CA2324353A1 - Polymer composite comprising a hydroxy-functionalized polyether or polyester and an inorganic filler and method for preparing the same - Google Patents

Polymer composite comprising a hydroxy-functionalized polyether or polyester and an inorganic filler and method for preparing the same Download PDF

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Publication number
CA2324353A1
CA2324353A1 CA002324353A CA2324353A CA2324353A1 CA 2324353 A1 CA2324353 A1 CA 2324353A1 CA 002324353 A CA002324353 A CA 002324353A CA 2324353 A CA2324353 A CA 2324353A CA 2324353 A1 CA2324353 A1 CA 2324353A1
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Canada
Prior art keywords
polymer composite
hydroxy
inorganic filler
functionalized polyether
composite
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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.)
Granted
Application number
CA002324353A
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French (fr)
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CA2324353C (en
Inventor
C. Alice Cheung
Christine A. Polansky
Jerry E. White
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Dow Global Technologies LLC
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Individual
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Publication of CA2324353A1 publication Critical patent/CA2324353A1/en
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Publication of CA2324353C publication Critical patent/CA2324353C/en
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Expired - Fee Related legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
    • 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
    • C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
    • C09D167/02—Polyesters derived from dicarboxylic acids and dihydroxy 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
    • C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
    • 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
    • C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
    • C08K3/013—Fillers, pigments or reinforcing additives
    • 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
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/28—Nitrogen-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
    • C08K3/34—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
    • C08K3/38—Boron-containing compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
    • C08L67/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J167/00—Adhesives based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Adhesives based on derivatives of such polymers
    • C09J167/02—Polyesters derived from dicarboxylic acids and dihydroxy 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
    • C08K3/24—Acids; Salts thereof
    • C08K3/26—Carbonates; Bicarbonates
    • C08K2003/262—Alkali metal carbonates
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
    • C08L2666/54—Inorganic substances

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Polyesters Or Polycarbonates (AREA)

Abstract

A polymer composite comprising a hydroxy-phenoxyether or hydroxy-phenoxy ester polymer matrix and an inorganic filler is prepared by melt-blending the polymer and the inorganic filler. The filler may be an inorganic metal oxide, metal hydroxide, metal carbonate, metal nitride, metal carbide or metal boride. Methods of polymer composite preparation involving in situ type polymerization may also be used.
The polymer composites have increased barrier capabilities compared to the unmodified polymers.

Claims (31)

1. A polymer composite comprising a hydroxy-functionalized polyether or polyester and an inorganic filler.
2. The polymer of Claim 1 wherein the inorganic filler is an inorganic oxide, hydroxide, carbonate, nitride, carbide, boride or mixture thereof.
3. The polymer composite of Claim 1 wherein the hydroxy-functionalized polyether or polyester is formed by the reaction of a dinucleophile and a monomer containing at least one epoxy moiety.
4. The polymer composite of Claim 1 wherein the hydroxy-functionalized polyether or polyester has repeating units represented by the formula:
wherein m is an integer from 5 to 1000, R1 is a divalent organic moiety which is primarily hydrocarbon; R3 is:
R4 is wherein R2 and R6 are independently divalent organic moieties which are primarily hydrocarbon; R5 is hydrogen or alkyl, m is an integer from 5 to 1000 and n is an integer from 0 to 100.
5. The polymer composite of Claim 4 wherein the hydroxy-functionalized polyether is formed by the reaction of a diglycidyl ether with a dicarboxylic acid.
6. The polymer composite of Claim 4 wherein the hydroxy-functionalized polyether is formed by the reaction of a diglycidyl ester with a bisphenol.
7. The polymer composite of Claim 4 wherein the hydroxy-functionalized polyester is formed by the reaction of a diglycidyl ester or an epihalohydrin with a dicarboxylic acid.
8. The polymer composite of Claim 1 wherein the hydroxy-functionalized polyether is represented by the formula:
wherein A is an amine moiety or a combination of different amine moieties; B
is a divalent organic moiety which is predominantly hydrocarbylene; R is alkyl or hydrogen;
and m is an integer from 5 to 1000.
9. The polymer composite of Claim 8 wherein A is 2-hydroxyethylimino-, 2-hydroxypropylimino-, piperazenyl, N,N'-bis(2-hydroxyethyl)-1,2-ethyienedimino-, and B is isopropylidenediphenylene, 1,3-phenylene, or 1,4-phenylene, and R5 is hydrogen.
10. The polymer composite of Claim 8 wherein the hydroxy-functionalized polyether is formed by the reaction of a diglycidyl ether or an epihalohydrin with a difunctional amine.
11. The polymer composite of Claim 1 wherein the hydroxy-functionalized polyether is represented by the formula:
wherein B is a divalent organic moiety which is primarily hydrocarbon, and R5 is alkyl or hydrogen, and m is an integer from 5 to 1000.
12. The polymer composite of Claim 11 wherein B is 1,3-phenylene, 1,4,-phenylene, sulfonyldiphenylene, oxydiphenylene, thiodiphenylene or isopropylidenediphenylene and R5 is hydrogen.
13. The polymer composite of Claim 11 wherein the hydroxy-functionalized polyether is formed by the reaction of an epihalohydrin or a diglycidyl ether with a bisphenol.
14. The polymer composite of Claim 1 wherein the hydroxy-functionalized polyether is represented by the formulae:
wherein R5 is hydrogen or alkyl, R7 and R9 are independently alkyl, substituted alkyl, aryl or substituted aryl, B and R8 are independently a divalent organic moiety that is substantially hydrocarbon, and m is an integer from 5 to 1000.
15. The polymer composite of Claim 14 wherein R5 is hydrogen, R7 and R9 are independently methyl, ethyl, propyl, butyl, 2-hydroxyethyl or phenyl and B
and R8 are independently 1,3-phenylene, 1,4,-phenylene, sulfonyldiphenylene, oxydiphenylene, thiodiphenylene or isopropylidenediphenylene.
16. The polymer composite of Claim 14 wherein the hydroxy-functionalized polyether is formed by the reaction of an unsubstituted monosulfonamide or an N,N'-disubstituted disulfonamide with a diglycidyl ether.
17. The polymer composite of Claim 1 wherein the inorganic filler is talc, mica, montmorillonite, hectorite, kaolinite, dickite, nacrite, halloysite, saponite, nontronite, beidellite, volhonskoite, sauconite, magadiite, medmontite, kenyaite, vermiculite, serpentine, chlorite, palygorskite, kulkeite, aliettite, sepiolite, alloohane, imogolite or a mixture thereof.
18. The polymer composite of Claim 17 wherein the inorganic filler is talc, mica, montmorillonite, hectorite or a mixture thereof.
19. The polymer composite of Claim 1 wherein the inorganic filler is a metal oxide, metal hydroxide, metal carbonate, mixed metal oxide, mixed metal hydroxide, mixed metal carbonate or a mixture thereof.
20. The polymer composite of Claim 1 wherein the inorganic filler is calcium oxide, magnesium oxide, zirconium oxide, titanium oxide, manganese oxide, iron oxide, aluminum oxide, calcium hydroxide, magnesium hydroxide, zirconium hydroxide, aluminum hydroxide, manganese hydroxide, iron hydroxide, calcium carbonate, magnesium carbonate, manganese carbonate, iron carbonate or zirconium carbonate.
21. The polymer composite of Claim 19 wherein the inorganic filler is calcium carbonate, calcium oxide, calcium hydroxide or a mixture thereof.
22. The polymer composite of Claim 1 wherein the inorganic filler is a metal nitride, metal carbide, or metal boride or a mixture thereof.
23. The polymer composite of Claim 1 wherein the inorganic filler is aluminum nitride, silicon nitride, iron nitride, silicon carbide, manganese carbide, iron carbide, iron boride, aluminum boride or manganese boride or a mixture thereof.
24. The polymer composite of Claim 21 wherein the aluminum nitride is silica-coated aluminum nitride.
25. The polymer composite of Claim 1 wherein the inorganic filler is at least 0.1 weight percent and not more than 90 weight percent of the final composite.
26. The polymer composite of Claim 1 formed by adding the inorganic filler to one or more of the monomers forming the hydroxy-functionalized polyether or polyester matrix and then polymerizing the monomers.
27. A method for forming the polymer composite of Claim 26 wherein the composite is made by reactive extrusion.
28. The composite of Claim 1 in the form of a coating, film, foam, laminate, fiber, hot-melt adhesive or molded article.
29. A method for forming a composite which comprises contacting a hydroxy-functionalized polyether or polyester, or a precursor to a hydroxy-functionalized polyether or polyester with an inorganic filler.
30. A method for forming a composite which comprises contacting a hydroxy-functionalized polyether or polyester, or a precursor to a hydroxy-functionalized polyether or polyester with an inorganic filler using compounding extrusion.
31. A fiber-reinforced composite comprising a resin matrix polymer reinforced with one or more reinforcing fiber or mat, wherein the resin matrix polymer is the composite of Claim 1.
CA002324353A 1998-03-20 1999-03-08 Polymer composite comprising a hydroxy-functionalized polyether or polyester and an inorganic filler and method for preparing the same Expired - Fee Related CA2324353C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US4530098A 1998-03-20 1998-03-20
US09/045,300 1998-03-20
PCT/US1999/005149 WO1999048962A1 (en) 1998-03-20 1999-03-08 Polymer composite comprising a hydroxy-functionalized polyether or polyester and an inorganic filler and method for preparing the same

Publications (2)

Publication Number Publication Date
CA2324353A1 true CA2324353A1 (en) 1999-09-30
CA2324353C CA2324353C (en) 2009-11-24

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CA002324353A Expired - Fee Related CA2324353C (en) 1998-03-20 1999-03-08 Polymer composite comprising a hydroxy-functionalized polyether or polyester and an inorganic filler and method for preparing the same

Country Status (13)

Country Link
EP (1) EP1070096B1 (en)
JP (1) JP2002507644A (en)
KR (1) KR20010042053A (en)
CN (1) CN1297465A (en)
AR (1) AR018788A1 (en)
AU (1) AU746116B2 (en)
BR (1) BR9909061A (en)
CA (1) CA2324353C (en)
DE (1) DE69932423T2 (en)
ES (1) ES2264256T3 (en)
PL (1) PL344139A1 (en)
WO (1) WO1999048962A1 (en)
ZA (1) ZA992222B (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2151830A1 (en) 2008-08-08 2010-02-10 pp-mid GmbH Polymer form body with conductive structures on the surface and method for its production
DE102008048459A1 (en) 2008-09-23 2010-03-25 Pp-Mid Gmbh Producing conductive structures on surface of polymer molded bodies, comprises providing polymer molded body from a polymer phase containing carbon nanotubes and thermally treating a surface of the polymer molded body
DE102008061051A1 (en) 2008-12-08 2010-06-10 Pp-Mid Gmbh Producing conductive structures on surface of polymer molded bodies, comprises providing polymer molded body from a polymer phase containing carbon nanotubes and thermally treating a surface of the polymer molded body
DE102009011538A1 (en) 2009-03-03 2010-09-09 Pp-Mid Gmbh Producing conductive structures on surface of polymer molded bodies, comprises providing polymer molded body from a polymer phase containing carbon nanotubes and thermally treating a surface of the polymer molded body

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CN100465216C (en) * 2005-12-30 2009-03-04 财团法人工业技术研究院 Nucleating agent of polytrimethylene terephthalate and injection moulding method
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JP5590481B2 (en) * 2008-01-17 2014-09-17 独立行政法人産業技術総合研究所 Composite polymer material and optical material including the same
CN101914293B (en) * 2010-08-17 2011-12-07 华中农业大学 Bamboo fiber-based full-biodegradable material and preparation method
CN101967275A (en) * 2010-10-25 2011-02-09 深圳市华力兴工程塑料有限公司 Nano magnesium carbonate modified fire protection engineering plastic and preparation method thereof
ITMI20110974A1 (en) 2011-05-30 2012-12-01 Pirelli HIGH-PERFORMANCE TIRE FOR VEHICLE WHEELS
ITMI20121623A1 (en) * 2012-09-28 2014-03-29 Pirelli TIRE FOR VEHICLE WHEELS
CN102924666A (en) * 2012-10-15 2013-02-13 深圳大学 Polymer/clay nano-composite material, preparation method thereof and nano-GFRP (Glass Fiber Reinforced Polymer) composite material
CN110484129B (en) 2019-07-02 2022-01-25 昆山联滔电子有限公司 Product with protective coating and preparation method thereof
CN111013976A (en) * 2019-12-10 2020-04-17 安徽省信誉机械有限责任公司 Treatment method for improving corrosion resistance and self-cleaning performance of stainless steel panel of rice noodle machine
CN114583254B (en) * 2022-03-04 2023-07-11 西安交通大学 Environment-adaptive solid composite electrolyte and preparation method and application thereof

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2151830A1 (en) 2008-08-08 2010-02-10 pp-mid GmbH Polymer form body with conductive structures on the surface and method for its production
DE102008048459A1 (en) 2008-09-23 2010-03-25 Pp-Mid Gmbh Producing conductive structures on surface of polymer molded bodies, comprises providing polymer molded body from a polymer phase containing carbon nanotubes and thermally treating a surface of the polymer molded body
DE102008061051A1 (en) 2008-12-08 2010-06-10 Pp-Mid Gmbh Producing conductive structures on surface of polymer molded bodies, comprises providing polymer molded body from a polymer phase containing carbon nanotubes and thermally treating a surface of the polymer molded body
DE102009011538A1 (en) 2009-03-03 2010-09-09 Pp-Mid Gmbh Producing conductive structures on surface of polymer molded bodies, comprises providing polymer molded body from a polymer phase containing carbon nanotubes and thermally treating a surface of the polymer molded body

Also Published As

Publication number Publication date
CA2324353C (en) 2009-11-24
KR20010042053A (en) 2001-05-25
DE69932423D1 (en) 2006-08-31
DE69932423T2 (en) 2007-02-01
BR9909061A (en) 2000-11-14
ZA992222B (en) 2000-10-10
ES2264256T3 (en) 2006-12-16
WO1999048962A1 (en) 1999-09-30
AU746116B2 (en) 2002-04-18
AR018788A1 (en) 2001-12-12
EP1070096B1 (en) 2006-07-19
AU2993799A (en) 1999-10-18
CN1297465A (en) 2001-05-30
JP2002507644A (en) 2002-03-12
PL344139A1 (en) 2001-10-08
EP1070096A1 (en) 2001-01-24

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