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WO2012016952A1 - Phyllosilicates stables à hautes températures à élargissement de couche accru - Google Patents

Phyllosilicates stables à hautes températures à élargissement de couche accru Download PDF

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Publication number
WO2012016952A1
WO2012016952A1 PCT/EP2011/063225 EP2011063225W WO2012016952A1 WO 2012016952 A1 WO2012016952 A1 WO 2012016952A1 EP 2011063225 W EP2011063225 W EP 2011063225W WO 2012016952 A1 WO2012016952 A1 WO 2012016952A1
Authority
WO
WIPO (PCT)
Prior art keywords
radical
imide group
organophilic
phyllosilicate
phyllosilicates
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.)
Ceased
Application number
PCT/EP2011/063225
Other languages
German (de)
English (en)
Inventor
Peter GRÖPPEL
André GRÜBEL
Rolf Mülhaupt
Michael Nedelcu
Meik Wissert
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.)
Siemens AG
Siemens Corp
Original Assignee
Siemens AG
Siemens Corp
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 Siemens AG, Siemens Corp filed Critical Siemens AG
Publication of WO2012016952A1 publication Critical patent/WO2012016952A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B33/00—Silicon; Compounds thereof
    • C01B33/20—Silicates
    • C01B33/36—Silicates having base-exchange properties but not having molecular sieve properties
    • C01B33/38—Layered base-exchange silicates, e.g. clays, micas or alkali metal silicates of kenyaite or magadiite type
    • C01B33/44—Products obtained from layered base-exchange silicates by ion-exchange with organic compounds such as ammonium, phosphonium or sulfonium compounds or by intercalation of organic compounds, e.g. organoclay material

Definitions

  • the present invention relates to the technical field of organophilic phyllosilicates, their preparation and their use in deformable molding compositions and in finished moldings or composite materials, in particular in nanocomposites (nanocomposites).
  • a process step is a
  • Layered silicate provided which comprises cations which at least two individual layers of the layered silicate
  • the organophilicating reagent comprises at least one imide group.
  • an organophilic layered silicate is proposed, which according to the process for the preparation of the organophilic
  • Layer silicate was produced. According to a further aspect of the invention, an organophilic layered silicate is proposed which comprises at least two individual layers
  • the individual layers are at least partially electrostatically connected by organic cations. At least part of the organic cations comprises an imide group. According to a further aspect of the invention, a use of such organophilic phyllosilicates in deformable
  • the organophilicating reagent comprises at least one imide group.
  • organophilic is to be understood as a substance which is dispersible in an organic material. The invention will be described below with reference to
  • FIGS 1A and 1B show formulas of two
  • Figures 2A, 2B, 2C, 2D show a chemical
  • FIG. 3 shows results of the thermal
  • TGA thermogravimetry
  • FIG. 4 shows results of
  • Figures 1A and 1B each show a formula for a chemical compound of imidamine-based
  • the organophilicizing reagent comprises at least one, preferably two or more functional imide groups 7a, 7b, 7c, 7d.
  • one or more or all of the imide groups of a compound comprise any choice of alkyl radical, alkenyl radical, aryl radical and / or an alkylaryl radical with or without further
  • R is an alkyl radical and / or an alkenyl radical and / or an aryl radical and / or an alkylaryl radical. R does not always have to be the same in a formula, but can be combined arbitrarily, which is through the
  • 3c may be an alkyl radical and 3d an aryl radical.
  • X is any cation 4
  • Organophilization of the layered silicate is replaced by the organophilic cation 5.
  • the cation 4 is therefore not part of the Organophil michsreagenzes.
  • Table 1 shows measured film widening d and thermal stabilities T d of organophilic sheet sililates
  • OSS layer expansions d and thermal stabilities T d of known OSS were measured, namely Montmorillonite (MMT), modified with octadecylamine
  • MMT-ODA Montmorillonite
  • MMT-DMODA dimethyloctadecyl ammonium modified montmorillonite
  • Table 1 also shows measured layer expansions d and thermal stabilities T of OSS in comparison with the above known OSS, namely, dodecenyl-modified montmorillonites (MMT-IA1), phthalate-modified montmorillonites (MMT-IA2 ), methyl-modified montmorillonite (MMT-IA3 / 4) and naphthyl-modified montmorillonite (MMT-IA5).
  • MMT-IA1 dodecenyl-modified montmorillonites
  • MMT-IA2 phthalate-modified montmorillonites
  • MMT-IA3 / 4 methyl-modified montmorillonite
  • MMT-IA5 naphthyl-modified montmorillonite
  • thermoplastics and thermosets new nanocomposites.
  • the nanocomposites, but also other composites with organophilic phyllosilicates are in exfoliated form
  • organophilic phyllosilicates are characterized by particularly high layer widening and outstanding
  • organophilic phyllosilicates with thermoplastics or
  • Imidamines offer through the easy accessibility and
  • Imidamine 1 (imidamine with dodecenyl radical) described: Under N2 atmosphere are 2 equivalents
  • DDSA Dodecynilsuccinic anhydride
  • DETA diethyl tetraamine
  • Figures 2A, 2B, 2C, 2D can be seen.
  • an anhydride 51a, 51b, 51c, 51d is treated with an amine 52a, 52b, 52c, 52d under preferred conditions 53a, 53b,
  • FIG. 2A imidamine with a dodecenyl radical (54a)
  • FIG. 2C imidamine with a methyl radical (54c);
  • Figure 2D imidamine with a naphthyl radical (54d).
  • the sheet silicates were first swollen in 80 ° C warm deionized water (H 2 O) 2 hours and
  • thermogravimetry results of the thermal characterization of the organophilic phyllosilicates by means of thermogravimetry (TGA) are shown in FIG.
  • the abscissa represents the temperature in ° C to which the organophilic sheet silicates were exposed, while the ordinate represents the weight percentage (mass wt.%).
  • Measurement curve 11 shows the temperature stability of already known dimethyloctadecylammonium (DMODA) modified montmorillonite (PGV).
  • DMODA dimethyloctadecylammonium
  • PSV modified montmorillonite
  • DMODA Dimethyloctadecylammonium
  • alkyl radical alkenyl radical, aryl radical and / or an alkylaryl radical

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Silicates, Zeolites, And Molecular Sieves (AREA)

Abstract

L'invention concerne des phyllosilicates stables à hautes températures à élargissement de couche accru. Ces phyllosilicates peut être produits selon les étapes de procédé suivantes : utilisation d'un phyllosilicate contenant des cations (4) qui relient électrostatiquement au moins deux couches individuelles d'un phyllosilicate; échange d'au moins une partie des cations (4) du phyllosilicate par des cations organiques (5) d'un réactif d'organophilisation (9a, 9b) contenant au moins un groupe imide (7).
PCT/EP2011/063225 2010-08-02 2011-08-01 Phyllosilicates stables à hautes températures à élargissement de couche accru Ceased WO2012016952A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE201010033029 DE102010033029A1 (de) 2010-08-02 2010-08-02 Hochtemperaturstabile Schichtsilikate mit erhöhter Schichtaufweitung
DE102010033029.9 2010-08-02

Publications (1)

Publication Number Publication Date
WO2012016952A1 true WO2012016952A1 (fr) 2012-02-09

Family

ID=44510938

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2011/063225 Ceased WO2012016952A1 (fr) 2010-08-02 2011-08-01 Phyllosilicates stables à hautes températures à élargissement de couche accru

Country Status (2)

Country Link
DE (1) DE102010033029A1 (fr)
WO (1) WO2012016952A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103012176A (zh) * 2012-12-03 2013-04-03 清华大学 一种长链烷基四羧基阴离子表面活性剂的制备方法

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4810734A (en) 1987-03-26 1989-03-07 Kabushiki Kaisha Toyota Chuo Kenkyusho Process for producing composite material
US4889885A (en) 1987-03-04 1989-12-26 Kabushiki Kaisha Toyota Chuo Kenkyusho Composite material containing a layered silicate
US4894411A (en) 1987-03-18 1990-01-16 Kabushiki Kaisha Toyota Chuo Kenkyusho Composite material and process for producing the same
WO1996008526A1 (fr) 1994-09-12 1996-03-21 Cornell Research Foundation, Inc. Nanocomposites stratifies de silicate-epoxy
WO1998010012A1 (fr) 1996-09-03 1998-03-12 Raychem Corporation Composites de polymere et d'argile organique
DE69907162T2 (de) 1998-02-20 2004-02-19 Vantico Ag Organophile phyllosilikate
EP1538183A1 (fr) * 2002-09-11 2005-06-08 Teijin Limited Film thermoplastique, composition de resine thermoplastique, et phyllosilicate
WO2005095506A1 (fr) * 2004-03-29 2005-10-13 Bridgestone Corporation Nanocomposite et procede associe
EP1702887A1 (fr) * 2003-09-18 2006-09-20 Teijin Limited Phyllosilicate et composition a base de resine thermoplastique contenant ce compose

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4889885A (en) 1987-03-04 1989-12-26 Kabushiki Kaisha Toyota Chuo Kenkyusho Composite material containing a layered silicate
US4894411A (en) 1987-03-18 1990-01-16 Kabushiki Kaisha Toyota Chuo Kenkyusho Composite material and process for producing the same
US4810734A (en) 1987-03-26 1989-03-07 Kabushiki Kaisha Toyota Chuo Kenkyusho Process for producing composite material
WO1996008526A1 (fr) 1994-09-12 1996-03-21 Cornell Research Foundation, Inc. Nanocomposites stratifies de silicate-epoxy
WO1998010012A1 (fr) 1996-09-03 1998-03-12 Raychem Corporation Composites de polymere et d'argile organique
DE69907162T2 (de) 1998-02-20 2004-02-19 Vantico Ag Organophile phyllosilikate
EP1538183A1 (fr) * 2002-09-11 2005-06-08 Teijin Limited Film thermoplastique, composition de resine thermoplastique, et phyllosilicate
EP1702887A1 (fr) * 2003-09-18 2006-09-20 Teijin Limited Phyllosilicate et composition a base de resine thermoplastique contenant ce compose
WO2005095506A1 (fr) * 2004-03-29 2005-10-13 Bridgestone Corporation Nanocomposite et procede associe

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
CLAYS, CLAY, MINERALS, vol. 52, no. 2, 2004, pages 171 - 179
FACHLITERATUR, CHEM. MATER., vol. 14, 2002, pages 3776 - 3785

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103012176A (zh) * 2012-12-03 2013-04-03 清华大学 一种长链烷基四羧基阴离子表面活性剂的制备方法

Also Published As

Publication number Publication date
DE102010033029A1 (de) 2012-02-02

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