EP2601254A1 - Mélanges polymères contenant des halogènes - Google Patents

Mélanges polymères contenant des halogènes

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Publication number
EP2601254A1
EP2601254A1 EP11736113.9A EP11736113A EP2601254A1 EP 2601254 A1 EP2601254 A1 EP 2601254A1 EP 11736113 A EP11736113 A EP 11736113A EP 2601254 A1 EP2601254 A1 EP 2601254A1
Authority
EP
European Patent Office
Prior art keywords
component
polymer mixture
polymer
mixture according
compound
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Withdrawn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
EP11736113.9A
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German (de)
English (en)
Inventor
Ingo Bellin
Klaus Hahn
Gregor Haverkemper
Horst Fischer
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Priority to EP11736113.9A priority Critical patent/EP2601254A1/fr
Publication of EP2601254A1 publication Critical patent/EP2601254A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • 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
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • 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
    • C08K5/02—Halogenated hydrocarbons

Definitions

  • the invention relates to polymer blends containing at least one polymer, at least one organic halogenated compound such as halogenated flame retardants, and at least one further compound for thermal stabilization of the organic halogenated compound.
  • Polymers are now used in many areas as materials in which the fire behavior of the materials used is of essential importance, for example in the construction sector, in living and clothing textiles or in vehicle construction. Therefore, the polymers used must also meet the applicable fire protection requirements.
  • a class of flame retardants commonly used in polymers are the halogenated organic flame retardants.
  • the effect of the halogenated flame retardants is that they release halogen radicals at elevated temperatures.
  • the halogen radicals interrupt the radical chain reactions that occur during combustion by trapping the radicals that support combustion. Hydrogen halides also frequently occur as intermediates.
  • a problem with the use of the halogenated organic flame retardant compounds in polymers is that the polymers often have to be mixed with flame retardants at elevated temperatures in order to achieve a uniform distribution of the flame retardants in the polymer matrix.
  • the polymers are often processed in forming processes that are carried out at elevated temperatures. At the temperatures required, the decomposition of a part of the halogenated flame retardants used often takes place. In particular in extrusion processes, the thermosensitive flame retardants are exposed to significant temperature loads due to the residence time and due to local, shear-induced temperature peaks. The additives can be degraded and the effective amount in the product can be reduced.
  • the hydrogen halide formed during the degradation of the additives has a corrosive effect on the systems used. It has therefore begun to add a stabilizer to the polymers in addition to the halogenated organic flame retardant, which decomposition of the Flame retardant in the processing of the polymers should prevent or at least reduce.
  • WO 2005/103133 A1 describes, for example, the addition of a thermally stabilizing amount of at least one acrylate or methacrylate polymer which melts in a temperature range from 50 to 150 ° C.
  • US 2003/0195286 A1 discloses a flame retardant additive composition with improved thermal stability containing an alkyl tin mercaptoalkanoate and a zeolite.
  • zinc compounds such as zinc stearate are used in combination with zeolites as thermal stabilizers.
  • EP 0 848 727 B1 describes flame retardant compositions containing hexabromocyclododecane and at least one halogenated epoxy resin as thermal stabilizer for the hexabromocyclododecane.
  • the hydrogen halides formed on decomposition of the halogenated flame retardants can be trapped by acid scavengers, as mentioned, for example, in WO 2009/065880.
  • acid scavengers for example, hydroxides of magnesium, aluminum or zinc or else alkali metal carbonates or alkali metal hydrogen carbonates are used for this purpose.
  • thermal stabilizers for the organic halogenated flame retardants there is a need for further thermal stabilizers which exhibit good activity on the stability of the flame retardants in the processing of the polymers and at the same time do not adversely affect the protective effect of the flame retardants.
  • the halogenated flame retardant and thermal stabilizer-treated polymers should continue to show good fire performance. This object is achieved by the use of compounds having a Versei- number of 80 to 300 mg KOH / g and an OH number of 200 to 800 mg KOH / g for the stabilization of halogenated flame retardants and by polymer blends containing (a) at least one polymer .
  • An object of the present invention is the use of compounds (c) having a saponification number of 80 to 300 mg KOH / g and an OH number of 200 to 800 mg KOH / g for the stabilization of halogenated organic compounds, in particular halogenated organic flame retardants. These compounds are used as component (c) in the polymer mixtures according to the invention.
  • (c) preferably has a saponification number of 100 to 250 mg KOH / g, particularly preferably 120 to 220 mg KOH / g. Also according to the invention preferably (c) has a hydroxyl number of 200 to 600 mg KOH / g, and more preferably from 220 to 500 mg KOH / g. Very particularly preferably, (c) has a saponification number of 100 to 220 mg KOH / g and an OH number of 200 to 600 mg KOH / g, and particularly preferably a saponification number of 120 to 200 mg KOH / g and an OH number of 220 to 500 mg KOH / g.
  • the hydroxyl number is determined according to the invention according to the German DIN standard DIN 53240.
  • the OH number means the amount of potassium hydroxide in milligrams, which is equivalent to the amount of acetic acid that reacts with the acetylation of one gram of the sample substance with this.
  • the saponification number is determined according to the invention according to DIN EN ISO 3681.
  • the saponification is the formation of potassium salts from derivatives of organic acids. and the saponification value as the amount of potassium hydroxide (KOH) in milligrams needed to saponify one gram of the product tested.
  • acid and / or epoxide groups are present in the compound to be investigated, these groups must be quantified in advance and taken into account in the determination of the hydroxyl or saponification number.
  • the amount of epoxide groups can e.g. are determined according to ASTM D 1652-04, the amount of acid groups can be determined, for example, according to DIN EN 12634.
  • the at least one compound used as component (c) preferably contains at most 1% by weight, preferably at most 0.5% by weight and particularly preferably at most 0.2% by weight of epoxide groups, based on the total weight of the compound according to ASTM 1652-04.
  • the epoxy group is understood as meaning the entire epoxide radical of the formula -C (H) OC (H 2 ) having a molecular weight of 43 g / mol.
  • the at least one compound used as component (c) has an acid number of at most 15 mg KOH / g, preferably at most 10 mg KOH / g and particularly preferably at most 5 mg KOH / g, determined according to DIN EN 12634.
  • the at least one compound used as component (c) most preferably contains at most the above-stated amounts of epoxide groups and at most the acid numbers given above.
  • the at least one compound used as component (c) contains carboxylic acid ester groups and free OH groups. According to a particularly preferred embodiment of the invention, the at least one compound used as component (c) contains as functional groups only OH and carboxylic ester groups. In this case, component (c) is very particularly preferably selected from polyesters which have been partially esterified with carboxylic acids.
  • a polyol according to the invention is a compound having at least two OH groups.
  • these include, for example, dihydric alcohols such as ethylene glycol, 1, 2-propylene glycol, 1, 3-propylene glycol, 1, 4-butanediol, 1, 3-butanediol, alcohols having 3 OH groups such as trimethylolmethane and glycerol, tetrahydric alcohols such as Threit, erythritol, Sorbitan (cyclic anhydride of sorbitol) and pentaerythritol, pentahydric alcohols such as arabitol, adonitol and xylitol, hexahydric alcohols such as sorbitol, mannitol and dicitric acid and sugars such as sucrose, trehalose and maltose.
  • dihydric alcohols such as ethylene glycol, 1, 2-propylene glycol, 1, 3-propylene glycol, 1, 4-
  • sorbitol is also called sorbitol, mannitol also mannitol, erythritol also erythrol, threitol also threitol, xylitol also xylitol, arabitol also arabitol and pentaerythritol also pentaerythritol.
  • Partially esterified means that at least one OH group is esterified and at least one OH group is free.
  • the carboxylic acid component of the partially esterified polyols for example, low fatty acids having 1 to 6 carbon atoms such as formic acid, acetic acid, propionic acid, acrylic acid, butyric acid, isobutyric acid, crotonic acid, pentanoic acid, isovaleric acid, hexanoic acid, sorbic acid, middle fatty acids having 7 to 1 1 carbon atoms and higher fatty acids with 12 to 30 carbon atoms are used.
  • low fatty acids having 1 to 6 carbon atoms such as formic acid, acetic acid, propionic acid, acrylic acid, butyric acid, isobutyric acid, crotonic acid, pentanoic acid, isovaleric acid, hexanoic acid, sorbic acid, middle fatty acids having 7 to 1 1 carbon atoms and higher fatty acids with 12 to 30 carbon atoms are used.
  • the medium and higher fatty acids include, for example, enanthic acid (C7), caprylic acid (C8), pelargonic acid (C9), capric acid (C10), undecanoic acid (C11), lauric acid (C12), tridecanoic acid (C13), myristic acid (C14), pentadecanoic acid (C14).
  • the at least one compound used as component (c) is selected from polyesters which are partially esterified with carboxylic acids
  • the partially esterified esters can be compounds of a certain carboxylic acid with a particular polyol; mixed esters of different carboxylic acids with one kind of polyols can also be mixed Esters of a carboxylic acid with different polyols and mixed esters of different carboxylic acids are used with different polyols.
  • (c) is selected from glycerol partially esterified with carboxylic acids, sorbitol, mannitol, sucrose, maltose, trehalose, sorbitan and mixtures thereof.
  • Component (c) is particularly preferably selected from polyesters which are partially esterified with fatty acids, particularly preferably from polyesters partially esterified with fatty acids with C 6 to C 24.
  • the at least one compound used as component (c) is particularly preferably selected from the group consisting of glycerol, in each case partially esterified with carboxylic acids with C6 to C24, sorbitan, trehalose, sucrose, maltose, sorbitol, mannitol and mixtures thereof ,
  • component (c) is selected from sorbitan monopalmitate, sorbitan monostearate, sorbitan monooleate, sorbitan monolaurate, Glycerol monopalmitate, glycerol monostearate, glycerol monooleate, glycerol monolaurate and mixtures thereof.
  • component (c) it is possible to use one of the abovementioned compounds, but also mixtures of two or more thereof.
  • the polymer mixtures according to the invention contain as component (b) at least one halogen-containing organic compound, which is preferably a halogenated organic flame retardant.
  • Halogen-containing or halogenated in the context of the present invention means that the corresponding compound contains at least one substituent selected from the group consisting of F, Cl, Br and I.
  • the at least one organic halogen-containing compound used as component (b) is preferably selected from the group consisting of bromine-containing compounds and compounds containing bromine and chlorine, in particular bromine-containing flame retardants and bromine- and chlorine-containing flame retardants.
  • component (b) preferably has a halogen content of at least 30% by weight, more preferably at least 40% by weight and most preferably at least 50% by weight, based on the organic halogen-containing compound.
  • Component (b) is preferably selected from the group consisting of bromine-containing flame retardants and bromine- and chlorine-containing flame retardants whose bromine content or bromine and chlorine content is at least 30% by weight, more preferably at least 40% by weight and very particularly preferably at least 50 wt .-%, based on the organic halogen-containing compound, is. Particularly preferred are aliphatic, cycloaliphatic and aromatic bromine-containing and chlorine and bromine-containing compounds.
  • aliphatic, cycloaliphatic and aromatic bromine compounds having a bromine content of at least 30 wt .-%, more preferably at least 40 wt .-% and most preferably at least 50 wt .-%, based on the organic halogen-containing compound such as hexabromocyclodecane, Pentabrommonochlorcyclohexan , Pentabromochlorochlorocyclohexane, Pentabromphenylallylether, Tetrabrombisphenol-A and its ethers, tetrabromophthalic anhydride,
  • component (b) is particularly preferably selected from hexabromocyclododecane, bromine-containing styrene-butadiene Copolymers and bromine and chlorine-containing styrene-butadiene copolymers.
  • the styrene-butadiene copolymers are preferably present in the form of block polymers.
  • the component (b) is usually in amounts of 0.05 to 5 wt .-%, preferably from 0, 1 to 4 wt .-% and particularly preferably from 0.5 to 2.5 wt .-%, based on the total weight of components (a), (b) and (c) used.
  • the weight ratio of component (c) to at least one organic halogen-containing compound is preferably in the range of 0.1 to 10.
  • Component (c) is preferably used in an amount of 0.05 to 5 wt.%, Preferably 0.1 to 1.5 4 wt .-% and particularly preferably from 0.1 to 2.5 wt .-%, based on the total weight of components (a), (b) and (c) used.
  • the polymer mixture contains at least one polymer as component (a), preferably the at least one polymer used as component (a) is thermoplastic.
  • thermoplastics are usually uncrosslinked linear or branched polymers, which can be repeatedly transferred by temperature change in a flowable or deformable state and solidified again.
  • Thermoplastic polymers are often processed at higher temperatures in a flowable or deformable state, for example by injection molding and extrusion. Especially in these processes, the flame retardants contained in the polymers must be stabilized.
  • component (a) is preferably selected from homopolymers and copolymers which contain vinylaromatic monomer units, in particular selected from homopolymers and copolymers which are composed of vinylaromatic monomer units.
  • vinyl aromatic monomer units are styrene and C 1 -C 4 -alkyl-substituted styrenes, such as alphamethylstyrene, betamethylstyrene, o-methylstyrene, m-methylstyrene, p-methylstyrene and ethylstyrene.
  • Styrene homopolymers and styrene copolymers are preferably used as components (a), particularly preferably glass-clear polystyrene (GPPS), impact polystyrene (HIPS), anionically polymerized polystyrene or impact polystyrene (A-IPS), styrene- ⁇ -methylstyrene copolymers, acrylonitrile-butadiene-styrene polymer ( ABS), styrene-acrylonitrile copolymers (SAN), acrylonitrile-styrene-acrylic ester copolymers (ASA), methacrylate-butadiene-styrene copolymers (MBS), methyl methacrylate-acrylonitrile-butadiene-styrene copolymers (MABS) or mixtures thereof or Mixtures of the aforementioned styrenes and homopolymers and copolymers with polyphenylene ether (PPE
  • the polymers and copolymers containing vinylaromatic monomer units mentioned can be used to improve the mechanical properties or for the temperature resistance optionally using compatibilizers with other thermoplastic polymers such as polyamine (PA), polyolefins such as polypropylene (PP) or polyethylene (PE), polyacrylates such as polymethyl methacrylate (PMMA ), Polycarbonate (PC), polyester esters such as polyethylene terephthalate (PET) or polybutylene terephthalate (PBT), polyethersulfones (PES), polyether ketones or polyether sulfides (PES) or mixtures thereof, usually in proportions of not more than 30% by weight in total , preferably in the range of 1 to 10 wt .-%, based on the total polymer mixture.
  • PA polyamine
  • PE polyolefins
  • PE polypropylene
  • PE polyethylene
  • PMMA polyacrylates
  • PC Polycarbonate
  • PET polyethylene terephthalate
  • PBT polybutylene
  • mixtures in the stated quantitative range are also possible, for example, with hydrophobically modified or functionalized polymers or oligomers, rubbers such as polyacrylates or polydienes, for example styrene-butadiene block copolymers or biodegradable aliphatic or aliphatic / aromatic copolyesters.
  • hydrophobically modified or functionalized polymers or oligomers rubbers such as polyacrylates or polydienes, for example styrene-butadiene block copolymers or biodegradable aliphatic or aliphatic / aromatic copolyesters.
  • Suitable compatibilizers are e.g. Maleic anhydride-modified styrene copolymers, polymers containing epoxy groups or organosilanes.
  • component (a) is selected from expandable / expanded styrene polymers.
  • This may be, for example, so-called expandable polystyrene (EPS) or extruded polystyrene foam (XPS).
  • Expandable / expanded styrene polymers generally contain one or more blowing agents in a homogeneous distribution in a proportion of 2 to 10% by weight, preferably 3 to 7% by weight, based on the polystyrene.
  • Suitable blowing agents are the physical blowing agents commonly used in EPS or XPS, such as aliphatic hydrocarbons having 2 to 7 carbon atoms, alcohols, ketones, ethers, carbon dioxide, water or halogenated hydrocarbons. Preference is given to using isobutane, n-butane, isopentane, n-pentane for EPS and C0 2 , ethanol, water and fluorinated hydrocarbons for XPS.
  • the polymer mixture according to the invention preferably contains
  • component (c) 0.05 to 5 parts by weight of component (c).
  • the polymer mixture contains
  • component (c) 0.1 to 4 parts by weight of component (c), and most preferably
  • component (c) 0.1 to 2.5 parts by weight of component (c).
  • the weight percentages are based on the total weight of components (a), (b) and (c).
  • the polymer mixture may comprise further additives customary in polymers, for example fillers, plasticizers, soluble and insoluble inorganic and / or organic dyes and pigments, athermanous compounds (eg graphite, carbon black, aluminum powder), UV Stabilizers and processing aids.
  • Their proportion is generally 0 to 45, preferably 0 to 20, in particular 0 (when present 0.2) to 10 wt .-%, based on the total weight of components (a), (b) and (c).
  • the preparation of the polymer mixtures according to the invention is carried out according to methods known per se by mixing the components. It may be advantageous to premix individual components. It is also possible to mix the components in solution or suspension while removing the solvent / suspension medium.
  • the evaporation of the solvent mixtures can be carried out, for example, in evaporation extruder.
  • the mixing of the components takes place in substance at temperatures in which the polymer or polymers used are meltable, for example by co-extrusion, kneading or rolling of the components.
  • Expandable propellant-containing styrenic polymers can be prepared in the extruder, for example, by the process described in WO 2009/065880 A2 and subsequently granulated.
  • the components (b) and (c) are preferably metered together.
  • the two components can either be initially introduced with the styrene polymer, but can also be dispersed together via a side stream extruder or in the form of a suspension and metered into the mainstream stream of the blowing agent-containing styrene polymer melt and extruded together through a die plate, preferably with subsequent sub-water granulation.
  • the process for the preparation of the polymer mixtures according to the invention thus comprises the steps
  • component (i) providing the component (a), (ii) adding component (b) and (c) to component (a) and / or separately
  • Another object of the present invention is the use of the polymer blends described above for the production of films, semi-finished products, foams, fibers and moldings.
  • the novel polymer blends can be processed by the known process of thermoplastic processing, for example by extrusion, injection molding, calendering, blow molding or sintering.
  • the invention also relates to the corresponding films, semi-finished products, foams, fibers and shaped articles containing a polymer mixture as described above.
  • Another object of the present invention is the use of compounds (c) having a saponification number of 80 to 300 mg KOH / g and an OH number of 200 to 800 mg KOH / g for the stabilization of halogenated flame retardants.
  • halogenated organic flame retardant (b) and optionally thermal stabilizer were placed in a test tube, which was closed with a rubber stopper, which had two glass tubes. Nitrogen was introduced through one glass tube and discharged through the second glass tube. The exhaust gas flow was passed through distilled water and the conductivity of the water was recorded as a function of time.
  • the hydrogen halide forming upon decomposition of the halo-containing flame retardants is introduced into the water by the carrier gas stream and increases its conductivity.
  • the stability time t st is used, which indicates the time after which the conductivity has changed by 50 ⁇ 5 * ⁇ 1 .
  • halogenated organic compounds used were the flame retardants hexabromocyclododecane (HBCD, CD 75-P from Chemtura Co.) and a brominated styrene-butadiene diblock copolymer (FR1, M w : 56000 g / mol, styrene block 37% by weight, 1, 2 - Vinyl content 72% by weight; prepared according to Example 8 of WO 2007/058736, with a Br content of about 60% by weight).
  • HBCD hexabromocyclododecane
  • FR1 brominated styrene-butadiene diblock copolymer
  • thermal stabilizers zinc stearate (Sigma Aldrich), hydrotalcite (Kyowa Chemical Industry Co.), Al (OH) 3 (Nabaltec AG), glycerol tristearate (Sigma Aldrich), zeolite A (Sigma Aldrich), glycerol (Sigma Aldrich), glycidyl methacrylate Copolymer (Joncryl ADR-4368 BASF SE), brominated epoxy resin (F2200 HM, ICL Industrial Products), Mg (OH) 2 (Albemerle Co.), sorbitan monolaurate (Sigma Aldrich), glycerol monostearate (Evonik Goldschmidt), glycerol monolaurate (Danisco) sorbitan monostearate ( Sigma Aldrich), sorbitan monooleate (Sigma Aldrich), sorbitan monopalmitate (Sigma Aldrich) and glycerol monooleate (Sigma Aldrich).
  • the corresponding expandable polystyrenes were first prepared by mixing 7% by weight of n-pentane into a polystyrene melt of PS 148G (viscosity number VZ: 83 ml / g, BASF SE). After cooling the propellant-containing polystyrene melt of originally 260 C ° to a temperature of 190 ° C, a polystyrene melt containing HBCD mixed with the respective stabilizer, mixed via a side stream extruder into the main stream. The mixture of Polystyrene melt, blowing agent, flame retardant and thermal stabilizer was conveyed at a rate of 60 kg / h through a die plate with 32 holes (nozzle diameter 0.75 mm).
  • HBCD flame retardant
  • the granules of expandable polystyrene were prefoamed by the action of flowing steam and, after 12 hours of storage, were sealed by further treatment with steam in a closed mold to form foam blocks with a density of 15 kg / m 3 .
  • the fire behavior of the foam panels was determined after storage for 72 hours at a foam density of 15 kg / m 3 in accordance with DIN 4102.
  • This test represents the stress due to a small, defined flame (match flame). Under this stress, the flammability and the flame propagation must be limited within a certain time. The test is carried out in a burner box equipped with a burner. The sample is flamed for 15 seconds and then the flame is removed. The duration between the start of the flame and the time at which the flame tip of the burning sample reaches a certain mark is measured, unless the flame goes out by itself.
  • the compounds having a saponification number of 80 to 300 mg KOH / g and an OH number of 200 to 800 mg KOH / g are very suitable for the stabilization of organic halogenated compounds.
  • the compounds to be used according to the invention show a significantly greater extension of time until the predetermined amount of halogenated compound is decomposed than the other thermal stabilizers known from the prior art.
  • V5 glycerol tristearate
  • V10 glycerin
  • V7 equal proportions of glycerol tristearate and glycerol
  • magnesium hydroxide which has proved to be the best stabilizer not according to the invention with respect to the stabilization of HBCD (see A, V11), reduces the flame resistance of expanded polystyrene foam equipped therewith to the extent that this polystyrene foam does not pass the B2 test exists (B, V12).
  • B, V12 the flame resistance of expanded polystyrene foam equipped therewith to the extent that this polystyrene foam does not pass the B2 test exists (B, V12).
  • B, V12 the known as a thermal stabilizer from the prior art hydrotalcite.
  • Polystyrene foam finished according to the invention with glycerol monostearate shows very good stabilization (see A, Example 5) and passes the B2 test (B, Example 9).

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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)
  • Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)

Abstract

La présente invention concerne des mélanges polymères contenant au moins un polymère, au moins un composé organique halogéné tel que des agents ignifuges halogénés, ainsi qu'au moins un autre composé de stabilisation thermique du composé organique halogéné, qui présente un degré de saponification de 80 à 300 mg KOH/g et un nombre OH de 200 à 800 mg KOH/g.
EP11736113.9A 2010-08-05 2011-07-28 Mélanges polymères contenant des halogènes Withdrawn EP2601254A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP11736113.9A EP2601254A1 (fr) 2010-08-05 2011-07-28 Mélanges polymères contenant des halogènes

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP10171986 2010-08-05
EP11736113.9A EP2601254A1 (fr) 2010-08-05 2011-07-28 Mélanges polymères contenant des halogènes
PCT/EP2011/063012 WO2012016906A1 (fr) 2010-08-05 2011-07-28 Mélanges polymères contenant des halogènes

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EP2601254A1 true EP2601254A1 (fr) 2013-06-12

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EP (1) EP2601254A1 (fr)
RU (1) RU2013109371A (fr)
WO (1) WO2012016906A1 (fr)

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