WO2010065467A1 - Branched and star-branched styrene polymers, telomers, and adducts, their synthesis, their bromination, and their uses - Google Patents

Branched and star-branched styrene polymers, telomers, and adducts, their synthesis, their bromination, and their uses Download PDF

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Publication number
WO2010065467A1
WO2010065467A1 PCT/US2009/066132 US2009066132W WO2010065467A1 WO 2010065467 A1 WO2010065467 A1 WO 2010065467A1 US 2009066132 W US2009066132 W US 2009066132W WO 2010065467 A1 WO2010065467 A1 WO 2010065467A1
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range
whole number
styrene
independently
brominated
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French (fr)
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WO2010065467A8 (en
Inventor
William J Layman
Charles H. Kolich
Arthur G. Mack
Jonathan P. Mccarney
Govindarajulu Kumar
Junzuo Wang
Jorge Morice
Zhongxin Ge
Bo Liu
Ravindra R. Joshi
Hoover B. Chew
Douglas W. Luther
Kimberly M. White
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Albemarle Corp
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Albemarle Corp
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Priority to MX2011005658A priority Critical patent/MX2011005658A/es
Priority to CA2744201A priority patent/CA2744201A1/en
Priority to JP2011539617A priority patent/JP2012510562A/ja
Priority to US13/130,105 priority patent/US8476373B2/en
Priority to CN2009801538697A priority patent/CN102272176A/zh
Priority to EP09804217A priority patent/EP2361269A1/en
Publication of WO2010065467A1 publication Critical patent/WO2010065467A1/en
Priority to IL213339A priority patent/IL213339A0/en
Anticipated expiration legal-status Critical
Publication of WO2010065467A8 publication Critical patent/WO2010065467A8/en
Ceased legal-status Critical Current

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    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L53/00—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
    • C08L53/005—Modified block copolymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L25/00—Compositions of, homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring; Compositions of derivatives of such polymers
    • C08L25/02—Homopolymers or copolymers of hydrocarbons
    • C08L25/04—Homopolymers or copolymers of styrene
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F112/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
    • C08F112/02—Monomers containing only one unsaturated aliphatic radical
    • C08F112/04—Monomers containing only one unsaturated aliphatic radical containing one ring
    • C08F112/06—Hydrocarbons
    • C08F112/12—Monomers containing a branched unsaturated aliphatic radical or a ring substituted by an alkyl radical
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F12/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
    • C08F12/02—Monomers containing only one unsaturated aliphatic radical
    • C08F12/04—Monomers containing only one unsaturated aliphatic radical containing one ring
    • C08F12/06—Hydrocarbons
    • C08F12/08—Styrene
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/18—Introducing halogen atoms or halogen-containing groups
    • C08F8/20—Halogenation
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/18—Introducing halogen atoms or halogen-containing groups
    • C08F8/20—Halogenation
    • C08F8/22—Halogenation by reaction with free halogens
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L25/00—Compositions of, homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring; Compositions of derivatives of such polymers
    • C08L25/02—Homopolymers or copolymers of hydrocarbons
    • C08L25/04—Homopolymers or copolymers of styrene
    • C08L25/06—Polystyrene
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L51/00—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
    • C08L51/04—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers grafted on to rubbers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L53/00—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L55/00—Compositions of homopolymers or copolymers, obtained by polymerisation reactions only involving carbon-to-carbon unsaturated bonds, not provided for in groups C08L23/00 - C08L53/00
    • C08L55/02—ABS [Acrylonitrile-Butadiene-Styrene] polymers
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    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
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    • C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
    • 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
    • C08K3/22—Oxides; Hydroxides of metals
    • C08K3/2279—Oxides; Hydroxides of metals of antimony
    • 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
    • C08K5/03—Halogenated hydrocarbons aromatic, e.g. C6H5-CH2-Cl
    • 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
    • C08L25/00—Compositions of, homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring; Compositions of derivatives of such polymers
    • C08L25/18—Homopolymers or copolymers of aromatic monomers containing elements other than carbon and hydrogen

Definitions

  • styrene telomer denotes styrene branched and/or star-branched addition product(s) having degrees of polymerization in the range of about 0 to about 1.1 and having less than about 10 GPC area% of the molecular weight distribution having an M w greater than 620 Daltons;
  • the value of "degrees of polymerization” can be satisfactorily estimated by calculating as if the material was a linear polymer. The calculation is, therefore, a reasonable approximation.
  • each C 6 H 5 is a phenyl group and each C 6 H a is a substituted phenyl group
  • n is a whole number and is in the range of 0 ⁇ n ⁇ 8
  • a is a whole number independently equal to 2, 3 or 4
  • b is a whole number independently equal to 0, 1, 2 or 3
  • c is a whole number independently equal to 1, 2, 3 or 4
  • the sum of a +b + c 6 for any discrete molecule.
  • each C 6 H 1 Br J is a brominated phenyl group and each C 6 H x ⁇ Br x is a brominated substituted phenyl group;
  • n is a whole number and is in the range of 0 ⁇ n ⁇ 8;
  • x is a whole number equal to 0 to 4;
  • y is a whole number equal to 0 to 4;
  • b is a whole number independently equal to 0, 2 or 3;
  • c is a whole number independently equal to 1, 2, 3 or 4;
  • i is a whole number equal to 0 to 4:
  • a feature of the process for preparing the branched or star-branched styrene polymeric, telomeric, and monomeric product distributions of this invention is the extent to which the reagents in the reaction mixture are uniformly dispersed.
  • the combination of significant agitation and dispersive mixing of the reagents in the reaction mixture is utilized in order to provide the product distributions of this invention. More specifically, the agitation and mixing used should be at least sufficient to maintain a substantially homogeneous concentration profile in the reaction mixture.
  • the quenching is effected using a protic solvent which, (i) if water is the quenching solvent, at least one phase cut is made to separate the organic and aqueous phases, and (ii) if a quenching solvent other than water is used, wash water is added to extract the quenching solvent and form an organic phase and an aqueous phase which are then separated by a phase cut.
  • a protic solvent which, (i) if water is the quenching solvent, at least one phase cut is made to separate the organic and aqueous phases, and (ii) if a quenching solvent other than water is used, wash water is added to extract the quenching solvent and form an organic phase and an aqueous phase which are then separated by a phase cut.
  • a commercial plant facility can be operated either on a batch, semi-batch, or continuous mode using balanced feeds as described above.
  • Step C) with the desire to obtain formulations having a substantially reduced level of the lowest molecular styrene addition product, the mono-adducts, it is advantageous to recover and recycle the distribution of mono-adducts. This is typically done by further stripping and is conveniently conducted using a WFE.
  • the recovered distribution of mono-adducts can be combined with the dried recovered CTA and/or dried TMEDA and recycled in the process in Step A) above.
  • the reactor was charged with the chain transfer agent(s) through a dip leg by means of a diaphragm pump.
  • Alkyl lithium, additional solvents and the amine promoter (TMEDA) were all fed subsurface to the stirred chain transfer agent(s) through the same dip leg.
  • Styrene was pumped into the reactor by means of a metering pump through a 3" cylindrical column (1.75" dia. -100 g) of Basic Aluminum Oxide (EMD Chemicals, Aluminum oxide 90, mesh 70-230, column chromatography grade) and delivered as a fine stream or spray above the surface of the reaction mixture through two 1/16" OD feed nozzles.
  • EMD Chemicals Basic Aluminum Oxide
  • Example 6 The procedure of Example 6 was repeated except that 129 ml (117.2 g, 1.13 mol) of styrene was fed over a 168 minute period to a reaction mass formed from 109 ml (95.5 g, 0.9 mol) o-xylene, 4.5 ml (0.009 mol) 2 M n-butyl lithium and 1.28 ml (0.99 g, 0.0086 mol) of TMEDA.
  • GPC analysis for the reaction mass excluding o-xylene is summarized in Table 1.
  • Example 6 The procedure of Example 6 was repeated except that 76.5 ml (69.6 g, 0.67 mol) of styrene dissolved in 36.2 mL o-xylene (31.9 g, 0.3 mol) was fed over a 242 minute period at about 115 0 C to a reaction mass formed from 84.1 g l-(2-methylphenyl)-3-phenylpropane (0.40 mol), 12.1 mL (10.6 g, 0.1 mol) o-xylene, 2.8 mL (0.0056 mol) n-butyl lithium (2 M in cyclohexane) and 0.83 mL (0.52 g, 0.0056 mol) TMEDA.
  • GPC analysis for the reaction mass excluding o-xylene is summarized in Table 2.
  • the initial form of the aluminum halide catalyst used in the processes of this invention is as AlCl 3 or AlBr 3 .
  • the AlCl 3 is desirably slurried in a suitable diluent.
  • AlCl 3 can be reacted by means of chloride bromide exchange (trans- halogenation) to produce a mixed or partially mixed chlorobromo aluminum trihalide with improved solubility in the liquid diluent.
  • chloride bromide exchange trans- halogenation
  • the bromination processes of this invention can be conducted as a batch, semi- batch or as a continuous process.
  • the solvent used in the bromination of the product distributions of this invention and reactor pre-charges can be selected from any of the following exemplary solvents; dichloromethane, dibromomethane, bromochloromethane, bromotrichloromethane, chloroform, 1,2-dibromoethane, 1,1-dibromoethane, l-bromo-2-chloroethane, 1,2- dichloroethane, 1,1,2-tribromoethane, 1,1,2,2-tetrabromoethane, 1,2-dibromopropane, 1- bromo-3-chloropropane, 1-bromobutane, 2-bromobutane, 2-bromo-2-methylpropane, 1- bromopentane, 1,5-dibromopentane, l-bromo-2-methylbutane, 1-bromohexane, 1- bromoheptane, bromocyclohexane, and
  • the amount of bromine fed is that amount required to achieve the desired bromination level sought assuming some small loss of bromine overhead with by-product HBr.
  • wt Br wt% Br • wt Substrate brommate d
  • the product distribution of this invention, brominating agent and AlBr 3 feeds should be made beneath the surface of the reactor contents/reaction mass and in close proximity to each other. It is a principle of this invention that the bromination of the product distributions of this invention should occur quickly.
  • the rates of reaction for the brominations of this invention are very fast due to reaction kinetics.
  • the rate-determining factor is the rate of mass transfer.
  • the use of proximate feeds is designed so that the reactants and catalyst are close, one to the other.
  • Another factor in assuring fast bromination is the feed of the AlBr 3 in solution with bromine.
  • the pressure in the reactor during the bromination is not critical, super- atmospheric pressures being the norm. However, very high pressures are not preferred in the context of equipment requirements and safety issues. Autogenous pressures are permissible.
  • Subsequent to the reactant and catalyst feeds it is permissible to allow the reaction mass to experience a ride time to ensure that bromination has ceased. It is permissible, when brominating at about 74 wt% bromine, to allow the temperature to warm to about 7 0 C to help facilitate consumption and react out as much of the fed bromine as is practical.
  • an aqueous phase is formed.
  • the pH of the sodium borohydride solution is such that the formed aqueous phase has a pH between about 10 and about 14 throughout the period that the formed aqueous phase is in contact with the organic phase.
  • aqueous caustic sodium borohydride treatment or wash can be used at any time after the water quench step and phase separation and on any recovered organic phase in the down stream, finishing sequence.
  • the resulting solids are separated from the water by conventional means, e.g. filtration and the like.
  • the separated solids are then dried by conventional drying techniques, again keeping in mind the T g of the solids.
  • the dried solids are the finished compositions of this invention.
  • the BCM can be either fresh or a BCM recycle heel from a previous run
  • Example cooling was provided through out the operation such that the reaction temperature remains close to -2 0 C.
  • the transfer of the reaction mixture was affected by gravity to the 6 L quench vessel through the bottom drain valve and the 3 /s" (9.5 mm) O.D. PTFE transfer line.
  • the bromination reactor was then recharged with another 816 g of dry BCM and the feeds continued at -6 to -2 0 C.
  • a second 60-minute co-feed and then a third 60-minute co-feed was conducted. Each time the reaction mass was quenched as below.
  • the quench vessel was previously charged with 1000 mL tap water (25 0 C) and stirred at 400 rpm to assure intimate mixing of the organic and aqueous phase.
  • the quench was exothermic and a 1O 0 C temperature rise was observed.
  • 10% sodium bisulfite was added until the red color associated with elemental Br 2 was quenched. Agitation was stopped and the organic phase allowed time to separate and settle.
  • the lower organic phase was physically separated and transferred to a 6 L wash vessel containing 1000 mL of 1 % NaBH 4 in aqueous 10% NaOH and gently stirred at room temperature while the 2 nd and then the 3 rd portions of the co-feed were completed.
  • Example BR-21 The procedure of Example BR-21 was used except that 500 g of SBSPD3b was combined with 1500 g of dry BCM and was co-fed with 1941.18 g of bromine containing 0.25 wt% AlBr 3 . The co-feed was conducted in three 60 minute periods with each co-feed fed to 1283 g heel of dry BCM. The workup procedure was that of Example Br-22. The process yielded 1345.7 grams of product, analyses of which are summarized in Table 4.
  • Example BR-21 The procedure of Example BR-21 was used except that 500 g of SBSPD5c was combined with 1500 g of dry BCM and was co-fed with 2389.83 g of bromine containing 0.25 wt% AlBr 3 . The co-feed was conducted in three 60 minute periods with each co-feed fed to 1283 g heel of dry BCM. The workup procedure was that of Example Br-22. The process yielded 1552.6 grams of product analyses of which are summarized in Table 4.
  • Example BR-21 The procedure of Example BR-21 was used except that 500 g of SBSPD5b was combined with 1500 g of dry BCM and was co-fed with 1985.07 g of bromine containing 0.25 wt% AlBr 3 . The co-feed was conducted in three 60 minute periods with each co-feed fed to 1283 g heel of dry BCM. The workup procedure was that of Example Br-22. The process yielded 1382.5 grams of product analyses of which are summarized in Table 4.
  • Example BR-21 The procedure of Example BR-21 was used except that 439.5 g of SBSPD5c was combined with 1318 g of dry BCM and was co-fed with 2501.77 g of bromine containing 0.25 wt% AlBr 3 . The co-feed was conducted in three 60 minute periods with each co-feed fed to 1333 g heel of dry BCM.
  • the workup procedure was that of Example Br-22. The work-up involved a heavy rag layer due to insoluble material. Multiple BCM washes of the rag were employed to recover as much product as possible. The washes were combined with the organic phase and treated as in Br-22. The process yielded 1264.95 grams of product analyses of which are summarized in Table 4.
  • Rxn denotes reaction
  • XRF denotes X-ray fluorescence test results
  • T g glass transition temperature as determined by differential scanning calorimetry (DSC)
  • TGA denotes thermogravimetric analysis
  • FP stands for final product
  • GPC denotes gel permeation chromatography result.
  • thermoplastic formulations Any of a number of conventional additives used in thermoplastic formulations may be used, in their respective conventional amounts, with the flame retardants of this invention.
  • conventional additives include plasticizers, antioxidants, fillers, pigments, UV stabilizers, lubricants, impact modifiers, and the like.
  • thermoset resin is a novolak resin
  • test tube With a constant nitrogen purge at 0.5 SCFH, the test tube is heated at 300 0 C in a molten salt bath (51.3% KNO 3 /48.7% NaNO 3 ) for 15 minutes followed by 5 minutes at ambient temperature. The test tube containing the sample is then replaced with a clean dry test tube, and the apparatus is purged with nitrogen for an additional 10 minutes with the empty test tube in the 300°C salt bath. The test tube, tubing and gas dispersion tubes are all rinsed with deionized water, and the rinse is combined quantitatively with the solutions in the three collection flasks.
  • molten salt bath 51.3% KNO 3 /48.7% NaNO 3
  • the article “a” or “an” if and as used herein is not intended to limit, and should not be construed as limiting, a claim to a single element to which the article refers. Rather, the article “a” or “an” if and as used herein is intended to cover one or more such elements, unless the text taken in context clearly indicates otherwise.
  • the invention may comprise, consist or consist essentially of the materials and/or procedures recited herein.

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  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Fireproofing Substances (AREA)
PCT/US2009/066132 2008-12-02 2009-11-30 Branched and star-branched styrene polymers, telomers, and adducts, their synthesis, their bromination, and their uses Ceased WO2010065467A1 (en)

Priority Applications (7)

Application Number Priority Date Filing Date Title
MX2011005658A MX2011005658A (es) 2008-12-02 2009-11-30 Polimeros, telomeros y aductos de estireno ramificados y ramificados en forma de estrella, su sintésis, bromacion y usos.
CA2744201A CA2744201A1 (en) 2008-12-02 2009-11-30 Branched and star-branched styrene polymers, telomers, and adducts their synthesis, their bromination, and their uses
JP2011539617A JP2012510562A (ja) 2008-12-02 2009-11-30 分岐および星型分岐スチレンの重合体、短鎖重合体、ならびに付加物、それらの合成、それらの臭素化、およびそれらの使用
US13/130,105 US8476373B2 (en) 2008-12-02 2009-11-30 Branched and star-branched styrene polymers, telomers, and adducts, their synthesis, their bromination, and their uses
CN2009801538697A CN102272176A (zh) 2008-12-02 2009-11-30 支化和星形支化的苯乙烯聚合物、调聚物和加合物，其合成、其溴化及其用途
EP09804217A EP2361269A1 (en) 2008-12-02 2009-11-30 Branched and star-branched styrene polymers, telomers, and adducts, their synthesis, their bromination, and their uses
IL213339A IL213339A0 (en) 2008-12-02 2011-06-02 Branched and star-branched styrene polymers, telomers, and adducts, their synthesis, their bromination, and their uses

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US11928508P 2008-12-02 2008-12-02
US61/119,285 2008-12-02

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