US20070222117A1 - Moulding Compound for Mouldings with High Weather Resistance - Google Patents

Moulding Compound for Mouldings with High Weather Resistance Download PDF

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Publication number
US20070222117A1
US20070222117A1 US11/579,329 US57932905A US2007222117A1 US 20070222117 A1 US20070222117 A1 US 20070222117A1 US 57932905 A US57932905 A US 57932905A US 2007222117 A1 US2007222117 A1 US 2007222117A1
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United States
Prior art keywords
weight
molding composition
copolymer
iso
parts
Prior art date
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Abandoned
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US11/579,329
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English (en)
Inventor
Werner Hoess
Michael Wicker
Klaus Schultes
Klaus Albrecht
Martin Mohrmann
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Roehm GmbH Darmstadt
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Roehm GmbH Darmstadt
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Assigned to ROEHM GMBH reassignment ROEHM GMBH ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: HOESS, WERNER, ALBRECHT, KLAUS, MOHRMANN, MARTIN, SCHULTES, KLAUS, WICKER, MICHAEL
Publication of US20070222117A1 publication Critical patent/US20070222117A1/en
Assigned to EVONIK ROHM GMBH reassignment EVONIK ROHM GMBH CHANGE OF NAME (SEE DOCUMENT FOR DETAILS). Assignors: ROHM GMBH
Abandoned legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/04—Homopolymers or copolymers of esters
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/04—Homopolymers or copolymers of esters
    • C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
    • C08L33/10—Homopolymers or copolymers of methacrylic acid esters
    • C08L33/12—Homopolymers or copolymers of methyl methacrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2205/00—Polymer mixtures characterised by other features
    • C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
    • 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
    • Y10T428/24—Structurally defined web or sheet [e.g., overall dimension, etc.]
    • Y10T428/24273—Structurally defined web or sheet [e.g., overall dimension, etc.] including aperture
    • 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
    • Y10T428/24—Structurally defined web or sheet [e.g., overall dimension, etc.]
    • Y10T428/24273—Structurally defined web or sheet [e.g., overall dimension, etc.] including aperture
    • Y10T428/24322—Composite web or sheet
    • 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
    • Y10T428/24—Structurally defined web or sheet [e.g., overall dimension, etc.]
    • Y10T428/24628—Nonplanar uniform thickness material
    • Y10T428/24669—Aligned or parallel nonplanarities
    • Y10T428/24694—Parallel corrugations
    • 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
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31855—Of addition polymer from unsaturated monomers
    • Y10T428/31909—Next to second addition polymer from unsaturated monomers

Definitions

  • the invention relates to a molding composition for molded parts with high weathering resistance.
  • EP 0 113 105 A1 describes heat-resistant methacrylate plastic mixtures composed of two copolymers.
  • Copolymer I is obtained via polymerization of methyl methacrylate, of an aromatic vinyl component, and of maleic anhydride
  • copolymer II is a polymer composed of from 80 to 100% by weight of methyl methacrylate and of from 0 to 20% by weight of other copolymerizable ethylenic monomers.
  • the copolymer I can be composed of from 50 to 98% by weight of methyl methacrylate, from 1 to 25% by weight of styrene, and from 1 to 25% by weight of maleic anhydride.
  • the preparation process is described as non-critical.
  • a specific proposal converts the monomers mentioned via partial polymerization to give a prepolymer in the presence of 2,2′-azobis(2,4-dimethylvaleronitrile) as initiator and of tert-dodecyl mercaptan as molecular-weight regulator.
  • the prepolymer is then polymerized first for 30 minutes at 80° C. and then again for 2 hours at 130° C.
  • the intention was to provide a molding composition whose weathering resistance has been further improved and whose MVR flowability (230° C./3.8 kg) in particular in the region advantageous for injection molding is from 2.5 to 5.0 cm 3 /10 min.
  • the intention is that the surface of specimens subjected to long-term weathering exhibit only very slight or no cracking.
  • the intention was that, when comparison is made with EP 0 113 105 A1, there is to be no or only very slight impairment of the Vicat softening temperature VST (ISO 306-B50), and that this is to achieve a value of 109° C.
  • the object is achieved via a molding composition, encompassing the following components
  • the inventive molding composition encompasses or is composed of the following components
  • the advantageous properties of the inventive molding composition are substantially based on the mixture of copolymer (I) with the (co)polymer (II).
  • a decisive factor for the properties improved in comparison with EP 0 113 105 A1 is the low molecular weight of the copolymer (I), characterized via a solution viscosity in chloroform at 25° C. (ISO 1628-Part 6) of less than or equal to 55 ml/g.
  • the molding composition can in many instances comprise not only the copolymer (I) and the (co)polymer (II) but also conventional additives, auxiliaries, and/or fillers, examples being colorants, pigments, or organic dyes, in the case of colored injection-molded parts.
  • a test specimen produced, for example via injection molding, from the inventive molding composition can have the following properties simultaneously.
  • the molding composition is further characterized in that the increase in yellowness index (DIN 6167, D65/10° illuminant, 3 mm) of a test specimen produced from the molding composition is not more than 1.5 units, preferably not more than 1.0 unit, after Xenotest weathering (DIN EN ISO 4893, Part 2) for 10 000 hours.
  • the increase in yellowness index (DIN 6167, D65/10° illuminant, 3 mm) of a test specimen produced from the molding composition is not more than 1.5 units, preferably not more than 1.0 unit, after Xenotest weathering (DIN EN ISO 4893, Part 2) for 10 000 hours.
  • the molding composition is characterized in that a test specimen produced from the molding composition has no cracking visible to the naked eye after Xenotest weathering (DIN EN ISO 4893, Part 2) for 5000 hours, indeed even after 10 000 hours.
  • the molding composition is characterized in that when the Taber 203 scratch hardness of a test specimen produced from the molding composition is determined using an applied force of 3.0 N the value obtained is not more than 3 ⁇ m crack depth, in particular not more than 2.8 ⁇ m crack depth.
  • the (co)polymer (II) is composed of from 80 to 100% by weight, preferably from 90 to 100% by weight, in particular from 99 to 100% by weight, of methyl methacrylate, styrene, and maleic anhydride. If appropriate, from 0 to 20% by weight, preferably from 0 to 10% by weight, in particular from 0 to 1% by weight, of other comonomers capable of free-radical polymerization can also be present, examples being ⁇ -methylstyrene or C1-C4-alkyl (meth)acrylates, in particular methyl acrylate, ethyl acrylate, or butyl acrylate, in particular n-butyl acrylate.
  • the copolymer (I) is particularly preferably composed only of units capable of free-radical polymerization and composed of methyl methacrylate, styrene, and maleic anhydride.
  • the solution viscosity of the copolymer (I) in chloroform at 25° C. is less than or equal to 55 ml/g, preferably less than or equal to 50 ml/g, in particular from 40 to 55 ml/g, particularly preferably from 43 to 50 ml/g.
  • M w weight-average of 95 000 g/mol
  • M w determination by means of gel permeation chromatography based on polymethyl methacrylate as calibration standard M w determination by means of gel permeation chromatography based on polymethyl methacrylate as calibration standard.
  • M w molecular weight M w can be determined by gel permeation chromatography or by a light-scattering method (see, for example, H. F. Mark et al., Encyclopedia of Polymer Science and Engineering, 2nd Edition, Vol. 10, pages 1 ff., J. Wiley, 1989).
  • Corresponding copolymers can be obtained in a manner known per se via free-radical polymerization.
  • EP-A 264 590 describes by way of example a process for preparation of a molding composition composed of a monomer mixture composed of methyl methacrylate, of a vinylaromatic compound, and of maleic anhydride, and, if appropriate, of a lower alkyl acrylate, where the polymerization is carried out to 50% conversion in the presence or absence of a non-polymerizable organic solvent, and where, starting at conversion of at least 50%, the polymerization is continued in the temperature range from 75 to 150° C. in the presence of an organic solvent as far as at least 80% conversion, and then the low-molecular-weight volatile constituents are evaporated.
  • JP-A 60 147 417 describes a process for preparation of a highly heat-resistant polymethacrylate molding composition in which a monomer mixture composed of methyl methacrylate and of maleic anhydride, and of at least one vinylaromatic compound is fed to a polymerization reactor suitable for solution polymerization or bulk polymerization at a temperature from 100 to 180° C. and is polymerized.
  • DE-A 44 40 219 describes another preparation process.
  • the copolymer (I) can be prepared by taking a monomer mixture composed of, for example, 6355 g of methyl methacrylate, 1271 g of styrene, and 847 g of maleic anhydride, and admixing 1.9 g of tert-butyl perneodecanoate and 0.85 g of tert-butyl 3,5,5-trimethylperoxyhexanoate as polymerization initiator and 19.6 g of 2-mercaptoethanol as molecular weight regulator, and 4.3 g of palmitic acid.
  • the resultant mixture can be charged to a polymerization cell and, for example, devolatilized for 10 minutes.
  • the mixture can then be polymerized in a water bath, for example for 6 hours at 60° C., and then for 30 hours at 55° C. water bath temperature. After about 30 hours, the polymerization mixture reaches its maximum temperature: about 126° C. Once the polymerization cell has been removed from the water bath, the polymer corresponding to component a) is further heat-conditioned in the polymerization cell for about 7 hours, for example at 117° C., in an oven under air.
  • the copolymer (II) is a (meth)acrylate (co)polymer whose solution viscosity in chloroform at 25° C. (ISO 1628-Part 6) is from 50 to 55 ml/g, preferably from 52 to 54 ml/g.
  • molecular weight M w can be determined by gel permeation chromatography or by a light-scattering method (see, for example, H. F. Mark et al., Encyclopedia of Polymer Science and Engineering, 2nd Edition, Vol. 10, pages 1 ff., J. Wiley, 1989).
  • the (co)polymer (II) is a homopolymer or copolymer composed of at least 80% by weight of methyl methacrylate and, if appropriate, up to 20% by weight of other monomers copolymerizable with methyl methacrylate.
  • the (co)polymer (II) is composed of from 80 to 100% by weight, preferably from 90 to 99.5% by weight, of methyl methacrylate units polymerized by a free-radical route and, if appropriate, of from 0 to 20% by weight, preferably from 0.5 to 10% by weight, of other comonomers capable of free-radical polymerization, e.g.
  • C1-C4-alkyl (meth)acrylates in particular methyl acrylate, ethyl acrylate, or butyl acrylate, preferably n-butyl acrylate.
  • the average molar mass M w of the copolymer (II) is preferably in the range from 90 000 g/mol to 200 000 g/mol, in particular from 100 000 g/mol to 150 000 g/mol.
  • the (co)polymer II can have been polymerized from from 95 to 99.5% by weight of methyl methacrylate and from 0.5 to 5% by weight, preferably from 1 to 4% by weight, of methyl acrylate.
  • the Vicat softening temperature VST (ISO 306-B50) of the (co)polymer (II) can be at least 107° C., preferably from 108 to 114° C.
  • the melt index MVR (ISO 1133, 230° C./3.8 kg) can, for example, be in the range greater than or equal to 2.5 cm 3 /10 min.
  • the molding composition can also comprise, alongside the polymer mixture composed of the copolymer (I) and of the (co)polymer (II), in a manner known per se, conventional additives, auxilaries, and/or fillers, examples being heat stabilizers, UV stabilizers, UV absorbers, antioxidants, and/or colorants, pigments, or organic dyes. It is preferable that the amount of conventional additives, auxiliaries, and/or fillers present is not more than 10% by weight, particularly preferably not more than 5% by weight, in particular not more than 2% by weight.
  • the molding composition can, if appropriate, also comprise absolutely no additives, auxiliaries, and/or fillers.
  • lubricants or mold-release agents are particularly important, and can reduce the level of, or entirely prevent, possible adhesion of the polymer mixture to the injection mold.
  • many moldings in particular, particularly injection-molded parts are non-transparent but have a color, therefore comprising colorants, pigments, or organic dyes, as additives.
  • Parts for outdoor uses generally comprise UV stabilizers, UV absorbers, or antioxidants for additional protection from weathering.
  • Lubricants can therefore be used as auxiliaries, examples being those selected from the group of the saturated fatty acids whose number of carbon atoms is less than C 20 , preferably from C 16 to C 18 , or from the saturated fatty alcohols whose number of carbon atoms is less than C 20 , preferably from C 16 to C 18 .
  • Quantitative proportions present are preferably very small, at most 0.25% by weight, for example from 0.05 to 0.2% by weight, based on the polymer mixture.
  • suitable materials are stearic acid, palmitic acid, industrial mixtures composed of stearic and palmitic acid.
  • suitable materials are n-hexadecanol, n-octadecanol, and industrial mixtures composed of n-hexadecanol and n-octadecanol.
  • Stearyl alcohol is a particularly preferred lubricant or mold-release agent.
  • the molding composition or polymer mixture can be prepared via dry blending of components a) and b), which may take the form of powder, beads, or preferably pellets.
  • copolymers (I) and the (co)polymer (II) are present 5 in a ratio of copolymers (I) to (co)polymer (II) which is from 95 to 5 to 5 to 95, preferably from 20 to 80 to 80 to 20, in particular from 20 to 60 to 80 to 40, in each case based on parts by weight.
  • the polymer mixture can also be processed via melting and mixing of the individual components in the melt, or via melting of dry premixes of the individual components, to give a ready-to-use molding composition. This can take place by way of example in single- or twin-screw extruders. The resultant extrudate can then be pelletized. Conventional additives, auxiliaries, and/or fillers c) can be directly admixed or can be added as required subsequently by the further processor.
  • the inventive molding composition can be used in a manner known per se to produce molded parts, entirely or to some extent via thermoplastic processing, in particular injection molding or extrusion, or via coextrusion or lamination, or else via lacquering.
  • a feature of the inventive moldings, due to the inventive molding composition present, is high weathering resistance, very little tendency toward yellowing, and very little tendency toward cracking.
  • the surface is also highly scratch-resistant.
  • the moldings are composed entirely or to some extent of the inventive molding composition, which is preferably composed to an extent of from 90 to 100% by weight of the copolymer (I) and of the (co)polymer (II), and, if appropriate, to an extent of from 0 to 10% by weight of conventional additives, auxiliaries, and/or fillers.
  • extruded moldings can be solid sheets, corrugated sheets, panels having cavities, in particular multiple-web sandwich panels, twin-web sandwich panels, triple-web sandwich panels, or quadruple-web sandwich panels, or sandwich panels with lattice geometry, or other sandwich panels.
  • Injection molded parts can by way of example be parts of household devices, of communications devices, of equipment for hobbies or for sports, or are bodywork parts, or are parts of bodywork parts in automobile construction, in shipbuilding, or in aircraft construction, examples being lamp covers, instrument covers, tachometer covers, displays, panels, or decorative strips.
  • Parts of moldings e.g. bodywork parts in automobile construction, in shipbuilding, or in aircraft construction, can be parts with a layer structure, where the inventive molding composition is used by way of example as external clear-lacquer layer and/or as internal layer provided with a colorant.
  • Typical examples of bodywork parts or parts of bodywork parts of automobiles are lamp covers, instrument covers, tachometer covers, panels, decorative strips, spoilers, roof modules, or exterior-mirror housings.
  • the inventive molding composition can be particularly advantageously used for the coating of surfaces or for the impregnation of wood, because it has high weathering resistance.
  • a possible method of application introduces the molding composition into an organic solvent or a solvent mixture and then processes it as a lacquer.
  • wood can be coated by the injection-molding process, by injecting a melt of the inventive molding composition over an article composed of wood, e.g. a control knob or a panel, in an injection mold.
  • the copolymer (I) is a copolymer composed of 75% by weight of methyl methacrylate, 15% by weight of styrene, and 10% by weight of maleic anhydride.
  • the procedure takes a monomer mixture composed of 6355 g of methyl methacrylate, 1271 g of styrene, and 847 g of maleic anhydride, and admixes this with 1.9 g of tert-butyl perneodecanoate and 0.85 g of tert-butyl 3,5,5-trimethylperoxyhexanoate as polymerization initiator, and 19.6 g of 2-mercaptoethanol as molecular weight regulator, and with 4.3 g of palmitic acid.
  • the resultant mixture is charged to a polymerization cell and devolatilized for 10 minutes.
  • the mixture can then be polymerized in a water bath, for example for 6 hours at 60° C., and then for 30 hours at 55° C. water bath temperature. After about 30 hours, the polymerization mixture reaches its maximum temperature: 126° C.
  • the polymer is further heat-conditioned in the polymerization cell for 7 hours, at 117° C., in an oven under air.
  • the resultant copolymer (I) is clear and almost colorless, and its V.N. (solution viscosity number to ISO 1628-6, 25° C., chloroform) is 48.7 ml/g.
  • the (co)polymer (II) used comprised: a commercially available copolymer composed of 99% by weight of methyl methacrylate and 1% by weight of methyl acrylate whose solution viscosity in chloroform at 25° C. (ISO 1628-Part 6) was about 53 ml/g.
  • the material used for comparison comprised:
  • Molding compositions A to D were prepared via mixing of the copolymers I, II, and, respectively, III.
  • a homogeneous pellet mixture was prepared via mixing for 5 minutes on a tumbling mixer.
  • the mixture was placed in the hopper of a single-screw extruder with 35 mm screw diameter and extruded at 230° C. melt temperature.
  • Extrudates were drawn from the extruder die head and were chopped by means of a pelletizer to give pellets after cooling in a water bath and then in an air-cooling section. This procedure was used to prepare mixtures composed of copolymer I and copolymer II, and also mixtures composed of copolymer II and copolymer III.
  • the following table includes the constitutions of the products, the tests carried out, and also the test results obtained.
  • the Xenotest to DIN EN ISO 4892, Part 2 (artificial weathering or irradiation in devices—filtered xenon arc irradiation) was carried out with a Beta LM Xenotest device.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Injection Moulding Of Plastics Or The Like (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Laminated Bodies (AREA)
  • Moulds For Moulding Plastics Or The Like (AREA)
US11/579,329 2004-05-05 2005-04-07 Moulding Compound for Mouldings with High Weather Resistance Abandoned US20070222117A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE102004022540.0 2004-05-05
DE200410022540 DE102004022540A1 (de) 2004-05-05 2004-05-05 Formmasse für Formkörper mit hoher Witterungsbeständigkeit
PCT/EP2005/003652 WO2005108486A1 (de) 2004-05-05 2005-04-07 Formmasse für formkörper mit hoher witterungsbeständigkeit

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2005/003652 A-371-Of-International WO2005108486A1 (de) 2004-05-05 2005-04-07 Formmasse für formkörper mit hoher witterungsbeständigkeit

Related Child Applications (1)

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US13/241,776 Continuation US8975337B2 (en) 2004-05-05 2011-09-23 Moulding compound for mouldings with high weather resistance

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Publication Number Publication Date
US20070222117A1 true US20070222117A1 (en) 2007-09-27

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US11/579,329 Abandoned US20070222117A1 (en) 2004-05-05 2005-04-07 Moulding Compound for Mouldings with High Weather Resistance
US13/241,776 Active US8975337B2 (en) 2004-05-05 2011-09-23 Moulding compound for mouldings with high weather resistance

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Application Number Title Priority Date Filing Date
US13/241,776 Active US8975337B2 (en) 2004-05-05 2011-09-23 Moulding compound for mouldings with high weather resistance

Country Status (14)

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US (2) US20070222117A1 (ko)
EP (1) EP1742997B1 (ko)
JP (1) JP4646254B2 (ko)
KR (1) KR101162388B1 (ko)
CN (1) CN1946797B (ko)
AT (1) ATE425219T1 (ko)
BR (1) BRPI0509589B1 (ko)
CA (1) CA2565476C (ko)
DE (2) DE102004022540A1 (ko)
HK (1) HK1099783A1 (ko)
MX (1) MXPA06012590A (ko)
PL (1) PL1742997T3 (ko)
SI (1) SI1742997T1 (ko)
WO (1) WO2005108486A1 (ko)

Cited By (40)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20030068369A1 (en) * 2001-01-30 2003-04-10 Mcallister Stephen Mark Pharmaceutical formulation
US20040104501A1 (en) * 2001-06-05 2004-06-03 Hans-Ulrich Petereit Method for injection moulding moulded bodies consisting of (meth) acrylate copolymers
US20040116567A1 (en) * 2001-02-07 2004-06-17 Gunter Schmitt Hot sealing compound for aluminum foils applied to polypropylene and polystyrene
US20050267250A1 (en) * 2002-09-16 2005-12-01 Roehn Gbmh & Co. Kg Articles made of pmma molding compound
US20060052515A1 (en) * 2002-12-19 2006-03-09 Roehm Gmbh & Co. Kg Process for producing aqueou dispersions
US20070122624A1 (en) * 2003-11-03 2007-05-31 Roehm Gmbh & Co. Kg Multilayered film made of (meth)acrylate copolymer and polycarbonate
US20070123610A1 (en) * 2000-09-04 2007-05-31 Roehm Gmbh & Co. Kg Pmma moulding compounds with improved impact resistance
US20070197703A1 (en) * 2005-01-14 2007-08-23 Roehm Gmbh Weather-Resistant Film For The Yellow Coloration Of Retro-Reflective Moulded Bodies
US20070276093A1 (en) * 2004-09-16 2007-11-29 Roehm Gmbh Use of Polyalkyl(Meth)Acrylate Bead Polymers and Moulding Material for Producing Extruded Moulded Parts With a Matt Surface
US20080035703A1 (en) * 2006-08-09 2008-02-14 Daewoong Suh Oxidation resistant solder preform
US20080132627A1 (en) * 2005-01-24 2008-06-05 Roehm Gmbh Impact-Resistant Poly(Meth)Acrylate Moulding Masses With High Thermal Stability
US20080161469A1 (en) * 2005-04-18 2008-07-03 Roehm Gmbh Thermoplastic Molding Material and Molding Elements Containing Nanometric Inorganic Particles for Making Said Molding Material and Said Molding Elements, and Uses Thereof
US20080188616A1 (en) * 2005-05-04 2008-08-07 Evonik Roehm Gmbh Method For Production of Bead Polymers With an Average Particle Size in the Range of 1 Micrometer to 40 Micrometers and Moulded Masses and Moulded Bodies Comprising Bead Polymers
US20080248298A1 (en) * 2003-09-26 2008-10-09 Roehm Gmbh & Co. Kg Method For Surface Hardening Substances By Application of Particularly Transparent Polymethacrylate Layers
US20080305335A1 (en) * 2002-02-06 2008-12-11 Roehm Gmbh & Co. Kg Core-shell structured silicone rubber graft polymers, impact-resistant modified molding compounds and molded bodies and method for producing the same
US20090226730A1 (en) * 2006-06-26 2009-09-10 Evonik Roehm Gmbh Transparent plastic composite
US7683131B2 (en) 2003-11-20 2010-03-23 Röhm GmbH & Co. KG Molding material containing a matting agent
US7695813B2 (en) 2002-12-19 2010-04-13 Roehm Gmbh & Co. Kg Core and shell particle for modifying impact resistance of a mouldable poly (meth) acrylate material
US20100098907A1 (en) * 2007-01-30 2010-04-22 Evonik Roehm Gmbh Molding compound for matt molded polyacrylate bodies
US20100098908A1 (en) * 2007-01-30 2010-04-22 Evonik Roehm Gmbh Moulding compositions for matt pmmi mouldings
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BRPI0509589B1 (pt) 2015-12-08
HK1099783A1 (en) 2007-08-24
KR101162388B1 (ko) 2012-07-04
ATE425219T1 (de) 2009-03-15
CN1946797B (zh) 2010-06-09
US20120015141A1 (en) 2012-01-19
US8975337B2 (en) 2015-03-10
DE102004022540A1 (de) 2005-12-08
JP4646254B2 (ja) 2011-03-09
EP1742997A1 (de) 2007-01-17
BRPI0509589A (pt) 2007-09-25
CA2565476A1 (en) 2005-11-17
CA2565476C (en) 2012-10-16
MXPA06012590A (es) 2006-12-15
EP1742997B1 (de) 2009-03-11
JP2007536417A (ja) 2007-12-13
SI1742997T1 (sl) 2009-08-31
KR20070034466A (ko) 2007-03-28
DE502005006814D1 (de) 2009-04-23
WO2005108486A1 (de) 2005-11-17
CN1946797A (zh) 2007-04-11

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