, carbon
  • structures may be partly or fully capped, preferably fully capped. Such is a clear advantage as the inner space can then be filled fully or almost fully. Having partly or fully capped hollow structures typically implies a careful selection and/or growth method of exoskeletons .
  • structures may be partly or fully provided with a partly or fully chemically modified surface.
  • structures can also comprise a modified surface.
  • the surface may be modified before providing the active compound, after providing the active compound, or during provision of the active compound.
  • the surface may be fully modified or partly modified, such as providing an adeguate amount of surface modifier.
  • the surface may be chemically modified in a variety of ways providing various characteristics thereto.
  • the active compound may be provided by precipitation on the surface .
  • the present coating may comprise 5- 99 wt.%, preferably 10-95 wt . % , more preferably 15-90 wt.%, even more preferably 20-80 wt.%, such as 50-75 wt.%, of at least one of a polymer of an epoxy resin, a phenolic resin, a polyurethane, a polyester, a polyamide, a polyimide, a silicone, an alkyd resin, an amino resin, and combinations thereof.
  • a polymer of an epoxy resin a phenolic resin, a polyurethane, a polyester, a polyamide, a polyimide, a silicone, an alkyd resin, an amino resin, and combinations thereof.
  • the exoskeleton particle size distribution may be a Gaussian- shaped size distribution.
  • the standard deviation in particle size may be very limited, such as wherein 3 ⁇ ( 3*average exoskeleton particle size),
  • an average exoskeleton particle may be from 1-lOOum, preferably
  • the present coating may comprise 2-20 Heteromonyphyta species, i.e. a limited number of species with well-defined characteristics, preferably 3-12 species, such as 5-10 species, each species having a different average size.
  • a first species may have an average size of 5 ⁇
  • a second species of 15 ⁇ and a third species of 50pm.
  • size distributions that are not overlapping, for instance in view of final characteristics of a coating, i.e. that within e.g. 3 ⁇ two adjacent size distributions do not overlap.
  • the present coating can be applied to a large number and variety of products.
  • the present method of modifying a natural carrier for controlled release may comprise providing natural porous silica exoskeletons structures of a Heteromonyphyta species, wherein the structures have an average height of 1 ⁇ -5000 um, an empty inner space with a cross section of 80 nm-49 ⁇ , and pores in the exoskeleton with an average size of 5-100 nm, wherein the inner space and pores of the structures is
  • the modifying method may comprise further steps.
  • the present carrier may be
  • Separation may e.g. be performed by suspending exoskeletons in a solvent, treating the suspension, such as by sonification, such that larger and smaller particles are spatially
  • an optional post- treatment on the obtained exoskeletons may be performed, or a combination of post-treatment steps.
  • an acid treatment may be performed, such as by providing a 1-5M acid, such as H2SO4, and mixing at room temperature at 50-500 rpm, such as 100-200 rpm, for a period of 1-24 hrs, such as 2-16 hrs, thereby removing impurities, such as metal species.
  • exoskeletons are typically washed with water, and dried, such as at 40-80 °C, typically at 50-60 °C, during 2-48 hrs, such as 12-24 hrs.
  • an alkaline treatment may be performed using a 10 _1 -10 "4 M, such as 10 "3 M alkaline solution, such as NaOH, during 1-3 hrs, such as 1.5 hrs, and further following the steps mentioned above.
  • a combination of an acid and alkaline post-treatment may be performed.
  • the present method of modifying a natural carrier for controlled release the active compound may be provided by ion exchange, typically after structural modification of the exoskeleton.
  • the present invention may relate to a method of forming the present coating or coating application comprising providing 1-20 wt . % of a hollow structure enclosing an internal space thereof, wherein the walls of the hollow structure is at least one natural porous silica exoskeleton of a Heteromonyphyta species, wherein the internal space and the surface of the hollow structure is provided with 0.1-100 vol.% of at least one of an organic and inorganic active compound, providing 5-99 wt . % of at least one of an uncured polymer, mixing the hollow structures and uncured polymer, applying the mixed polymer to a surface, and curing the polymer, wherein wt.%/vol.% are based on a total weight/volume of the
  • the present invention may relate to a method of forming the present coating or coating application comprising providing 1-20 wt.% of a hollow structure enclosing an internal space thereof, wherein the walls of the hollow structure is at least one natural porous silica exoskeleton of a Heteromonyphyta species, wherein the internal space and the surface of the hollow structure is provided with 0.1-100 vol.% of at least one of an organic and inorganic active compound, providing 5-99 wt.% of at least one of a thermoplastic polymer in a solvent, mixing the hollow structures and polymer, such as by extrusion, applying the mixed polymer to a surface, and increasing the temperature, wherein wt.%/vol.% are based on a total weight/volume of the coating/hollow structure.
  • the method of forming the present coating may further comprises providing 1-40 wt.% of a hollow structure enclosing an internal space thereof, preferably 2-30 wt.%, more
  • the walls of the hollow structure is at least one natural porous silica exoskeleton of a Heteromonyphyta species, wherein the exoskeleton is produced in a bioreactor, wherein both the internal space and the surface of the hollow structure is provided with 0.1-100 vol.% of at least one of an organic and inorganic active compound. It has been found that especially for exoskeletons produced in a bioreactor much high loadings of filler can be provided to coatings with a more controlled particle size and property distribution.
  • FIG. 6 shows microscope images of (a-b) Cerium Nitrate and (c-d) Ce- DE mixed with Ancamine®2500 just after mixing (a, c) and after 1 hour (b, d) . Images illustrate the yellowing process in the case of the salt-amine couple and its absence in the case of the Ce-DE amine one. Image confirms the strong reduction of the yellowing when the Ce-salt is included in an exoskeleton nanoporous micro particle.
  • Figure 1 shows a set of SEM images and EDX spectra of the diatom exoskeletons before (la and lc) and after (lb and lc) the purification process as well as the particle size
  • FIG. 5 Microscope images of polished AA2024-T3 before, during, and after 7 days of immersion in 0.05M NaCl (a) without corrosion inhibitor (b) 0.05mM Ce( 03)3 and (c) Ce- doped DE containing 0.05 m Ce(N03) 3. Note, images during immersion do not represent real sizes due to the distortion by the solution.
  • the present invention is demonstrated for an epoxy-amine coating on an aerospace aluminium alloy AA2024-T3 system.
  • Cerium nitrate was used as the corrosion inhibitor giving an excellent corrosion inhibition in the copper-rich aluminium alloy. Cerium nitrate was here stored into refined
  • Diatomaceous earth Diafil 525 mainly consisting of
  • the as-received diatomaceous earth consists of 89.0 wt. % amorphous silica (S1O2) , a tapped powder bulk density of 0.42 g/cm 3 and a mean particle size of 12 ⁇ .
  • the DE may be post-treated in order to remove impurities. Almost all impurities can thereby be removed.
  • the treated DE shows a somewhat better behaviour, e.g. in terms of release of active compound over time and in amount.
  • AA2024-T3 metal sheets were cut into pieces of 25x50 mm prior to surface modification and coating application.
  • the metal surface preparation consisted of the following sequential steps: (i) removal of native oxide layer and
  • the organic coatings were prepared using a mixture of
  • PVC concentration
  • Figure 1 shows a set of SEM images and EDX spectra of the diatom exoskeletons before (la and lc) and after (lb and lc) the purification process as well as the particle size
  • Magnesium (Mg) were also detected and assigned to impurity oxides (A1203, Fe203, CaC03, CaO, and MgO) .
  • the purifying process used was not capable of fully removing oxide
  • impurities The presence of the impurities in the clean DE did not have an effect on the ulterior cerium doping when the doping procedure proposed in this work was employed. As the impurities did not have a significant effect in the doping it was decided to skip the acid and alkali post-treatments to simplify the process.
  • the XRD spectra for the Ce-DE shows the amorphous silica baseline combined with crystalline peaks corresponding to Ce(N03) 3 .
  • the increased intensity of the peaks compared to pure Ce (N0 3 ) 3.6H 2 0 is presumably caused by the decrease of water in the crystal lattice due to drying and localized deposition on the diatom silica surface.
  • the results confirm that, during the doping process, the cerium inhibitor did not change its crystalline structure and remained as an inorganic salt primarily inside the diatom exoskeletons body space and nanopores, thereby confirming the success of the developed doping procedure.
  • Figure 4 shows the SEM-EDS micrograph of a fractured epoxy coating containing Ce-DE particles.
  • the fractured plane shows a DE cylindrical particle (from the top) embedded in the epoxy matrix.
  • the EDS analysis further confirmed the presence of high cerium concentrations inside the exoskeleton with a low carbon signal of the polymeric matrix thereby confirming the cerium inhibitor remained in the inner volume of the DE when the Ce-DE particles were mixed with the epoxy coating. This is a critical requirement of the localized long term corrosion protection.
  • Figure 5 (a) shows that pitting corrosion on AA2024 occurs within the first 3h of immersion in 0.05 M NaCl, indicating the susceptibility to localized corrosion in salt water for this alloy. The initiation of pitting did not occur when
  • a new biobased carrier for corrosion inhibition is introduced.
  • the use of diatom algae silica exoskeletons provides protection of AA2024-T3 structures by cerium nitrate corrosion inhibitor. Corrosion protection levels comparable to those given by a coating containing potassium dichromate were obtained. High protection levels are achieved, a reduction of unwanted reactions, a high inhibitor storage in the silica cages and the fast and sustained release of the cerium
  • inhibitor loaded algae exoskeleton particles for sustained corrosion inhibition is not restricted to cerium and epoxy coatings on aluminium substrates but should be regarded as being generic with a high versatility and potential for developing

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  • Wood Science & Technology (AREA)
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Abstract

La présente invention concerne un revêtement comprenant un support naturel à des fins de libération contrôlée d'un composé, tel qu'une protection métallique, un produit comprenant ledit revêtement ou l'application du revêtement, un procédé de modification d'un support naturel à des fins de libération contrôlée, et des procédés de formation dudit revêtement ou d'application de revêtement, où le support naturel est choisi parmi les exosquelettes d'une espèce d'Heterokontophyta.
PCT/NL2018/050161 2017-03-15 2018-03-15 Diatomées comme supports naturels à des fins de libération contrôlée pour protection et revêtements métalliques Ceased WO2018169397A1 (fr)

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NL2018517A NL2018517B1 (en) 2017-03-15 2017-03-15 Diatoms as natural carriers for controlled release for metal protection and coating applications
NL2018517 2017-03-15

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WO2018169397A1 true WO2018169397A1 (fr) 2018-09-20

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114560739A (zh) * 2022-03-14 2022-05-31 重庆大学 一种硅藻土基复合有机硅肥及其制备方法和用途

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1024181A1 (fr) 1999-01-29 2000-08-02 DaimlerChrysler AG Couche anti-corrosion
WO2010148158A1 (fr) 2009-06-17 2010-12-23 Isp Investments Inc. Procédé de préparation de substances actives biocides stables, microencapsulées et à libération lente et composition apparentée
AU2012101866A4 (en) * 2012-12-21 2013-01-31 Macadamia Oils Of Australia Pty Ltd Controlled Release Biodegradable Fertiliser

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1024181A1 (fr) 1999-01-29 2000-08-02 DaimlerChrysler AG Couche anti-corrosion
WO2010148158A1 (fr) 2009-06-17 2010-12-23 Isp Investments Inc. Procédé de préparation de substances actives biocides stables, microencapsulées et à libération lente et composition apparentée
AU2012101866A4 (en) * 2012-12-21 2013-01-31 Macadamia Oils Of Australia Pty Ltd Controlled Release Biodegradable Fertiliser

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114560739A (zh) * 2022-03-14 2022-05-31 重庆大学 一种硅藻土基复合有机硅肥及其制备方法和用途

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