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WO2000020363A1 - Nouveaux 1,2-bis(phenyl) tetrafluoro ethanes bromes et procedes d'ignifugation de materiaux inflammables - Google Patents

Nouveaux 1,2-bis(phenyl) tetrafluoro ethanes bromes et procedes d'ignifugation de materiaux inflammables Download PDF

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Publication number
WO2000020363A1
WO2000020363A1 PCT/US1999/022859 US9922859W WO0020363A1 WO 2000020363 A1 WO2000020363 A1 WO 2000020363A1 US 9922859 W US9922859 W US 9922859W WO 0020363 A1 WO0020363 A1 WO 0020363A1
Authority
WO
WIPO (PCT)
Prior art keywords
bis
phenyl
bromine
accordance
tetra
Prior art date
Application number
PCT/US1999/022859
Other languages
English (en)
Inventor
Charles J. Mazac
Leonard J. Chyall
Paul Kleindl
Mark L. Robin
Original Assignee
Great Lakes Chemical Corporation
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Great Lakes Chemical Corporation filed Critical Great Lakes Chemical Corporation
Priority to EP99951704A priority Critical patent/EP1119536A1/fr
Priority to AU64090/99A priority patent/AU6409099A/en
Publication of WO2000020363A1 publication Critical patent/WO2000020363A1/fr

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Classifications

    • 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
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
    • C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
    • C07C17/12—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms in the ring of aromatic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
    • C07C17/18—Preparation of halogenated hydrocarbons by replacement by halogens of oxygen atoms of carbonyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
    • C07C25/18—Polycyclic aromatic halogenated hydrocarbons

Definitions

  • the present invention relates to bromine- containing 1 , 2 -bis (phenyl) tetrafluoroethanes of the formula:
  • Decabromodiphenyl alkanes such as decabromodiphenyl methane and decabromodiphenyl ethane are known compounds that are useful as flame retardants, as disclosed in Hussain U.S. Patent No. 5,008,477.
  • the compounds are prepared by brominating diphenyl alkane, in the presence of a bromination catalyst such as A1C1 3 and/or AlBr 3 , at a temperature of about 50°C to about 60°C, wherein the alkane group has 1-10 carbon atoms. It has been found, in accordance with the present invention, that the above- defined bromine-containing 1,2-bis (phenyl) tetrafluoro- ethylene compounds can be prepared and exhibit improved flame retardancy to flammable materials .
  • novel compounds in accordance with the present invention have the general formula:
  • the compounds of formula I can be used as synthesis intermediates for the preparation of agricultural and pharmaceutical compounds, and can also be used as flame retardants.
  • novel compounds in accordance with the present invention have the general formula:
  • novel compounds are any of the following compounds :
  • the compounds of formula I may be prepared in a number of ways.
  • the compounds may be prepared via the reaction of 1, 2-bis (phenyl) - tetrafluoroethane with a bromination agent, such as elemental bromine in fuming sulfuric acid:
  • the amount of bromine reacted with the 1, 2-bis (phenyl) tetrafluoroethane reactant is readily controlled by adjusting the molar ratio of bromine to 1,2 -bis (phenyl) tetrafluoroethane. Excess bromine favors the formation of the more highly brominated compounds of the present invention, whereas lower amounts of bromine favor the production of the less heavily brominated compounds of the present invention.
  • bromination agents may be employed, for example, elemental bromine in the presence of a Lewis acid, or N-bromo compounds such as N-bromosuccinimide and dibromodimethylhydantoin.
  • the 1, 2-bis (phenyl) tetrafluoroethane precursor may be prepared via the reaction of benzil with a fluorination agent, such as SF 4 or diethylaminosulfur trifluoride (DAST)
  • the bromine-containing 1, 2-bis (phenyl) tetra- fluoroethane should be incorporated into or onto the flammable material in an amount sufficient to obtain the desired flame retardancy, which varies with the particular flammable material in which the compound (s) is incorporated.
  • the amount of compound (s) incorporated into the flammable material is in the range of about 2% to about 50% by weight of flammable material, preferably about 5% to about 30%, based on the weight of flammable material .
  • the bromine-containing 1, 2-bis (phenyl) tetra- fluoroethanes of the present invention are useful for flame retardation of any flammable material , including monomers and oligomers, but are particularly advantageous for flame retarding thermoplastic and thermosetting polymers and copolymers.
  • examples include polyolefins, polyurethanes , polyamides, polyimides, polycarbonates, polyethers, polyesters, epoxy resins, polyphenols, and elastomers, such as natural rubber, butyl rubber, and polysilanes.
  • the oligomers and polymers may be cross-linked or non cross-linked and may contain typical additives, such as plasticizers, stabilizers, antioxidants, fillers, pigments and the like.
  • the flame retardant compounds of the present invention can be compounded into the flammable material at any stage of processing, e.g., added to the monomer or oligomer prior to, during, or after polymerization, or during extrusion, melt blending, or molding of the flammable material, e.g., polymer.
  • the recovered solid was washed with several portions of water and methylene chloride and identified by nuclear magnetic resonance (NMR) , mass spectrometry (MS) , Fourier Transform Infra Red (FTIR) , and bromine content analysis as 1, 2-bis (pentabromophenyl) tetrafluoroethane .
  • NMR nuclear magnetic resonance
  • MS mass spectrometry
  • FTIR Fourier Transform Infra Red
  • bromine content analysis 1, 2-bis (pentabromophenyl) tetrafluoroethane .
  • This example demonstrates the flame retardancy properties of the 1, 2 -bis (pentabromophenyl) tetra- fluoroethane compound.
  • a small-scale "Mini-Max" bowl mixer was employed to compound 1,2 -bis (pentabromophenyl) tetrafluoroethane (BPTFE) and 1, 2-bis (pentabromophenyl) ethane (BPE) , a commercially available flame retardant, into high impact polystyrene.
  • BPTFE 1,2 -bis (pentabromophenyl) tetrafluoroethane
  • BPE 1, 2-bis (pentabromophenyl) ethane
  • the lower oxygen index (LOI) and the Underwriters Laboratories UL-94 rating were then determined for the samples.
  • the results shown in Table 1 indicate that the flame retardant performance of the new compound is identical to that of the commercial product.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Fireproofing Substances (AREA)

Abstract

L'invention porte sur des 1,2-bis(phényl) tétrafluoro éthanes contenant du brome de formule (I) dans laquelle x=1-5, et y=0-5, et sur un procédé de préparation de ces composés. Lesdits composés, qui servent d'intermédiaires dans la production de composés présentant une activité pharmaceutique ou agricole, peuvent également servir d'ignifuges.
PCT/US1999/022859 1998-10-07 1999-10-04 Nouveaux 1,2-bis(phenyl) tetrafluoro ethanes bromes et procedes d'ignifugation de materiaux inflammables WO2000020363A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP99951704A EP1119536A1 (fr) 1998-10-07 1999-10-04 Nouveaux 1,2-bis(phenyl) tetrafluoro ethanes bromes et procedes d'ignifugation de materiaux inflammables
AU64090/99A AU6409099A (en) 1998-10-07 1999-10-04 Novel bromine-containing 1,2-bis(phenyl) tetrafluoro ethanes and method of imparting flame retardancy to flammable materials

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US10333498P 1998-10-07 1998-10-07
US60/103,334 1998-10-07

Publications (1)

Publication Number Publication Date
WO2000020363A1 true WO2000020363A1 (fr) 2000-04-13

Family

ID=22294628

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1999/022859 WO2000020363A1 (fr) 1998-10-07 1999-10-04 Nouveaux 1,2-bis(phenyl) tetrafluoro ethanes bromes et procedes d'ignifugation de materiaux inflammables

Country Status (3)

Country Link
EP (1) EP1119536A1 (fr)
AU (1) AU6409099A (fr)
WO (1) WO2000020363A1 (fr)

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB934970A (en) * 1961-12-05 1963-08-21 Kalk Chemische Fabrik Gmbh Process for the production of bromine derivatives of aromatic compounds containing more than three bromine atoms
US5741949A (en) * 1994-10-05 1998-04-21 Great Lakes Chemical Corporation Continuous bromination process and products thereof

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB934970A (en) * 1961-12-05 1963-08-21 Kalk Chemische Fabrik Gmbh Process for the production of bromine derivatives of aromatic compounds containing more than three bromine atoms
US5741949A (en) * 1994-10-05 1998-04-21 Great Lakes Chemical Corporation Continuous bromination process and products thereof

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
CHRISTY M E ET AL: "2-, 3-, and 4-(.alpha.,.alpha.,.beta.,.beta.-Tetrafluorophenethyl)b enzylamines. A new class of antiarrhythmic agents", J. MED. CHEM. (JMCMAR);1977; VOL.20 (3); PP.421-30, Merck Sharp and Dohme Res. Lab.;West Point; Pa., XP002125328 *
HASEK W R ET AL: "The chemistry of sulfur tetrafluoride. II The fluorination of organic carbonyl compounds", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY., vol. 82, 1960, AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC., US, pages 543 - 551, XP002125300, ISSN: 0002-7863 *
MATHEY F ET AL: "Reactions of molybdenum hexafluoride with functionalized aldehydes and ketones", TETRAHEDRON (TETRAB);1975; VOL.31 (5); PP.391-401, Inst. Natl. Rech. Chim. Appl.;Vert-le-Petit; Fr., XP002125329 *

Also Published As

Publication number Publication date
EP1119536A1 (fr) 2001-08-01
AU6409099A (en) 2000-04-26

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