CA2455841A1 - Flame retardant compositions - Google Patents

Flame retardant compositions Download PDF

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Publication number
CA2455841A1
CA2455841A1 CA002455841A CA2455841A CA2455841A1 CA 2455841 A1 CA2455841 A1 CA 2455841A1 CA 002455841 A CA002455841 A CA 002455841A CA 2455841 A CA2455841 A CA 2455841A CA 2455841 A1 CA2455841 A1 CA 2455841A1
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CA
Canada
Prior art keywords
bis
composition according
component
sterically hindered
hindered amine
Prior art date
Legal status (The legal status 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 status listed.)
Granted
Application number
CA002455841A
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French (fr)
Other versions
CA2455841C (en
Inventor
Nikolas Kaprinidis
Douglas Wayne Horsey
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF Schweiz AG
Original Assignee
Ciba Specialty Chemicals Holding Inc.
Nikolas Kaprinidis
Douglas Wayne Horsey
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.)
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Application filed by Ciba Specialty Chemicals Holding Inc., Nikolas Kaprinidis, Douglas Wayne Horsey filed Critical Ciba Specialty Chemicals Holding Inc.
Publication of CA2455841A1 publication Critical patent/CA2455841A1/en
Application granted granted Critical
Publication of CA2455841C publication Critical patent/CA2455841C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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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
    • C08K5/16—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
    • 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
    • C08K5/16—Nitrogen-containing compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L27/00—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 a halogen; Compositions of derivatives of such polymers
    • C08L27/02—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 a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment
    • C08L27/12—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 a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment containing fluorine atoms
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L27/00—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 a halogen; Compositions of derivatives of such polymers
    • C08L27/02—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 a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment
    • C08L27/12—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 a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment containing fluorine atoms
    • C08L27/18—Homopolymers or copolymers or tetrafluoroethene

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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)

Abstract

Organic polymeric substrates, for example polyolefins such as polypropylene, can be made flame retardant by the incorporation of a synergistic mixture of (i.) a sterically hindered amine of the nitroxyl, hydroxylamine, alkoxyamine or hydroxyalkoxyamine class, and (ii.) a fluorinated polyolefin. Advantageously, a further flame retardant may be added, without the need of adding an antimony synergist. The compositions of the invention combine good flame retardant properties with light stability and good mechanical properti es.

Claims (17)

1. A flame retardant composition which comprises (A) an organic polymer substrate, (B) an effective flame retarding amount of a mixture of (i.) at least one sterically hindered amine of the nitroxyl, hydroxylamine, alkoxyamine or hydroxyalkoxyamine class, and (ii.) at least one fluorinated polyolefin.
2. A composition according to claim 1 containing as additional component (iii.) at least one compound selected from the group consisting of the halogenated flame retardants.
3. A composition according to claim 1 containing no antimony compounds or antimony compounds in an amount less than 1 % by weight based on the weight of the polymer component A.
4. A composition according to claim 1 containing no filler or a filler in an amount less than than 3 % by weight based on the weight of the polymer component A.
5. A composition according to claim 1 in which the polymer component A is a thermoplastic polymer.
6. A composition according to claim 1 in which the polymer component A is selected from the group of resins consisting of the polyolefins, the thermoplastic olefins, styrenic polymers and copolymers, ABS and polymers which contain hetero atoms, double bonds or aromatic rings; especially wherein component A is selected from the group of resins consisting of polyethylene, polypropylene or copolymers thereof.
7. A composition according to claim 1 in which the sterically hindered amine of the nitroxyl, hydroxylamine, alkoxyamine or hydroxyalkoxyamine class is compound containing a group of the formula (I) or (II) in which G is hydrogen or methyl, and G1 and G2, independently of one another, are hydrogen, methyl or together are a substituent =O, and has a molecular weight from the range 170 - 10000 g/mol.
8. A composition according to claim 7 wherein the sterically hindered amine is selected from the compounds (a) the reaction product of 2,4-bis[(1-cyclohexyloxy-2,2,6,6-piperidin-4-yl)butylamino]-6-chloro-s-triazine with N,N'-bis(3-aminopropyl)ethylenediamine);
(b) 1-cyclohexyloxy-2,2,6,6-tetramethyl-4-octadecylaminopiperidine;
(c) bis(1-octyloxy-2,2,6,6-tetramethylpiperidin-4-yl) sebacate;
(d) 2,4-bis[(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)butylamino]-6-(2-hydroxyethylamino-s-triazine;
(e) bis(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl) adipate;
(h) 2,4-bis[(1-cyclohexyloxy-2,2,6,6-piperidin-4-yl)butylamino]-6-chloro-s-triazine;
(i) 1-(2-hydroxy-2-methylpropoxy)-4-octadecanoyloxy-2,2,6,6-tetramethylpiperidine; or (j) the compound of formula in which n is from 1 to 15.
9. A composition according to claim 1 in which the fluorinated polyolefin (component ii) is selected from polytetrafluoroethylene, tetrafluoroethylene-hexafluoropropylene resin or copolymers thereof prepared using minor amounts of fluorine-free ethylenically unsaturated monomers.
10. A composition according to claim 9 in which the fluorinated polyolefin (component ii) is polytetrafluoroethylene of particle size below 1000 micron.
11. A composition according to claim 1 in which the sterically hindered amine of component (i) is contained in an amount from 0.1 to 10% by weight based on the weight of the polymeric substrate (A); and in which the fluorinated polyolefin (component ii) is contained in an amount from 0.01 to 2% by weight based on the weight of the polymeric substrate (A).
12. A composition according to claim 2 in which the halogenated flame retardant of component (iii) is selected from the group consisting of organic aromatic halogenated compounds; organic cycloaliphatic or polycycloaliphatic halogenated compounds;
and organic aliphatic halogenated compounds.
13. A composition according to claim 12 in which the halogenated flame retardant of component (iii) is selected from the group consisting of chloroalkyl phosphate esters, polybrominated diphenyl oxide, decabromodiphenyl oxide, tris[3-bromo-2,2-bis(bromomethyl)propyl] phosphate, bis(2,3-dibromopropyl ether) of bisphenol A, brominated epoxy resin, ethylene-bis(tetrabromophthalimide), bis(hexachlorocyclopentadieno)cyclooctane, chlorinated paraffins, 1,2-bis(tribromophenoxy)ethane, tetrabromo-bisphenol A, ethylene bis-(dibromo-norbornanedicarboximide), bis-(hexachlorocyclopentadieno) cyclooctane, tris-(2,3-dibromopropyl)-isocyanurate, and ethylene-bis-tetrabromophthalimide.
14. A composition according to claim 1 containing a further component selected from pigments, dyes, plasticizers, phenolic antioxidants, thixotropic agents, levelling assistants, basic costabilizers, nitrone stabilizers, amine oxide stabilizers, benzofuranone stabilizers, UV
absorbers, sterically hindered amines, metal passivators, metal oxides, organophosphorus compounds, hydroxylamines, non-halogenated flame retardants, and mixtures thereof;
especially phenolic antioxidants, calcium stearate, zinc stearate, phosphite and phosphonite stabilizers, benzofuranone stabilizers, UV absorbers of the 2-(2'-hydroxyphenyl)benzotriazole and 2-(2-hydroxyphenyl)-1,3,5-triazine classes, and sterically hindered amines.
15. A process for imparting light stability and flame retardancy to an organic polymeric substrate, which process comprises adding to said polymeric substrate a mixture of (i.) a sterically hindered amine of the nitroxyl, hydroxylamine, alkoxyamine or hydroxyalkoxyamine class, and (ii.) a fluorinated polyolefin.
16. A flame retardant additive combination comprising (i.) a sterically hindered amine of the nitroxyl, hydroxylamine, alkoxyamine or hydroxyalkoxyamine class, and (ii.) a fluorinated polyolefin.
17. A molded polymer article comprising (i.) a sterically hindered amine of the nitroxyl, hydroxylamine, alkoxyamine or hydroxyalkoxyamine class, and (ii.) a fluorinated polyolefin.
CA2455841A 2001-08-15 2002-08-06 Flame retardant compositions Expired - Fee Related CA2455841C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US31251701P 2001-08-15 2001-08-15
US60/312,517 2001-08-15
PCT/EP2002/008767 WO2003016388A1 (en) 2001-08-15 2002-08-06 Flame retardant compositions

Publications (2)

Publication Number Publication Date
CA2455841A1 true CA2455841A1 (en) 2003-02-27
CA2455841C CA2455841C (en) 2011-01-04

Family

ID=23211813

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2455841A Expired - Fee Related CA2455841C (en) 2001-08-15 2002-08-06 Flame retardant compositions

Country Status (8)

Country Link
US (1) US20040198875A1 (en)
EP (1) EP1423465B1 (en)
JP (1) JP4389248B2 (en)
AT (1) ATE432313T1 (en)
CA (1) CA2455841C (en)
DE (1) DE60232452D1 (en)
TW (1) TWI301134B (en)
WO (1) WO2003016388A1 (en)

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Also Published As

Publication number Publication date
ATE432313T1 (en) 2009-06-15
JP4389248B2 (en) 2009-12-24
DE60232452D1 (en) 2009-07-09
US20040198875A1 (en) 2004-10-07
EP1423465B1 (en) 2009-05-27
TWI301134B (en) 2008-09-21
EP1423465A1 (en) 2004-06-02
WO2003016388A1 (en) 2003-02-27
JP2005500421A (en) 2005-01-06
CA2455841C (en) 2011-01-04

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