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WO2015102302A1 - Copolymère de poly(téréphthalate de cyclohexylènediméthylène) présentant une résistance aux chocs, une résistance à la décoloration et une réflexibilité améliorées et produit de résine moulé formé à partir de ce dernier - Google Patents

Copolymère de poly(téréphthalate de cyclohexylènediméthylène) présentant une résistance aux chocs, une résistance à la décoloration et une réflexibilité améliorées et produit de résine moulé formé à partir de ce dernier Download PDF

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Publication number
WO2015102302A1
WO2015102302A1 PCT/KR2014/012830 KR2014012830W WO2015102302A1 WO 2015102302 A1 WO2015102302 A1 WO 2015102302A1 KR 2014012830 W KR2014012830 W KR 2014012830W WO 2015102302 A1 WO2015102302 A1 WO 2015102302A1
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Prior art keywords
copolymer
poly
terephthalate
group
weight
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PCT/KR2014/012830
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English (en)
Korean (ko)
Inventor
이수민
김종량
김태영
백지원
이부연
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SK Chemicals Co Ltd
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SK Chemicals Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • C08L83/10—Block- or graft-copolymers containing polysiloxane sequences
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
    • C08G63/695—Polyesters containing atoms other than carbon, hydrogen and oxygen containing silicon
    • C08G63/6954—Polyesters containing atoms other than carbon, hydrogen and oxygen containing silicon derived from polxycarboxylic acids and polyhydroxy compounds
    • C08G63/6956—Dicarboxylic acids and dihydroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/42—Block-or graft-polymers containing polysiloxane sequences
    • C08G77/445—Block-or graft-polymers containing polysiloxane sequences containing polyester sequences

Definitions

  • the present invention relates to a poly (cyclonuclear dimethyl dimethylene terephthalate) copolymer having improved layer strength, discoloration resistance and reflectivity and a resin molded article formed therefrom.
  • Poly (alkylene terephthalate) (Poly (alkylene terephthalate)) has excellent physical properties such as wear resistance, durability, thermal stability, and is widely used as a material for fibers, films, molded articles and the like.
  • Such poly (alkylene terephthalate) is typically poly (ethylene terephthalate) (hereinafter referred to as 'PET'), poly (butylene terephthalate) (P y (butylene terephthalate), referred to as " ⁇ " ), Poly (cyclonuylene dimethylene terephthalate) (Poly (1,4-cyclohexylenedimethylene terephthalate), hereinafter 'PCT') and the like have been commercialized.
  • the increasing PCT is attracting attention as a new material that can overcome the problems of polyester materials such as PET and PBT, namely, deterioration of moldability due to slow crystallization rate and limitation of use due to low thermal deformation silverness.
  • PCTs are composed of terephthalic acid ( ⁇ ') or dimethyl terephthalate (, ⁇ ).
  • Ester of 1,4-cyclohexanedimethanol hereinafter referred to as 'CHDM'
  • crystalline polyesters produced by transesterification and polycondensation reactions.
  • PCT has excellent heat resistance, chemical resistance, hygroscopicity, and flowability compared to general-purpose polyesters PET and PBT, among which heat deflection temperature7> 245 ⁇ 260 ° C, continuous (continuous-use) temperature 7 ⁇ 130 to 150 ° C. has a characteristic. Accordingly, PCT is liquid crystalline Super engineering, the only non-wholly aromatic polyester commercialized except for polyester, means metal-substituted engineering plastics such as polyamide, polyphenylene sulfide, liquid crystalline polymer Belongs to plastic group.
  • PCTs are used in electronic materials where surface mounting technology is advanced at high temperatures, or in light emitting diodes (LEDs) that are constantly exposed to heat and light while the product is in use . It is applied to the use of a housing or a reflector.
  • LEDs light emitting diodes
  • the present invention is to provide a poly (cyclonuclear dimethyl dimethylene terephthalate) copolymer which enables the provision of a resin molded article having excellent discoloration resistance and reflectivity while having improved impact strength.
  • the present invention is to provide a resin molded article formed from the poly (cyclonuclear silane dimethylene terephthalate) copolymer.
  • R 1 to R 4 are each independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 18 carbon atoms;
  • D 1 and D 2 are each independently a C1 to "20 aliphatic hydro car invoke, or cycloaliphatic having 4 to 10 carbon atoms dihydro car invoking gt;
  • L 1 and L 2 are each independently a hydroxy group or a hydroxy phenyl group
  • n and m is an integer of from 5 to 300 r each independently.
  • the repeating units derived from the polysiloxane compound may be included as 0.1 to 30 parts by weight 0/0 of the total weight of the copolymer.
  • the poly (cyclonuclearylenedimethylene terephthalate) copolymer can have a weight average molecular weight of 10,000 to 100,000 and a number average molecular weight of 10,000 to 50,000.
  • the esterification reaction is based on 100 parts by weight of a diol compound containing 1,4-cyclonucleic acid dimethane, a dicarboxylic acid compound containing terephthalic acid, dimethyl terephthalate or a mixture thereof 90 to 90 1 10 parts by weight, and may be carried out using a composition comprising 0.01 to 10 parts by weight of the polysiloxane compound.
  • the composition for the esterification reaction trimethyl phosphate (trimethyl phosphate), triethyl phosphate (triethyl phosphate), triphenyl phosphate (triphenyl phosphate), triethyl phosphono acetate (triethyl
  • phosphorus stabilizers selected from the group consisting of phosphonoacetate, phosphoric acid, and phosphorous acid may be further included in an amount of 0.001 to 5 parts by weight based on 100 parts by weight of the diol compound.
  • the esterification reaction may be performed for 120 to 600 minutes under a temperature of 230 to 290 ° C and a pressure of 0.01 to 3.0 kg / cm 2 .
  • the catalyst is titanium oxide, titanium chelate compound, tetra-n-propyl titanate, tetra-isopropyl titanate, tetra-butyl titanate, tetra-isobutyl titanate, and butyl-isopropyl It may be one or more titanium-based catalyst selected from the group consisting of titanate.
  • the polycondensation reaction may be performed for 60 to 360 minutes under a temperature of 290 to 320 ° C and a pressure of 0.1 to ZO torr.
  • the resin molded article formed from the said poly (cyclonuclear silane dimethylene terephthalate) copolymer is provided.
  • the resin molded article may exhibit an impact strength (ASTM D256) of 20 J / m or more for a 1/8 "thick specimen at 25 ° C.
  • the resin molded article may exhibit a physical property of Color L * -b * value is 95% or more compared to the initial value under the phase silver after standing for 48 hours at 140 ° C.
  • the resin molded article may exhibit physical properties of reflectance of at least 95% of the initial value at room temperature after leaving for 48 hours at 14 CTC.
  • Such a resin molded article can be used for the purpose of the housing or reflector for LED.
  • a poly (cyclonuylene dimethyl dimethylene terephthalate) copolymer according to specific embodiments of the present invention, a method for preparing the same, and a resin molded article formed therefrom will be described in more detail.
  • Poly (cyclonuclear dimethyl dimethylene terephthalate) copolymer comprising a repeating unit derived from a polysiloxane compound represented by the following formula (2)
  • R 1 to R 4 are each independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 18 carbon atoms;
  • D 1 and D 2 are each independently an aliphatic hydrocarbyl group having 1 to 20 carbon atoms, or an alicyclic hydrocarbyl group having 4 to 10 carbon atoms;
  • L 1 and L 2 are each independently a hydroxy group or a hydroxy phenyl group
  • n and m are each independently an integer of 5 to 300.
  • the PCT copolymer is a copolymer including a basic repeating unit of the PCT as shown in Formula 1 and a repeating unit by a polysiloxane compound as shown in Formula 2.
  • Such PCT copolymers have improved intrinsic properties compared to conventional PCTs, and thus are improved without additional additives, as compared to conventionally known PCT compounds (i.e., compositions comprising additives applied for the purpose of improving PCT and physical properties). It is possible to provide a resin molded article having physical properties (in particular, improved impact strength, discoloration resistance and reflectivity, etc.).
  • the repeating unit of Chemical Formula 1 may include a diol compound (eg, 1,4-cyclohexanedimethane) and a dicarboxylic acid compound (eg, terephthalic acid, dimethyl terephthalate Or a mixture thereof) and the polycondensation reaction.
  • a diol compound eg, 1,4-cyclohexanedimethane
  • a dicarboxylic acid compound eg, terephthalic acid, dimethyl terephthalate Or a mixture thereof
  • n is not particularly limited. However, according to an embodiment of the present invention, n may be 5 or more, preferably 5 to 300, or 5 to 200, or 5 to 150, or 5 to 100, which may be advantageous for securing physical properties of the PCT copolymer.
  • polysiloxane compound represented by Formula 2 is polycondensed together with the reaction product of the esterification reaction of the diol compound and the dicarboxylic acid compound, and the repeating unit derived therefrom may be included in the copolymer.
  • R 1 to R 4 are each independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 18 carbon atoms.
  • R 1 to R 4 are each independently an alkyl group such as methyl, ethyl, propyl or butyl; Or an aryl group such as a phenyl or naphthyl group, and the hydrogen atom included in the alkyl group and the aryl group is unsubstituted or substituted with an alkyl group having 1 to 5 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an aryl group having 6 to 10 carbon atoms, and the like. Can be.
  • D 1 and D 2 are each independently an aliphatic hydrocarbyl group having 1 to 20 carbon atoms, or an alicyclic hydrocarbyl group having 4 to 10 carbon atoms.
  • the D 1 and D 2 are each independently It may be an alkyl group having 1 to 5 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an aryl group having 6 to 10 carbon atoms.
  • L 1 and L 2 are terminal groups having a hydroxy group, and may each independently be a hydroxy group or a hydroxy phenyl group.
  • m is 5 or more, preferably 5 to 300, or 5 to 200, or 5 to 150, or 5 to 100, and the expression of the effect of introducing the repeating unit derived from the polysiloxane compound and the PCT aerial It may be advantageous to secure the properties of the coalescence.
  • the polysiloxane compound represented by Formula 2 may have a weight average molecular weight of 500 to 15,000, preferably 1,000 to 15,000, or 1,000 to 12,000, according to the introduction of repeating units derived from the polysiloxane compound. It may be advantageous to express the effect and to secure the physical properties of the PCT copolymer.
  • the repeating unit derived from the polysiloxane compound is 0.1 to 30 weight 0 /., Or 0.1 to 25 weight%, or 1 to 20 weight 0 / or 1 to 15 of the total weight of the copolymer it is preferably included in a weight 0/0.
  • the content ratio of the repeating unit is preferably adjusted in the above range.
  • Such poly (cyclonucleosildimethylene terephthalate) copolymers have a weight average molecular weight of 10,000 to 100,000, or 30,000 to 8,000; Having a number average molecular weight of 10,000 to 50,000, or 15,000 to 35,000 may be advantageous for the expression of suitable mechanical properties.
  • the poly (cyclonucleosildimethylene terephthalate) copolymer may have an intrinsic viscosity of 1.1 dl / g or less, or 0.5 to 1.0 dl / g, which may be advantageous for ensuring proper processability.
  • the esterification reaction the esterification reaction
  • Dialkyl compounds containing 1,4-cyclonucleic acid dimethane and dicarboxylic acid compounds including terephthalic acid, dimethyl terephthalate or a mixture thereof can be mainly used.
  • esterification reaction includes ethylene glycol, diethylene glycol,
  • Diol compounds such as 1,4-butanediol, 1,3-propane diol and neopentyl glycol; Isophthalic acid, naphthalene 2,6-dicarboxylic acid, 2,6-naphthalenedicarboxylic acid, dimethylisophthalate, dimethyl naphthalene 2,6-dicarboxylic acid, dimethyl 2,6-naphthalenedicarboxylate Dicarboxylic acid compounds such as may be used together.
  • the diol compound 80 mol% or more of 1,4- cyclonucleic acid dimethane is used as the diol compound, and terephthalic acid, dimethyl terephthalate or a mixture thereof is used as the dicarboxylic acid compound. Preference is given to using at least 80 mol%.
  • the esterification reaction is 90 to 1 10 parts by weight, or 80 to 100 parts by weight, or 75 to 90 parts by weight of the dicarboxylic acid compound relative to 100 parts by weight of the diol compound It is preferably carried out using the composition comprising.
  • the polysiloxane compound may be mixed with 0.01 to 10 parts by weight, or 0.1 to 10 parts by weight, or 1 to 5 parts by weight based on 100 parts by weight of the diol compound used in the esterification reaction. That is, the polysiloxane, while fully expressing the effect of improving the stratification strength according to the introduction of repeating units derived from the polysiloxane compound, may include a problem that it may be impossible to discharge from the inside of the reactor to the outside during the manufacturing process when the excess amount of the repeating units is included. It is preferable that the addition amount of a compound is adjusted in the above-mentioned range.
  • the esterification reaction of the catalyst can be performed in the presence.
  • the titanium-based catalyst is titanium oxide, titanium chelate compound, tetra-n-propyl titanate, tetra-isopropyl titanate, tetra-n-butyl titanate, tetra-isobutyl titanate, and butyl- At least one compound selected from the group consisting of isopropyl titanate.
  • the titanium-based catalyst is preferably adjusted so that the content of the titanium element contained in the catalyst relative to the weight of the final PCT copolymer is 20 ppm or less. That is, while inducing an appropriate polycondensation reaction, the amount of the catalyst in consideration of the yellowing of the resin (increased color-b) due to side reactions or the decrease in molecular weight of the resin due to side reactions may be caused when the excess amount of the catalyst is added. Is preferably adjusted in the above-described range.
  • a phosphorus stabilizer may be further used in the esterification reaction to ensure thermal stability.
  • phosphorus stabilizers include trimethyl phosphate, triethyl phosphate, triphenyl phosphate, triethyl phosphonoacetate, phosphoric acid, and phosphorous acid. It may be one or more compounds selected from the group consisting of.
  • the phosphorus stabilizer may be included in an amount of 0.001 to 5 parts by weight, or 0.01 to 5 parts by weight, 0.01 to 1 part by weight, based on 100 parts by weight of the compound, in order to sufficiently express the effect of the addition of the stabilizer. have.
  • the phosphorus stabilizer is preferably adjusted so that the content of phosphorus element included in the stable relative to the weight of the final PCT copolymer is 30 ppm or less. This is because when the content of the phosphorus-based stabilizer exceeds 30 ppm, the color of the copolymer may be deteriorated and the catalytic activity of the polycondensation reaction may be degraded, thereby affecting the reaction time and the degree of polymerization.
  • This esterification reaction can be carried out under conventional conditions, and preferably for 120 to 600 minutes under silver conditions of 230 to 290 ° C and pressure conditions of 0.01 to 3.0 kg / cm 2 .
  • the step of polycondensation reaction for the product obtained by the esterification reaction can be performed.
  • the polycondensation reaction can be carried out continuously with the esterification reaction.
  • the polycondensation reaction may be carried out under conventional conditions, preferably 60 to 360 minutes under a temperature of 290 to 320 ° C and a pressure of 0.1 to 2.0 torr.
  • a conventional resin processing process such as extruding the product of the condensation reaction to prepare pellets, and crystallizing the pellets to solid phase polymerization, may be necessary. May be included.
  • a resin molded article formed from the above-mentioned poly (cyclonuclear dimethyl dimethylene terephthalate) copolymer.
  • the resin molded article is formed using the PCT copolymer, as compared with resin molded articles formed using conventionally known PCT compounds (i.e., compositions comprising PCT and additives applied for the purpose of improving physical properties), It can exhibit improved physical properties (particularly improved impact strength, discoloration resistance and reflectivity) without the additive of. .
  • the resin molded article has a layer strength of 20 J / m or more, preferably 20 to 100 J / m, or 20 to 85 J / m, for a 1/8 "thick specimen at 25 ° C. (ASTM D256) Can be represented.
  • the resin molded article may exhibit excellent heat resistance and discoloration resistance after being left at 140 ° C. for 48 hours at a Color L * -b * value of 95% or more compared to the initial value at room temperature.
  • the resin molded article has a reflectance of 450 nm or more after being left at 140 ° C. for 48 hours at 95% or more of the initial value at room temperature, and can maintain excellent reflectivity even in a poor environment.
  • Such resin molded articles can be suitably used for applications such as housings for LEDs, reflectors for LEDs, and housings for various light emitting devices, which are continuously exposed to heat and light, and electronics for which surface mount technology is applied at high temperatures. It can also be applied to the field of materials.
  • the poly (cyclonuclear silane dimethylene terephthalate) copolymer according to the present invention exhibits excellent intrinsic physical properties, thereby enabling the provision of a resin molded article having improved impact strength, discoloration resistance and reflectivity without additional additives.
  • a resin molded article can maintain excellent initial properties even in an environment in which continuous heat and light are applied, and can be suitably used for applications such as a housing or reflector for an LED.
  • R 1 to R 4 are each methyl group, D 1 and D 2 are each a propylene group, L 1 and L 2 are each a hydroxy group, Mw 2,253), and about 0.15 g of titanium oxide based catalyst (Sachtleben's Hombifast PC
  • R 1 to R 4 are each a methyl group
  • D 1 and D 2 are each a propylene group
  • L 1 and L 2 are each a hydroxy group
  • Mw 2,253, and about 4.1 g of titanium oxide catalyst (Sachtleben Hombifast PC, 15% catalytic increase effective Ti ratio) was added to the reaction vessel, and the esterification reaction was carried out while the temperature was raised to 280 ° C for 3 hours at normal pressure. Subsequently, the polycondensation reaction was carried out for 150 minutes under the conditions of 300 ° C.
  • R 1 To R 4 are each a methyl group, D 1 and D 2 are each a propylene group, L 1 and L 2 are each a hydroxy group, Mw 2,253), and about 35.8 g of titanium oxide Catalysts (Sachtleben's Hombifast PC, Effective Ti Ratio in Catalysts
  • R 1 to R 4 are each a methyl group, D 1 and D 2 are each a propylene group, L 1 and L 2 are each a hydroxy group, Mw 2,253), and about 0.15 g of titanium oxide based A catalyst (Sachtleben's Hombifast PC, 15% effective Ti ratio in the catalyst) was added to the reactor, and the esterification reaction was performed by raising the temperature to 280 ° C for 3 hours at normal pressure.
  • a catalyst Sudleben's Hombifast PC, 15% effective Ti ratio in the catalyst
  • R 1 to R 4 are each a methyl group, D 1 and D 2 are each a propylene group, L 1 and L 2 are each a hydroxy group, Mw 1,418), and about 0.15 g of titanium oxide catalyst (Sachtleben's Hombifast PC, effective Ti ratio in the catalyst
  • R 1 to R 4 are each a methyl group
  • D 1 and D 2 are each a propylene group
  • L 1 and L 2 are each a hydroxy group, Mw 4,172)
  • about 0.15 g of titanium oxide based Catalyst (Sachtleben's Hombifast PC, Effective Ti Ratio in Catalyst
  • R 1 to R 4 are each a methyl group, D 1 and D 2 are each a propylene group, L 1 and L 2 are each a hydroxy group, Mw 9,178), and about 0.15 g of titanium oxide bran
  • a catalyst Sachtleben's Hombifast PC, 15% effective Ti ratio in the catalyst was added to the reactor and sublimed to 280 ° C for 3 hours at atmospheric pressure. The esterification reaction proceeded.
  • Effective Ti ratio of 1, 4-cyclohexanedimethanol (trans 70 %), about 1.5 kg of terephthalic acid, about 0.4 g of triethyl phosphate, and, about 0.15 g of the titanium oxide-based catalyst (Sachtleben Corporation Hombifast PC, the catalyst of from about 1.7 kg 15%) was added to the reactor, and the esterification reaction was performed while raising the temperature to 280 ° C for 3 hours at normal pressure. Subsequently, the product obtained by the esterification reaction was subjected to a condensation reaction for 150 minutes under conditions of 300 ° C. and 0.5 to 1 torr.
  • Equation 2 A was 0.247 as Huggins constant, and c was 1.2 g / dl as the concentration value.
  • Test Example 2 For each specimen prepared using the PCT resin obtained through the examples and comparative examples, the initial Color L -b * value at room temperature was measured according to the CIE LAB index. Then, the color L ' -b ' value over time after leaving the same specimen at 140 ° C was measured, and the results are shown in Table 1 and Table 2.
  • CIE LAB indicator was used for color measurement.
  • CIE LAB system is yellow to the human senses the colors - blue, green - "as defined by the color space coordinates, L 'in the CIE based on the opposite saekseol such as red brightness value (from 0 to 100; 0 is black, 100 is white ), a ' value is green-red ([+] is red based on 0, [-] is green), and b ' value is yellow-blue ([+] is yellow based on 0, [-] is Blue).
  • Notched Izod was measured according to ASTM D256 under 25 ° C. on a 1/8 "thick specimen prepared using each PCT resin obtained through Examples and Comparative Examples, and the results are shown in Table 5 below. Indicated. Table 5
  • the specimen using the PCT co-polymer according to the embodiments showed a high impact strength of 20 J / m or more, and has a layer strength of about 2 times improved compared to the specimen according to the comparative examples Confirmed. Furthermore, according to the embodiments
  • the specimen using PCT copolymer showed 95% or more of Cc) br L * -b * value and reflectance after aging, and it was confirmed that it can maintain high reflectance while maintaining excellent discoloration resistance compared to the comparative examples. It became.

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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)
  • Polyesters Or Polycarbonates (AREA)

Abstract

La présente invention concerne un copolymère de poly(téréphthalate de cyclohexylènediméthylène) et un produit de résine moulé formé à partir de ce dernier. Le copolymère de poly(téréphthalate de cyclohexylènediméthylène) selon la présente invention présente d'excellentes propriétés physiques intrinsèques et permet de fournir un produit de résine moulé ayant une résistance aux chocs, une résistance à la décoloration et une réflexibilité améliorées sans additifs particuliers. Le produit de résine moulé peut conserver d'excellentes propriétés physiques initiales même dans un environnement dans lequel chaleur et lumière sont continuellement appliquées, et peut ainsi être utilisé de manière appropriée pour des boîtiers de DEL, des réflecteurs et analogues.
PCT/KR2014/012830 2013-12-30 2014-12-24 Copolymère de poly(téréphthalate de cyclohexylènediméthylène) présentant une résistance aux chocs, une résistance à la décoloration et une réflexibilité améliorées et produit de résine moulé formé à partir de ce dernier Ceased WO2015102302A1 (fr)

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