WO2014173908A1 - Composition améliorée et son utilisation comme agent ignifugeant - Google Patents

Composition améliorée et son utilisation comme agent ignifugeant Download PDF

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WO2014173908A1
WO2014173908A1 PCT/EP2014/058154 EP2014058154W WO2014173908A1 WO 2014173908 A1 WO2014173908 A1 WO 2014173908A1 EP 2014058154 W EP2014058154 W EP 2014058154W WO 2014173908 A1 WO2014173908 A1 WO 2014173908A1
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group
radical
formula
chain
melamine
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PCT/EP2014/058154
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German (de)
English (en)
Inventor
Rudolf Pfaendner
Elke METSCH-ZILLIGEN
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Zylum Beteiligungsgesellschaft Mbh & Co. Patente Ii Kg
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Publication of WO2014173908A1 publication Critical patent/WO2014173908A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K21/00—Fireproofing materials
    • C09K21/06—Organic materials
    • C09K21/12—Organic materials containing phosphorus
    • 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
    • C08K5/01—Hydrocarbons
    • 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
    • C08K5/49—Phosphorus-containing compounds
    • C08K5/5399—Phosphorus bound to nitrogen

Definitions

  • the present invention relates to a composition which is particularly suitable as a flame retardant.
  • flame retardants are usually added to the plastic with the aim of preventing the ignition for a certain time or to significantly delay the spread of fire.
  • Traditional flame retardants are based on chlorine- and bromine-containing compounds (in conjunction with antimony trioxide), on phosphorus-containing and nitrogen-containing compounds and on inorganic hydroxides. In recent times, halogen-free flame retardant solutions are preferred for environmental reasons.
  • flame retardants there are a variety of flame retardants, which are usually used substrate-specific for a particular polymer and a specific application according to the underlying standards.
  • plastics z. B from the group of polyolefins, such as. As polypropylene or polyethylene, polystyrenes and polyurethanes. These have been particularly sensitive proved to be flammable. In particular, for applications in the field of household electronics, in the transport sector (cars, trains, aircraft, ships) or for building materials and furniture so there is a strong demand
  • Aluminum trihydroxide (ATH).
  • ATH Aluminum trihydroxide
  • phosphorus-containing heptazine derivatives are suitable as flame retardants for plastics, textiles, wood products, paper, cardboard, plasters, insulation materials, building material composites and polymeric foams.
  • Radical generators It has surprisingly been found that the combination of a phosphorus-containing heptazine derivative (a) with at least one compound (b) from the group of radical generators leads to a synergistic effect of the flameproofing effect.
  • compositions according to the invention since it allows the addition of radical generators to achieve an improved flame retardancy with reduced material costs.
  • the compounds (a) used are symmetrical phosphorus-containing heptazine derivatives represented by the formula (Ib),
  • R 1; R 2 , and R 3 independently represent a radical selected from the group a, consisting of a straight-chain or branched-chain (Ci-Ci 2 ) -alkyl radical, a (C 3 -C 7 ) -cycloalkyl radical, a straight-chain or branched-chain (Ci -C 2) alkenyl, a straight or branched (Ci-Ci 2) alkoxy, furyl, furanyl, benzofuranyl, thienyl, thiazolyl, benzothiazolyl, thiadiazolyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, pyrazinyl, benzothienyl, morpholinyl, thiomorpholinyl, Piperidinyl, piperazinyl, pyrrolidinyl, pyrimidinyl, imidazolinyl, pyrazolid
  • the group ⁇ comprises the above substituents in a form which have no halogen-containing groups.
  • the group ⁇ is therefore preferably in non-halogenated form.
  • the phosphorus-containing heptazine derivatives (a) used according to the invention are usually air-stable and colorless / white.
  • R 1; R 2 , and R 3 of the phosphorus-containing heptazine derivative (a) according to the above formula (lb) are each an aromatic radical which is above
  • Oxygen is bound, esp. -O-phenyl (phenoxy) or in each case m-kresyloxy, -1-naphthyloxy or 2-naphthyloxy or 2-biphenyloxy or 4-biphenyloxy.
  • the phosphorus-containing heptazine derivatives (a) which can also be referred to as melem phosphoranylides according to the invention can be the melamine, melamine or melon derivatives, by appropriate selection of the radicals with regard to the physical and chemical properties of the resulting links
  • This class of substances can be advantageously varied and thus tailored in a simple manner specifically for a particular application.
  • the inventively used phosphorus-containing heptazine derivatives (a) the phosphorus melamine, melamine and melon derivatives as part of a flame retardant composition so for example advantageous increased solubility of the derivative in a plastic to be protected as well as better adaptation the
  • Heptazine, melamine, melamine and melone derivatives have the advantage that they can be designed halogen-free with respect to a flame retardant with respect to the radicals Ri, R 2 and R 3 and thus in comparison to the halogen-containing radicals Ri, R 2 and R 3 and thus in comparison to the halogen-containing radicals Ri, R 2 and R 3 and thus in comparison to the halogen-containing radicals Ri, R 2 and R 3 and thus in comparison to the halogen-containing
  • the phosphorus-containing heptazine, melamine, melam and melone derivatives may also be in the form of oligomer or polymer, with the latter containing, for example, structural units which contain two or more bridging phosphine groups or
  • Phosphazene linkages are exemplified as shown in formula (2b) below for heptazine derivatives:
  • Preferred bridges for R 2 are -O-phenyl-1,3-O-, -O-phenyl-1,4-O- and -O-naphthyl-O-. It is possible that the polymers are also present in crosslinking form.
  • Radical generators are in the context of the present invention, compounds which can generate by thermal and radiation-induced cleavage esp. By light radicals.
  • a comprehensive presentation of such radical generators (also called free radical generator or radical initiators) can be found, for. See, for example, E.T. Denisov, T.G. Denisova, T.S. Pokidova, Handbook of free radical initiators, Wiley 2003.
  • free radical generators such as peroxides or hydroperoxides, are used in the polymerization of monomers and in the synthesis of plastics and are required for these applications
  • suitable free radical generators for the applications herein are those which have sufficient thermal stability for the plastics or coating processing processes, i. form during processing no or only very small amounts of radicals and only at higher temperatures, as they occur only in case of fire, spontaneously generate radicals.
  • the respective processing processes and temperatures for coatings and plastic processing processes are known to the person skilled in the art.
  • Composition is such that the at least one compound from the group of radical generators comprises one or more compounds having at least one functional group selected from compounds with
  • composition according to the invention is designed such that it comprises at least one compound from the group of radical generators, with the proviso that it is not a compound having a NOR (alkoxyamine) group.
  • the radical generators used for the processing of plastics in the melt, it is advantageous for the radical generators used to have a thermal stability of at least 150 ° C., preferably of at least 180 ° C., very preferably of at least 200 ° C.
  • the thermal stability of a compound can be z. B. by thermogravimetric analysis (TGA) are determined, wherein the weight loss is measured by decomposition at a certain temperature. Sufficient thermal stability is determined if at the measurement temperature no or only a low percentage decomposition tolerable for the incorporation process is detected.
  • Suitable free radical generators therefore preferably consist of molecules with the structural elements
  • sulfur compounds are also Thiuramsulfide such. Tetramethylthiuram disulfide, dithiocarbamates, e.g. Zinkdiethyldithiocarbamat or Natriumdimethyldithiocarbamat, mercaptobenzothiazoles such.
  • Example of a polysulfide is elemental sulfur, other polysulfides are described for example in US 4218332.
  • the preparation of suitable azo compounds is for example in M. Aubert et. al. Macromol. Be. Eng. 2007, 292, 707-714 or in WO 2008101845, the preparation of hydrazones and azines in M. Aubert et al., Pol. Adv. Technol. 2011, 22, 1529-1538, the preparation of triazenes in W. Pawelec et al., Pol. Degr. Rod. 2012, 97, 948-954.
  • Disulfides, polysulfides, thiols, thiuram sulfides, dithiocarbamates, mercaptobenzothiazoles and sulfenamides are commercially available.
  • Disulfides and polysulfides are preferred among the described structural elements, a particularly preferred compound being distearyl disulfide, which is commercially available under the tradename Hostanox (RTM) from Clariant SE.
  • RTM Hostanox
  • C-C radical generators are compounds which can generate tertiary carbon radicals by thermal or radiation-induced cleavage, in particular by light.
  • C-C radical generators are described, for example, in E.T. Denisov, T.G.
  • C-C radical generators that decompose thermally induced above 180 ° C.
  • Polycumyl-1,3 (CAS No. 25822-44-0).
  • polycumyl-1,4 and / or the polycumyl-1,3 n in the range of 2 to 1,000, particularly preferably in the range of 2 to 20.
  • Polycumyl can be prepared by polyrecombination of 1,4-diisopropylbenzene or 1,3-diisopropylbenzene by reaction with inorganic or organic peroxides as described e.g. By V.V. Korshak in Polymer Science USSR, 1 (1960), 341-350 and in Polymer Science USSR, 3 (1962), 925-935. This gives high molecular weight products
  • composition according to the invention is such that compound (b) is selected from the group of radical generators dicumyl (CAS No. 1889-67-4, formula 5).
  • the composition of the invention is such that compound (b) is selected from the group of radical generators polycumyl-1,4 (CAS No. 25822-43-9, formula 6).
  • the polycumyl-1,4 is present such that n is in the range from 2 to 1000, more preferably in the range from 2 to 20.
  • mixtures of different radical generators can be used, for. B. radical generators, a different
  • Dicumyl and polycumyl are commercial products, the z. B. from United Initiators GmbH & Co KG, Pullach, Germany are available.
  • the present invention also relates to the use of a composition as described above as a flame retardant, in particular for plastics and coatings.
  • Suitable plastics are: a) polymers of olefins or diolefins such. As polyethylene (LDPE, LLDPE, VLDPE, MDPE, HDPE), metallocene PE (m-PE), polypropylene, polyisobutylene, poly-4-methyl-pentene-l, polybutadiene, polyisoprene, polycyclooctene, and copolymers in the form of statistical Gradient or block structures such.
  • LDPE polyethylene
  • LLDPE low density polyethylene
  • VLDPE low density polyethylene
  • MDPE low density polyethylene
  • HDPE high density polyethylene
  • m-PE metallocene PE
  • polypropylene polyisobutylene
  • poly-4-methyl-pentene-l polybutadiene
  • polyisoprene polycyclooctene
  • copolymers in the form of statistical Gradient or block structures such.
  • EP Polypropylene-polyethylene
  • EPM ethylene-vinyl acetate
  • EVA ethylene-acrylic ester
  • SBS polystyrene, polymethylstyrene, styrene-butadiene, styrene-butadiene-styrene (SBS), styrene-isoprene, styrene-butadiene-acrylonitrile (ABS), styrene-acrylonitrile-acrylate (ASA) styrene-maleic anhydride polymers including corresponding graft copolymers such as z. Styrene on butadiene or maleic anhydride on SBS; c) halogen-containing polymers such.
  • B polyvinyl chloride and
  • polyvinylidene chloride d) polymers of unsaturated esters such.
  • unsaturated esters such as polyacrylates and
  • Polymethacrylates such as PMMA, polyacrylonitrile; e) polymers of unsaturated alcohols and derivatives, e.g.
  • Polyvinyl alcohol polyvinyl acetate, polyvinyl butyral; f) polyacetals, such as. For example, polyoxymethylene; g) polyphenylene oxides and blends with polystyrene; h) polyurethanes, in particular linear polyurethanes; i) polyamides such as. As polyamide-6, 6.6., 6.10. 4.6, 6.12, 12.12., Polyamide 11, polyamide 12 and (partially) aromatic polyamides such. For example, polyphthalamides; j) polyimides, polyamideimides, polyetherimides, polyketones, polysulfones,
  • Polyethersulfones polyphenylene sulfide
  • polyesters such as polyethylene terephthalate and polybutylene terephthalate, polylactic acid;
  • compositions according to the invention are used as flame retardants for plastics from the group of polyolefins, polystyrenes and polyurethanes.
  • polyolefins such as polyethylene, polypropylene or diene elastomers, copolymers of these polymers and their blends with other polymers.
  • the plastic contains 5-30% of the flame retardant combination.
  • Flame retardants nor flame retardants and / or additives are added.
  • Suitable further additives are, for example, from the group of UV absorbers, light stabilizers, stabilizers, the
  • Filler deactivators nucleating agents, toughening agents, plasticizers, lubricants, rheology modifiers, processing aids, pigments, dyes, optical brighteners, antimicrobials, antistatics, slip agents, antiblocking agents, coupling agents, dispersants, compatibilizers, oxygen scavengers, acid scavengers, marking agents and / or antifogging agents.
  • Suitable further flame retardants are, for. B. a) inorganic
  • Flame retardants such.
  • Mg-Al silicates MgC0 3 , huntite, hydromagnesite or halloysite and Sb 2 0 3 , Sb 2 0 5 , M0O3, zinc stannate, zinc hydroxystannate, b) nitrogen-containing flame retardants such.
  • Phosphorus-containing flame retardants e.g. red phosphorus, phosphates such.
  • red phosphorus e.g. red phosphorus
  • phosphates such as resorcinol diphosphate, bisphenol A diphosphate and their oligomers, triphenyl phosphate, phosphinates such.
  • salts of hypophosphorous acid and its derivatives such as
  • Diphenyloxides tris (3-bromo-2,2-bis (bromomethyl) propyl phosphate, ethylene bis (tetrabromophthalimide), tetrabromo-bisphenol A, brominated polystyrene, brominated polybutadiene, brominated epoxy resin,
  • the plastic preferably contains 5-30% total of flame retardants.
  • the compositions contain in particular acid scavengers, for. B. based on salts of long-chain acids such. B.
  • Antioxidants the phosphites / phosphonites and / or light stabilizers from the group of hindered amines (HALS) and / or dispersants.
  • HALS hindered amines
  • Suitable light stabilizers for example compounds on the basis of 2- (2 'hydroxyphenyl) benzotriazoles are, 2-hydroxybenzophenones, esters of benzoic acids, acrylates, oxamides, and 2- (2-hydroxyphenyl) -l, 3,5-triazines.
  • Suitable phenolic antioxidants are, for example, alkylated monophenols, alkylated hydroquinones, tocopherols, alkylidenebisphenols,
  • Pentaerythritol tetrakis [3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate, tris (3,5-di-tert-butyl-4-hydroxyphenyl) isocyanurate, 1,3,5-trimethyl-2 , 4,6-tris (3,5-di-tert-butyl-4-hydroxyphenyl) isocyanurate, 1,3,5-trimethyl-2,4,6-tris (3,5-di-tert-butyl-4 - hydroxybenzyl) benzene, triethylene glycol bis [3- (3-tert-butyl-4-hydroxy-5-methylphenyl) propionate, N, N , -hexane-1,6-diyl-bis [3- (3,5-) di-tert-butyl-4-hydroxyphenyl) propionic acid amide.
  • Suitable phosphites / phosphonites are, for example:
  • Triphenyl phosphite diphenyl alkyl phosphites, phenyl dialkyl phosphites,
  • Tri (nonylphenyl) phosphite Tri (nonylphenyl) phosphite, trilauryl phosphites, trioctadecyl phosphite,
  • Diisodecylpentaerythritol diphosphite bis (2,4-di-tert-butylphenyl) pentaerythritol diphosphite, bis (2,4-di-cumylphenyl) pentaerythritol diphosphite, bis (2,6-di-tert-butyl-4-methylphenyl) pentaerythritol diphosphite, diisodecyloxypentaerythritol diphosphite, bis ( 2,4-di-tert-butyl-6-methylphenyl) pentaerythritol diphosphite, bis (2,4,6-tris (tert-butylphenyl) pentaerythritol diphosphite, tristearylsorbitol triphosphite, tetrakis (2,4-di-tert-butylphenyl) -4,4
  • Suitable stabilizers are aminic antioxidants and
  • Hydroxylamine or N-oxides (nitrones) and thiosynergists such as distearyl thiodipropionate or dilauryldithiopropionate.
  • hindered amines examples include 1,1-bis (2,2,6,6-tetramethyl-4-piperidyl) succinate, bis (l, 2,2,6,6-pentamethyl-4-piperidyl) sebazate, bis (l octyloxy-2,2,6,6-tetramethyl-4-piperidyl) sebacate, bis (l, 2,2,6, 6-pentamethyl-4-piperidyl) -n-butyl-3,5-di-tert- butyl 4-hydroxybenzyl malonate, the
  • Suitable dispersants are, for example:
  • Polyacrylates e.g. B. copolymers with long-chain side groups, polyacrylate block copolymers, alkylamides: z. N, N'-l, 2-ethanediyl-bisoctadecanamide,
  • Sorbitan esters e.g. As monostearyl sorbitan esters, titanates and zirconates, reactive copolymers with functional groups z.
  • monostearyl sorbitan esters titanates and zirconates, reactive copolymers with functional groups z.
  • functional groups z For example, polypropylene-co-acrylic acid,
  • the incorporation of the above-described flame retardants and the additional additives in the plastic is carried out by conventional processing methods, whereby preferably the polymer is melted and mixed with the flame retardants and optionally other additives, preferably by mixers, kneaders and extruders. As processing machines are preferred extruders such. B.
  • Ring extruders, co-kneaders which are preferably equipped with a vacuum degassing.
  • the processing can be carried out under air or under inert gas conditions if necessary.
  • Various flame retardants and additives can be added separately or as a mixture in the form of
  • the extrusions of the polypropylene samples (DOW C766-03) are made at a temperature of 190 ° C and a screw speed of 150 rpm on a DSM Micro 5cc twin-screw extruder.
  • the residence time of the mixture in bypass operation is 60 s.
  • the desired mixture of polymer and additives is first mixed manually in a beaker and fed in small portions to the micro-extruder. If the volume of the device is filled with melt, the material remains in the device for a further 60 s (dwell time) and is then drained off.
  • the resulting plastic strands are granulated (Pell-Tec SD 50 pure).
  • Test specimens for the fire test are produced from the granules at a temperature of 220 ° C and a pressure of 2 t on a hydraulic 10 t press (Werner & Pfleiderer). For this purpose, the granules are filled into the mold and these transferred into the already preheated press. At a pressure of 0.5 t, the granules are first melted for 60 seconds. When the melting time has elapsed, the pressure is increased to 2 t and kept constant for a further 3 min. While maintaining the contact pressure, the mold is cooled to 60 ° C and then removed the sample body.
  • the specimens are in accordance with the standard
  • Table 1 Compositions in polypropylene (example: 7H DPE) and
  • Dicumyl and polycumyl were purchased from United Initiators GmbH & Co KG Germany
  • compositions even when reducing the total amount of
  • Comparative Example 3 proves that the radical generator used alone has no effect as a flame retardant, since the specimens already burn completely at the first flame.
  • Example 4 dicumyl was replaced by distearyl disulfide (Hostanox SE 10, manufacturer: Clariant SE) (Example 4),
  • Example 6 obtained from Aldrich Germany, deviating at a pressing temperature of 200 ° C made

Abstract

L'invention concerne une composition qui présente des propriétés améliorées, en particulier en tant qu'agent ignifugeant, et son utilisation comme agent ignifugeant, en particulier pour des matières plastiques, par exemple sous la forme de pièces moulées par injection, de films, de revêtements, de mousses, de fibres, de câbles et de tubes.
PCT/EP2014/058154 2013-04-23 2014-04-22 Composition améliorée et son utilisation comme agent ignifugeant WO2014173908A1 (fr)

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DE102013006937.8A DE102013006937A1 (de) 2013-04-23 2013-04-23 Verbesserte Zusammensetzung und deren Verwendung als Flammschutzmittel

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