Sterically hindered phenolic phosphonates and polycarbonate resin composition using the same
Disclosed herein is a sterically hindered phenolic phosphonate resin compound represented by the following Chemical Formula 1. The present invention also provides a polycarbonate resin composition including the sterically hindered phenolic phosphonate resin compound as a flame retardant. wherein R 1 is a C 1 -C 6 alkyl group or a C 6 -C 14 aryl group; each R 2 is independently a C 1 -C 6 linear alkyl group or a C 3 -C 6 branched alkyl group; and each n is independently 1-3.
1. A sterically hindered phenolic phosphonate compound represented by the following Chemical Formula 1:
wherein R 1 is a C 1 -C 6 alkyl group or a C 6 -C 14 aryl group; each R 2 is independently a C 1 -C 6 linear alkyl group or a C 3 -C 6 branched alkyl group; and each n is 3.
2. A sterically hindered phenolic phosphonate compound of claim 1 , wherein at least one R 2 is a C 3 -C 6 branched alkyl and R 1 is C 6 -C 14 aryl.
3. A sterically hindered phenolic phosphonate compound of claim 2 , wherein at least one R 2 is t-butyl.
4. A sterically hindered phenolic phosphonate compound of claim 3 , wherein each R 2 is t-butyl.
5. A sterically hindered phenolic phosphonate compound of claim 1 , wherein at least one R 2 is C 1 -C 6 linear alkyl and R 1 is C 6 -C 14 aryl.
6. A sterically hindered phenolic phosphonate compound of claim 5 , wherein at least one R 2 is methyl.
7. A sterically hindered phenolic phosphonate compound of claim 6 , wherein each R 2 is methyl.
8. A method of preparing a sterically hindered phenolic phosphonate compound comprising reacting a phenolic compound represented by the following Chemical Formula 2 with a halogenated phosphonate compound represented by the following Chemical Formula 3
wherein each R 2 is independently a C 1 -C 6 linear alkyl group or a C 3 -C 6 branched alkyl group; and n is 3,
wherein R 1 is a C 1 -C 6 alkyl group or a C 6 -C 14 aryl group; and X is Cl or Br.
9. The method of claim 8 , wherein said sterically hindered phenolic phosphonate compound is prepared by reflux-reacting an equivalent of a halogenated phosphonate compound and two equivalents of a phenolic compound.
10. A method of improving flame retardancy of a thermoplastic resin comprising adding a sterically hindered phenolic phosphonate compound as defined in claim 1 as a flame retardant to said thermoplastic resin.
11. The method of claim 10 , wherein said thermoplastic resin comprises a polycarbonate.
12. A flameproof polycarbonate resin composition comprising:
about 100 parts by weight of a base resin comprising a polycarbonate resin; and
about 0.5 to about 20 parts by weight of a sterically hindered phenolic phosphonate compound represented by the following Chemical Formula 1:
wherein R 1 is C 1 -C 6 alkyl or C 6 -C 14 aryl; each R 2 is independently C 1 -C 6 linear alkyl or C 3 -C 6 branched alkyl; and each n is 3.
13. The flameproof polycarbonate resin composition of claim 12 , wherein said base resin comprises about 50 to about 100% by weight of a polycarbonate resin and about 0 to about 50% by weight of a rubber modified styrenic resin.
14. The flameproof polycarbonate resin composition of claim 13 , wherein said rubber modified styrenic resin comprises about 20 to about 100% by weight of a graft copolymer resin and about 0 to about 80% by weight of a vinyl copolymer resin.
15. The flameproof polycarbonate resin composition of claim 14 , wherein:
said graft copolymer resin is prepared by graft-polymerizing about 5 to about 65% by weight of a rubbery polymer, about 30 to about 95% by weight of an aromatic vinyl monomer, about 1 to about 20% by weight of a monomer copolymerizable with the aromatic vinyl monomer, and about 0 to about 15% by weight of a monomer for providing processability and heat resistance; and
said vinyl copolymer resin is prepared by copolymerizing about 60 to about 90% by weight of an aromatic vinyl monomer, about 10 to about 40% by weight of a monomer copolymerizable with the aromatic vinyl monomer and about 0 to about 30% by weight of a monomer for providing processability and heat resistance.
16. The flameproof polycarbonate resin composition of claim 12 , further comprising about 10 parts by weight or less of an aromatic phosphate ester compound represented by the following Chemical Formula 5 based on 100 parts by weight of the base resin
wherein each R 3 , R 4 , and R 5 is independently hydrogen or a C 1 -C 4 alkyl group; X is a C 6 -C 20 aryl group or a C 1 -C 10 alkyl-substituted C 6 -C 20 aryl group; and n is 0-4.
17. The flameproof polycarbonate resin composition of claim 12 , further comprising at least one additive selected from the group consisting of plasticizers, heat stabilizers, antioxidants, anti-dripping agents, compatibilizers, light-stabilizers, pigments, dyes, inorganic fillers and combinations thereof
18. A molded article molded from the polycarbonate resin composition as defined in claim 12 , wherein the molded article has an average combustion time of about 0.5 seconds or less after a first round of combustion measured for specimens having a thickness of about ⅛″ and a size of about 125 mm by 13 mm in accordance with UL 94 VB.
19. The flameproof polycarbonate resin composition of claim 12 , wherein at least one R 2 is a C 3 -C 6 branched alkyl and R l is C 6 -C 14 aryl.
20. The flameproof polycarbonate resin composition of claim 19 , wherein at least one R 2 is t-butyl.
21. The flameproof polycarbonate resin composition of claim 20 , wherein each R 2 is t-butyl.
22. The flameproof polycarbonate resin composition of claim 12 , wherein at least one R 2 is C 1 -C 6 linear alkyl and R 1 is C 6 -C 14 aryl.
23. The flameproof polycarbonate resin composition of claim 22 , wherein at least one R 2 is methyl.
24. The flameproof polycarbonate resin composition of claim 23 , wherein each R 2 is methyl.