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WO2008151993A1 - Composition polymère transparente, à transformabilité thermoplastique et élastomère, stable aux uv et présentant de bonnes propriétés d'adhérence - Google Patents

Composition polymère transparente, à transformabilité thermoplastique et élastomère, stable aux uv et présentant de bonnes propriétés d'adhérence Download PDF

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Publication number
WO2008151993A1
WO2008151993A1 PCT/EP2008/057083 EP2008057083W WO2008151993A1 WO 2008151993 A1 WO2008151993 A1 WO 2008151993A1 EP 2008057083 W EP2008057083 W EP 2008057083W WO 2008151993 A1 WO2008151993 A1 WO 2008151993A1
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WO
WIPO (PCT)
Prior art keywords
polymer composition
component
weight
composition according
blocks
Prior art date
Application number
PCT/EP2008/057083
Other languages
German (de)
English (en)
Inventor
Holger Wickel
Jens Dieter Erler
Original Assignee
Kraiburg Tpe Gmbh & Co. Kg
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 Kraiburg Tpe Gmbh & Co. Kg filed Critical Kraiburg Tpe Gmbh & Co. Kg
Publication of WO2008151993A1 publication Critical patent/WO2008151993A1/fr

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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
    • 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
    • C08L53/025—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 modified
    • 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
    • C09D153/00—Coating compositions based on block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers
    • C09D153/02—Vinyl aromatic monomers and conjugated dienes
    • C09D153/025—Vinyl aromatic monomers and conjugated dienes modified
    • 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
    • C09J153/00—Adhesives based on block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers
    • C09J153/02—Vinyl aromatic monomers and conjugated dienes
    • C09J153/025—Vinyl aromatic monomers and conjugated dienes modified
    • 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
    • C08L2666/02—Organic macromolecular compounds, natural resins, waxes or and bituminous materials

Definitions

  • Transparent, thermoplastically processable, elastomeric polymer composition with UV stability and good adhesion properties.
  • the invention relates to a transparent, thermoplastically processable, elastomeric polymer composition with UV stability and good adhesion properties on engineering thermoplastics, as well as the use of this composition for the production of composite parts.
  • thermoplastic elastomers based on alkenyl aromatic block copolymers
  • TPE-S styrene block copolymers
  • TPE-S triblock copolymers of the type ABA, consisting of two styrene end blocks A and a middle block B, for example, of a polymerized diene (polydiene) such as 1,3-butadiene ⁇ Styrene-butadiene-styrene, SBS) or isoprene (styrene-isoprene-styrene, SIS).
  • polydiene polymerized diene
  • SBS Styrene-butadiene-styrene
  • SIS isoprene
  • MuItiblock polymers such as ABABA or radial polymers such as (AB) n X with n> 2, wherein X is derived from a coupling reagent such as divinylbenzene or a silane (US 3,985,830).
  • the blndblöcke A different ABA polymer chains form below their glass transition temperature amorphous domains, - since the blndblöcke A are connected by the middle blocks B arises in this way a network structure of hard polystyrene domains and a soft B matrix, which causes the elastomeric character.
  • the A domains Upon heating above its glass transition temperature, the A domains are reversibly softened and the polymer becomes thermoplastically processable. Since the indices of refraction of the polystyrene blocks and the center block are generally different per se, the optical properties such as transparency and light scattering are essentially determined by the size of the polystyrene moraines, which is essentially determined by the length of the blocks.
  • the polydiene midblocks can also be selectively hydrogenated to produce polymers with a saturated midblock.
  • Such polymers are disclosed, for example, in US 3,595,942.
  • hydrogenation of SBS results in SEBS ⁇ styrene-ethylene / butylene-styrene ⁇ .
  • more than 90% of the double bonds are reduced, as a side reaction even a small proportion ( ⁇ 10%) of the aromatic rings can be partially hydrogenated.
  • the middle blocks can also contain polymerized styrene;
  • the distribution of styrene and diene in the midblocks may be randomly "C", "random", or "tapered.”
  • 7,169,848 B2 discloses a specific type of monoalkenyl aromatic / diene distribution one or more regions of the B blocks adjacent to the A blocks have an above-average content of diene, while one or more regions not adjacent to the A blocks contain an above-average monoalkenyl aromatic content, moreover, the distribution is not blocky, which means that at most 40% of the monoalkenyl aromatic units in the B block have two monoalkenyl aromatic moieties as neighbors, the remainder having at least one diene moiety as neighbor
  • the measurement of this property can be made by 1 H-NMR as in US Pat No. 7,169,848 B2.
  • thermoplastic elastomers of the type alkenyl aromatic block copolymer and in the two-component injection molding on engineering thermoplastics in particular those with polar groups such as PC, ABS, PC / ABS mixtures, PBT, PETG, Zylar or PMMA adhere also known.
  • polar groups such as PC, ABS, PC / ABS mixtures, PBT, PETG, Zylar or PMMA
  • a further component which imparts adhesion is generally also required.
  • thermoplastic elastomer compositions of styrene block copolymers which contain thermoplastic elastomeric co-polyesters (TPE-E) as a component which promotes adhesion.
  • TPE-S thermoplastic elastomeric co-polyesters
  • TPE-U thermoplastic elastomeric polyurethanes
  • SBS Styrene-butadiene-styrene-styrene-styrene-styrene-styrene-styrene-styrene-styrene-styrene-styrene-styrene-styrene-styrene-styrene-styrene-styrene-styrenethacrylate-styrene-styrene-styrene-styrene-styrene-styrene-styrene-styrene-styrene-styrene-styrene-styrene-styrene-styrene-styrene-styrene-styrene-styrene-styrene-styrene-styrene-styrene-styrene
  • Hydrogenated styrenic block copolymer compositions e.g.
  • SEBS styrene-ethylene / butylene-styrene
  • endblock-compatible resin show inadequate adhesion to engineering thermoplastics having polar groups.
  • the A blocks have number average molecular weights between The total content of monoalkenyl aromatic is 15-75% by weight (US 2003/0181584 A1) and 20-80% by weight, respectively -% (US 2003/0181585 A1).
  • WO 03/066769 A1 and US 2003/0176574 A1 disclose the use of hydrogenated styrene block copolymers with controlled styrene distribution in the middle block in
  • thermoplastically processable, elastomeric composition which is transparent, has good UV stability, has very good mechanical properties such as high tensile strength, as well as on engineering thermoplastics, in particular on polar thermoplastics such as PC, ABS, PC / ABS compounds, PBT, PETG, Zylar or PMMA adheres well.
  • polar thermoplastics such as PC, ABS, PC / ABS compounds, PBT, PETG, Zylar or PMMA adheres well.
  • compositions comprising the following components:
  • thermoplastic elastomeric block C ⁇ polymere having at least two end blocks A of polymerized monoalkenyl aromatic and at least one middle block B of polymerized and then hydrogenated conjugated dienes and monoalkenyl aromatic, wherein
  • the number average molecular weight of component (a) is between 80,000 and 240,000
  • the number average molecular weight of the individual endblocks is between 10,000 and 36,000
  • the proportion of monoalkenyl aromatic, relative to the weight of component (a), is 35-80%
  • the proportion of monoalkenyl aromatic in the end blocks, with respect to the weight of component ⁇ a ⁇ , is 20-40%
  • the proportion of monoalkenyl aromatic in the middle blocks, in relation to the weight of the middle blocks, is 15-75%
  • compositions adhere, for example in the
  • Two-component injection molding good on engineering thermoplastics and especially on thermoplastics with polar groups.
  • they are characterized by high transparency and UV stability. Typical are transmission values above 85% and haze values below 50%, preferably below 20%, according to ASTM D 1003, Method A, and at least 500 hours until the first signs of yellowing occur under UV radiation according to DIN EN ISO 4892-2.
  • composition is e.g. for the manufacture of medical equipment, razor handles, switches, controls on equipment, mobile phones,
  • the component consists of one or more thermoplastic elastomeric block copolymers having at least two end blocks A of polymerized monoalkenyl aromatics and at least one middle block B of polymerized and then hydrogenated conjugated
  • the diene is, for example, 1,3-butadiene or substituted 1,3-butadienes such as isoprene, piperylene, 2,3-dimethyl-1,3-butadiene, 1-phenyl-1,3-butadiene, or else a mixture of different dienes, - butadiene is preferred.
  • the monoalkenyl aromatic may be, for example, styrene, alpha-methylstyrene, para-methylstyrene, vinylnaphthalene, para-butylstyrene, or else a mixture of different monoalkenylaromatics; Styrene is preferred.
  • the proportion of hydrogenated diene units is preferably 90% or greater; furthermore, up to 10% of the monoalkenylaromatics may also be hydrogenated or partially hydrogenated.
  • the middle blocks B preferably contain polymerized conjugated dienes and polymerized monoalkenyl aromatics in a controlled distribution, as in US Pat. No. 7,169,848 B2 described.
  • one or more regions of the B blocks adjacent to the A blocks contain an above-average proportion of diene, while one or more regions not adjacent to the A blocks contain an above-average monoalkenyl aromatic content.
  • the distribution is not blocky.
  • the weight of the end blocks accounts for 20-40%, preferably 25-35%. Furthermore, in view of good adhesion, a certain minimum weight of the end blocks is necessary, and a certain maximum weight, in order to ensure high transparency and good processability.
  • the number average weight of a single endblock is between 10,000 and 36,000, preferably between 15,000 and 28,000, and more preferably between 18,000 and 22,000.
  • the molecular weights of the polymers can be measured by gel permeation chromatography (GPC) against polystyrene standards with chlorobenzene as the eluent.
  • the total amount of monoalkenyl aromatic, based on the weight of component (a), is 35-80%, preferably 40-70%, and most preferably 44-60%.
  • Lower levels of monoalkenyl aromatic lead to no longer sufficient adhesion to polar thermoplastics, higher proportions reduce the elasticity.
  • the proportion of monoalkenyl aromatic in the B blocks, based on the weight of the B blocks should be at least 15%; however, to ensure adequate elasticity and processability, 75% should not be exceeded. Preference is given to a proportion of 18-55%, and particularly preferred are 20-45%.
  • Suitable polymers are available, for example, from Kraton under the name "Kraton A”.
  • the adhesion-promoting component is an endblock-compatible resin or a mixture of such.
  • Suitable examples are aromatic resins, such as homo- and co-polymers of vinyl toluene, styrene, alpha-methlystyrene, coumarone or indene.
  • the weight-average molecular weight is preferably from 1000 to 40,000 in view of the hardness of the composition.
  • Examples are coumarone-indene resins, polyindene resins, poly (methylindene) resins, polystyrene resins, vinyltoluene-alpha-methylstyrene resins, and alpha-methylstyrene resins. resins.
  • Such resins are offered under the names “HERCURES”, “ENDEX”, “KRISTALEX”, “NEVCHEM”, “PICCOTEX” and “PICCOLASTIC”.
  • ENDEX 155 and KRISTALEX F115 Eastman with softening temperatures of about 155 and 115 0 C are preferred.
  • the resin component There are used 25 to 100 parts by weight of the resin component, preferably 30 to 80 parts by weight, and particularly preferably 40 to 60 parts by weight. High resin contents increase the hardness of the composition and its adhesion to polar thermoplastics. For resin contents of less than 25 parts by weight, the adhesion becomes insufficient.
  • middle block compatible oils for example, vegetable oils or mineral oils can be used. Preference is given to paraffinic and / or naphthenic white oils. With regard to the use of the compositions for the
  • the oil is contained at 40-150 parts by weight, preferred are 60-120 parts by weight.
  • thermoplastic, monoalkenyl aromatic-block aromatic copolymers such as SBS, SIS or SEBS, as well as pigments, dyes, waxes, additional plasticizers, stabilizers and / or processing aids.
  • the composition may contain, in addition to the oil, a polyvinyl plasticizer, typically between 10 and 60 parts by weight.
  • Suitable polymeric plasticizers are midblock-compatible, soft polymers, such as, for example, hydrogenated polydienes or copolymers of diene and monoalkenyl aromatic monomers, preferably of 1,3-butadiene and styrene, or else middle block-compatible resins, such as, for example, aliphatic, cycloaliphatic or hydrogenated aromatic hydrocarbon resins having preferred number average molecular weights between 200 and 1500.
  • Suitable middle block-compatible resins are commercially available, for example, under the names ESCOREZ, REGALITE or REGALREZ.
  • the polymer compositions according to the invention can be prepared and processed in the usual way.
  • composition can be carried out, for example, by extrusion. the melt take place; preferred is the use of a
  • Twin-screw extruder Typical speeds are between 250 and 450 min -1 and temperatures between 160 and 24O 0 C.
  • the granules of the composition can then be further processed, for example by injection molding, typically temperatures between 190 and 250 0 C are used.
  • composition is suitable for two-component injection molding processes for the production of composite parts with technical thermopolasts.
  • Examples 1-4 are suitable for two-component injection molding processes for the production of composite parts with technical thermopolasts.
  • Examples 1-4 demonstrate an embodiment of the invention.
  • the weight proportions of the individual components are given in Table 1.
  • Example 1 a mixture of the polymers “Kraton RP 6935 * and” Kraton RP 6936 "in the ratio 30/70 is used as component (a).
  • the molecular weight and styrene content averages of this mixture are also given in Table 1.
  • Kraton RP 6935 is a hydrogenated styrene-butadiene triblock copolymer with controlled styrene distribution in the middle block and has a number average molecular weight (Mn) of about 210000.
  • Mn number average molecular weight
  • the styrene content is 58%
  • the end block styrene content is 30%. From these values result a number average molecular weight of each endblock of about 32,000, and a midblock styrene content, based on the number average molecular weight of the midblock, of 40%.
  • the weight average molecular weights (Mw) are 240000 (total) and 36000 ⁇ final block, respectively).
  • Kraton RP 6936 also a hydrogenated styrene-butadiene triblock copolymer with controlled styrene distribution in the middle block, has a number average molecular weight of about 120,000, with a styrene content of 39% and an endblock styrene content of 30% the number-average molecular weight of the individual endblocks, each about 18,000, and a midblock styrene content, based on the molecular weight of the midblock, of 13%.
  • the weight average molecular weights are 140000 (total) and 21000 (final block), respectively.
  • compositions in Examples 2-4 contain as component (a) the hydrogenated styrene-butadiene triblock copolymer Kraton EDF 8257, which has a controlled styrene distribution in the middle block and the number average molecular weight of which is 120000; the hydrogenated styrene-butadiene triblock copolymer Kraton EDF 8257, which has a controlled styrene distribution in the middle block and the number average molecular weight of which is 120000;
  • the respective weight-average values are 130000 and 19500, respectively.
  • the total styrene content is 58% and the middle-block styrene content, based on the weight of the middle block, is 40%.
  • the molecular weight determination of the polymers was carried out by means of gel permeation chromatography (GPC) from solutions with a concentration of 1 g / L with chlorobenzene as the eluent at a flow rate of 0.55 mL / min.
  • GPC gel permeation chromatography
  • EHDEX 155" (Eastman) is an endblock-compatible aromatic hydrocarbon resin having a softening point of 155 ° C and a weight average molecular weight of about 9,000;
  • Kristalex F115 is an alpha-methylstyrene-based endblock compatible resin having a weight average molecular weight of about 2,000 and a softening point of about 115 ° C .; the compositions are softer than with Endex 155.
  • the Prepared compositions according to the invention From the components, with the aid of a co-rotating Berstorff ZE25 twin-screw extruder, the Prepared compositions according to the invention. In this case, rotational speeds between 250 and 450 min -1 and temperatures between 160 and 24O 0 C were used, the throughput was 8-15 kg / h The resulting, transparent granules were then further processed by injection molding at 190-250 0 C to test specimens for measuring the properties.
  • test specimens for measuring the mechanical and optical properties as well as the UV resistance were produced with a Demag injection molding machine and stored for at least 16 hours before being subjected to the tests.
  • the hardness according to DIN 53505 / ISO868 was determined with conventional hardness testers. Tensile strengths (ZFS) and elongations at break (BD) according to DIN 53504 / ISO 37 and tear propagation resistances (WRW) according to DIN / ISO 34-1, method B (b) were measured with a Zwick ZO10 tensile tester.
  • the adhesion of the compositions according to the invention to engineering thermoplastics was determined according to Renault Standard D41 1916.
  • a 2 mm thick composite part with a technical thermoplastic, eg PC, ABS, PC / ABS, PBT, PETG or PMMA, as a hard component was produced on a Ferromatik MILLACRON 2K injection molding machine.
  • the peel resistance was then measured with a Zwick tensile testing machine ZO10.
  • the hard component was clamped in a movable carriage and fixed the consisting of the inventive composition elastomeric component with a clamp. The measurement was made at a pulling speed of 100 mm / min perpendicular to the adhesive surface.
  • Examples 5 and 6 contain a polymeric plasticizer called TSM (Taylored Softening Modifier). It is a hydrogenated copolymer of styrene and butadiene having a number average molecular weight below 80,000 and a weight ratio of styrene / butadiene of 40/60.
  • TSM Teylored Softening Modifier
  • ESCOREZ 5320 is a midblock-compatible resin which also functions as a polymeric plasticizer in Examples 7 and S. It is a cycloaliphatic hydrocarbon resin having a number average molecular weight of about 350 and a softening temperature of about 125 ° C.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Medicinal Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Injection Moulding Of Plastics Or The Like (AREA)
  • Manufacture Of Macromolecular Shaped Articles (AREA)

Abstract

L'objet de l'invention est une composition polymère transparente, thermoplastique, élastomère et stable par rapport aux UV qui adhère à des matières thermoplastiques lors du moulage par injection à deux composants, en particulier à ceux contenant des groupes polaires. Cette composition comprend trois composants : (a) un copolymère bloc élastomère ayant au moins deux blocs d'extrémité A, constitués de composés aromatiques monoalcényle polymérisés, et au moins un bloc central B constitué de diènes conjugués polymérisés et ensuite hydrogénés, et des composés aromatiques de monoalcényle polymérisés, (b) une résine compatible avec les blocs d'extrémité et (c) une huile compatible avec le bloc central.
PCT/EP2008/057083 2007-06-13 2008-06-06 Composition polymère transparente, à transformabilité thermoplastique et élastomère, stable aux uv et présentant de bonnes propriétés d'adhérence WO2008151993A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102007027156A DE102007027156A1 (de) 2007-06-13 2007-06-13 Transparente, thermoplastisch verarbeitbare, elastomere Polymerzusammensetzung mit UV-Stabilität und guten Haftungseigenschaften
DE102007027156.7 2007-06-13

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WO2008151993A1 true WO2008151993A1 (fr) 2008-12-18

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PCT/EP2008/057083 WO2008151993A1 (fr) 2007-06-13 2008-06-06 Composition polymère transparente, à transformabilité thermoplastique et élastomère, stable aux uv et présentant de bonnes propriétés d'adhérence

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Publication number Priority date Publication date Assignee Title
WO2020126804A1 (fr) 2018-12-20 2020-06-25 Actega Ds Gmbh Composition élastomère thermoplastique

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20030181584A1 (en) * 2002-02-07 2003-09-25 Kraton Polymers U.S. Llc Elastomeric articles prepared from controlled distribution block copolymers
EP1707596A1 (fr) * 2005-03-14 2006-10-04 Kraton Polymers Research B.V. Copolymère hydrogéné à blocs pour les moulages sur les thermoplastiques.

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US3149182A (en) 1957-10-28 1964-09-15 Shell Oil Co Process for preparing block copolymers utilizing organolithium catalysts
US3595942A (en) 1968-12-24 1971-07-27 Shell Oil Co Partially hydrogenated block copolymers
US3985830B1 (en) 1974-07-15 1998-03-03 Univ Akron Star polymers and process for the preparation thereof
JP2888305B2 (ja) 1989-09-13 1999-05-10 大成プラス株式会社 熱融着性に優れた熱可塑性弾性体組成物
JP3210059B2 (ja) 1992-02-17 2001-09-17 大成プラス株式会社 熱融着性に優れた熱可塑性弾性体組成物
US7169848B2 (en) 2002-02-07 2007-01-30 Kraton Polymers U.S. Llc Block copolymers and method for making same
US20070066753A1 (en) * 2005-09-16 2007-03-22 Ehrlich Martin L Highly processible compounds of high MW conventional block copolymers and controlled distribution block copolymers

Patent Citations (2)

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Publication number Priority date Publication date Assignee Title
US20030181584A1 (en) * 2002-02-07 2003-09-25 Kraton Polymers U.S. Llc Elastomeric articles prepared from controlled distribution block copolymers
EP1707596A1 (fr) * 2005-03-14 2006-10-04 Kraton Polymers Research B.V. Copolymère hydrogéné à blocs pour les moulages sur les thermoplastiques.

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