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(12) United States Patent (10) Patent No.: US 8,889,770 B2 Narayan Et Al

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(12) United States Patent (10) Patent No.: US 8,889,770 B2 Narayan Et Al US00888977OB2 (12) United States Patent (10) Patent No.: US 8,889,770 B2 Narayan et al. (45) Date of Patent: *Nov. 18, 2014 (54) BROMINATED FLAME RETARDANT, (58) Field of Classification Search ANTMONY OXDE FREE POLYMER USPC ......... 524/100, 281, 299, 371, 405, 417,423, FORMULATIONS 524/424, 429, 430, 432, 433,442 See application file for complete search history. (75) Inventors: Subramaniam Narayan, West Lafayette, IN (US); Harry A. Hodgen, Battle Ground, IN (US) (56) References Cited (73) Assignee: Chemtura Corporation, Middlebury, U.S. PATENT DOCUMENTS CT (US) 3,760,003 A 9, 1973 Asadorian et al. 3,883,613 A 5/1975 Cooper (*) Notice: Subject to any disclaimer, the term of this 4,024,093 A 5, 1977 Abolins et al. patent is extended or adjusted under 35 4,888,370 A 12/1989 Freitaget al. U.S.C. 154(b) by 87 days. 5,143,955 A 9, 1992 Kendall et al. 2006.0167143 A1 7/2006 Borade et al. This patent is Subject to a terminal dis 2007/0040154 A1 2/2007 Murakami claimer. 2010, 0160516 A1 6, 2010 Timberlake et al. 2010, O292376 A1 11/2010 Timberlake et al. 2011, 0004003 A1 1/2011 Nishihara et al. (21) Appl. No.: 13/567,420 2011/O184107 A1* 7/2011 Timberlake ................... 524,371 (22) Filed: Aug. 6, 2012 FOREIGN PATENT DOCUMENTS (65) Prior Publication Data WO WO 2009/084800 A1 T 2009 US 2013/OO53482 A1 Feb. 28, 2013 * cited by examiner Related U.S. Application Data Primary Examiner — Kriellion Sanders (60) Provisional application No. 61/527.262, filed on Aug. (74) Attorney, Agent, or Firm — Joseph Suhadolnik; 25, 2011. Chemtura Corporation; George Romanik (51) Int. C. CSK 3/04 (2006.01) (57) ABSTRACT CSK5/06 (2006.01) CSK 3/3492 (2006.01) Antimony free flame retardant compositions are prepared by COSL 25/06 (2006.01) combining a polymer resin, certain halogenated polyphe COSL 55/02 (2006.01) nylene ether flame retardants and a non-brominated phenoxy CSK5/00 (2006.01) oligomer or polymer Such as a poly-phenylene ether, arylox C09K2I/08 (2006.01) yester, or aryloxycarbonate. The present antimony free flame COSL 7/2 (2006.01) retardant compositions also typically have more desirable (52) U.S. C. physical properties than similar compositions comprising CPC ................. C08K5/06 (2013.01); C08K 5/0066 antimony trioxide and other flame retardant. In particular (2013.01); C09K2I/08 (2013.01); C08L 71/12 embodiments, ATO free flame retardant HIPS and PC/ABS (2013.01) compositions are provided. USPC ........... 524/100; 524/281: 524/299; 524/371; 524/405; 524/417:524/423: 524/424; 524/429: 524/430; 524/432: 524/433; 524/442 8 Claims, No Drawings US 8,889,770 B2 1. 2 BROMINATED FLAME RETARDANT, PPOs are often not very effective as flame retardants on ANTMONY OXDE FREE POLYMER their own and are more often added to polymer resins to FORMULATIONS improve physical properties such as dimensional stability, mechanical and dielectric strength etc. In many Such appli This application claims benefit under 35 USC 119(e) of 5 cations where PPO is used, other flame retardant additives or U.S. Provisional Application No. 61/527.262 filed Aug. 25. packages, such as phosphinates, halogenated flame retardants 2011, the disclosure of which is incorporated herein by ref metal synergists etc., are incorporated when flame retardance CCC. is required. Excellent flame retardant activity is obtained without the U.S. Published Patent Application No. 2006/0167143 dis use of antimony Synergists or similar metal based synergists 10 closes a composition which comprises a compatibilized poly in compositions comprising select a halogenated polyphe (arylene ether)/polyamide blend, a phosphinate flame retar nylene ether flame retardant and a non-brominated phenoxy oligomer or polymer Such as a poly-phenylene ether, arylox dant and a flame retardant augment selected from the group yester, or aryloxycarbonate. consisting of melamine polyphosphate, Zinc borate, low melt 15 ing glass and talc. BACKGROUND U.S. Pat. No. 420,393, discloses a self-extinguishing ther moplastic molding composition, such as rubber-modified The addition of flame retardants to polymer resins during high-impact polystyrene, with improved mechanical proper processing is well known. Flame-retardant additives can be ties and good flame resistance comprising styrene resin, categorized in general by three basic mechanisms. Vapor polyphenylene ether resin, a halogenated aromatic frame phase flame-retardants work in the vaporphase by free radical retardant compound, an antimony containing compound and flame poisoning, which removes active free radicals that pro an additive selected from the group consisting of polyesters mote further exothermic reactions. The ubiquitous haloge and, polyethylene. nated flame-retardants are believed to function as vaporphase U.S. Pat. No. 4,024,093 discloses a flame retardant ther flame-retardants. Often, these compounds are used along 25 moplastic molding composition comprising polyphenylene with Synergists, e.g., antimony Synergists. Condensed-phase ether resin, a vinyl aromatic resin, an aromatic halogenated flame-retardants promote the formation of char in the solid flame retardant; and a flame retardant amount of an organic phase to form an insulating layer which protects the flam iron. U.S. Pat. No. 5,143,955 discloses a composition com mable substrate from the fire and reduces the emission of prising a polyphenylene ether resin, e.g., poly(2,6-dimethyl Volatile flammable gases into the fire. Many phosphorus and 30 1,4-phenylene)ether, a high impact polystyrene resin, a bro silicone-based flame retardants are believed to function as condensed-phase flame-retardants. Heat sink flame-retar minated aromatic flame retardant and a high molecular dants work via endothermic reactions by releasing water and/ weight polystyrene resin. or carbon dioxide, which quench the fire. U.S. Pat. No. 7,816,430 discloses a curable composition Halogenated organic compounds, including oligomeric 35 for a printed wiring board comprising a cyanate ester com and polymeric materials are widely used and are highly effec pound and/or a prepolymer thereof, a specific epoxy resin, a tive flame retardant additives for polymer resins. Examples of monovalent phenol and a polyphenylene ether resin. The commercially available brominated flame retardants include composition can further comprise a brominated flame retar tetrabromobisphenol A, bis(2,3-dibromopropyl ether), dant. Among the list of possible flame retardants is bromi hexabromocyclododecane, tris(tribromoneopenyl)phos 40 nated polyphenylene ether. phate, poly(pentabromobenzyl acrylate), decabromodiphe Aryloxy carbonates, such as the widely used bis-phenol A nyl oxide, tris(tribromophenyl)cyanurate, tris-dibromopro polycarbonate (BPA-PC) and similar materials, are commer pyl isocyanurate, brominated polystyrenes and poly cially available thermoplastic polymers. PCs may be used as (bromostyrenes). the Sole or predominate polymer in a plastic article, and also In order to meet high flame retardance standards in ther 45 find use in various blends, for example, PC-ABS blends. moplastics, for example, the UL-94 V-0 standard, haloge Polycarbonates are not typically associated with flame retar nated flame retardants are generally blended with a synergist, dant activity. most commonly antimony trioxide (ATO). However, for Halogenated polyphenyl ethers are known flame retar compliance with Voluntary environmental standards, the use dants. U.S. Pat. No. 3,760.003 discloses compounds of the of antimony trioxide has been restricted due to its chemical 50 hazard classification. Also, the use of synergists can lead to challenges in coloring, increased cost, and can in some cases negatively impact polymer properties. It would therefore be highly desirable to limit or eliminate antimony compounds and similar synergists from polymer compositions. 55 Thermoplastic polyphenylene oxide resins, such as poly mers of 2,6-dimethylphenol, are commercially available and OCC are most often encountered as polymer additives or as part of a polymer blend, e.g., polyamide blends and high impact wherein each X is independently C1 or Br. each m is indepen polystyrene, i.e., HIPS. 60 dently a number from 0 to 5. p is a number from 0 to 4, and n Polyphenylene ethers (PPE), also called polyphenylene is a number from 1 to 5, which are useful as flame retardants oxides (PPO), are inherently flame resistant. U.S. Pat. No. in polymer resins such as polyester, polystyrene and ABS. 4,888,370 discloses the use of PPO as a flame retardant addi Published US Pat. Appl. 2011/004.0003 and 20110184107, tive in polyamide. U.S. Published Patent Application No. and copending U.S. application Ser. No. 13/248.387, pub 2010/0292376 discloses the use of polyphenylene ethers as a 65 lished as US 20120065297, the disclosures of which are flame retardant adjuvant in polymer resins comprising ben incorporated herein by reference, disclose mixtures of bro Zylic phosphine oxide flame retardants. minated aryl ether oligomers as flame retardants. US 8,889,770 B2 3 4 It has been found that certain of these halogenated poly R" and Rashalogen are bromine, the halogen content of the ether flame retardants can interact with Synergists, adjuvants halogenated aryl ether oligomer(s) is from 50 to about and other materials differently than many similar halogenated 83 wt %, e.g., a halogen content of from about 65 to about 83 aromatic flame retardants. Very Surprising is the discovery wt %, In some particular embodiments the oligomeric or poly that the halogenated polyethers having at least three haloge meric phenyoxy material is a polyphenylene ether. In other nated aromatic rings are more effective than decabromo particular embodiments the oligomeric or polymeric diphenyl ether when used in combination with phenoxy con phenyoxy material is an aryl carbonate comprising phenoxy taining materials such as polyphenylene ethers, aryl moieties, e.g., bis-phenol-A-polycarbonate. The phenoxy carbonates and the like, e.g., non-halogenated PPOs.
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