WO2014099397A1 - Flame retardant polymer compositions - Google Patents

Flame retardant polymer compositions Download PDF

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Publication number
WO2014099397A1
WO2014099397A1 PCT/US2013/073335 US2013073335W WO2014099397A1 WO 2014099397 A1 WO2014099397 A1 WO 2014099397A1 US 2013073335 W US2013073335 W US 2013073335W WO 2014099397 A1 WO2014099397 A1 WO 2014099397A1
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Prior art keywords
bismuth
bis
group
composition according
phosphate
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PCT/US2013/073335
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English (en)
French (fr)
Inventor
Robert Arechederra
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POLYAD SERVICES LLC
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POLYAD SERVICES LLC
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Priority to JP2015549440A priority Critical patent/JP6313331B2/ja
Priority to US14/651,236 priority patent/US10227482B2/en
Priority to EP13864772.2A priority patent/EP2935430B1/en
Publication of WO2014099397A1 publication Critical patent/WO2014099397A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
    • C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
    • C08L23/10—Homopolymers or copolymers of propene
    • C08L23/12—Polypropene
    • 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
    • C08K13/00—Use of mixtures of ingredients not covered by one single of the preceding main groups, each of these compounds being essential
    • C08K13/02—Organic and inorganic ingredients
    • 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
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
    • 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
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
    • C08K3/20—Oxides; Hydroxides
    • 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
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/0066—Flame-proofing or flame-retarding additives
    • 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
    • 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
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
    • C08K5/3432—Six-membered rings
    • C08K5/3435—Piperidines
    • 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
    • C09K21/08—Organic materials containing halogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2201/00—Properties
    • C08L2201/02—Flame or fire retardant/resistant
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2201/00—Properties
    • C08L2201/08—Stabilised against heat, light or radiation or oxydation

Definitions

  • the present invention is aimed at flame retardant polymer compositions, especially thermoplastic polymer compositions.
  • the invention pertains to flame retardant polymer compositions comprising certain bismuth compounds, e.g. BiOCI, in combination with traditional organobromine flame retardants.
  • the polymer substrate is selected from the group consisting of polypropylene, polyethylene, thermoplastic olefin (TPO), ABS, high impact polystyrene, polycarbonate and polyethylene terephthalate.
  • the polymer substrate may also be thermoplastic polyurethane, thermoplastic elastomer, polymethylmethacrylate, rubbers, polyesters, polyacrylonitrile or polyoxymethylene.
  • These metal complexes may be in the free form or fixed on substrates, typically on activated magnesium chloride, titanium(lll) chloride, alumina or silicon oxide. These catalysts may be soluble or insoluble in the polymerisation medium.
  • the catalysts can be used by themselves in the polymerisation or further activators may be used, typically metal alkyls, metal hydrides, metal alkyl halides, metal alkyl oxides or metal alkyloxanes, said metals being elements of groups la, lla and/or Ilia of the Periodic Table.
  • the activators may be modified conveniently with further ester, ether, amine or silyl ether groups. These catalyst systems are usually termed Phillips, Standard Oil Indiana, Ziegler (-Natta), TNZ (DuPont), metallocene or single site catalysts (SSC).
  • Copolymers of monoolefins and diolefins with each other or with other vinyl monomers for example ethylene/propylene copolymers, linear low density polyethylene (LLDPE) and mixtures thereof with low density polyethylene (LDPE), propylene/but-1-ene copolymers,
  • PCHE polycyclohexylethylene
  • PVCH polyvinylcyclohexane
  • dibromobenzoic acid dibromostyrene (DBS) and its derivatives
  • the organobromine flame retardant is preferably decabromodiphenyl ether, tris[3-bromo- 2,2-bis(bromomethyl)propyl] phosphate or brominated polystyrene.
  • the combination of the bismuth compounds and one or more organobromine flame retardants is synergistic.
  • Suitable sterically hindered hydrocarbyloxyamine light stabilizers are for example:
  • Non-halogenated phosphorous-based flame retardants are compounds that include phosphorous, such as triphenyl phosphates, phosphate esters, phosphonium derivatives, phosphonates, phosphoric acid esters and phosphate esters, and those described in U.S. Patent No. 7,786,199.
  • Phosphorous-based flame retardants are usually composed of a phosphate core to which is bonded alkyl (generally straight chain) or aryl (aromatic ring) groups.
  • Examples include red phosphorous, inorganic phosphates, insoluble ammonium phosphate, ammonium polyphosphate, ammonium urea polyphosphate, ammonium orthophosphate, ammonium carbonate phosphate, ammonium urea phosphate, diammonium phosphate, ammonium melamine phosphate, diethylenediamine polyphosphate, dicyandiamide polyphosphate, polyphosphate, urea phosphate, melamine pyrophosphate, melamine orthophosphate, melamine salt of dimethyl methyl phosphonate, melamine salt of dimethyl hydrogen phosphite, ammonium salt of boron-polyphosphate, urea salt of dimethyl methyl phosphonate, organophosphates, phosphonates and phosphine oxide.
  • phosphorous-based flame retardants include methylamine boron- phosphate, cyanuramide phosphate, magnesium phosphate, ethanolamine dimethyl phosphate, cyclic phosphonate ester, trialkyi phosphonates, potassium ammonium phosphate, cyanuramide phosphate, aniline phosphate, trimethylphosphoramide, tris(1-aziridinyl)phosphine oxide, bis(5,5-dimethyl-2-thiono-1 ,3,2-dioxaphosphorinamyl)oxide, dimethylphosphono-N- hydroxymethyl-3-propionamide, tris(2-butoxyethyl)phosphate,
  • phosphorous acts through zinc halide or zinc oxyhalide, which accelerate the decomposition of halogen sources and promote char formation.
  • UV absorbers selected from hydroxyphenylbenzotriazole,
  • hydroxyphenyltriazine benzophenone and benzoate UV absorbers, organic phosphorus stabilizers, hydroxylamine stabilizers, benzofuranone stabilizers, amine oxide stabilizers, hindered phenol antioxidants and/or hindered amine light stabilizers.
  • the further additives are for instance employed at levels of about 0.1 to about 10% by weight, based on the weight of the polymer substrate.
  • Further additives are for instance selected from the group consisting of pigments, dyes, plasticizers, phenolic antioxidants, thixotropic agents, levelling assistants, basic costabilizers, nitrone stabilizers, amine oxide stabilizers, benzofuranone stabilizers, UV absorbers, sterically hindered amine light stabilizers, metal passivators, metal oxides, organophosphorus
  • Hindered amine light stabilizers include for example the condensate of 1-(2-hydroxyethyl)-2,2,6,6-tetramethyl-4-hydroxypiperidine and succinic acid, MW 3100-4000
  • oligomeric compound which is the condensation product of 4,4'-hexa- methylenebis(amino-1 ,2,2,6,6-pentaamethylpiperidine) and 2,4-dichloro-6-[(1 ,2,2,6,6- pentaamethylpiperidin-4-yl)butylamino]-s-triazine end-capped with 2-chloro-4,6- bis(dibutylamino)-s-triazine,
  • Hydroxylamine stabilizers are for example ⁇ , ⁇ -dibenzylhydroxylamine, N,N- diethylhydroxylamine, N,N-dioctylhydroxylamine, ⁇ , ⁇ -dilaurylhydroxylamine, N,N- didodecylhydroxylamine, N,N-ditetradecylhydroxylamine, ⁇ , ⁇ -dihexadecylhydroxylamine, N,N- dioctadecylhydroxylamine, N-hexadecyl-N-tetradecylhydroxylamine, N-hexadecyl-N- heptadecylhydroxylamine, N-hexadecyl-N-octadecylhydroxylamine, N-heptadecyl-N- octadecylhydroxylamine, N-methyl-N-octadecylhydroxylamine or N,N-di(hydrogenated tallow)hydroxy
  • the amine oxide stabilizer is for example GENOX EP, a di(Ci 6 -C 18 )alkyl methyl amine oxide, CAS# 204933-93-7.
  • Benzoate UV absorbers are for instance esters of substituted and unsubstituted benzoic acids, as for example 4-tert-butylphenyl salicylate, phenyl salicylate, octylphenyl salicylate, dibenzoyl resorcinol, bis(4-tert-butylbenzoyl) resorcinol, benzoyl resorcinol, 2,4-di-tert- butylphenyl 3,5-di-tert-butyl-4-hydroxybenzoate, hexadecyl 3,5-di-tert-butyl-4-hydroxybenzoate, octadecyl 3,5-di-tert-butyl-4-hydroxybenzoate, 2-methyl-4,6-di-tert-butylphenyl 3,5-di-tert-butyl- 4-hyd roxybenzoate .
  • Dyes are any of the colorants which dissolve completely in the plastic used or are present in molecularly dispersed form and therefore can be used to provide high-transparency, non-diffusion coloring of polymers.
  • Other dyes are organic compounds which fluoresce in the visible portion of the electromagnetic spectrum, e.g. fluorescent dyes. Dyes may be included singly or in any combination in amounts typically of up to about 5% by weight, based on the weight of the polymer substrate.
  • Desirable fillers include but are not limited to titanium dioxide, silicon carbide, silica (and other oxides of silica, precipitated or not), lead carbonate, zinc white, lithopone, zircon, corundum, spinel, apatite, barytes powder, barium sulfate, carbon black, dolomite, calcium carbonate, talc and hydrotalcite compounds of the ions Mg, Ca, or Zn with Al, Cr or Fe and C0 3 and/or HP0 4 , hydrated or not; quartz powder, hydrochloric magnesium carbonate, glass fibers, clays, alumina, and other metal oxides and carbonates, metal hydroxides, chrome, phosphorous, silica, silicone, and blends thereof. These fillers may particularly include any other fillers and porous fillers and supports known in the art.
  • Present component b) and optional further additives can also be sprayed onto the polymer substrate. They are able to dilute other additives (for example the conventional additives indicated above) or their melts so that they can be sprayed also together with these additives onto the polymer. Addition by spraying during the deactivation of the polymerization catalysts is particularly advantageous, it being possible to carry out spraying using, for example, the steam used for deactivation.
  • Embodiment 1 A flame retardant composition which comprises
  • Embodiment 8 A composition according to any of embodiments 1 through 7 where the organobromine flame retardants are selected from the group consisting of tetrabromobisphenol A (TBBPA), tetrabromophthalate esters, bis(2,3- dibromopropyloxy)tetrabromobisphenol A, brominated carbonate oligomers based on TBBPA, brominated epoxy oligomers based on condensation of TBBPA and epichlorohydrin, copolymers of TBBPA and 1 ,2-dibromoethane; dibromobenzoic acid, dibromostyrene (DBS) and its derivatives; ethylenebromobistetrabromophthalimide, dibromoneopentyl glycol,
  • TBBPA tetrabromobisphenol A
  • tetrabromophthalate esters bis(2,3- dibromopropyloxy)tetrabromobisphenol A
  • Embodiment 10 A composition according to any of embodiments 1 through 9, further comprising one or more sterically hindered hydrocarbyloxyamine stabilizers.
  • Embodiments 13 A composition according to any of embodiments 1 through 11 , further comprising one or more additional flame retardants selected from the group consisting of
  • Embodiment 14 A composition according to any of embodiments 1 through 13 further comprising one or more additives selected from the group consisting of pigments, dyes, plasticizers, phenolic antioxidants, thixotropic agents, levelling assistants, basic costabilizers, nitrone stabilizers, amine oxide stabilizers, benzofuranone stabilizers, UV absorbers, sterically hindered amine light stabilizers, metal passivators, metal oxides, organophosphorus
  • Embodiment 15 A composition according to any of embodiments 1 through 13 further comprising one or more additives selected from the group consisting of phenolic antioxidants, calcium stearate, zinc stearate, phosphite or phosphonite stabilizers, benzofuranone stabilizers, 2-(2'-hydroxyphenyl)benzotriazole, 2-(2-hydroxyphenyl)-1 ,3,5-triazine or benzoate UV absorbers and sterically hindered amine light stabilizers.
  • additives selected from the group consisting of phenolic antioxidants, calcium stearate, zinc stearate, phosphite or phosphonite stabilizers, benzofuranone stabilizers, 2-(2'-hydroxyphenyl)benzotriazole, 2-(2-hydroxyphenyl)-1 ,3,5-triazine or benzoate UV absorbers and sterically hindered amine light stabilizers.
  • dibromocyclooctane trisbromoneopentanol, tris(tribromophenyl)triazine, 2,3-dibromopropanol, tribromoaniline, tribromophenol, tetrabromocyclopentane, tetrabromobiphenyl ether, tetrabromodipentaerythritol, decabromodiphenyl ether, tetrabromophthalic anhydride, pentabromotoluene, pentabromodiphenyl ether, pentabromodiphenyl oxide, pentabromophenol, pentabromophenyl benzoate, pentabromoethylbenzene, hexabromocyclohexane,
  • Embodiment 20 An additive composition according to any of embodiments 16 through 19, which is in the form of a one pack system selected from the group consisting of pellets, pastilles, flakes and granules.
  • Embodiment 21 A method for providing a flame retardant polymer composition, said method comprising incorporating into a thermoplastic polymer substrate an effective flame retarding amount of a combination of one or more bismuth compounds selected from the group consisting of bismuth oxychloride, bismuth oxyfluoride, bismuth oxybromide, bismuth oxyiodide and bismuth oxynitrate and one or more organobromine flame retardants.
  • Embodiment 25 A composition according to any of embodiments 1 through 15, further comprising zinc oxide.
  • Embodiment 29 Use of a combination of one or more bismuth compounds selected from the group consisting of bismuth oxychloride, bismuth oxyfluoride, bismuth oxybromide, bismuth oxyiodide and bismuth oxynitrate and one or more organobromine flame retardants towards providing flame retardancy to a thermoplastic polymer substrate.
  • High density polyethylene (HDPE) samples are compounded at 200°C in a laboratory extruder and injection molded into strips according to Example 1.
  • the samples contain 25% decabromodiphenyl ether, 2% BiOCI and loadings of ZnO of from 4% to 10%.
  • Samples also contain 0.4% IRGANOX 1010, 0.3% ethylene bis-stearamide wax and 0.2% calcium stearate. Percents are by weight, remainder being HDPE.
  • the strips all achieve a UL 94 V0 rating.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
PCT/US2013/073335 2012-12-20 2013-12-05 Flame retardant polymer compositions Ceased WO2014099397A1 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
JP2015549440A JP6313331B2 (ja) 2012-12-20 2013-12-05 難燃性ポリマー組成物
US14/651,236 US10227482B2 (en) 2012-12-20 2013-12-05 Flame retardant polymer compositions
EP13864772.2A EP2935430B1 (en) 2012-12-20 2013-12-05 Flame retardant polymer compositions

Applications Claiming Priority (4)

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US201261739842P 2012-12-20 2012-12-20
US61/739,842 2012-12-20
US201361835893P 2013-06-17 2013-06-17
US61/835,893 2013-06-17

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EP (1) EP2935430B1 (https=)
JP (1) JP6313331B2 (https=)
AR (1) AR094184A1 (https=)
TW (1) TWI638038B (https=)
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EP2935430A4 (en) 2016-05-25
JP6313331B2 (ja) 2018-04-18
EP2935430B1 (en) 2019-05-29
TW201428093A (zh) 2014-07-16
US10227482B2 (en) 2019-03-12
JP2016501963A (ja) 2016-01-21
US20150322252A1 (en) 2015-11-12
EP2935430A1 (en) 2015-10-28
TWI638038B (zh) 2018-10-11

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