WO1985003511A1 - Polyolefine dotee de bonnes proprietes d'adherence - Google Patents

Polyolefine dotee de bonnes proprietes d'adherence Download PDF

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Publication number
WO1985003511A1
WO1985003511A1 PCT/FI1984/000015 FI8400015W WO8503511A1 WO 1985003511 A1 WO1985003511 A1 WO 1985003511A1 FI 8400015 W FI8400015 W FI 8400015W WO 8503511 A1 WO8503511 A1 WO 8503511A1
Authority
WO
WIPO (PCT)
Prior art keywords
acid
polyolefin
adhesion
silane
ldpe
Prior art date
Application number
PCT/FI1984/000015
Other languages
English (en)
Inventor
Christer BERGSTRÖM
Leena Piitulainen
Original Assignee
Neste Oy
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 to PCT/FI1984/000015 priority Critical patent/WO1985003511A1/fr
Application filed by Neste Oy filed Critical Neste Oy
Priority to GB08521526A priority patent/GB2162853B/en
Priority to DE19843490656 priority patent/DE3490656T/de
Priority to NL8420026A priority patent/NL8420026A/nl
Priority to AT0906284A priority patent/ATA906284A/de
Priority to DE3490656A priority patent/DE3490656C2/de
Priority to CH4367/85A priority patent/CH667659A5/de
Priority to BE0/212375A priority patent/BE898893A/fr
Priority to FR8402459A priority patent/FR2559775B1/fr
Publication of WO1985003511A1 publication Critical patent/WO1985003511A1/fr
Priority to NO85853860A priority patent/NO164909C/no
Priority to DK448685A priority patent/DK448685D0/da
Priority to SE8504544A priority patent/SE458928B/sv

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L43/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing boron, silicon, phosphorus, selenium, tellurium or a metal; Compositions of derivatives of such polymers
    • C08L43/04—Homopolymers or copolymers of monomers containing silicon
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F255/00—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F255/00—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00
    • C08F255/02—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00 on to polymers of olefins having two or three carbon atoms
    • 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
    • C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
    • 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
    • C08K5/54—Silicon-containing compounds
    • C08K5/541—Silicon-containing compounds containing oxygen
    • C08K5/5415—Silicon-containing compounds containing oxygen containing at least one Si—O bond

Definitions

  • the present invention concerns a modified polyolefin with good adhesion properties towards metals and towards the surfaces of substances containing polar groups.
  • polyolefins such as polyethylene and poly ⁇ propylene
  • their adhesive capacity to metals and to polar polymers is poor.
  • Attempts have been made to improve the adhesivity by many different methods.
  • the adhesivity ⁇ of poly ⁇ olefins to polar polymers has also been improved by admixing thereto a polymer with good adhesion or by copolymerising poly- ethylene with comonomers containing functional groups.
  • Functional groups giving better adhesiveness may also be produced by grafting various polar compounds to the polyolefin chains, such as acrylic acid, methacrylic acid and their derivatives (e.g. salts), and maleic anhydride.
  • Silane-modified polylolefin can be produced from high pressure polyethylene (LDPE) , low pressure polyethylene (HDPE, LLDPE), polypropylene (PP) or their copolymers and from homopolymer/copolymer mixtures by ⁇ > ⁇ admixing to them 0.01-10 % by weight unsaturated alkoxysilane and 0.01-0.5 % by weight of a radical former.
  • LDPE high pressure polyethylene
  • HDPE low pressure polyethylene
  • PP polypropylene
  • the grafting may take place before or in connection with the processing step.
  • the silane to be grafted to polyolefin may be any unsaturated alkoxysilane appropriate to the purpose.
  • unsaturated alkoxysilane appropriate to the purpose.
  • Such are e.g. vinyl- trimethoxysilane, vinyltriethoxysilane, vinyltris(betamethoxy ⁇ ethoxy)silane, or gammamethacryloxypropyltrimethoxysilane.
  • radical former it is possible for radical former to use any substance which forms radicals at the processing temperature but not at the homogenizing stage in the compound manufacturing.
  • peroxide compounds such as dicumylperoxide.
  • Hydrolysable alkoxysilanes were originally developed for improving the iscibility of polymers and inorganic fillers (to serve as coupling agents) .
  • the alkoxy groups of the silanes are hydrolysed to hydroxy groups, and thereafter ensues condensation with the hydroxyl groups on the surface of the fillers.
  • the alkoxy groups there is a group (there are groups) having such a chemical composition that it is (they are) well miscible with the polymer. Since the alkoxy groups of the silanes condensate under effect of water (and of a catalyst, e.g. dibutylstannic dilaurate) , one has begun to use silanes in cross-linking techniques.
  • This idea is based on unsaturated alkoxy silane being grafted with the aid of peroxide to the polymer, and cross-linking does not take place until after completion of the finished product, with the aid of water or steam. It is possible in this way to machine the polymer at high temperatures without risk of cross-linking, and the cross- linking step is also less expensive as regards both energy expenditure and investments.
  • silanes are used towards cross- linking, a condensing catalyst must always be present.
  • silane-grafted LDPE and LDPE containing catalyst are added into a conventional cable extruder, while in Maillefer's system all raw material components are directly added into a cable extruder of special design, wherein the grafting takes place. It has been noted in connection with cable manufacturing that certain silane-grafted LDPE brands adhere to aluminium.
  • the object of the invention is to provide a modified polyolefin containing silane having good adhesion properties with regard to metals and polar plastics and in which the silane must not necessarily be grafted to the polyolefin by using radical formers.
  • the modified polyolefin of the invention is characterized in that it contains 80-99.8 % polyolefin (LDPE, LLDPE, HDPE, PP or copolymers or polymer mixtures of these), 0.01-10 % alkoxysilane and 0.01-10 % carboxylic acid in order to improve the adhesion properties.
  • the modified polyolefin of the invention may be manufactured from high pressure polyethylene (LDPE) , low pressure polyethylene (HDPE, LLDPE) , polypropylene (PP) or from their copolymers or from mixtures of their homopolymers and copolymers.
  • LDPE high pressure polyethylene
  • HDPE low pressure polyethylene
  • LLDPE low pressure polyethylene
  • PP polypropylene
  • the alkoxysilanes may be grafted to the polyolefin chain by using 0.01-0.5 % by weight of a radical former (such as dicumyl peroxide) . Grafting may take place either before the processing step or in connection therewith.
  • a radical former such as dicumyl peroxide
  • Silanes of this kind are, for instance, vinyltrimethoxy- silane, vinyltriethoxysilane, vinyltris (betamethoxyethoxy) silane or gammamethacr loxypropyltrime hoxy silane .
  • the long-chain fatty acid may be any fatty acid having a hydro ⁇ carbon chain longer than five carbons. It may be saturated, un ⁇ saturated, polyunsaturated, branched or substituted. This group includes for instance myristic acid, stearic acid, behenylic acid, oleic acid, linolic acid, linolenic acid, ricinolic acid.
  • polyolefin grafted with silane must not be treated too long at elevated temperatures. It has been found that the adhesion properties can be optimated with regard to the temperature and delay time in the extruder.
  • the heat treatment of silane-grafted polyolefin can be minimized by allowing the grafting to take place only at the processing step. It is possible to dissolve the radical former in silane and either to process the mixture of polyolefin, silane and radical or first to prepare a compound at a temperature so low that no grafting takes place.
  • the silane-grafted polyolefin contains a long-chain fatty acid, the adhesive properties depend in the same way on the extruder temperature and the delay time.
  • the adhesive properties of mixtures of polyolefin, silane and fatty acid depend on the extruder temperature and on the delay time. The lower the delay time, the better the adhesive properties. However, when the plastic courses become joined, the temperature must be as high as possible and the delay time at high temperature and high pressure as long as possible in order that sufficient adhesion might be achieved.
  • the modified polyolefin of the invention may be used in various ways in applications in which good adhesion to polyamide and to other materials containing polar groups is implied. Of such uses may be mentioned for instance the coating of polyamide tubes and bottles directly with modified polyolefin, or the use of modified polyolefin as an intermediate or adhesive layer when coating polyamide tubes, bottles or other objects. Moreover, there may be mentioned the use of polyolefin according to the invention as film which sticks to polyamide and to other polar surfaces and, in addition, to the polyolefin itself. One may also contemplate coextruded multi-ply films, such as combination films of polyamide and modified polyolefin, and compound films of polyamide, modified polyolefin and common polyolefin.
  • modified polyolefin of the invention may be applied as such or as coating of other films or as adhesive agent between other films, depending on the objective in each particular case.
  • Aluminium, steel and other metal tubes, sheet or other objects may be coated with the modified polyolefin of the invention, or it may be used as an intermediate substance.
  • the silane must usually be grafted to the polyolefin.
  • VTMOEO (betamethoxyethoxy)silane
  • i IPO was also carried out with polyester sheet (PET) and steel sheet at 180 C and 210 C.
  • pre ⁇ heating was given for 90 s, the pressure was raised in 30 s and it was kept at joining pressure height (20 bar) for 40 s.
  • From the specimens thus produced five test samples were cut, which had width 20 mm and length 125 mm.
  • the samples were stored for three days at 23°C and 50 % R.H.
  • the tensile strength reflecting the adhesion was measured with an Instron tension testing apparatus, employing the pulling rate of 100 mm/min. The force required for detaching the different layers could be read from the recorder graph, and the adhesion in Ncm could be calculated therefrom.
  • the effect of stearic acid on the adhesivity to polyamide of LDPE grafted with vinyltrimethoxysilane was studied.
  • the radical former used in the grafting step was 0.05 % of dicumylperoxide .(DCP) .
  • OMPI two-layer coextrusion by the film blowing method was carried out.
  • the ultimate temperature of the silane-modified LDPE was 190 C and that of the polyamide, 240 C, and the molten polymers combined in the nozzle. Since there was rather little silane-modified LDPE and the coextrusion line was rather primitive, uniform conditions and films with uniform thickness were hard to achieve. However, the observation can be made from these films that by using 3 % VTMO and 1 % stearic acid in the LDPE so good adhesion to the poly ⁇ amide course was achieved that the courses could not be separated. It is also noted that no gels occurred in the LDPE modified in this manner.
  • the adhesion was studied in the case that LDPE modified with VTMO and stearic acid is pressed onto polyester (PET) and steel. Two different temperatures were used in the pressing step (180 C and 210 C) . Table 5 below reveals that good adhesion both to poly ⁇ ester and to steel was obtained by grafting VTMO to LDPE. Lowering of the pressing temperature to 180 C caused the adhesions to be reduced, but they were still fairly good. On addition of stearic acid, the adhesions both to polyester and to steel were reduced, and when moreover the peroxide was omitted, they were even further impaired.
  • Table 8 reveals that carboxylic acid improves the adhesion properties of silane-modified polyolefin also in coextrusion with a polar plastic. This test is better consistent with actual conditions in the sense that the pressing time is very short but the temperature high. With isostearic acid so good adhesion is achieved in this way that it cannot be measured. With other acids adhesion is also obtained, even when the silane has not been grafted.
  • the example also demonstrates how hydrolysis of grafted silane prevents the forming of adhesion. The hydrolysis of silane is accelerated when water and/or a condensation catalyst is present, and already grafted silane (Sioplas E) is readily hydrolysed.

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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)
  • Laminated Bodies (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Graft Or Block Polymers (AREA)
  • Paints Or Removers (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

Polyoléfine modifiée dotée de bonnes propriétés d'adhérence par rapport aux métaux et aux surfaces de matériaux contenant des groupes polaires. La polyoléfine contient entre 80 et 90,8% de polyoléfine (LDPE, LLDPE, HDPE, PP) ou leurs copolymères ou mélanges polymères), entre 0,01 et 10% d'alkoxysilane et entre 0,01 et 10% d'un acide gras à chaîne longue pour améliorer les propriétés d'adhérence. L'alkoxysilane est greffé sur la polyoléfine à l'aide d'un groupe formant des radicaux libres, ou l'alkoxysilane a été ajouté à la polyoléfine sans greffage. L'acide gras à chaîne longue est l'acide stéarique, l'acide myristique, l'acide béhénylique, l'acide oléique, l'acide linoléique, l'acide linolinique ou l'acide ricinolique. L'alkoxy silane est un vinyle triméthoxysilane, un vinyle triéthoxysilane, un vinyle tri(bétaméthoxyéthoxy) silane ou un gammaéthacrylopropyltriméthoxysilane.
PCT/FI1984/000015 1984-02-03 1984-02-03 Polyolefine dotee de bonnes proprietes d'adherence WO1985003511A1 (fr)

Priority Applications (12)

Application Number Priority Date Filing Date Title
DE3490656A DE3490656C2 (fr) 1984-02-03 1984-02-03
GB08521526A GB2162853B (en) 1984-02-03 1984-02-03 Polyolefin with good adhesion properties
DE19843490656 DE3490656T (de) 1984-02-03 1984-02-03 Polyolefin mit guten Haftungseigenschaften
NL8420026A NL8420026A (nl) 1984-02-03 1984-02-03 Polyolefine met goede adhesie-eigenschappen.
AT0906284A ATA906284A (de) 1984-02-03 1984-02-03 Polyolefin mit guten haftungseigenschaften
PCT/FI1984/000015 WO1985003511A1 (fr) 1984-02-03 1984-02-03 Polyolefine dotee de bonnes proprietes d'adherence
CH4367/85A CH667659A5 (de) 1984-02-03 1984-02-03 Modifiziertes polyolefin.
BE0/212375A BE898893A (fr) 1984-02-03 1984-02-13 Polyolefine ayant de bonnes proprietes d'adherence
FR8402459A FR2559775B1 (fr) 1984-02-03 1984-02-17 Polyolefine avec de bonnes proprietes d'adherence
NO85853860A NO164909C (no) 1984-02-03 1985-09-30 Polyolefin med gode adhesjonsegenskaper.
DK448685A DK448685D0 (da) 1984-02-03 1985-10-02 Polyolefin med gode adhaesionsegenskaber
SE8504544A SE458928B (sv) 1984-02-03 1985-10-02 Med alkoxisilan modifierad polyolefin med goda vidhaeftningsegenskaper

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/FI1984/000015 WO1985003511A1 (fr) 1984-02-03 1984-02-03 Polyolefine dotee de bonnes proprietes d'adherence

Publications (1)

Publication Number Publication Date
WO1985003511A1 true WO1985003511A1 (fr) 1985-08-15

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ID=8556353

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/FI1984/000015 WO1985003511A1 (fr) 1984-02-03 1984-02-03 Polyolefine dotee de bonnes proprietes d'adherence

Country Status (11)

Country Link
AT (1) ATA906284A (fr)
BE (1) BE898893A (fr)
CH (1) CH667659A5 (fr)
DE (2) DE3490656T (fr)
DK (1) DK448685D0 (fr)
FR (1) FR2559775B1 (fr)
GB (1) GB2162853B (fr)
NL (1) NL8420026A (fr)
NO (1) NO164909C (fr)
SE (1) SE458928B (fr)
WO (1) WO1985003511A1 (fr)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0394090A1 (fr) * 1989-04-19 1990-10-24 Vetrotex Saint-Gobain Emulsion aqueuse à base de polyoléfines greffées, procédé d'obtention et emploi, notamment dans les compositions d'apprêt
US5242969A (en) * 1989-04-19 1993-09-07 Vetrotex-Saint Gobain Aqueous polyolefin emulsions and method of forming same
WO1994020550A1 (fr) * 1993-03-01 1994-09-15 Ppg Industries, Inc. Polyoelfines chlorees modifiees, dispersions aqueuses desdites polyolefines et leur utilisation dans des compositions de revetement
US5993562A (en) * 1996-08-13 1999-11-30 Ppg Industries Ohio, Inc. Method, composition, and kit for abrasive cleaning of fluid delivery systems
EP1394198A1 (fr) * 2002-07-25 2004-03-03 Wacker Polymer Systems GmbH & Co. KG Polymères hydrophobes modifiés
US10086588B2 (en) * 2013-12-20 2018-10-02 Zeon Corporation Resin material and resin film

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA1261499A (fr) * 1984-11-22 1989-09-26 Tatsuo Kinoshita Copolymere ethylenique statistique modifie
JPH0667994B2 (ja) * 1986-06-11 1994-08-31 住友化学工業株式会社 シラン変性エチレン共重合体、その製造方法およびその共重合体からなる接着剤
EP0252061A1 (fr) * 1986-07-04 1988-01-07 Cableries Et Corderies Du Hainaut S.A. Procédé de production de polymères et copolymères vinyliques réticulables par greffage d'un composé hydrolysable du silane
ES2026931T3 (es) * 1987-10-14 1992-05-16 Cray Valley Sa Un procedimiento para producir un copolimero de etileno silano modificado.
FI902479A (fi) * 1990-05-18 1991-11-19 Neste Oy Eten-vinylsilansampolymer och dess framstaellning.
DE19536961A1 (de) * 1995-10-04 1997-04-10 Henkel Kgaa Polyolefin-basierte Formteile und Folien mit permanent verbesserten Oberflächeneigenschaften
FR2842516B1 (fr) * 2002-07-18 2004-10-15 Saint Gobain Vetrotex Composition d'ensimage pour verranne, procede utilisant cette composition et produits resultants
DE102008002163A1 (de) 2008-06-02 2009-12-03 Wacker Chemie Ag Bindemittel auf der Basis von alpha-silangruppenhaltigen Polymeren
DE102009028353A1 (de) 2009-08-07 2011-04-14 Wacker Chemie Ag Bindemittel auf der Basis von silangruppenhaltigen hochverzweigten Polyolefinen

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DE2444829A1 (de) * 1974-09-19 1976-04-08 Kabel Metallwerke Ghh Verfahren zur herstellung von durch aufpfropfen einer silanverbindung in anwesenheit von feuchtigkeit vernetzbaren thermoplasten oder elastomeren
DE2611491A1 (de) * 1975-03-20 1976-09-23 Sekisui Chemical Co Ltd Aufschaeumbare und vernetzbare polyaethylenzusammensetzung, verfahren zur herstellung derselben und erzeugung von vernetzten polyaethylenschaeumen
DE2151270B2 (de) * 1970-10-14 1979-02-08 Dow Corning Ltd., London Verfahren zur Vernetzung von Polyolefinen

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JPS5316747A (en) * 1976-07-30 1978-02-16 Showa Electric Wire & Cable Co Ltd Manufacture of crosslinked polyolefin extrusion molded articles
US4400429A (en) * 1980-12-22 1983-08-23 National Distillers And Chemical Corporation Tree retardant additive composition for polymeric insulation
AT383992B (de) * 1983-03-07 1987-09-10 Neste Oy Mehrschichtiger, polyolefin enthaltender verbundfilm

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Publication number Priority date Publication date Assignee Title
DE2151270B2 (de) * 1970-10-14 1979-02-08 Dow Corning Ltd., London Verfahren zur Vernetzung von Polyolefinen
DE2444829A1 (de) * 1974-09-19 1976-04-08 Kabel Metallwerke Ghh Verfahren zur herstellung von durch aufpfropfen einer silanverbindung in anwesenheit von feuchtigkeit vernetzbaren thermoplasten oder elastomeren
DE2611491A1 (de) * 1975-03-20 1976-09-23 Sekisui Chemical Co Ltd Aufschaeumbare und vernetzbare polyaethylenzusammensetzung, verfahren zur herstellung derselben und erzeugung von vernetzten polyaethylenschaeumen

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Chemical Abstracts, Vol 89(1978), abstract No 147611w, Nishizawa, hitoshi; Kato Masahiro Shimanuki, Horoshi; Suyama, Saichi *
Chemical Abstracts, Vol 98(1983), abstract No 108241s, Guede,I. Mueller,V. Tolstaya,S.N.; Kozlov, G.V; Ignatkina, T.I. *

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0394090A1 (fr) * 1989-04-19 1990-10-24 Vetrotex Saint-Gobain Emulsion aqueuse à base de polyoléfines greffées, procédé d'obtention et emploi, notamment dans les compositions d'apprêt
FR2646164A1 (fr) * 1989-04-19 1990-10-26 Saint Gobain Vetrotex Emulsion aqueuse a base de polyolefines greffees procede d'obtention et emploi, notamment dans les compositions d'appret
US5242969A (en) * 1989-04-19 1993-09-07 Vetrotex-Saint Gobain Aqueous polyolefin emulsions and method of forming same
US5389440A (en) * 1989-04-19 1995-02-14 Vetrotex Saint-Gobain Finish composition for coating and protecting a reinforcing substrate
TR26575A (tr) * 1989-04-19 1995-03-15 Saint Gobain Vetrotex ASILANMIS POLIOLEFIN KüKENLI SULU EMüLSIYON, ELDE EDILME YÖNTEMI VE ÖZELLIKLE APRE BILESIMLERINDE KULLANIMI
WO1994020550A1 (fr) * 1993-03-01 1994-09-15 Ppg Industries, Inc. Polyoelfines chlorees modifiees, dispersions aqueuses desdites polyolefines et leur utilisation dans des compositions de revetement
US5993562A (en) * 1996-08-13 1999-11-30 Ppg Industries Ohio, Inc. Method, composition, and kit for abrasive cleaning of fluid delivery systems
EP1394198A1 (fr) * 2002-07-25 2004-03-03 Wacker Polymer Systems GmbH & Co. KG Polymères hydrophobes modifiés
US7183358B2 (en) * 2002-07-25 2007-02-27 Wacker Polymer Systems Gmbh & Co. Kg Hydrophobically modified polymers
US10086588B2 (en) * 2013-12-20 2018-10-02 Zeon Corporation Resin material and resin film

Also Published As

Publication number Publication date
DE3490656T (de) 1986-02-20
FR2559775B1 (fr) 1988-02-12
SE458928B (sv) 1989-05-22
FR2559775A1 (fr) 1985-08-23
GB2162853B (en) 1987-08-12
BE898893A (fr) 1984-05-30
NO164909B (no) 1990-08-20
NL8420026A (nl) 1985-12-02
SE8504544L (sv) 1985-10-02
NO853860L (no) 1985-09-30
DK448685A (da) 1985-10-02
ATA906284A (de) 1990-12-15
DE3490656C2 (fr) 1989-04-20
SE8504544D0 (sv) 1985-10-02
GB8521526D0 (en) 1985-10-02
CH667659A5 (de) 1988-10-31
DK448685D0 (da) 1985-10-02
NO164909C (no) 1990-11-28
GB2162853A (en) 1986-02-12

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