CA2205789A1 - Process for hydrophobicizing particles, and their use as fillers in polymer masterbatches - Google Patents

Process for hydrophobicizing particles, and their use as fillers in polymer masterbatches

Info

Publication number
CA2205789A1
CA2205789A1 CA002205789A CA2205789A CA2205789A1 CA 2205789 A1 CA2205789 A1 CA 2205789A1 CA 002205789 A CA002205789 A CA 002205789A CA 2205789 A CA2205789 A CA 2205789A CA 2205789 A1 CA2205789 A1 CA 2205789A1
Authority
CA
Canada
Prior art keywords
group
formula
particles
process according
alkyl
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.)
Abandoned
Application number
CA002205789A
Other languages
French (fr)
Inventor
Ahti August Koski
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.)
Bayer Inc
Original Assignee
Bayer Inc
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 Bayer Inc filed Critical Bayer Inc
Priority to CA002205789A priority Critical patent/CA2205789A1/en
Priority to KR19997010752A priority patent/KR20010012789A/en
Priority to CN98805249A priority patent/CN1257524A/en
Priority to JP54974398A priority patent/JP2001527599A/en
Priority to EP98922548A priority patent/EP0983317A1/en
Priority to AU75165/98A priority patent/AU7516598A/en
Priority to US09/082,378 priority patent/US6420456B1/en
Priority to PCT/CA1998/000499 priority patent/WO1998053004A1/en
Priority to CA002288607A priority patent/CA2288607A1/en
Priority to ZA984299A priority patent/ZA984299B/en
Priority to TW087107869A priority patent/TW472074B/en
Publication of CA2205789A1 publication Critical patent/CA2205789A1/en
Abandoned legal-status Critical Current

Links

Classifications

    • 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
    • C08K9/04—Ingredients treated with organic substances
    • C08K9/06—Ingredients treated with organic substances with silicon-containing 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
    • C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
    • C09C1/28—Compounds of silicon
    • C09C1/30—Silicic acid
    • C09C1/3081—Treatment with organo-silicon 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
    • C09C3/12—Treatment with organosilicon compounds
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2002/00—Crystal-structural characteristics
    • C01P2002/02—Amorphous compounds
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2002/00—Crystal-structural characteristics
    • C01P2002/80—Crystal-structural characteristics defined by measured data other than those specified in group C01P2002/70
    • C01P2002/88—Crystal-structural characteristics defined by measured data other than those specified in group C01P2002/70 by thermal analysis data, e.g. TGA, DTA, DSC
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2004/00—Particle morphology
    • C01P2004/50—Agglomerated particles
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2004/00—Particle morphology
    • C01P2004/60—Particles characterised by their size
    • C01P2004/61—Micrometer sized, i.e. from 1-100 micrometer
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2006/00—Physical properties of inorganic compounds
    • C01P2006/12—Surface area
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2006/00—Physical properties of inorganic compounds
    • C01P2006/22—Rheological behaviour as dispersion, e.g. viscosity, sedimentation stability
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2006/00—Physical properties of inorganic compounds
    • C01P2006/90—Other properties not specified above
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
    • Y10T428/2982—Particulate matter [e.g., sphere, flake, etc.]
    • Y10T428/2991—Coated
    • Y10T428/2993—Silicic or refractory material containing [e.g., tungsten oxide, glass, cement, etc.]
    • Y10T428/2995—Silane, siloxane or silicone coating

Abstract

Particles are hydrophobicized by treatment with a compound containing amino and silane groups, followed by treatment with a silane compound containing a hydrophobic group. The invention is particularly useful for treating hydrophilic mineral particles. The treated particles can be used, for example, as fillers in polymer masterbatches.

Claims (26)

1. A process for treating particles to render them hydrophobic, which process comprises (a) treating particles with a compound of formula I
or an acid addition or quaternary ammonium salt thereof, in which at least one of R1, R2 and R3, is a hydroxyl group or a hydrolysable group, R4 is a divalent group that is resistant to hydrolysis at the Si-R4 bond, R5 is hydrogen, a C1-30 alkyl or C2-30 mono-, di- or triunsaturated alkenyl group, or R5 is a group of formula in which x is an integer from 2 to 10, R13 and R14 are each hydrogen, C1-18 alkyl, C2-18 mono-, di- or triunsaturated alkenyl, phenyl, a group of formula wherein b is an integer from 1 to 10, or a group of formula wherein c is an integer from 1 to 10 and R22 and R23 which may be the same or different, are each hydrogen, C1-10 alkyl or C2-10 alkenyl, provided that there is no double bond in the position alpha to the nitrogen atom, or a group of formula -[(CH2)r NH]d-H
wherein r is an integer from 1 to 6 and d is an integer from 1 to 4;
R6 may be any of the groups defined for R5, or R5 and R6 may together form a divalent group of formula in which A is a -CHR or -NR group in which R is hydrogen or a C1-30 alkyl or C2-30 alkenyl group, or A is an oxygen or sulfur atom and t and v are each 1, 2, 3 or 4; provided that the sum of t and v does not exceed 6; and (b) thereafter adding to the treated particles a compound of the formula II

in which R15, R16 and R17 have the same definitions as R1, R2 and R3, defined above and R12 is a C8-30 alkyl group, a C8-30 mono-, di- or triunsaturated alkenyl group, either of which can be interrupted by one or more aryl groups, or a group of formula or an acid addition or quaternary ammonium salt thereof in which R18 is a divalent group resistant to hydrolysis at the Si-R18 bond, R19 is hydrogen, a C1-30 alkyl group, a C2-30 mono-, di- or triunsaturated alkenyl group, an aromatic group that is substituted by a C1-20 alkyl or C2-20 mono-, di- or triunsaturated alkenyl group, and R20 may be any of the groups defined for R19, with the provisos that R19 and R20 do not have a tertiary carbon atom adjacent to the nitrogen atom and that at least one of R19 and R20 has a carbon chain at least 8 carbon atoms in length uninterrupted by any heteroatom.
2. A process according to claim 1 wherein the treatment is carried out in an aqueous dispersion and a coupling agent is added to the aqueous dispersion after the addition of the compound of formula I but before the addition of the compound of formula II.
3. A process according to claim 1 or 2 wherein the particles are mineral particles that are hydrophilic and have surface hydroxyl groups.
4. A process according to claim 2 or 3 wherein the aqueous dispersion of particles is treated with the compound of formula I in the form of its acid addition salt or quaternary ammonium salt.
5. A process according to claim 2, 3 or 4 which includes the further step of admixing the hydrophobicized particles with a polymer material.
6. A process according to any one of claims 1 to 5 which includes the further step of admixing the hydrophobicized particles with a polymer solution and forming the mixture into a polymer masterbatch.
7. A process according to claim 6 wherein the polymer is one or more of IIR, HIIR, IR, EPDM, SBR, BR, NBR, HNBR, HSRE, natural rubber, polystyrene, polychloroprene, epichlorohydrin (ECO), chlorinated polyethylene, silicone, and ABS.
8. A process according to any one of claims 1 to 7 wherein the particles are silica particles.
9. A process according to any one of claims 1 to 8 wherein R1 is selected from the group consisting of hydroxyl groups, groups of formula OC p H2p+1' where p has a value from 1 to 10 and the alkyl chain may be interrupted by one or more oxygen atoms, phenoxy, acetoxy, chloro, bromo, iodo, ONa, OLi, OK, amino and mono- and dialkylamino, R2 is selected from the group consisting of hydroxyl groups, groups of formula OC p H2p+1 where p has a value from 1 to 10 and the alkyl chain may be interrupted by one or more oxygen atoms, phenoxy, acetoxy, ONa, OLi, OK, amino, mono- and dialkylamino, C1-10 alkyl, C2-10 mono- and di- unsaturated alkenyl, phenyl and groups of formula wherein R4, R5, R6 are as defined in claim 1.
10. A process according to any one of claims 1 to 9 wherein R15 is selected from the group consisting of hydroxyl groups, groups of formula OC p H2p+1' where p has a value from 1 to 10 and the alkyl chain may be interrupted by one or more oxygen atoms, phenoxy, acetoxy, chloro, bromo, iodo, ONa, OLi, OK, amino and mono- and dialkylamino, R16 is selected from the group consisting of hydroxyl groups, groups of formula OC p H2p+1 where p has a value from 1 to 10 and the alkyl chain may be interrupted by one or more oxygen atoms, phenoxy, acetoxy, ONa, OLi, OK, amino, mono- and dialkylamino, C1-10 alkyl, C2-10 mono- and di- unsaturated alkenyl, phenyl and groups of formula in which R18 is a divalent group resistant to hydrolysis.
11. A process according to any one of claims 2 to 10 wherein the coupling agent is selected from the group consisting of bis[3-(triethoxysilyl)propyl] tetrasulfane, bis[3-(triethoxysilyl)propyl] tetrasulfane, and bis[2-(trimethoxysilyl)ethyl] tetrasulfane.
12. A process according to any one of claims 1 to 11 wherein the compound of formula I is N-oleyl-N-(3-trimethoxy-silyl)propyl ammonium dichloride.
13. A process according to any one of claims 1 to 12 wherein the compound of formula II is N-oleyl-N-(3-trimethoxysilyl)propyl ammonium dichloride.
14. A polymer masterbatch which comprises a polymer and a particulate filler that has been hydrophobicized by a process according to any one of claims 1 to 13.
15. A rubber masterbatch which comprises an elastomer and a particulate filler that has been hydrophobicized by a process according to any one of claims 1 to 13.
16. A polymer or rubber masterbatch according to claim 14 or 15 wherein the filler particles are selected from the group consisting of silica, silicates, clay, titanium dioxide and alumina.
17. Particles that have been hydrophobicized by a process according to any one of claims 1 to 13.
18. Particles of claim 17 wherein the mineral particles are selected from the group consisting of silica, silicates, clay, titanium dioxide and alumina.
19. A rubber masterbatch comprising elastomer and filler particles that have been treated with a coupling agent, compound of formula I, and compound of formula II, wherein:
(a) the elastomer comprises one or more of IIR, HIIR, IR, EPDM, SBR, BR, NBR, HNBR, natural rubber, polystyrene, polychloroprene, epichlorohydrin (ECO), chlorinated polyethylene, silicone, ABS;
(b) the filler particles are selected from silica, silicates, clay, titanium dioxide, and alumina, and are present in an amount of from about 5 to 250 parts per hundred rubber;
(c) the coupling agent is present in an amount of between 0 and 20 % by weight filler particles (dry weight), and preferably between about 2 and about 10 % by weight of filler particles (dry weight);
(d) the compound of formula I, and is present in an amount of between 0.1 to 20 % by weight of filler particles (dry weight), preferably between about 0.25 and about 10 % by weight of filler particles (dry weight) and most preferably between about 0.5 and about 2 % by weight of filler particles (dry weight), wherein the compound of formula I is or an acid addition or quaternary ammonium salt thereof, in which at least one of R1, R2 and R3, is a hydroxyl or hydrolysable group, R4 is a divalent group that is resistant to hydrolysis at the Si-R4 bond, R5 is hydrogen, a C1-30 alkyl or C2-30 mono-, di- or triunsaturated alkenyl group, or R5 is a group of formula in which x is an integer from 2 to 10, R13 and R14 are each hydrogen, C1-18 alkyl, C2-18 mono-, di- or triunsaturated alkenyl, phenyl, a group of formula or a group of formula CH2CH2NH2, R6 may be any of the groups defined for R5, or R5 and R6 may together form a divalent group of formula in which A is a -CH2- group or an oxygen or sulfur atom and t and v are each 1, 2, 3 or 4; provided that the sum of t and v does not exceed 6, and (e) the compound of formula II, and is present in an amount of between about 0.5 and 20 % by weight of filler particle (dry weight), wherein the compound of formula II is:

in which R15, R16 and R17 have the same definitions as R1, R2 and R3, defined above, and R12 is C8-30 alkyl, C8-30 mono-, di- or triunsaturated alkenyl, or a group of formula or an acid addition or quaternary ammonium salt thereof in which R4 is a divalent group resistant to hydrolysis at the Si-R4 bond, R5 is hydrogen C1-30 alkyl, C2-30 mono-, di- or triunsaturated alkenyl, a group of formula -ArC w H2w+1 in which Ar represents a divalent aromatic group and w is an integer from 1 to 20, and R6 may be any of the groups defined for R5, with the proviso that at least one of R5 and R6 must have an uninterrupted carbon chain at least 8 carbon atoms in length.
20. A rubber masterbatch according to claim 19 wherein the filler particles are selected from the group consisting of silica, silicates, clay, titanium dioxide and alumina.
21. A rubber masterbatch according to claim 19 wherein the coupling agent is selected from the group consisting of bis[3-(trimethoxysilyl)propyl] tetrasulfane, bis-[3-(triethoxy-silyl)propyl] tetrasulfane, and bis[3-(trimethoxysilyl)ethyl]
tetrasulfane.
22. A rubber masterbatch according to claim 19 wherein the compound of formula I is N-oleyl-N-(3-trimethoxysilyl)-propyl ammonium dichloride.
23. A rubber masterbatch according to claim 19 wherein the compound of formula II is N-oleyl-N-(3-trimethoxysilyl)-propyl ammonium dichloride.
24. A polymer material admixed with filler particles selected from the group consisting of silica, silicates, clay, titanium dioxide and alumina, which filler particles have been hydrophobicized by a process according to any one of claims 1 to 13.
25. Use of a polymer masterbatch containing a filler that has been hydrophobicized by a process according to any one of claims 1 to 13 in a rubber vulcanizate, tire, tire tread hose or shoe sole.
26. Use of particles that have been hydrophobicized by a process according to any one of claims 1 to 13 as a filler in toners, alkyd paints or anti-foaming preparations.
CA002205789A 1997-05-22 1997-05-22 Process for hydrophobicizing particles, and their use as fillers in polymer masterbatches Abandoned CA2205789A1 (en)

Priority Applications (11)

Application Number Priority Date Filing Date Title
CA002205789A CA2205789A1 (en) 1997-05-22 1997-05-22 Process for hydrophobicizing particles, and their use as fillers in polymer masterbatches
KR19997010752A KR20010012789A (en) 1997-05-22 1998-05-21 Process for Hydrophobicizing Particles, and Their Use as Fillers in Polymer Masterbatches
CN98805249A CN1257524A (en) 1997-05-22 1998-05-21 Process for hydrophobicizing particles, and their use as fillers in polymer masterbatches
JP54974398A JP2001527599A (en) 1997-05-22 1998-05-21 Methods for rendering particles hydrophobic and their use as fillers in polymer masterbatches
EP98922548A EP0983317A1 (en) 1997-05-22 1998-05-21 Process for hydrophobicizing particles, and their use as fillers in polymer masterbatches
AU75165/98A AU7516598A (en) 1997-05-22 1998-05-21 Process for hydrophobicizing particles, and their use as fillers in polymer masterbatches
US09/082,378 US6420456B1 (en) 1997-05-22 1998-05-21 Process for hydrophobicizing particles, and their use as fillers in polymer masterbatches
PCT/CA1998/000499 WO1998053004A1 (en) 1997-05-22 1998-05-21 Process for hydrophobicizing particles, and their use as fillers in polymer masterbatches
CA002288607A CA2288607A1 (en) 1997-05-22 1998-05-21 Process for hydrophobicizing particles, and their use as fillers in polymer masterbatches
ZA984299A ZA984299B (en) 1997-05-22 1998-05-21 Process for hydrophobicizing particles and their use as fillers in polymer masterbatches
TW087107869A TW472074B (en) 1997-05-22 1998-05-21 Process for hydrophobicizing particles, and their use as fillers in polymer masterbatches

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CA002205789A CA2205789A1 (en) 1997-05-22 1997-05-22 Process for hydrophobicizing particles, and their use as fillers in polymer masterbatches
US09/082,378 US6420456B1 (en) 1997-05-22 1998-05-21 Process for hydrophobicizing particles, and their use as fillers in polymer masterbatches

Publications (1)

Publication Number Publication Date
CA2205789A1 true CA2205789A1 (en) 1998-11-22

Family

ID=25679354

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002205789A Abandoned CA2205789A1 (en) 1997-05-22 1997-05-22 Process for hydrophobicizing particles, and their use as fillers in polymer masterbatches

Country Status (8)

Country Link
US (1) US6420456B1 (en)
EP (1) EP0983317A1 (en)
JP (1) JP2001527599A (en)
CN (1) CN1257524A (en)
AU (1) AU7516598A (en)
CA (1) CA2205789A1 (en)
WO (1) WO1998053004A1 (en)
ZA (1) ZA984299B (en)

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