WO2009080597A2 - Procédé pour préparer un hydroxyde double lamellaire organiquement modifié - Google Patents

Procédé pour préparer un hydroxyde double lamellaire organiquement modifié Download PDF

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Publication number
WO2009080597A2
WO2009080597A2 PCT/EP2008/067576 EP2008067576W WO2009080597A2 WO 2009080597 A2 WO2009080597 A2 WO 2009080597A2 EP 2008067576 W EP2008067576 W EP 2008067576W WO 2009080597 A2 WO2009080597 A2 WO 2009080597A2
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WIPO (PCT)
Prior art keywords
nonionic surfactant
metal ion
organic acid
layered double
process according
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PCT/EP2008/067576
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English (en)
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WO2009080597A3 (fr
Inventor
Robin Winters
Elwin Schomaker
Boen O
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Akzo Nobel N.V.
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Publication of WO2009080597A2 publication Critical patent/WO2009080597A2/fr
Publication of WO2009080597A3 publication Critical patent/WO2009080597A3/fr

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    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B13/00—Oxygen; Ozone; Oxides or hydroxides in general
    • C01B13/14—Methods for preparing oxides or hydroxides in general
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01F—COMPOUNDS OF THE METALS BERYLLIUM, MAGNESIUM, ALUMINIUM, CALCIUM, STRONTIUM, BARIUM, RADIUM, THORIUM, OR OF THE RARE-EARTH METALS
    • C01F7/00—Compounds of aluminium
    • C01F7/78—Compounds containing aluminium and two or more other elements, with the exception of oxygen and hydrogen
    • C01F7/784—Layered double hydroxide, e.g. comprising nitrate, sulfate or carbonate ions as intercalating anions
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01F—COMPOUNDS OF THE METALS BERYLLIUM, MAGNESIUM, ALUMINIUM, CALCIUM, STRONTIUM, BARIUM, RADIUM, THORIUM, OR OF THE RARE-EARTH METALS
    • C01F7/00—Compounds of aluminium
    • C01F7/78—Compounds containing aluminium and two or more other elements, with the exception of oxygen and hydrogen
    • C01F7/784—Layered double hydroxide, e.g. comprising nitrate, sulfate or carbonate ions as intercalating anions
    • C01F7/785—Hydrotalcite
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/41—Preparation of salts of carboxylic acids
    • C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2002/00—Crystal-structural characteristics
    • C01P2002/20—Two-dimensional structures
    • C01P2002/22—Two-dimensional structures layered hydroxide-type, e.g. of the hydrotalcite-type

Definitions

  • the invention relates to a process for preparing organically modified layered double hydroxides. That is: layered double hydroxides containing an organic anion as a charge-balancing anion.
  • Processes for preparing such organically modified layered double hydroxides are generally known and are generally performed in water.
  • the organic modification i.e. the charge-balancing anion
  • the use of water in these processes causes the final dried product to have a considerable amount of water and to form alkaline suspensions when re- dispersed in water.
  • the considerable amount of water in and the alkalinity of conventionally prepared layered double hydroxides may change the mechanical and physical properties of the resulting material when blended into polymeric matrices, for instance by causing depolymerization.
  • fatty acids leads to the formation of inhomogeneous suspensions containing agglomerates of fatty acid. This is due to the fact that the solubility in water of the fatty acids is limited and decreases with the pH and since the pH during preparation of the layered double hydroxide drops, the solubility of the fatty acid decreases during said process, leading to fatty acid agglomerates and deposits in the reactor.
  • WO 2007/065877 prepared layered double hydroxides in the presence of an organic solvent which is miscible with water and in which at least 5 g/l of a charge-balancing anion precursor can be dissolved.
  • an organic solvent which is miscible with water and in which at least 5 g/l of a charge-balancing anion precursor can be dissolved.
  • a further object is to provide a process in which agglomerate formation is reduced or even prevented.
  • LDH organically modified layered double hydroxide
  • step (b) reacting said divalent metal ion source and said trivalent metal ion source in said aqueous suspension or solution to obtain a layered double hydroxide, wherein an organic acid and a nonionic surfactant are added to the aqueous suspension or solution before, during or after step (b), and wherein the amount of nonionic surfactant is between 0.1 and 10 wt%, based on the total weight of organic acid and nonionic surfactant.
  • the organic acid and the nonionic surfactant can be added simultaneously or separately at different stages in the process of the invention.
  • the nonionic surfactant is added to the suspension or solution before addition of the organic acid.
  • the nonionic surfactant and the organic acid are added simultaneously, as a mixture.
  • the organic acid and/or the nonionic surfactant are added to the suspension or solution before or while step (b) proceeds.
  • the organically modified layered double hydroxide is prepared in one step, which generally renders the process simpler and quicker, and consequently more attractive economically.
  • step (b) It is also envisaged to add part of the organic acid and/or nonionic surfactant prior to or during step (b), and to add the remaining part after the layered double hydroxide is formed.
  • the organic acid and the nonionic surfactant are added to an already prepared layered double hydroxide.
  • This already prepared layered double hydroxide preferably contains, prior to the addition of the organic acid and the nonionic surfactant, an inorganic charge-balancing anion selected from the group consisting of hydroxide, nitrate, chloride, bromide, phosphate, phosphonate, sulfonate, sulfate, bisulfate, and mixtures thereof, preferably hydroxide, nitrate, chloride, bromide, and mixtures thereof, and most preferably hydroxide. Therefore, the present invention also relates to a process for preparing an organically modified layered double hydroxide comprising an organic anion as charge-balancing anion, the process comprising the steps of:
  • Nonionic surfactants are amphiphathic molecules consisting of a nonpolar hydrophobic portion attached to a polar hydrophilic portion.
  • the hydrophobic portion in the nonionic surfactants used in the process of the present invention preferably is a linear or branched hydrocarbon chain containing 9-24, preferably 10-22, and most preferably 12-20 carbon atoms.
  • nonionic surfactants examples include alcohol ethoxylates, alkyl phenol ethoxylates, fatty acid ethoxylates, sorbitan esters and their ethoxylated derivatives, ethoxylated fats and oils, amine ethoxylates, ethylene oxide- propylene oxide copolymers, surfactants derived from mono- and polysaccharides such as alkyl polyglucosides, and glycehdes. Ethoxylated surfactants are preferred, while ethoxylated alcohols are the most preferred nonionic surfactants for use in the process of the present invention.
  • Suitable ethoxylated nonionic surfactants preferably comprise at least 6 ethylene oxide moieties, more preferably 10-25 ethylene oxide moieties, and most preferably 15-25 ethylene oxide moieties.
  • Nonionic surfactants are generally classified according to their HLB value.
  • M hp equals the number of ethylene oxide moieties times their molecular weight (44 g/mol).
  • the HLB value of the surfactant to be used in the process of the present invention preferably is at least 10, more preferably at least 12, and most preferably at least 14.
  • the amount of nonionic surfactant used in the process of the invention is between 0.1 and 10 percent by weight (wt%), based on the total weight of organic acid and surfactant.
  • the amount is at least 0.2 wt%, more preferably at least 0.3 wt%, and most preferably at least 0.5 wt%, and preferably at most 8 wt%, more preferably at most 5 wt%, and most preferably at most 4 wt%.
  • the nonionic surfactant can be used alone or in combination with other non- ionic surfactants or in combination with ionic surfactants, such as anionic surfactants.
  • the organic acid preferably comprises at least 2 carbon atoms, more preferably at least 8 carbon atoms, even more preferably at least 10 carbon atoms, and most preferably at least 12 carbon atoms.
  • the organic acid preferably comprises at most 1 ,000 carbon atoms, more preferably at most 500 carbon atoms, even more preferably at most 100 carbon atoms, and most preferably at most 50 carbon atoms.
  • the organic acid is a fatty acid having from 8 to 22 carbon atoms. Such a fatty acid may be saturated or unsaturated.
  • suitable fatty acids are caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, arachidic acid, decenoic acid, palmitoleic acid, oleic acid, linoleic acid, linolenic acid, and mixtures thereof.
  • the organic acid is a rosin- based acid. Rosin is derived from natural sources, is readily available, and is relatively inexpensive compared to synthetic organic acids.
  • Typical examples of natural sources of rosin are gum rosin, wood rosin, and tall oil rosins. Rosin commonly is a suspension of a wide variety of different isomers of monocarboxylic tricyclic rosin acids usually containing about 20 carbon atoms. The tricyclic structures of the various rosin acids differ mainly in the position of AIN 3254 R
  • rosin is a suspension of substances comprising levopimaric acid, neoabietic acid, palustric acid, abietic acid, dehydroabietic acid, seco-dehydroabietic acid, tetrahydroabietic acid, pimaric acid, and isopimaric acid.
  • Rosin derived from natural sources also includes rosins, i.e. rosin suspensions, modified notably by polymerization, isomerization, disproportionation, hydrogenation, and Diels-Alder reactions with acrylic acid, anhydrides, and acrylic acid esters. Rosin can also be modified or chemically altered by introducing an organic group, an anionic group or a cationic group.
  • the organic group may be a substituted or unsubstituted aliphatic or aromatic hydrocarbon having 1 to 40 carbon atoms.
  • the anionic group may be any anionic group known to the man skilled in the art, such as a carboxylate or a sulfonate.
  • the organic acid is a mixture of fatty acid and rosin.
  • the divalent metal ion source and the trivalent metal ion source used in the processes of the present invention can be any source known to the man skilled in the art. These sources include soluble salts of the divalent and/or trivalent metal ions as well as insoluble or partially insoluble divalent and trivalent metal ion sources, or mixtures thereof.
  • soluble salts refers to divalent and trivalent metal ion sources that dissolve completely in water and form a clear solution at room temperature.
  • insoluble or partially insoluble metal ion sources refers to sources that do not dissolve completely in water and form a suspension at room temperature.
  • Examples of soluble salts of metal ion sources are nitrates, chlorides, perchlorates, and aluminates.
  • Examples of insoluble or partially insoluble divalent and trivalent metal ion sources are oxides, hydroxides, and carbonates.
  • the sources are insoluble or partially soluble.
  • Most preferably, the divalent and trivalent metal ion sources are oxides or hydroxides.
  • Examples of divalent metal ions are Zn 2+ , Mn 2+ , Ni 2+ , Co 2+ , Fe 2+ , Cu 2+ , Sn 2+ , Ba 2+ , Ca 2+ , and Mg 2+ .
  • Examples of trivalent metal ions are Al 3+ , Cr 3+ , Fe 3+ , Co 3+ , Mn 3+ , Ni 3+ , Ce 3+ , and Ga 3+ .
  • suitable magnesium sources which are insoluble or partially insoluble are magnesium oxide, magnesium hydroxide, magnesium hydroxycarbonate, magnesium bicarbonate, dolomite, and sepiolite.
  • the aluminium source which is insoluble or partially insoluble typically is a hydroxide or an oxide of aluminium.
  • aluminium trihydroxides such as gibbsite and bayerite
  • aluminium oxohydroxides such as boehmite, diaspore or goethite, and transition aluminas, which are known to the man skilled in the art.
  • the use of the above insoluble or partially soluble divalent and trivalent metal ion sources is more environment-friendly than the use of the salts, because it does not result in a salty waste stream.
  • the insoluble or partially soluble divalent and trivalent metal ion sources, and in particular the magnesium and aluminium sources are generally less expensive than the corresponding salts.
  • the insoluble or partially soluble divalent and/or trivalent metal ion sources are milled prior to step (b).
  • the divalent and/or trivalent metal ion sources generally have a d50 value of less than 20 ⁇ m and a d90 value of less than 50 ⁇ m.
  • the d50 value is less than 15 ⁇ m and the d90 value is less than 40 ⁇ m, more preferably the d50 value is less than 10 ⁇ m and the d90 value is less than 30 ⁇ m, even more preferably the d50 value is less than 8 ⁇ m and the d90 value is less than 20 ⁇ m, and most preferably the d50 value is less than 6 ⁇ m and the d90 value is less than 10 ⁇ m.
  • the particle size distribution can be determined using methods known to the man skilled in the art, e.g. laser AIN 3254 R
  • divalent and trivalent metal ion sources are magnesium and aluminium sources, it further may reduce the amount of impurities such as gibbsite or brucite in the resulting layered double hydroxide.
  • the reaction between the divalent metal ion source and the trivalent metal ion source in the suspension or solution can be conducted at a temperature between about 30 0 C and the boiling point of the suspension or solution at atmospheric pressure.
  • the temperature generally is from 40 to 120 0 C, preferably from 50 to 100°C, and most preferably from 60 to 90 0 C.
  • the reaction can also be conducted at a pressure above atmospheric pressure and a temperature which generally is above the boiling point of the suspension or solution at atmospheric pressure.
  • the pressure generally is from 1 bar to 200 bar, preferably from 2 bar to 150 bar, and most preferably from 3 bar to 100 bar.
  • a temperature of 100°C or higher preferably from 100°C to 300 0 C, more preferably from 110°C to 250°C, and most preferably from 120 0 C to 200°C can be used. If temperatures above the normal boiling point are used, the pressure applied is generally autogenous.
  • the required time for the reaction between the divalent metal ion source and the trivalent metal ion source in the suspension or solution depends on the temperature, pressure, and metal sources used, but generally takes about 30 min to 24 hours, preferably 1 -6 hours, and most preferably 2-4 hours.
  • the LDH, the organic acid, and the nonionic surfactant are preferably contacted at a temperature between about 30°C and the boiling point of the suspension or solution at atmospheric pressure.
  • the temperature generally is from 40 to 150 0 C, preferably from 50 to 120°C, and most preferably from 60 to 90°C.
  • the pressure generally is from 1 bar to 6 bar, preferably 1 to 3 bar, and most preferably 1 to 2 bar. At pressures higher than 1 bar, a temperature of AIN 3254 R
  • 100 0 C or higher preferably from 100 0 C to 150°C, more preferably from 110 0 C to 140°C, and most preferably from 120°C to 130 0 C can be used. If temperatures above the normal boiling point are used, the pressure applied is generally autogenous.
  • the required time for the contacting the LDH with the organic acid and the nonionic surfactant depends on the temperature and pressure, but generally takes about 20 min to 6 hours, preferably 40 min to 3 hours and most preferably 1 -2 hours.
  • the process of the invention can be conducted in the absence of CO2 or carbonates in the precursor suspension, so as to ascertain that no carbonate is incorporated into the layered double hydroxide as charge-balancing anion.
  • the organically modified layered double hydroxide that results from the process of the present invention comprises an organic anion as charge-balancing anion.
  • charge-balancing anion refers to anions that compensate for the electrostatic charge deficiencies of the crystalline LDH sheets.
  • the charge-balancing anions may be situated in the interlayer, on the edge or on the outer surface of the stacked LDH layers. Such anions situated in the interlayer of stacked LDH layers are referred to as intercalating ions.
  • the organically modified layered double hydroxide (LDH) resulting from the process of the present invention has a layered structure corresponding to the general formula:
  • M 2+ is a divalent metal ion such as Zn 2+ , Mn 2+ , Ni 2+ , Co 2+ , Fe 2+ , Cu 2+ , Sn 2+ , Ba 2+ , Ca 2+ , Mg 2+ , and is most preferably Mg 2+
  • M 3+ is a trivalent metal ion such as Al 3+ , Cr 3+ , Fe 3+ , Co 3+ , Mn 3+ , Ni 3+ , Ce 3+ , and Ga 3+ , and is most preferably AIN 3254 R
  • X z ⁇ is a charge-balancing anion, at least part of which is derived from the organic acid.
  • X z ⁇ is an organic anion derived from the organic acid.
  • at least 10%, more preferably at least 30%, even more preferably at least 60%, and most preferably at least 90% of the total amount of intercalating anions X z ⁇ is derived from a fatty acid or rosin.
  • the LDH may be in any crystal form known in the art. If the LDH is a hydrotalcite, the hydrotalcite may be a polytype having 3Hi, 3H 2 , 3Ri or 3R 2 stacking, for example.
  • the organically modified layered double hydroxide obtained by the process of the present invention is particularly suitable for use in a polymeric matrix.
  • the organically modified layered double hydroxide may be delaminated or exfoliated.
  • delamination is defined as a reduction of the mean stacking degree of the LDH particles by at least partial de-layering of the LDH structure, thereby yielding a material containing significantly more individual LDH sheets per volume.
  • exfoliation is defined as complete delamination, i.e. disappearance of periodicity in the direction perpendicular to the LDH sheets, leading to a random dispersion of individual layers in a medium, thereby leaving no stacking order at all.
  • TEM transmission electron microscopy
  • the organically modified layered double hydroxides prepared with the process of the invention to have a distance between the individual layers of above 1.5 nm.
  • This renders the layered double hydroxides easily processable in the polymeric matrix, and it further enables easy delamination and/or exfoliation of the layered double hydroxide, resulting in a mixture of the organically modified layered double hydroxide and the polymer matrix with improved physical properties.
  • the distance between the layers is at least 1.5 nm, more preferably at least 1.6 nm, even more preferably at least 1.8 nm, and most preferably at least 2 nm.
  • the distance between the individual layers can be determined using X-ray diffraction and transmission electron microscopy (TEM), as outlined above.
  • the distance between the individual layers includes the plate thickness of one of the individual layers.
  • organically modified layered double hydroxides were prepared using the following surfactants:
  • General procedure 1 was performed using these surfactants in amounts ranging from 0.5 to 16 wt%, based on the total weight of fatty acid and surfactant.
  • anionic surfactants resulted in agglomeration of the fatty acid.
  • the best results with anionic surfactants were obtained with sodium C-14-16 olefin sulfonate, but still these suspensions contained fatty acid agglomerates and the final pH of the suspension was higher than 8.
  • the use of a combination of an anionic surfactant (sodium Ci 4- i6 olefin sulfonate) and a nonionic surfactant (tridecyl alcohol 6 EO) gave some improvement in the extent of agglomeration, although agglomerates were still present.
  • nonionic surfactants in amounts of more than 10 wt% (based on the total weight of fatty acid and surfactant) resulted in foaming.
  • General procedure 2 was performed using stearyl alcohol 16 EO as the surfactant.
  • the surfactant was used in an amount of 2.5 wt%, based on the total weight of fatty acid and surfactant.
  • a homogeneous LDH slurry was obtained with a pH of 8.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Geology (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Compounds Of Alkaline-Earth Elements, Aluminum Or Rare-Earth Metals (AREA)

Abstract

L'invention porte sur un procédé pour préparer un hydroxyde double lamellaire organiquement modifié comprenant un anion organique en tant qu'anion d'équilibrage de charge par (a) la préparation d'une suspension ou solution aqueuse comprenant une source d'ion de métal divalent, une source d'ion de métal trivalent et de l'eau et (b) la réaction de ladite source d'ion de métal divalent et de ladite source d'ion de métal trivalent dans ladite suspension ou solution aqueuse pour obtenir un hydroxyde double lamellaire, un acide organique et un agent tensioactif non ionique étant ajoutés à la suspension ou solution aqueuse avant, pendant ou après l'étape (b) et la quantité de l'agent tensioactif non ionique se situant entre 0,1 et 10 % en poids, sur la base de la masse totale de l'acide organique et de l'agent tensioactif non ionique.
PCT/EP2008/067576 2007-12-19 2008-12-16 Procédé pour préparer un hydroxyde double lamellaire organiquement modifié WO2009080597A2 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
EP07123538.6 2007-12-19
EP07123538 2007-12-19
US1562807P 2007-12-20 2007-12-20
US61/015,628 2007-12-20

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WO2009080597A2 true WO2009080597A2 (fr) 2009-07-02
WO2009080597A3 WO2009080597A3 (fr) 2009-09-11

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2263976A1 (fr) * 2009-06-03 2010-12-22 Akzo Nobel Chemicals International B.V. Hydroxyde à double couche avec une morphologie spécifique, sa préparation et utilisation
WO2012150439A1 (fr) 2011-05-04 2012-11-08 Isis Innovation Limited Préparation d'hydroxydes doubles lamellaires
WO2016096626A1 (fr) * 2014-12-17 2016-06-23 Unilever N.V. Composition de support pour actifs volatils
EP3333217A1 (fr) 2016-12-12 2018-06-13 Scg Chemicals Co. Ltd. Composition polymère

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101450677B1 (ko) * 2013-08-06 2014-10-15 주식회사 두본 중화제를 포함하는 첨가제 조성물

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996005140A1 (fr) * 1994-08-15 1996-02-22 Aluminum Company Of America Synthese d'hydrotalcite et de composes apparentes, a partir de deux poudres
WO2007065859A1 (fr) * 2005-12-06 2007-06-14 Akzo Nobel N.V. Procede permettant de preparer un hydroxyde double lamellaire organiquement modifie
WO2007065861A1 (fr) * 2005-12-06 2007-06-14 Akzo Nobel N.V. Argile comprenant des ions organiques permettant d'equilibrer les charges et materiaux nanocomposites comprenant cette argile
WO2007065877A1 (fr) * 2005-12-06 2007-06-14 Akzo Nobel N.V. Procede destine a la preparation d'un hydroxyde double en couches organiquement modifie

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996005140A1 (fr) * 1994-08-15 1996-02-22 Aluminum Company Of America Synthese d'hydrotalcite et de composes apparentes, a partir de deux poudres
WO2007065859A1 (fr) * 2005-12-06 2007-06-14 Akzo Nobel N.V. Procede permettant de preparer un hydroxyde double lamellaire organiquement modifie
WO2007065861A1 (fr) * 2005-12-06 2007-06-14 Akzo Nobel N.V. Argile comprenant des ions organiques permettant d'equilibrer les charges et materiaux nanocomposites comprenant cette argile
WO2007065877A1 (fr) * 2005-12-06 2007-06-14 Akzo Nobel N.V. Procede destine a la preparation d'un hydroxyde double en couches organiquement modifie

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2263976A1 (fr) * 2009-06-03 2010-12-22 Akzo Nobel Chemicals International B.V. Hydroxyde à double couche avec une morphologie spécifique, sa préparation et utilisation
WO2012150439A1 (fr) 2011-05-04 2012-11-08 Isis Innovation Limited Préparation d'hydroxydes doubles lamellaires
WO2016096626A1 (fr) * 2014-12-17 2016-06-23 Unilever N.V. Composition de support pour actifs volatils
EP3333217A1 (fr) 2016-12-12 2018-06-13 Scg Chemicals Co. Ltd. Composition polymère
WO2018108362A1 (fr) 2016-12-12 2018-06-21 Scg Chemicals Co., Ltd. Composition polymère
US11193013B2 (en) 2016-12-12 2021-12-07 Scg Chemicals Co., Ltd. Polymer composition

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TW200946455A (en) 2009-11-16

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