WO2005095421A1 - Strukturoptimierte haftvermittler für polymerwerkstoffe, verwendung davon und daraus hergestellter verbundwerkstoff - Google Patents
Strukturoptimierte haftvermittler für polymerwerkstoffe, verwendung davon und daraus hergestellter verbundwerkstoff Download PDFInfo
- Publication number
- WO2005095421A1 WO2005095421A1 PCT/EP2005/051348 EP2005051348W WO2005095421A1 WO 2005095421 A1 WO2005095421 A1 WO 2005095421A1 EP 2005051348 W EP2005051348 W EP 2005051348W WO 2005095421 A1 WO2005095421 A1 WO 2005095421A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- composite material
- filler
- epoxy
- adhesion promoter
- adhesion promoters
- Prior art date
Links
- 239000002318 adhesion promoter Substances 0.000 title claims abstract description 23
- 239000002131 composite material Substances 0.000 title claims abstract description 16
- 239000002861 polymer material Substances 0.000 title description 2
- 239000000945 filler Substances 0.000 claims abstract description 23
- 150000001875 compounds Chemical class 0.000 claims abstract description 12
- 239000004593 Epoxy Substances 0.000 claims description 7
- 229920000642 polymer Polymers 0.000 claims description 7
- 239000011159 matrix material Substances 0.000 claims description 6
- GWGHARNRKUWIEF-UHFFFAOYSA-N triethyl oxiran-2-ylmethyl silicate Chemical compound CCO[Si](OCC)(OCC)OCC1CO1 GWGHARNRKUWIEF-UHFFFAOYSA-N 0.000 claims description 6
- 239000003822 epoxy resin Substances 0.000 claims description 5
- 229920000647 polyepoxide Polymers 0.000 claims description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000000919 ceramic Substances 0.000 claims description 4
- 239000000835 fiber Substances 0.000 claims description 4
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 4
- 239000000843 powder Substances 0.000 claims description 4
- 239000010453 quartz Substances 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- -1 alkyl radical Chemical class 0.000 claims description 3
- 150000001412 amines Chemical group 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- 229910052582 BN Inorganic materials 0.000 claims description 2
- PZNSFCLAULLKQX-UHFFFAOYSA-N Boron nitride Chemical compound N#B PZNSFCLAULLKQX-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 150000005840 aryl radicals Chemical class 0.000 claims description 2
- 239000011248 coating agent Substances 0.000 claims description 2
- 238000000576 coating method Methods 0.000 claims description 2
- PMHQVHHXPFUNSP-UHFFFAOYSA-M copper(1+);methylsulfanylmethane;bromide Chemical compound Br[Cu].CSC PMHQVHHXPFUNSP-UHFFFAOYSA-M 0.000 claims description 2
- WMWXXXSCZVGQAR-UHFFFAOYSA-N dialuminum;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3] WMWXXXSCZVGQAR-UHFFFAOYSA-N 0.000 claims description 2
- 239000010459 dolomite Substances 0.000 claims description 2
- 229910000514 dolomite Inorganic materials 0.000 claims description 2
- 239000004744 fabric Substances 0.000 claims description 2
- 229910044991 metal oxide Inorganic materials 0.000 claims description 2
- 150000004706 metal oxides Chemical class 0.000 claims description 2
- 239000010445 mica Substances 0.000 claims description 2
- 229910052618 mica group Inorganic materials 0.000 claims description 2
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 claims description 2
- 229910010271 silicon carbide Inorganic materials 0.000 claims description 2
- 239000006004 Quartz sand Substances 0.000 claims 1
- 239000010454 slate Substances 0.000 claims 1
- 238000004132 cross linking Methods 0.000 abstract 1
- 239000007822 coupling agent Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 229910000077 silane Inorganic materials 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- 230000017525 heat dissipation Effects 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 239000012454 non-polar solvent Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000005046 Chlorosilane Substances 0.000 description 1
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- JEZFASCUIZYYEV-UHFFFAOYSA-N chloro(triethoxy)silane Chemical compound CCO[Si](Cl)(OCC)OCC JEZFASCUIZYYEV-UHFFFAOYSA-N 0.000 description 1
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical compound Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 239000012764 mineral filler Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012778 molding material Substances 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/025—Silicon compounds without C-silicon linkages
-
- 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
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/20—Oxides; Hydroxides
- C08K3/22—Oxides; Hydroxides of metals
-
- 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
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
- C08K5/541—Silicon-containing compounds containing oxygen
- C08K5/5435—Silicon-containing compounds containing oxygen containing oxygen in a ring
-
- 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
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
- C08K5/544—Silicon-containing compounds containing nitrogen
-
- 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
- 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
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/20—Oxides; Hydroxides
- C08K3/22—Oxides; Hydroxides of metals
- C08K2003/2227—Oxides; Hydroxides of metals of aluminium
Definitions
- the invention relates to a new chemical compound that can be used as an adhesion promoter, for example in the wetting of fillers in composite materials.
- composite materials with a very high degree of filling of heat-conductive materials are developed, which form a heat-conducting bridge between the element to be cooled and the cooling.
- Coupling agents are usually chemical compounds based on organosilicon with two different reactive groups, which adhere and / or react both to the interface of the solid surface of the filler and to the polymer matrix.
- silanes of the general formula (RO) 3 -Si-R are used as adhesion promoters.
- R is usually an alkyl radical (methyl, ethyl, propyl), R represents an alkylamine, vinyl, acrylic or alkyl epoxy radical. These compounds are usually used to coat the surfaces of various mineral fillers to improve adhesion.
- a disadvantage of the known adhesion promoters is that they reduce the strength values of the composite materials.
- the bending strength and the impact strength of the composite materials, which are also filled with adhesion promoters, are poor.
- the invention relates to a compound of the following general structure
- R can be identical or unequal to R, R 'and R' 'and can be a branched or unbranched alkoxy or alkyl radical having 1 to 10 carbon atoms, R' identical or unequal to R and R '' and an alkyl or aryl radical with 1 to 10 carbon atoms and
- R '' may be the same or different than R and R 'and an epoxy, prim. Sec tert Amine residue can represent.
- the invention also relates to a composite material comprising at least one polymer matrix and a filler, at least part of the filler being partially or completely wetted with a compound as described above as an adhesion promoter.
- the invention relates to the use of the glycidoxytrialkoxysilane as an adhesion promoter in the coating of ceramic fillers.
- adhesion promoter presented here has a new structural element.
- An oxygen atom has been introduced in the field of silicon-carbon bonding, which contributes to increased flexibility and resistance of the connection to stress.
- This compound is easily accessible synthetically and has proven to be just as stable to hydrolysis as the epoxysilane adhesion promoters already used in technology.
- the preparation is carried out very simply by mixing the components in a non-polar solvent and cooling, according to the scheme: The chlorosilane Si (R 3 ) Cl is added dropwise to a solution of the epoxide in a non-polar solvent.
- Ceramic fillers that can be used are coarse to fine-grained, splintered, spherical, platelet-shaped and / or short-fiber inorganic fillers for use in epoxy resin systems.
- quartz powder, quartz material, aluminum oxide, aluminum oxide hydrate, aluminum nitride, boron nitride, silicon carbide, mica, dolomite, shale powder or other metal oxides, or mixtures thereof, could be mentioned in detail in this context.
- Fillers and / or fibers can only achieve their full effectiveness if they are firmly attached to the plastic matrix.
- the filler can be in fiber form and / or in fabric form.
- the filler can be completely or partially coated with the coupling agent.
- the use concentration and the mode of application of the adhesion promoter must be determined specifically for each surface system.
- the individual filler is either precoated with the adhesion promoter and then processed further to form a test specimen or the silane becomes added to the polymer-filler mixture in situ.
- a glycidoxytriethoxysilane of the following structure is formed:
- a resin system which contains epoxy and / or isocyanate groups is preferably used as the epoxy resin system.
- the concentration of the individual adhesion promoters was varied between 0.2-2.0% by mass based on the thermoanalytical measurement data. Between 0.3-1.2 mass% are also particularly preferred.
- Polymer system epoxy / anhydride system with amine derivative as accelerator.
- the filler content was 65% by volume, which corresponds to 86% by weight of aluminum oxide.
- the curing was carried out according to the following temperature profile: 12h 80 ° C, 4h 90 ° C, 3h 100 ° C, 12h 140 ° C.
- the average Tg was between 94-102 ° C.
- the expansion coefficient was 14 ppm / ° K (at 20-50 ° C) and
- the thermal conductivity was 3 W / mK.
- the average molding material density was 3 g / cm 3 .
- the fillers are coated with the new coupling agent using the usual methods.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Description
Claims
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102004016336.7 | 2004-04-02 | ||
DE102004016336 | 2004-04-02 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2005095421A1 true WO2005095421A1 (de) | 2005-10-13 |
Family
ID=34963271
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2005/051348 WO2005095421A1 (de) | 2004-04-02 | 2005-03-23 | Strukturoptimierte haftvermittler für polymerwerkstoffe, verwendung davon und daraus hergestellter verbundwerkstoff |
Country Status (1)
Country | Link |
---|---|
WO (1) | WO2005095421A1 (de) |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2651479A1 (de) * | 1976-11-11 | 1978-05-18 | Schering Ag | Elastisches klebemittel |
US20020010302A1 (en) * | 2000-07-21 | 2002-01-24 | Toagosei Co., Ltd | Moisture-curing reactive hot-melt adhesive for weather strip flocking, flocked weather strip, and process for producing flcoked weather strip |
EP1394817A1 (de) * | 2000-11-21 | 2004-03-03 | Nissan Chemical Industries Ltd. | Elektrisch leitfähige Oxid Partikel und Verfahren zu ihrer Herstellung |
-
2005
- 2005-03-23 WO PCT/EP2005/051348 patent/WO2005095421A1/de active Application Filing
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2651479A1 (de) * | 1976-11-11 | 1978-05-18 | Schering Ag | Elastisches klebemittel |
US20020010302A1 (en) * | 2000-07-21 | 2002-01-24 | Toagosei Co., Ltd | Moisture-curing reactive hot-melt adhesive for weather strip flocking, flocked weather strip, and process for producing flcoked weather strip |
EP1394817A1 (de) * | 2000-11-21 | 2004-03-03 | Nissan Chemical Industries Ltd. | Elektrisch leitfähige Oxid Partikel und Verfahren zu ihrer Herstellung |
Non-Patent Citations (33)
Title |
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ABE T. ET AL., J. FLUORINE CHEM., vol. 97, no. 1-2, 1999, pages 229 - 238 * |
DATABASE BEILSTEIN [online] BEILSTEIN INSTITUTE FOR ORGANIC CHEMISTRY, FRANKFURT-MAIN, DE; 20 July 1992 (1992-07-20), XP002331710, retrieved from XFIRE Database accession no. BRN 4306426 * |
DATABASE BEILSTEIN [online] BEILSTEIN INSTITUTE FOR ORGANIC CHEMISTRY, FRANKFURT-MAIN, DE; 24 January 1994 (1994-01-24), XP002331708, retrieved from XFIRE Database accession no. BRN 6379128 * |
DATABASE BEILSTEIN [online] BEILSTEIN INSTITUTE FOR ORGANIC CHEMISTRY, FRANKFURT-MAIN, DE; 25 July 2001 (2001-07-25), XP002331709, retrieved from XFIRE Database accession no. BRN 8765029, BRN 8768452 * |
DATABASE BEILSTEIN [online] BEILSTEIN INSTITUTE FOR ORGANIC CHEMISTRY, FRANKFURT-MAIN, DE; 7 March 2000 (2000-03-07), XP002331711, retrieved from XFIRE Database accession no. BRN8309091 * |
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; ANOSOV, V. P.: "Vibrational spectra of compounds containing silicon and nitrogen", XP002331719, retrieved from STN Database accession no. 1979:143700 * |
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; HAUBOLD, WOLFGANG ET AL: "Diborane(4) molecules with boron atoms with different coordination numbers", XP002331717, retrieved from STN Database accession no. 1984:603250 * |
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; KHLEBNIKOVA, T. D. ET AL: "1-triethylsiloxy-2-(N,N-dialkylamino)alkanes as novel potential corrosion inhibitors of hydrosulfide corrosion of petroleum industry equipment", XP002331712, retrieved from STN Database accession no. 2001:7840 * |
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DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; KREBS, ROLAND ET AL: "Pentacoordinate silicon: intramolecular coordination of O-fluorosilyl derivatives of N,N-disubstituted aminoethanols and of N-fluorosilyl substituted derivatives of trimethylethylenediamine", XP002331714, retrieved from STN Database accession no. 1985:523568 * |
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