EP0985002A2 - Composition de polycetone renforcee - Google Patents

Composition de polycetone renforcee

Info

Publication number
EP0985002A2
EP0985002A2 EP98922978A EP98922978A EP0985002A2 EP 0985002 A2 EP0985002 A2 EP 0985002A2 EP 98922978 A EP98922978 A EP 98922978A EP 98922978 A EP98922978 A EP 98922978A EP 0985002 A2 EP0985002 A2 EP 0985002A2
Authority
EP
European Patent Office
Prior art keywords
elastomer
amine
polymer composition
functionalised
block
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Withdrawn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
EP98922978A
Other languages
German (de)
English (en)
Inventor
James Graham Bonner
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.)
BP Chemicals Ltd
Original Assignee
BP Chemicals Ltd
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
Priority claimed from GBGB9711129.8A external-priority patent/GB9711129D0/en
Priority claimed from GBGB9717355.3A external-priority patent/GB9717355D0/en
Application filed by BP Chemicals Ltd filed Critical BP Chemicals Ltd
Publication of EP0985002A2 publication Critical patent/EP0985002A2/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Withdrawn legal-status Critical Current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
    • C08L73/00—Compositions of macromolecular compounds obtained by reactions forming a linkage containing oxygen or oxygen and carbon in the main chain, not provided for in groups C08L59/00 - C08L71/00; Compositions of derivatives of such polymers

Definitions

  • the present invention relates to polymer compositions containing a polyketone polymer which have improved toughness.
  • polyketones are defined as linear polymers having an alternating structure of (a) units derived from carbon monoxide and (b) units derived from one or more olefinically unsaturated compounds.
  • Such polyketones have the formula:
  • Polyketones have use as thermoplastics for the production of e.g. containers or parts for the automotive industry. Such uses require the polymer to have suitable impact properties. Accordingly, it is known to incorporate into polyketones additives which improve the impact resistance properties of the polymer.
  • US 5,369,170 relates to a composite system comprising an aminated modified polyolefin and a linear alternating polymer of carbon monoxide and at least one ethylenically unsaturated hydrocarbon.
  • the composite structure is produced by reacting a polyolefin with excess amine to form an imide with a free primary amine and causing the primary amine to react with a polyketone chain to form a pyrrole. These reactions can occur during a blending process. Compatibilisation is said to be achieved by the formation of polyketone/polyolefin graft copolymers at the interface of the polymers.
  • the present invention relates to a polymer composition which comprises: (A) a major amount of a polyketone having a linear alternating structure of (a) units derived from carbon monoxide and (b) units derived from one or more olefinically unsaturated compounds; and (B) a minor amount of an amine functionalised elastomer wherein the amount of amine incorporated in the elastomer is from about 0.01 to 2.0% by weight of the total weight of component (B).
  • the amount of amine incorporated in the elastomer is from 0.05 to 1.0% by weight of the total weight of component (B).
  • the optimum amount of amine varies depending on the elastomer.
  • the amine functionalised elastomer is an amine functionalised polyolefinic or styrenic elastomer.
  • the polyolefinic elastomer which is functionalised with the amine can be a copolymer of an olefin e.g. propylene with ethylene, butene or other unsaturated aliphatic hydrocarbons or ethylene with propylene and a diene. Such copolymers are known and any such polymer can be used. It is preferred that the polyolefinic elastomer is an ethylene-propylene rubber or an ethylene/propylene/diene polymer (EPDM), most preferably EPDM. EPDM is an amorphous elastomeric polyolefin having a random distribution of units derived from ethylene, propylene and one or more dienes (e.g. dicyclopentadiene or hexa-l,4-diene) along the polymer backbone.
  • EPDM ethylene/propylene/diene polymer
  • the styrenic elastomer which is functionalised with the amine can be a styrenic block copolymer.
  • the term "styrenic block copolymer” is used to indicate a thermoplastic elastomer characterised by at least one block of units derived from one or more vinyl aromatic hydrocarbons (A block) and at least one block of units derived from one or more olefins other than a vinyl aromatic hydrocarbon (B block).
  • the vinyl aromatic hydrocarbon useful as the precursor of A blocks has a vinyl group attached directly to an aromatic ring.
  • Preferred vinyl aromatic compounds are styrene and substituted styrenes.
  • Illustrative substituted styrenes include ⁇ -methyl styrene, ⁇ -ethylstyrene, p-methylstyrene, m-methylstyrene, p- ethylstyrene, m-isopropylstyrene, divinyl benzene, ⁇ ,4-dimethylstyrene, chlorostyrene and vinyl benzene chloride.
  • Olefins useful as precursors of the B blocks include ethylene, propylene, butylene, and dienes (e.g.
  • the styrenic block copolymer has the structure A-B-A.
  • the block copolymer may be partially hydrogenated. Hydrogenation of block copolymers is well known in the art.
  • styrenic block copolymers examples include styrene-ethylene/butylene- styrene block terpolymer (SEBS), styrene-butadiene-styrene block terpolymer (SBS) and styrene-isoprene-styrene block terpolymer (SIS).
  • SEBS styrenic block copolymers are sold by Shell under the trade name of Kraton and by Asahi under the trade name of Tuftec.
  • Component (B) of the polymer composition of the present invention may comprise a mixture of two or more amine functionalised elastomers.
  • the amine functionalised elastomer may be obtained by (a) graft copolymerising an elastomer, preferably a polyolefinic or styrenic elastomer, with at least one polymerisable ethylenically unsaturated carboxylic acid or derivative thereof and (b) reacting the resulting graft copolymer with a compound (C) which has at least two primary or secondary amino groups at least one of which is a primary amino group.
  • Polymerisable ethylenically unsaturated carboxylic acids and derivatives thereof which are graft copolymerised with the elastomer include, for example, acrylic acid, methacrylic acid, maleic acid, itaconic acid, citraconic acid, mesaconic acid, maleic anhydride, 4-methyl cyclohex-4-ene-l,2-dicarboxylic acid anhydride, bicyclo (2.2.2) oct-5-ene-2,3-dicarboxylic acid anhydride, 1,2,3,4,5,8,9,10- octahydronaphthalene-2,3 dicarboxylic acid anhydride, 2-oxa-l,3-diketospiro (4.4) non-7-ene, bicyclo (2.2.1) hept-5-ene-2,3-dicarboxylic acid anhydride, maleopimaric acid, tetrahydrophthalic anhydride, x-methyl-bicyclo (2.2.1) hept
  • maleic anhydride is used.
  • the amount which is graft copolymerised with a polyolefinic elastomer is typically from 0.001 to 30%, preferably from 0.1 to 10% more preferably from 0.15 to 5 % by weight of the graft copolymer.
  • the amount of maleic anhydride which is graft copolymerised with a styrenic elastomer is typically from 0.001 to 5%, preferably from 0.05 to 3% more preferably from 0.5 to 2 % by weight of the graft copolymer.
  • Methods for preparing graft copolymers are well known and any suitable method can be used to prepare the graft copolymer of the elastomer and the polymerisable ethylenically unsaturated carboxylic acid or derivative thereof.
  • One such suitable method comprises blending together the elastomer and the polymerisable ethylenically unsaturated carboxylic acid or derivative thereof in the presence of a free radical initiator, such as an organic peroxide or hydroperoxide, at a temperature which is above the melting point of the elastomer and which provides a suitable half-life of the free radical initiator.
  • a free radical initiator such as an organic peroxide or hydroperoxide
  • This grafting process can be carried out using known mixing equipment such as, for example, a Brabender mixer, a Banbury mixer or a roll mill.
  • the grafting process is carried out in a closed vessel.
  • a convenient method of preparing the graft copolymer is therefore to extrude the elastomer, the polymerisable ethylenically unsaturated carboxylic acid or derivative thereof and an organic peroxide or hydroperoxide through a single or multiple screw extruder.
  • the elastomer may be dissolved or suspended in a solvent and the resulting solution or suspension is mixed with the polymerisable ethylenically unsaturated carboxylic acid or derivative thereof and the free radical initiator.
  • the compound (C) having at least two primary or secondary amino groups at least one of which is a primary group which is reacted with the graft copolymer is preferably a diamine having two primary amino groups and up to 16 carbon atoms inclusive and at least two carbon atoms between the primary amino groups.
  • the diamines suitably contain aromatic moieties linking the amino groups as illustrated by phenylenediamine, 4,4'-diaminobiphenyl and di(4-aminophenyl) ether, or the diamines contain cycloaliphatic linking moieties such as in the case of di(4-aminocyclohexyl)methane or 1,4-diaminocyclooctane.
  • the preferred diamines are the acyclic terminal primary diamines of the formula: NH 2 (CH 2 ) n H 2 (I) wherein n is an integer from 2 to 16 inclusive.
  • Such polymethylenediamines include trimethylenediamine, tetramethylenediamine, hexamethylenediamine, decamethylenediamine, dodecamethylenediamine and hexadecamethylenediamine.
  • the compound (C) which is reacted with the graft copolymer can also suitably be a polyalkylene polyamine, or a mixture thereof, having the formula:- H 2 N(R-NH) n H (II) wherein R is a divalent aliphatic hydrocarbon group having 2 to 4 carbon atoms and n is an integer in the range from 1 to 10. More preferably the amine is a polyalkylene polyamine of the formula (II) wherein R is the group -CH 2 CH 2 - and n has a value of 2 to 6, i.e. a polyethylene polyamine.
  • polyethylene polyamines examples include triethylene tetramine and tetraethylene pentamine.
  • Hydroxyalkyl amines for example ethanolamine, diethanolamine, 2- hydroxypropylamine and N-hydroxy-ethyl ethylenediamines, and the like may also be used as the compound (C).
  • compound (C) can be a compound of formula (III), H 2 N(CHR 1 CHR 2 O) personallyCHR 3 CHR 4 NH 2 (III) wherein one of R 1 and R 2 is hydrogen and the other is hydrogen or lower alkyl, preferably C 2 -C6 alkyl, more preferably methyl, and n is an integer from 1 to 40, preferably 1 to 10, more preferably 1 to 7, for example 2 to 7, one of R 3 and R 4 is hydrogen and the other is hydrogen or lower alkyl, preferably C 2 -C 6 alkyl, more preferably methyl.
  • the amount of compound (C) which is reacted with the graft copolymer is from 0.01 to 2.0%, preferably from 0.05 to 1.0% by weight of the amine functionalised graft copolymer.
  • the optimum amount of compound (C) varies depending on the graft copolymer.
  • Compound (C) can be reacted with the graft copolymer having an elastomeric backbone which has been grafted with at least one polymerisable ethylenically unsaturated carboxylic acid or derivative thereof, in several ways; a preferred method is to react them in the melt by melt mixing them in known mixing equipment e.g. a Brabender mixer, a Banbury mixer or a roll mill or twin screw extruder.
  • known mixing equipment e.g. a Brabender mixer, a Banbury mixer or a roll mill or twin screw extruder.
  • an amine functionalised polyolefinic elastomer may be obtained via a "masked” polymerisation as described in "High Performance
  • an amine functionality may be introduced using a direct polymerisation of ethylene and propylene or ethylene, propylene and a diene with an amine functionalised monomer.
  • the amine functionality needs to be deactivated (masked) prior to introduction into the polymerisation medium and is regenerated during a demasking operation which is an integral part of the polymerisation process.
  • the amine functionality is believed to be randomly distributed along the polyolefinic elastomer chain.
  • the amine functionality is pendant from the backbone of the polyolefinic elastomer.
  • This architecture requires the amine functionality to be polymerised into the polyolefinic elastomeric chain through an olefin to which the "masked" amine functionality is chemically linked.
  • Examples of amine functionalised polyolefinic elastomers which may be obtained via this "masked" copolymerisation include EPDM-amine and ethylene-propylene-amine.
  • polyketones are defined as linear polymers having an alternating structure of (a) units derived from carbon monoxide and (b) units derived from one or more olefinically unsaturated compounds.
  • Suitable olefinic units are those derived from C 2 to C 20 alpha-olefins or substituted derivatives thereof or arylaliphatic olefinically unsaturated compounds such as styrene or alkyl substituted derivatives of styrene. It is preferred that such olefin or olefins are selected from C 2 to C ⁇ normal alpha-olefins (i.e.
  • the olefin units are either derived from ethylene or most preferred of all from a mixture of ethylene and one or more C 3 to C O normal alpha-olefin(s) especially propylene or butene.
  • the molar ratio of ethylene units to C 3 to C_ normal alpha-olefin units is greater than or equal to 1 most preferably between 2 and 30.
  • the polyketones employed in the invention preferably have a number average molecular weight of from 1000 to 500,000, preferably from 15,000 to 300,000, more preferably from 40,000 to 200,000 as determined by gel permeation chromatography.
  • the melting point of the polyketones is preferably between 175 and 300°C, preferably from 180 to 225°C.
  • the amine functionalised elastomer is incorporated in the polyketone in an amount of between 0.5 and 50% by weight, preferably from 5 to 40% and more preferably from 10 to 30% by weight, based on the weight of the polyketone plus amine functionalised elastomer.
  • Particularly preferred amine functionalised elastomers include a SEBS block terpolymer grafted with maleic anhydride and subsequently reacted with an amine (compound (C)).
  • compositions of the present invention may also contain conventional additives such as antioxidants, stabilisers, processing aids, fillers etc.
  • the present invention provides a polyketone polymer composition having significant impact strength improvement.
  • the scope of the present invention extends to moulded or extruded articles including containers (for example, bottles, trays, cups), automotive parts, sheets and profile sections comprising the polymer composition as defined hereinbefore.
  • a further aspect of the invention relates to the use of an amine functionalised elastomer to increase the impact strength of a polyketone polymer.
  • the following Examples illustrate the invention.
  • the Melt Flow Rate (MFR) of the polyketone was measured using a Davenport Melt Index Tester. Tests were carried out at a temperature of 240°C or 250°C and an applied load of 1.2 kg or 5 kg. The MFR was calculated from the mass of extrudate pushed through a die (2.095 mm diameter) over a 30 second period on application of the load 4 minutes after charging the polymer into the barrel of the instrument at a temperature of 240°C or 250°C. Otherwise standard MFR procedures were followed (e.g. ISO 1133).
  • Polyketone/amine functionalised elastomer compositions were prepared using a PRISM TSE16 co-rotating twin screw extruder.
  • the extruder was operated at a screw speed of 200rpm and with the following set of temperatures: zone 1 (feed) 195-200°C; zone 2, 205-215°C; zone 3 (die) 215-230°C.
  • zone 1 (feed) 195-200°C; zone 2, 205-215°C; zone 3 (die) 215-230°C zone 1 (feed) 195-200°C; zone 2, 205-215°C; zone 3 (die) 215-230°C.
  • zone 1 (feed) 195-200°C
  • zone 2, 205-215°C zone 3 (die) 215-230°C.
  • the appropriate amount of amine functionalised elastomer was either preblended with the polyketone prior to being fed into the extruder or fed independently via an additional feeder.
  • Appropriate levels of stabilisers and antioxidants were premixed with the polyketone
  • the elastomer used was a maleic anhydride modified styrene- ' ethylene/butene-styrene (SEBS) block terpolymer (Kraton FG1901X) supplied by SEBS.
  • SEBS maleic anhydride modified styrene- ' ethylene/butene-styrene
  • the reaction with the amine was carried out by processing the maleic anhydride modified SEBS block terpolymer in the presence of a quantity of 1,12- diaminododecane using a PRISM TSE16 co-rotating twin screw extruder.
  • the extruder operated at a screw speed of 150rpm and with the following set of temperatures: zone 1 (feed) 180°C: zone 2, 200°C: zone 3 (die) 210°C.
  • zone 1 (feed) 180°C: zone 2, 200°C: zone 3 (die) 210°C.
  • zone 1 (feed) 180°C: zone 2
  • zone 3 zone 3
  • the maleic anhydride modified SEBS block terpolymer and diamine were premixed and fed to the extruder at a rate which ensured a 35% torque on the screws during production.
  • the polyketone used was a terpolymer of ethylene, propylene and carbon monoxide having a melting point of 212°C and a melt flow rate (MFR) of
  • the polyketone/amine functionalised elastomer composition was compression moulded into plaques, 150 x 150 x 4mm, using the following conditions:
  • Cooling Crash cooled with water.
  • Example 1 was repeated except that the graft copolymer used was a maleic anhydride modified styrene-ethylene/butene-styrene (SEBS) block terpolymer supplied by Asahi Chemical (Tuftec M1962).
  • SEBS maleic anhydride modified styrene-ethylene/butene-styrene
  • Tuftec M1962 Asahi Chemical
  • the polyketone used had a melting point of 189°C and a melt flow rate (MFR) of 44g/10minutes at 240°C/ 5kg.
  • Polyketone/amine functionalised elastomer compositions were prepared using a PRISM TSE16 co-rotating twin screw extruder.
  • the extruder was operated at a screw speed of 175rpm and with the following set of temperatures: zone l(feed) 190-195°C; zone 2, 215-225°C; zone 3(die) 225-230°C.
  • zone amine functionalised elastomer was either preblended with the polyketone prior to being fed into the extruder or fed independently via an additional feeder.
  • Appropriate levels of stabilisers and antioxidants were premixed with the polyketone.
  • Extruder outputs were maintained at a level to give constant 50% torque on the screws.
  • the polyketone used was a terpolymer of ethylene, propylene and carbon monoxide, and had a melting point of 218°C and a melt flow rate(MFR) of 106g/10mins with a 1.2 kg load at 250°C.
  • the amine functionalised elastomer was an amine functionalised ethylene-propylene rubber (Paratone 8950) supplied by Exxon Chemicals (Paramins).
  • the polyketone/amine functionalised elastomer was injection moulded into tensile bars using a Battenfeld BA230 injection moulder machine. Samples for Izod impact testing were machined from these and tested as in Example 1.

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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)

Abstract

Composition polymère contenant (A) une quantité principale d'une polycétone présentant une structure linéaire alternée comprenant (a) des motifs dérivés de monoxyde de carbone et (b) des motifs dérivés d'un ou plusieurs composés oléfiniquement insaturés; et (B) une quantité mineure d'un élastomère fonctionnalisé par une amine dans lequel la quantité d'amine introduite dans l'élastomère est comprise entre 0,01 et 2,0 % en poids par rapport au poids total du composant. Grâce à une sélection soigneuse de la quantité d'amine qui est introduite dans l'élastomère, on accroît la résilience de la polycétone.
EP98922978A 1997-05-29 1998-05-27 Composition de polycetone renforcee Withdrawn EP0985002A2 (fr)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
GBGB9711129.8A GB9711129D0 (en) 1997-05-29 1997-05-29 Toughened polyketones composition
GB9711129 1997-05-29
GB9717355 1997-08-16
GBGB9717355.3A GB9717355D0 (en) 1997-08-16 1997-08-16 Toughened polyketones composition
PCT/GB1998/001532 WO1998054261A2 (fr) 1997-05-29 1998-05-27 Composition de polycetone renforcee

Publications (1)

Publication Number Publication Date
EP0985002A2 true EP0985002A2 (fr) 2000-03-15

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Family Applications (1)

Application Number Title Priority Date Filing Date
EP98922978A Withdrawn EP0985002A2 (fr) 1997-05-29 1998-05-27 Composition de polycetone renforcee

Country Status (4)

Country Link
EP (1) EP0985002A2 (fr)
JP (1) JP2002500692A (fr)
AU (2) AU7543698A (fr)
WO (2) WO1998054261A2 (fr)

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US6099926A (en) * 1997-12-12 2000-08-08 Intella Interventional Systems, Inc. Aliphatic polyketone compositions and medical devices
US6093463A (en) * 1997-12-12 2000-07-25 Intella Interventional Systems, Inc. Medical devices made from improved polymer blends
KR101755708B1 (ko) * 2011-09-09 2017-07-10 현대자동차주식회사 내충격성 및 유연성이 향상된 폴리케톤 조성물
KR101705647B1 (ko) * 2015-05-27 2017-02-10 주식회사 효성 폴리케톤 섬유로 이루어지는 플렉시블 컨테이너 및 이의 제조방법
KR102386124B1 (ko) 2015-10-02 2022-04-14 삼성전자주식회사 고분자 조성물, 고분자 조성물의 제조 방법, 전자기기 및 전자기기의 제조 방법
KR101867940B1 (ko) * 2017-01-19 2018-06-15 주식회사 효성 말레산무수물 그라프트 고무를 적용한 폴리케톤 조성물
KR101849200B1 (ko) * 2017-01-19 2018-04-16 주식회사 효성 충격강도가 개선된 폴리케톤 조성물
CN107513263B (zh) * 2017-10-19 2020-08-04 威海联桥新材料科技股份有限公司 一种热塑性弹性体垫片材料及其生产方法
CN109666256A (zh) * 2018-11-15 2019-04-23 广州敬信高聚物科技有限公司 一种无卤阻燃热塑性弹性体组合物及其制备方法和应用

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US4520169A (en) * 1982-09-02 1985-05-28 E. I. Du Pont De Nemours And Company Elastomeric sol/gel blends
EP0345854B1 (fr) * 1988-06-08 1993-12-22 Shell Internationale Researchmaatschappij B.V. Composition de polymères
US4900789A (en) * 1988-12-22 1990-02-13 Shell Oil Company Polymer blend of carbon monoxide/olefin copolymer and conjugated alkadiene
JPH04214724A (ja) * 1990-02-12 1992-08-05 Shell Internatl Res Maatschappij Bv 一酸化炭素とエチレン性不飽和化合物との鎖状交互ポリマーを含むポリケトンポリマーブレンド
US5162432A (en) * 1990-04-12 1992-11-10 Shell Oil Company Polyketone polymer blends
US5369170A (en) * 1993-12-13 1994-11-29 Shell Oil Company Composite systems of polyketone and aminated, modified polyolefins

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Also Published As

Publication number Publication date
AU7543798A (en) 1998-12-30
WO1998054261A2 (fr) 1998-12-03
JP2002500692A (ja) 2002-01-08
WO1998054262A1 (fr) 1998-12-03
AU7543698A (en) 1998-12-30
WO1998054261A3 (fr) 1999-03-04

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