EP2486094A1 - Mélanges polymères de polystyrène avec des copolymères séquencés styrène-butadiène - Google Patents

Mélanges polymères de polystyrène avec des copolymères séquencés styrène-butadiène

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Publication number
EP2486094A1
EP2486094A1 EP10760696A EP10760696A EP2486094A1 EP 2486094 A1 EP2486094 A1 EP 2486094A1 EP 10760696 A EP10760696 A EP 10760696A EP 10760696 A EP10760696 A EP 10760696A EP 2486094 A1 EP2486094 A1 EP 2486094A1
Authority
EP
European Patent Office
Prior art keywords
styrene
film
weight
butadiene
components
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.)
Withdrawn
Application number
EP10760696A
Other languages
German (de)
English (en)
Inventor
Norbert Niessner
Rogelio Chavez
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.)
BASF SE
Original Assignee
BASF SE
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 BASF SE filed Critical BASF SE
Priority to EP10760696A priority Critical patent/EP2486094A1/fr
Publication of EP2486094A1 publication Critical patent/EP2486094A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L25/00—Compositions of, homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring; Compositions of derivatives of such polymers
    • C08L25/02—Homopolymers or copolymers of hydrocarbons
    • C08L25/04—Homopolymers or copolymers of styrene
    • C08L25/06—Polystyrene
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
    • C08J9/0061—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof characterized by the use of several polymeric components
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2201/00—Foams characterised by the foaming process
    • C08J2201/02—Foams characterised by the foaming process characterised by mechanical pre- or post-treatments
    • C08J2201/03—Extrusion of the foamable blend
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2325/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring; Derivatives of such polymers
    • C08J2325/02—Homopolymers or copolymers of hydrocarbons
    • C08J2325/04—Homopolymers or copolymers of styrene
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2453/00—Characterised by the use of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives of such polymers
    • C08J2453/02—Characterised by the use of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives of such polymers of vinyl aromatic monomers and conjugated dienes
    • 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
    • C08K5/04—Oxygen-containing compounds
    • C08K5/10—Esters; Ether-esters
    • C08K5/109—Esters; Ether-esters of carbonic acid, e.g. R-O-C(=O)-O-R
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L53/00—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
    • C08L53/02—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers of vinyl-aromatic monomers and conjugated dienes

Definitions

  • the invention relates to a mixture comprising a) 1 to 40 wt .-% of a styrene-butadiene-styrene block copolymer
  • d) contains 0.1 to 20 wt .-% of a foam-forming additive, wherein the sum of components a) to d) 100 wt .-% results.
  • DE-A-44 16 862 discloses expandable styrene polymers for elastic polystyrene foams containing polystyrene and styrene-butadiene-styrene block copolymers.
  • the document refers exclusively to expandable styrene polymers, i. polystyrene beads obtainable via suspension polymerization with e.g. Pentane as blowing agent, which foams by temperature / steam, but does not give an intimate blend with the other components.
  • foams of polyolefin / polystyrene resin mixtures are known, which are formed by mixing a polyolefin resin and a polystyrene resin in the presence of a hydrogenated styrene-butadiene block copolymer, as well as extrusion foams from the resulting Resin composition in the presence of a blowing agent.
  • US Pat. No. 6,268,046 discloses foamable mixtures comprising two different styrene polymers with CO2 as blowing agent. It is described that elastomeric styrene / butadiene copolymer is added to increase the overall elasticity of the molded articles.
  • EP-A-1 730 221 From EP-A-1 730 221 (WO-A-2005/095501) are known foams of polystyrene containing low molecular weight random styrene-butadiene copolymers. This results in a reduction in the compressive strength and flexural strength of the foam from 60 to 40 days.
  • Foams based on expandable polystyrene, a blowing agent and styrene-butadiene block copolymers are known from EP-A-1 930 365.
  • Foamed films for use in a microwave oven are known from JP-A-08/041 233.
  • the desired effect high temperature resistance with gradual improvement of the toughness
  • DE-A-10 2004 055 539 discloses mixtures comprising mineral fillers and thermoplastic elastomers based on styrene.
  • a disadvantage of the aforementioned polymers is that no way is described to improve both toughness and stiffness of foams.
  • the present invention had the object to remedy the aforementioned disadvantages. Accordingly, new and improved blends were found which a) 1 to 40 wt .-% of a styrene-butadiene-styrene block copolymers with
  • the mixtures according to the invention comprise, preferably consisting of 1 to 40 wt .-%, preferably 2 to 30 wt .-%, particularly preferably 5 to 10 wt .-% of styrene-butadiene-styrene block copolymers (component A), 60 to 99 wt.
  • component A preferably 70 to 98 wt .-%, particularly preferably 90 to 95 wt .-% of polystyrene (component B), 0 to 50 wt .-%, preferably 0.1 to 20 wt .-%, particularly preferably 1 to 10% by weight of a filler (component C) and 0.1 to 20% by weight, preferably 0.2 to 15% by weight, particularly preferably 0.5 to 10% by weight, of an additive (component D) , Component A:
  • styrene and butadiene are generally predominantly, preferably at least 95%, particularly preferably 98%, in particular 99%, very preferably 100% in polymerized form.
  • the content of at least one copolymerized styrene monomer is 60 to 95 wt .-%, preferably 65 to 90 wt .-%, particularly preferably 70 to 80 wt .-% (component a1.).
  • the content of at least one copolymerized diene moiety monomers is 5 to 40 wt .-%, preferably 10 to 35 wt .-%, particularly preferably 20 to 30 wt .-%.
  • Suitable diene components are, for example, butadiene, pentadiene, dimethylbutadiene and isoprene, preferably butadiene and isoprene, more preferably butadiene.
  • comonomers may also be added to these monomers, e.g. Acrylates.
  • the monomers mentioned in DE-A 196 33 626 on page 3, lines 5-50 under M1-M10 are suitable as comonomers.
  • the block copolymers known as such are prepared by anionic polymerization in a manner known to those skilled in the art. Usually mono-, bi- or multifunctional alkali metal alkyls, aryls or aralkyls are used as initiators.
  • Examples include n-butyllithium and sec-butyllithium called.
  • the preferred solution polymerization may be carried out in an aliphatic, aromatic or cycloaliphatic hydrocarbon such as benzene, toluene, hexane, cyclohexane, heptane, octane, with or without addition of further substances, e.g. Ethern, done.
  • so-called retarders e.g. Magnesium or aluminum organyls are added.
  • the living chains can be terminated with a chain stopper.
  • Proton-active substances such as e.g.
  • the living chain ends for example a styrene-butadiene block
  • suitable coupling means often forming a mixture of linear and star-shaped (with n arms) styrene-butadiene block copolymers.
  • the block structure is essentially formed by first anionically polymerizing styrene alone, resulting in a styrene block. After consumption of the styrene monomers, the monomer is changed by adding monomeric butadiene and polymerizing anionically to form a butadiene block (so-called sequential polymerization).
  • the obtained diblock polymer S-B can be polymerized by renewed monomer exchange on styrene to form a triblock polymer S-B-S, if desired.
  • triblock copolymers B-S-B The same applies analogously for triblock copolymers B-S-B.
  • the two styrene blocks can have the same size (same molecular weight, ie symmetrical structure S1-B-S1) or different sizes (different sizes). different molecular weight so unbalanced structure S1-B-S2) be.
  • S1-B-S1 symmetrical structure
  • S1-B-S2 different sizes
  • S1-B-S2 different molecular weight so unbalanced structure
  • BSB block sequences SSB or S1-S2-B, or SBB or S-B1-B2
  • the above are the indices for the block sizes (block lengths or molecular weights).
  • the block sizes depend, for example, on the monomer amounts used and the polymerization conditions.
  • blocks BIS may also be present.
  • the blocks BIS are also soft and contain butadiene and styrene, for example randomly distributed or as tapered
  • styrene-butadiene block copolymers four-block and polyblock copolymers are also suitable.
  • Said block copolymers may have a linear structure (described above). However, branched and star-shaped structures are preferred. Branched block copolymers are obtained in a known manner, e.g. by grafting reactions of polymeric "side branches" onto a polymer backbone.
  • Star shaped block copolymers are e.g. by reacting the living anionic chain ends with an at least bifunctional coupling agent.
  • an at least bifunctional coupling agent are described, for example, in US-A-3,985,830, US-A-3,280,084, US-A-3,637,554 and US-A-4,091,053.
  • epoxidized glycerides for example epoxidized linseed oil or soybean oil
  • silicon halides such as SiCU
  • di-vinylbenzene di-vinylbenzene
  • polyfunctional aldehydes ketones, esters, anhydrides or epoxides.
  • Carbonates such as diethyl carbonate or ethylene carbonate (1,3-dioxolan-2-one) are also preferred.
  • dimerization are dichlorodialkylsilanes, dialdehydes such as terephthalaldehyde and esters such as ethyl formate or ethyl acetate.
  • star-shaped block copolymers By coupling identical or different polymer chains one can produce symmetrical or asymmetrical star structures, ie the individual star branches can be identical or different, in particular contain different blocks S, B, B / S or different block sequences. Further details on star-shaped block copolymers can be found, for example, in WO-A 00/58380.
  • Styrene-butadiene-styrene block copolymers having a styrene content of 60 to 95% by weight of styrene are, for example, K-Resin 01, K-Resin 03, K-Resin 05, K-Resin 10, Styrolux® 684D, Styrolux® 693 D and Styrolux ® 3G55.
  • Component B Component B:
  • Suitable styrene polymers are all customary polymers based on styrene monomers.
  • styrene monomers all vinylaromatic monomers can be used, for example styrene, ⁇ -methylstyrene, p-methylstyrene, ethylstyrene, tert-butylstyrene, vinylstyrene, vinyltoluene, 1,2-diphenylethylene, 1,1-diphenylethylene or mixtures thereof.
  • the styrenic polymers may be rubber-free or rubber-containing.
  • the former includes polystyrene (GPPS), the latter being commonly referred to as impact, for example, impact polystyrene (HIPS).
  • the rubbers contained in the impact-resistant styrene polymers are in particular those based on diene monomers.
  • Suitable diene monomers are all polymerizable dienes, in particular 1,3-butadiene, 1,3-pentadiene, 1,3-hexadiene, 2,3-dimethylbutadiene, isoprene, piperylene or mixtures thereof. Preference is 1, 3-butadiene (in short: butadiene).
  • the process is characterized in that the styrene polymer used is polystyrene (GPPS), impact-modified polystyrene (HIPS), or mixtures thereof. Particular preference is given to using GPPS.
  • HIPS high-impact polystyrene
  • the preparation of the styrene polymers can be effected in a manner known per se, for example by mass, solution, emulsion, suspension or precipitation polymerization of the monomers, or combinations of these types of polymerization.
  • the radical, anionic or cationic initiators known to the person skilled in the art, as well as other auxiliaries, are used for this purpose.
  • the rubber-containing (impact-modified) styrene polymers have a rubber content of 0.1 to 12% by weight.
  • the rubber-containing styrenic polymers preferably have weight-average molecular weights of 80,000 to 500,000, in particular 100,000 to 400,000 g / mol
  • the rubber-free styrene polymers preferably have weight-average molecular weights of 100,000 to 500,000, in particular 120,000 to 400,000 g / mol.
  • the styrene polymers used as starting material, the known additives and processing aids (short: additives) in the usual amounts for these substances contain, for example, lubricants or mold release agents, colorants such as pigments or dyes, flame retardants, antioxidants, light stabilizers, fibrous and powdery fillers or reinforcing agents or antistatic agents, and other additives, or mixtures thereof.
  • the styrene polymers used may also contain mineral oil in amounts of 0 to less than 8 wt .-%.
  • Such products are commercially available, e.g. Polystyrol® 143E from BASF.
  • Such to less than 8 wt .-% mineral oil-containing styrene polymers can be used particularly advantageous if the product mineral oil-containing styrene polymers with a particularly high mineral oil content, for example 20 to 50 wt .-%, to be produced.
  • mineral oil all, usually from mineral resources (petroleum, lignite, coal, wood, peat) obtained, liquid distillation products are suitable. They usually consist of mixtures of saturated hydrocarbons and are usually unsaponifiable. Suitable mineral oils are e.g. Petrol, diesel oils, heating oils, lubricating oils, kerosene or insulating oils. Also liquid paraffins, ie mixtures of purified, saturated aliphatic hydrocarbons, are suitable.
  • the suitable mineral oils have a density of 0.75 to 1, 0 g / ml according to DIN 51757 at 15 ° C, and a viscosity (kinematic) of 50 to 90 mm 2 / s according to DIN 51562 at 40 ° C, on.
  • white oils especially those which are approved as additives for styrene polymers (polystyrenes, etc.) with food contact, food law.
  • white oil Vinog® 70 from Wintershall AG, a mineral oil having the following properties:
  • the mineral oil content of the mineral oil-containing styrene polymer is at least 8% by weight. It is preferably at most 50% by weight. More preferably, the mineral oil content is 8 to 50 wt .-%, and in particular it is 10 to 50 wt .-%. Most preferably, it is 15 to 40 wt .-%.
  • Component C All commercially available mineral fillers such as talc, calcium carbonate, titanium dioxide, magnesium sulfate, magnesium oxide, calcium oxide, aluminum oxide, preferably talc, calcium carbonate and titanium dioxide.
  • Component D All commercially available mineral fillers such as talc, calcium carbonate, titanium dioxide, magnesium sulfate, magnesium oxide, calcium oxide, aluminum oxide, preferably talc, calcium carbonate and titanium dioxide.
  • blowing agents such as carbon dioxide with or without alcohol, nitrogen, butane, pentane or chemical blowing agents such as sodium carbonate, potassium carbonate or reaction products of citric acid.
  • blowing agents such as carbon dioxide with or without alcohol, nitrogen, butane, pentane or chemical blowing agents such as sodium carbonate, potassium carbonate or reaction products of citric acid.
  • component B is melted, and component A is already introduced into the extruder as a mixture with B or, alternatively, via an additional metering. Both components are now heated beyond the glass stage of B, so that they melt in the extruder.
  • component C is added as a mixture with A and / or B or, alternatively, by separate dosing. Separate doses may be, for example: gear pumps (in the case of liquid / pasty components), melt extruder, plug screw.
  • component D is added.
  • a chemical blowing agent e.g. a mixture of citric acid and sodium bicatbonate - component D can also be added together as a mixture with A and / or B.
  • Component D is a physical blowing agent, it is preferably in the plastic or molten state of the melt, consisting of the components A, B and optionally C, added.
  • Physical blowing agents are those which are present in the gaseous state under the respective extrusion temperatures and at atmospheric pressure (1 bar).
  • the resulting mixture of components A to D is then extruded through a die, typically forming a semi-finished product (film, film, tube, tube, etc.) which has a foam structure due to the spontaneous expansion of the pressurized blowing agent.
  • melt extruder which usually has the purpose to cool the low-viscosity mixture AD and thus to convert into a higher viscous melt
  • a melt is cooled to 1 10 to 150 ° C.
  • Typical extrusion temperatures are 100 to 300 ° C, preferably 1 10 to 275 ° C and particularly preferably 120 to 250 ° C.
  • the mixtures according to the invention can be used in or as
  • Foamed films for food packaging of all kinds (such as meat trays, vegetable trays),
  • a star-shaped S / B block copolymer was prepared according to Example 17 of WO-A-2000/058380 (in the following Table A: Example 6).
  • component B polystyrene having a mean viscosity number of 96 (measured as 0.5 wt .-% solution in dimethylformamide [DMF] at 23 ° C) was used.
  • the foam samples were extruded on a tandem machine. This consisted of a first extruder for melting the polymer and for mixing the blowing agent and a second extruder for cooling the blowing agent-containing melt. Styrene-butadiene-styrene block copolymer and polystyrene were fed to the first extruder. The polymer was melted at 210 ° C and the foam-forming additive was injected together at one point. The blowing agent used was carbon dioxide. The propellant-containing melt was then in a second

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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)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)

Abstract

L'invention concerne un mélange comprenant : a) 1 à 40% en poids d'un copolymère séquencé styrène-butadiène-styrène présentant 1.) 60 à 95% en poids d'un monomère de styrène et 2.) 5 à 60% en poids d'un monomère de diène, b) 60 à 99% en poids d'un polymère de styrène, c) 0 à 50% en poids d'une charge, et d) 0,1 à 20% en poids d'un additif moussant, la somme des composants a) à d) s'élevant à 100% en poids.
EP10760696A 2009-10-09 2010-10-05 Mélanges polymères de polystyrène avec des copolymères séquencés styrène-butadiène Withdrawn EP2486094A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP10760696A EP2486094A1 (fr) 2009-10-09 2010-10-05 Mélanges polymères de polystyrène avec des copolymères séquencés styrène-butadiène

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP09172692 2009-10-09
EP10760696A EP2486094A1 (fr) 2009-10-09 2010-10-05 Mélanges polymères de polystyrène avec des copolymères séquencés styrène-butadiène
PCT/EP2010/064778 WO2011042405A1 (fr) 2009-10-09 2010-10-05 Mélanges polymères de polystyrène avec des copolymères séquencés styrène-butadiène

Publications (1)

Publication Number Publication Date
EP2486094A1 true EP2486094A1 (fr) 2012-08-15

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EP10760696A Withdrawn EP2486094A1 (fr) 2009-10-09 2010-10-05 Mélanges polymères de polystyrène avec des copolymères séquencés styrène-butadiène

Country Status (3)

Country Link
US (1) US20120208909A1 (fr)
EP (1) EP2486094A1 (fr)
WO (1) WO2011042405A1 (fr)

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US8440764B2 (en) 2010-05-07 2013-05-14 Styrolution GmbH Molding composition with reduced light scattering
AT516041B1 (de) * 2014-08-26 2016-02-15 Ifn Holding Ag Fenster

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WO2011042405A1 (fr) 2011-04-14
US20120208909A1 (en) 2012-08-16

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