3-phenyl-benzofuran-2-one derivatives containing phosphorus as stabilizers
The invention relates to a composition comprising an organic material susceptible to oxidative, thermal or light-induced degradation and a compound of formula I-P, I-O or I-M Further embodiments are a compound of formula I-P, I-O or I-M, a process for protection of the organic material by the compound, the use of the compound for stabilizing the organic material, an additive composition comprising the compound, a process for manufacturing the compound and intermediates involved therein.
1. A composition, comprising:
a) an organic material susceptible to oxidative, thermal or light-induced degradation, and
b) a compound (101), (102), (103), (104), (105), (106), (107), (108) or (109):
2. The composition according to claim 1 , wherein the organic material is a polymer, an oligohydroxy compound, a wax, a fat or a mineral oil.
3. The composition according to claim 2 , wherein the organic material is a polymer, which is a polyolefin or a copolymer thereof, a polystyrene or a copolymer thereof, a polyurethane or a copolymer thereof, or a polyether, and which is obtained by a method comprising:
polymerizing an epoxide, an oxetane or tetrahydrofuran, or a copolymer thereof, a polyester or a copolymer thereof, a polycarbonate or a copolymer thereof, a poly(vinyl chloride) or a copolymer thereof, a poly(vinylidene chloride) or a copolymer thereof, a polysulfone or a copolymer thereof, a polybutadiene or a copolymer thereof, a poly(vinyl acetate) or a copolymer thereof, a poly(vinyl alcohol) or a copolymer thereof, a poly(vinyl acetal) or a copolymer thereof, or a polyamide or a copolymer thereof.
4. The composition according to claim 1 , wherein component b) is present in the composition in an amount of 0.0005% to 10% based on the weight of component a).
5. The composition according to claim 1 , further comprising:
as a component c), a first further additive.
6. The composition according to claim 5 , which comprises as component c) a phenolic antioxidant, which is tetrakis-[β-(3,5-di-tert-butyl-4-hydroxyphenyl)-propionyloxymethyl]methane or stearyl β-(3,5-di-tert-butyl-4-hydroxyphenyl)-propionate.
7. The composition according to claim 5 , which comprises as component c) a phosphite, which is tris-(2,4-di-tert-butylphenyl) phosphite.
8. The composition according to claim 5 , wherein the first further additive comprises at least one selected from the group consisting of a phosphite or phosphorite different to component b), an acid scavenger, a phenolic antioxidant, and an aminic antioxidant.
9. The composition according to claim 8 , wherein the further additive comprises a phenolic antioxidant, which is an ester of P-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid.
10. The composition according to claim 8 , further comprising:
as a component d), a second further additive, which is a phosphite or phosphorite different to component b), an acid scavenger, a phenolic antioxidant or an aminic antioxidant,
with the proviso that component d) is a different substance than component c).
11. The composition according to claim 1 , wherein component (h) is compound (101) as defined in claim 1 .
12. The composition according to claim 1 , wherein component (b) is compound (102) as defined in claim 1 .
13. The composition according to claim 1 , wherein component (h) is compound (103) as defined in claim 1 .
14. The composition according to claim 1 , wherein component (b) is compound (104) as defined in claim 1 .
15. The composition according to claim 1 , wherein component (b) is compound (105) as defined in claim 1 .
16. The composition according to claim 1 , wherein component (b) is compound (106) as defined in claim 1 .
17. The composition according to claim 1 , wherein component (b) is compound (107) as defined in claim 1 .
18. The composition according to claim 1 , wherein component (b) is compound (108) as defined in claim 1 .
19. The composition according to claim 1 , wherein component (b) is compound (109) as defined in claim 1 .
20. A process for protecting an organic material susceptible to oxidative, thermal or light-induced degradation, the process comprising incorporating the organic material into, or applying the organic material onto, a compound (101), (102), (103), (104), (105), (106), (107), (108) or (109):
21. The process according to claim 20 , wherein:
the organic material is a polymer;
the incorporating into the polymer is carried out at a temperature between 135° C. to 350° C.; and
the polymer is a polyolefin or a copolymer thereof, a polystyrene or a copolymer thereof, a polyurethane or a copolymer thereof, or a polyether, which is obtained by a method comprising polymerizing an epoxide, an oxetane or tetrahydrofuran, or a copolymer thereof, a polyester or a copolymer thereof, a polycarbonate or a copolymer thereof, a poly(vinyl chloride) or a copolymer thereof, a poly(vinylidene chloride) or a copolymer thereof, a polysulfone or a copolymer thereof, a polybutadiene or a copolymer thereof, a poly(vinyl acetate) or a copolymer thereof, a poly(vinyl alcohol) or a copolymer thereof, a poly(vinyl acetal) or a copolymer thereof, or a polyamide or a copolymer thereof.
22. A compound (101), (102), (103), (104), (105), (106), (107), (108) or (109):
23. The compound according to claim 22 , wherein the compound is compound (101).
24. The compound according to claim 22 , wherein the compound is compound (102).
25. The compound according to claim 22 , wherein the compound is compound (103).
26. The compound according to claim 22 , wherein the compound is compound (104).
27. The compound according to claim 22 , wherein the compound is compound (105).
28. The compound according to claim 22 , wherein the compound is compound (106).
29. The compound according to claim 22 , wherein the compound is compound (107).
30. The compound according to claim 22 , wherein the compound is compound (108).
31. The compound according to claim 22 , wherein the compound is compound (109).
32. An additive composition, comprising:
b) a compound (101), (102), (103), (104), (105), (106), (107), (108) or (109); and
c) a first further additive, which is a phosphite or phosphorite different to component b), an acid scavenger, a phenolic antioxidant or an aminic antioxidant:
33. The additive composition according to claim 32 , which comprises, as component c), a phenolic antioxidant, which is an ester of β-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid.
34. The additive composition according to claim 32 , further comprising:
as a component d), a second further additive, which is a phosphite or phosphonite different to component b), an acid scavenger, a phenolic antioxidant or an aminic antioxidant,
with the proviso that component d) is a different substance than component c).