US20020111403A1 - Flame retardant polyester compositions - Google Patents

Flame retardant polyester compositions Download PDF

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Publication number
US20020111403A1
US20020111403A1 US09/738,620 US73862000A US2002111403A1 US 20020111403 A1 US20020111403 A1 US 20020111403A1 US 73862000 A US73862000 A US 73862000A US 2002111403 A1 US2002111403 A1 US 2002111403A1
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Prior art keywords
composition
containing compound
polyester
ratio
amount
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US09/738,620
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English (en)
Inventor
Johannes Gosens
Gerrit De Wit
Tieb Aouraghe
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General Electric Co
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Individual
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Priority to US09/738,620 priority Critical patent/US20020111403A1/en
Assigned to GENERAL ELECTRIC COMPANY reassignment GENERAL ELECTRIC COMPANY ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: AOURAGHE, TIEB, DE WIT, GERRIT, GOSENS, JOHANNES CORNELIS
Priority to DE60136220T priority patent/DE60136220D1/de
Priority to EP01994154A priority patent/EP1349890B1/fr
Priority to JP2002558420A priority patent/JP2004517994A/ja
Priority to PCT/US2001/046432 priority patent/WO2002057352A1/fr
Publication of US20020111403A1 publication Critical patent/US20020111403A1/en
Priority to US10/234,742 priority patent/US6737455B2/en
Abandoned legal-status Critical Current

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    • 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
    • C08K5/51—Phosphorus bound to oxygen
    • C08K5/52—Phosphorus bound to oxygen only
    • C08K5/521—Esters of phosphoric acids, e.g. of H3PO4
    • C08K5/523—Esters of phosphoric acids, e.g. of H3PO4 with hydroxyaryl compounds
    • 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
    • C08K5/29—Compounds containing one or more carbon-to-nitrogen double bonds
    • C08K5/31—Guanidine; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
    • C08K5/3477—Six-membered rings
    • C08K5/3492—Triazines
    • 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

  • thermoplastic polyester compositions and in particular to halogen-free, flame retardant thermoplastic polyester compositions.
  • Thermoplastic polyester compositions such as poly(alkylene terephthalates) have valuable characteristics including strength, toughness, high gloss and solvent resistance. Polyesters therefore have utility as materials for a wide range of applications, from automotive parts to electric and electronic appliances. Because of their wide use, particularly in electronic applications, it is desirable to provide flame retardancy to polyesters.
  • One particular set of conditions commonly accepted and used as a standard for flame retardancy is that which is set forth in Underwriter's Laboratories, Inc. Bulletin 94 which proscribes certain conditions by which material are rated for self-extinguishing characteristics.
  • Another set of conditions commonly accepted and used (especially in Europe) as a standard for flame retardancy is the so-called Glow Wire Test (GWT), the International standard IEC 695-2-1/2.
  • GWT Glow Wire Test
  • JP 03-281652 to Mitsubishi Petrochemical discloses FR polyester compositions comprising 100 parts of a polyester resin, 30-250 parts of a filler, 5-50 parts of melamine cyanurate, and 5-50 parts of a P-containing FR compound.
  • JP 06-157880 to Akzo Kashima, Mitsubishi Petrochemical describes a polyester (100 parts) with 30-250 pts of a filler, 5-50 parts of melamine cyanurate and 5-50 parts of an aromatic phosphate.
  • JP11209587 to Kaneka discloses a polyester composition with a) 20-59% Glass and mineral filler in a ratio of 3/2-1/4, b) melamine cyanurate and c) 15-32% P-compound with P-compound/Melamine cyanurate ratio of 1/1-1/3, and d) 0.01-2% Fluoro resin.
  • Non-halogenated flame retardants for polyesters are described in the literature. Although good FR-properties can be obtained upon high enough amounts of the FR-ingredients, the materials lack good mechanical properties as impact and/or have insufficient color stability upon heat aging. Desirable enhanced properties and deficiencies can be overcome by the proper choice of the P-compound and the right amounts of N- and P-compounds in relation which each other and in relation with the type and amount of the present polyester. Good balance of ductility, flame retardancy and color stability upon oven aging can be obtained by a flame retardant polyester composition comprising, based on the total composition,
  • N-containing compound selected from the group of triazine, guanidine, or (iso)cyanurate compounds
  • P-containing compound selected from the group of BPA-diphosphates or phosphoramides
  • a halogen-free, flame retardant polyester composition comprises, based on the total composition,
  • N-containing compound selected from the group of triazine, guanidine, or (iso)cyanurate compounds
  • P-containing compound selected from the group of BPA-diphosphates or phosphoramides
  • the flame retardant polyester composition includes a flame retarding quantity of one or a mixture of nitrogen-containing compounds, selected from the group of triazine, guanidine, or (iso)cyanurate compounds.
  • nitrogen-containing compounds selected from the group of triazine, guanidine, or (iso)cyanurate compounds.
  • examples of such compounds are the 1,3,5-triazine compounds as for instance 2,4,6-triamine-1,3,5-triazine (melamine), melam, melem, melon, ammeline, ammelide, 2-ureidomelamine, acetoguanamine, benzoguanamine, diaminephenyltriazine or mixtures thereof.
  • Especially salts/adducts of these compounds with (iso)cyanuric acid (as eg melamine cyanurate), boric acid, and/or phosphoric acid (including the so called melamine polyphosphate) can be used in the composition.
  • Preferred compounds include the cyanuric acid derivatives of 1,3,5-triazine-compounds as melamine cyanurate.
  • the nitrogen-containing compounds are used in combination with one or more phosphorous-containing compounds as described below, since the combination appears to impart better flame retardant properties than where either component is used alone.
  • a suitable class of phosphorous compounds is the class of diphosphates of the general structure (OR1)(OR2)P( ⁇ O)—OXO—P( ⁇ O)(OR3(OR4) (optionally including some oligomeric higher phosphates), for instance made out of POCl3, a diphenol compound HO—X—OH with X is a group with at least 2 aryl unit (such as bisphenol A), and mono-hydroxy compound(s) ROH (R1, R2, R3, R4 might be equal or different), such as phenol.
  • Other suitable phosphorus compounds are phosphoramides such as tetraxylyl piperazine diphosphoramide.
  • R1 is an amine residue
  • R2 and R3 are independently an alkoxy residue, aryloxy residue, aryloxy residue containing at least one alkyl or one halogen substitution or mixture thereof, or amine residue.
  • the phosphoramide have a glass transition point of at least about 0° C., preferably of at least about 10° C., and most preferably of at least about 20° C.
  • Another phosphoramide comprises a phosphoramide having a glass transition temperature of at least about 0° C., preferably of at least about 10° C., and most preferably of at least about 20° C., of the formula:
  • each A is independently phenyl, 2,6-dimethylphenyl, or 2,4,6-trimethylphenyl.
  • composition may further optionally comprise various fillers and other additives known in the art, particular glass fibers in an amount of up to about 40 weight percent, and 0.01 to about 2.0 weight percent of at least one anti-dripping agent which retards the tendency of the composition to drip when subjected to burning conditions.
  • Suitable polyesters that can be blend with the used poly(ethylene terephthalate) include those derived from an aliphatic or cycloaliphatic diol, or mixtures thereof, containing from 2 to about 10 carbon atoms and at least one aromatic dicarboxylic acid.
  • Preferred polyesters are derived from an aliphatic diol and an aromatic dicarboxylic acid having repeating units of the following general formula:
  • n is an integer of from 2 to 6
  • R is a C6-C20 aryl radical comprising a decarboxylated residue derived from an aromatic dicarboxylic acid.
  • aromatic dicarboxylic acids represented by the decarboxylated residue R are isophthalic or terephthalic acid, 1,2-di(p-carboxyphenyl)ethane, 4,4′-dicarboxydiphenyl ether, 4,4′ bisbenzoic acid, and mixtures thereof. All of these acids contain at least one aromatic nucleus. Acids containing fused rings can also be present, such as in 1,4-1,5- or 2,6-naphthalene dicarboxylic acids.
  • the preferred dicarboxylic acids are terephthalic acid, isophthalic acid, naphthalene dicarboxylic acid or a mixtures thereof.
  • the aliphatic polyols include glycols, such as propylene glycol, butanediol, hydroquinone, resorcinol, trimethylene glycol, 2-methyl-1,3propane glycol, hexamethylene glycol, decamethylene glycol, cyclohexane dimethanol, or neopentylene glycol.
  • glycols such as propylene glycol, butanediol, hydroquinone, resorcinol, trimethylene glycol, 2-methyl-1,3propane glycol, hexamethylene glycol, decamethylene glycol, cyclohexane dimethanol, or neopentylene glycol.
  • polyesters with minor amounts, e.g., from about 0.5 to about 30 percent by weight, of units derived from aliphatic acids and/or aliphatic polyols to form copolyesters.
  • the aliphatic polyols include glycols, such as poly(ethylene glycol).
  • Such polyesters can be made following the teachings of, for example, U.S. Pat. Nos. 2,465,319 and 3,047,539.
  • polyesters are poly(ethylene terephthalate) (“PET”) as main polyester, poly(1,4-butylene terephthalate), (“PBT”), and poly(propylene terephthalate) (“PPTI”).
  • PET poly(ethylene terephthalate)
  • PBT poly(1,4-butylene terephthalate)
  • PPTI poly(propylene terephthalate)
  • a preferred PBT resin is one obtained by polymerizing a glycol component at least 70 mole %, preferably at least 80 mole %, of which consists of tetramethylene glycol and an acid component at least 70 mole %, preferably at least 80 mole %, of which consists of terephthalic acid, and polyester-forming derivatives therefore.
  • the preferred glycol component can contain not more than 30 mole %, preferably not more than 20 mole %, of another glycol, such as ethylene glycol, trimethylene glycol, 2-methyl-1,3-propane glycol, hexamethylene glycol, decamethylene glycol, cyclohexane dimethanol, or neopentylene glycol.
  • another glycol such as ethylene glycol, trimethylene glycol, 2-methyl-1,3-propane glycol, hexamethylene glycol, decamethylene glycol, cyclohexane dimethanol, or neopentylene glycol.
  • the preferred acid component can contain not more than 30 mole %, preferably not more than 20 mole %, of another acid such as isophthalic acid, 2,6-naphthalene dicarboxylic acid, 2,7-naphthalene dicarboxylic acid, 1,5-naphthalene dicarboxylic acid, 4,4′-diphenyl dicarboxylic acid, 4,4′-diphenoxyethane dicarboxylic acid, p-hydroxy benzoic acid, sebacic acid, adipic acid and polyester-forming derivatives thereof.
  • another acid such as isophthalic acid, 2,6-naphthalene dicarboxylic acid, 2,7-naphthalene dicarboxylic acid, 1,5-naphthalene dicarboxylic acid, 4,4′-diphenyl dicarboxylic acid, 4,4′-diphenoxyethane dicarboxylic acid, p-hydroxy benzoic acid, sebacic acid, adipic acid and polyester-forming derivatives thereof
  • Block copolyester resin components are also useful, and can be prepared by the transesterification of (a) straight or branched chain poly(1,2ethylene terephthalate) and (b) a copolyester of a linear aliphatic dicarboxylic acid and, optionally, an aromatic dibasic acid such as terephthalic or isophthalic acid with one or more straight or branched chain dihydric aliphatic glycols.
  • branched high melt viscosity resins which include a small amount of e.g., up to 5 mole percent based on the terephthalate units, of a branching component containing at least three ester forming groups.
  • the branching component can be one which provides branching in the acid unit portion of the polyester, or in the glycol unit portion, or it can be hybrid.
  • branching components are tri- or tetracarboxylic acids, such as trimesic acid, pyromellitic acid, and lower alkyl esters thereof, and the like, or preferably, polyols, and especially preferably, tetrols, such as pentaerythritol, triols, such as trimethylolpropane; or dihydroxy carboxylic acids and hydroxydicarboxylic acids and derivatives, such as dimethyl hydroxyterephthalate, and the like.
  • branched poly(1,4-butylene terephthalate) resins and their preparation are described in Borman, U.S. Pat. No. 3,953,404, incorporated herein by reference.
  • small amounts e.g., from 0.5 to 15 percent by weight of other aromatic dicarboxylic acids, such as isophthalic acid or naphthalene dicarboxylic acid, or aliphatic dicarboxylic acids, such as adipic acid, can also be present, as well as a minor amount of diol component other than that derived from 1,4-butanediol, such as ethylene glycol or cyclohexylenedimethanol, etc., as well as minor amounts of trifunctional, or higher, branching components, e.g., pentaerythritol, trimethyl trimesate, and the like.
  • the preferred stabilizers include an effective amount of an acidic phosphate salt; an acid, alkyl, aryl or mixed phosphite having at least one hydrogen or alkyl group; a Group IB or Group IIB metal phosphate salt; a phosphorous oxo acid, a metal acid pyrophosphate or a mixture thereof.
  • the acidic phosphate salts include sodium dihydrogen phosphate, mono zinc phosphate, potassium hydrogen phosphate, calcium dihydrogen phosphate and the like.
  • the phosphites may be of the formula:
  • R1, R2, and R3 are independently selected from the group consisting of hydrogen, alkyl and aryl with the proviso that at least one of R1, R2, and R3 is hydrogen or alkyl.
  • the phosphate salts of a Group IB or Group IIB metal include zinc phosphate, copper phosphate and the like.
  • the phosphorous oxo acids include phosphorous acid, phosphoric acid, polyphosphoric acid or hypophosphorous acid.
  • polyacid pyrophosphates maybe of the formula:
  • M is a metal
  • x is a number ranging from 1 to 12 and y is a number ranging 1 to 12
  • n is a number from 2 to 10
  • z is a number from 1 to 5 and the sum of (xz)+y is equal to n+2.
  • Inorganic fillers can impart additional beneficial properties such as thermal stability, increased density, stiffness and texture.
  • Typical inorganic fillers include but are not limited to alumina, amorphous silica, anhydrous aluminum silicates, mica, feldspar, clays, talc, glass flake, glass fibers, glass microspheres, wollastonite, metal oxides such as titanium dioxide, zinc oxide, ground quartz, and t he like.
  • Preferred inorganic fillers include zinc oxide, barium sulfate and fiberglass as well as mixtures of the above. Barium sulfate may be in the form of the naturally occurring barites or as synthetically derived barium sulfate.
  • the particle size may vary, and is preferably from about 0.1 to about 50 microns, most preferably from about 1 to about 15 microns.
  • fibrous (filamentous) glass can be untreated, but preferably, it will be treated with silane or titanate coupling agents, e.g.
  • Useful filamentous glass is well known to those skilled in the art and is widely available from a number of manufacturers.
  • fibrous glass filaments comprised of lime-aluminum borosilicate glass that is relatively soda free, commonly known as “E” glass.
  • E lime-aluminum borosilicate glass
  • other glasses are useful where electrical properties are not so important, e.g., the low soda glass commonly known as “C” glass.
  • the filaments are made by standard processes, e.g., by steam or air blowing, flame blowing and mechanical pulling.
  • the preferred filaments for plastic reinforcement are made by mechanical pulling.
  • Exemplary filament diameters are in the range from about 0.00012 to 0.00075 inch.
  • the glass filaments may be bundled into fibers and the fibers bundled in turn to yarns, ropes or rovings, or woven into mats, and the like, as is required by the particular end use of the composition.
  • the compositions include from 0 to about 60 weight percent, preferably from about 10 to about 50 weight percent, and most preferably from about 25 to about 40 weight of the total composition.
  • Glass fibers are typically used in quantities from about 0 to about 60 weight percent, preferably from about 10 to about 40 weight percent.
  • the compositions may also contain one or a mixture of reinforcing filler.
  • Suitable fillers include silica; silicates such as talc or mica; carbon black; and reinforcing fibers, such as carbon fiber, aramide fiber or glass fiber.
  • Glass fibers may be composed of E-glass or alkali metal silicate glass and may comprise short, chopped glass fibers with a circular cross section ranging in diameter from about 2 ⁇ 10 ⁇ 4 to 8 ⁇ 10 ⁇ 4 inch and about 0.2 to 2 cm in length. Such glass fibers are normally supplied by the manufacturers with a surface treatment compatible with the polymer component of the composition, such as a siloxane or polyurethane sizing.
  • the reinforcing filler is normally included at a level of from about 1 to 40 parts by weight, more preferably from about 5 to 35 parts by weight, per 100 parts by weight of the total polymer composition.
  • the composition may also include one or more anti-dripping agents which have the properties of preventing or retarding resin from dripping while the resin is subjected to burning conditions.
  • anti-dripping agents include silicone oils, silica (which also serves as a reinforcing filler), asbestos and fibrillating-type of fluorine-containing polymers.
  • fluorine-containing polymers include fluorinated polyolefins such as polytetrafluoroethylene, tetrafluoroethylene/hexafluoropropylene copolymers, tetrafluoroethylene/ethylene copolymers, polyvinylidene fluoride and polychlorotrifluoroethylene.
  • Preferred such fluorine-containing polymers have a melt viscosity at 3500C of about 1.0 ⁇ 104 to 1.0 ⁇ 1014 poises.
  • the anti-dripping agent is added to the composition at a level of about 0.05 to 5 parts by weight, more preferably from about 0.1 to 4 parts by weight, based on the weight of the total polymer composition.
  • compositions may also contain other conventional additives used in polyester polymer compositions such as stabilizers, mold release agents, plasticizers and processing aids.
  • the compositions can be prepared by a number of procedures.
  • the polyester composition, optional amorphous additives, impact modifier and filler and/or reinforcing glass is put into an extrusion compounder with resinous components to produce molding pellets.
  • the resins and other ingredients are dispersed in a matrix of the resin in the process.
  • the ingredients and any reinforcing glass are mixed with the resins by dry blending, then either fluxed on a mill and comminuted, or then are extruded and chopped.
  • the composition and any optional ingredients can also be mixed and directly molded, e.g., by injection or transfer molding techniques. Preferably, all of the ingredients are freed from as much as water as possible.
  • compounding should be carried out to ensure that the residence time in the machine is short; the temperature is carefully controlled; the friction heat is utilized; and an intimate blend between the resin composition and any other ingredients is obtained.
  • the ingredients are pre-compounded, pelletized and then molded.
  • Pre-compounding can be carried out in conventional equipment. For example, after pre-drying the polyester composition (if necessary) e.g., for four hours at 120° C., a single screw extruder is fed with a dry blend of the ingredients, the screw employed having a long transition section to ensure proper melting.
  • a twin screw extrusion machine e.g., an extruder with i.e. intermeshing co-rotating screws can be fed with resin and additives at the feed port and reinforcing additives (and other additives) fed downstream. In either case, a generally suitable melt temperature will be about 230 to 300° C.
  • the pre-compounded composition can be extruded and cut up into molding compounds such as conventional granules, pellets, etc., by standard techniques.
  • composition can then be molded in any equipment conventionally used for thermoplastic compositions, e.g., a Newbury type injection molding machine with conventional cylinder temperatures, e.g., 230 to 280° C., and conventional mold temperatures, e.g. 55 to 95° C.
  • a Newbury type injection molding machine with conventional cylinder temperatures, e.g., 230 to 280° C., and conventional mold temperatures, e.g. 55 to 95° C.
  • All formulations are made by dry-blending of ingredients with exception of BPA-diphosphate, RDP and glass fiber.
  • the blends are subsequently compounded on a WP 25 mm co-rotating extruder, where RDP or BPA-DP and Glass are fed separately down-stream the extruder.
  • Temperature setting was 50-140-265-260-260-260-260-260-275 C, vacuum 0.2 bar and RPM of 300.
  • Molding is done on a Engel 35 tons with temperature setting of 245-255-265-265 (from throat to nozzle) and a mold temperature of 70 C for the PBT-based formulations and 80 C for the PET-based formulations (or otherwise stated). Prior to molding the pellets were pre-dried at 120 C for 4 hrs.
  • TSAN PTFE/SAN blend of PTFE/SAN 50/50
  • test specimen The flammability of test specimen is also evaluated according to the standard UL-94 protocol, vertical burning. Ratings of V0 indicate test samples with the best resistance to burning, whereas V1 and V2 ratings in that order indicate a lessening degree of resistance to burning (V2 with drippings).
  • Test specimen are evaluated for Izod Impact in accordance with ISO 180. The color of test specimen after oven aging during 500 hours at 150 degrees C. were visually inspected.
  • Formulations and test results are shown in the table. Amounts are part by weight. It has been surprisingly found that the right balance of properties can be obtained. The following are observations relating to the results. Formulations based on BPA-DP or X4PIP do not show dark brown discoloration upon oven aging (500 hrs at 150 C), in contrast to RDP-containing formulations (Reference samples #1, #3 and #4). Samples with a PET/PBT ratio ⁇ 55/45 (Reference samples #1, #2, and #3) do not have a V0 rating, even not at high amounts of P- and N-compounds.
  • Samples with a ratio of P+N-cpds/Polyester ⁇ 0.3 for PET/PBT>55/45 show no V0 rating (Reference samples #5, #6 and #7).
  • Reference sample #8 versus #9 shows that an anti-dripping agent is needed for a V0 rating.
  • Samples with a ratio of P+N-cpds/Polyester>0.6 for a PET/PBT>55/45 show impact properties below 25 kJ/m2 (Reference sample #12), in contrast with samples with a ratio ⁇ 0.6.
  • Samples with a P-/N-compound ratio ⁇ 0.8 also show bad impact (Reference sample #5 versus #6, and #11 versus #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)
US09/738,620 2000-12-15 2000-12-15 Flame retardant polyester compositions Abandoned US20020111403A1 (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
US09/738,620 US20020111403A1 (en) 2000-12-15 2000-12-15 Flame retardant polyester compositions
DE60136220T DE60136220D1 (de) 2000-12-15 2001-12-07 Flammhemmende polyesterzusammensetzungen
EP01994154A EP1349890B1 (fr) 2000-12-15 2001-12-07 Compositions de polyester ignifuges
JP2002558420A JP2004517994A (ja) 2000-12-15 2001-12-07 難燃性ポリエステル組成物
PCT/US2001/046432 WO2002057352A1 (fr) 2000-12-15 2001-12-07 Compositions de polyester ignifuges
US10/234,742 US6737455B2 (en) 2000-12-15 2002-09-03 Flame retardant polyester compositions

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Application Number Priority Date Filing Date Title
US09/738,620 US20020111403A1 (en) 2000-12-15 2000-12-15 Flame retardant polyester compositions

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US10/234,742 Continuation US6737455B2 (en) 2000-12-15 2002-09-03 Flame retardant polyester compositions

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EP (1) EP1349890B1 (fr)
JP (1) JP2004517994A (fr)
DE (1) DE60136220D1 (fr)
WO (1) WO2002057352A1 (fr)

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US20050137297A1 (en) * 2003-12-17 2005-06-23 General Electric Company Flame-retardant polyester composition
US20060142439A1 (en) * 2002-11-27 2006-06-29 Grigory Titelman Fire retarded styrene polymer compositions
US20080153968A1 (en) * 2004-11-03 2008-06-26 Elkem As High Performance Engineering Plastics and Additive For Use in Engineering Plastics
US20080292797A1 (en) * 2001-10-19 2008-11-27 Terufumi Iwaki Agent and method for flame-retardant processing of polyester-based fiber products
US20110126831A1 (en) * 2007-08-28 2011-06-02 Fernandez Pernia Jorge Portable essence vaporizer
US8604105B2 (en) 2010-09-03 2013-12-10 Eastman Chemical Company Flame retardant copolyester compositions
TWI579205B (zh) * 2012-12-14 2017-04-21 中本包裝股份有限公司 耐熱食品容器及其製造方法
US9828163B2 (en) * 2011-12-16 2017-11-28 Nakamoto Packs Co., Ltd. Heat-resistant food container and its manufacturing method

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US7101923B2 (en) * 2003-10-03 2006-09-05 General Electric Company Flame-retardant thermoset composition, method, and article
JP4526865B2 (ja) * 2004-04-30 2010-08-18 Ｓａｂｉｃイノベーティブプラスチックスジャパン合同会社 ポリエステル樹脂製光反射体
JP5114656B2 (ja) * 2006-05-17 2013-01-09 東洋紡株式会社 難燃性樹脂組成物
US8268916B2 (en) * 2006-09-25 2012-09-18 Federal-Mogul World Wide, Inc. Flame-retardant compound and method of forming a continuous material therefrom
US20080112876A1 (en) * 2006-11-09 2008-05-15 Indspec Chemical Corporation Method of Stabilizing Resorcinol Resins and Gel Compositions Made Therefrom
US8178208B2 (en) * 2006-12-01 2012-05-15 Sabic Innovative Plastives IP B.V. Polyester compositions, methods of manufacture, and uses thereof
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US20030022969A1 (en) 2003-01-30
EP1349890B1 (fr) 2008-10-15
DE60136220D1 (de) 2008-11-27

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