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 1-P, 1-O or I-M. Further embodiments are a compound of formula 1-P, 1-O or 1-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 of formula I-P, I-O or I-M:
wherein:
Y P , Y O and Y M are oxygen or represent a covalent bond;
when Y P , Y O and Y M are oxygen,
R 1P represents one of the subformulae II-P, II-O or II-M:
R 1O represents one of the subformulae II-O or II-M,
R 1M represents the subformulae II-M, or
R 1P together with R 2P , R 1O together with R 2O and R 1M together with R 2M represent one of the subformulae III, IV or V:
or
R 1P , R 1O and R 1M are C 6 -C 10 -aryl, which is unsubstituted or substituted by C 1 -C 8 -alkyl, C 1 -C 8 -alkoxy, halogen or one phenyl, C 1 -C 18 -alkyl, C 3 -C 16 -cycloalkyl, C 7 -C 13 -aralkyl, C 2 -C 18 -alkenyl, C 2 -C 30 -alkyl, which is interrupted by one or more oxygen atoms, or C 2 -C 16 -alkyl, which is interrupted by one sulfur atom,
R 2P represents one of the subformulae II-P, II-O or II-M,
R 2O represents one of the subformulae II-O or II-M,
R 2M represents the subformulae II-M, or
R 2P together with R 1P , R 2O together with R 1O and R 2M together with R 1M represent one of the subformulae III, IV or V, or
R 2P , R 2O and R 2M are C 6 -C 10 -aryl, which is unsubstituted or substituted by C 1 -C 8 -alkyl, C 1 -C 8 -alkoxy, halogen or one phenyl, C 1 -C 18 -alkyl, C 3 -C 16 -cycloalkyl, C 7 -C 13 -aralkyl, C 2 -C 18 -alkenyl, C 2 -C 30 -alkyl, which is interrupted by one or more oxygen atoms, or C 2 -C 16 -alkyl, which is interrupted by one sulfur atom;
when Y P , Y O and Y M represent a covalent bond,
R 1P represents one of the subformulae II-P, II-O or II-M,
R 1O represents one of the subformulae II-O or II-M,
R 1M represents the subformulae II-M, or
R 1P , R 1O and R 1M are C 6 -C 10 -aryl, which is unsubstituted or substituted by C 1 -C 8 -alkyl, C 1 -C 8 -alkoxy, halogen or one phenyl, C 1 -C 18 -alkyl, C 3 -C 16 -cycloalkyl, C 7 -C 13 -aralkyl, C 2 -C 18 -alkenyl, C 2 -C 30 -alkyl, which is interrupted by one or more oxygen atoms, or C 2 -C 16 -alkyl, which is interrupted by one sulfur atom,
R 2P , R 2O and R 2M are C 6 -C 10 -aryl, which is unsubstituted or substituted by C 1 -C 8 -alkyl, C 1 -C 8 -alkoxy, halogen or one phenyl, or halogen;
R 4 , R 5 , R 6 and R 7 are independently from each other hydrogen or C 1 -C 8 -alkyl,
R P2 , R P3 , R P5 and R P6 are independently from each other hydrogen or C 1 -C 8 -alkyl,
R O1 , R O2 , R O5 and R O6 are independently from each other hydrogen or C 1 -C 8 -alkyl,
R M1 , R M3 , R M5 and R M6 are independently from each other hydrogen or C 1 -C 8 -alkyl,
R a1 , R a2 , R a3 and R a4 are independently from each other hydrogen or C 1 -C 8 -alkyl,
R b1 , R b2 , R b3 , R b4 , R b5 and R b6 are independently from each other hydrogen or C 1 -C 8 -alkyl, and
R c1 , R c2 , R c3 and R c4 are independently from each other hydrogen or C 1 -C 8 -alkyl.
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.
4. The composition according to claim 1 , wherein:
R 4 and R 6 are hydrogen,
R 5 and R 7 are independently from each other hydrogen or C 1 -C 8 -alkyl,
R P2 and R P6 are independently from each other hydrogen or C 1 -alkyl,
R P3 and R P5 are independently from each other hydrogen or C 1 -C 4 -alkyl,
R O1 and R O6 are independently from each other hydrogen or C 1 -C 8 -alkyl,
R O2 is hydrogen or C 1 -alkyl,
R O5 is hydrogen or C 1 -C 4 -alkyl,
R M1 is hydrogen or C 1 -alkyl,
R M3 and R M5 are independently from each other hydrogen or C 1 -C 4 -alkyl,
R M6 is hydrogen or C 1 -C 8 -alkyl,
R a1 , R a2 , R a3 and R a4 are independently from each other hydrogen or C 1 -C 4 -alkyl,
R b1 , R b2 , R b3 , R b4 , R b5 and R b6 are independently from each other hydrogen or C 1 -C 4 -alkyl, and
R c1 , R c2 , R c3 and R c4 are independently from each other hydrogen or C 1 -C 4 -alkyl.
5. The composition according to claim 1 , wherein:
Y P , Y O and Y M are oxygen or represent a covalent bond;
when Y P , Y O and Y M are oxygen,
R 1P represents one of the subformulae II-P, II-O or II-M,
R 1O represents one of the subformulae II-O or II-M,
R 1M represents the subformulae II-M, or
R 1P together with R 2P , R 1O together with R 2O and R 1M together with R 2M represent one of the subformulae III, IV or V, or
R 1P , R 1O and R 1M are C 6 -C 10 -aryl, which is unsubstituted or substituted by C 1 -C 8 -alkyl, C 1 -C 18 -alkyl or C 3 -C 16 -cycloalkyl, and
R 2P represents one of the subformulae II-P, II-O or II-M,
R 2O represents one of the subformulae II-O or II-M,
R 2M represents the subformulae II-M, or
R 2P together with R 1P , R 2O together with R 1O and R 2M together with R 1M represent one of the subformulae III, IV or V, or
R 2P , R 2O and R 2M are C 6 -C 10 -aryl, which is unsubstituted or substituted by C 1 -C 8 -alkyl, C 1 -C 18 -alkyl or C 3 -C 16 -cycloalkyl;
when Y P , Y O and Y M represent a covalent bond,
R 1P represents one of the subformulae II-P, II-O or II-M,
R 1O represents one of the subformulae II-O or II-M,
R 1M represents the subformulae II-M, or
R 1P , R 1O and R 1M are C 6 -C 12 -aryl, which is unsubstituted or substituted by C 1 -C 8 -alkyl, C 1 -C 18 -alkyl or C 3 -C 16 -cycloalkyl, and
R 2P , R 2O and R 2M are C 6 -C 10 -aryl, which is unsubstituted or substituted by C 1 -C 8 -alkyl, or fluoro.
6. The composition according to claim 1 , wherein:
the compound of component b) is a compound of formula I-P or I-O;
Y P and Y O are oxygen or represent a covalent bond;
when Y P and Y O are oxygen,
R 1P , R 2P , R 1O or R 2O does not represent the subformulae II-M; and
when Y P and Y O represent a covalent bond,
R 1P or R 1O does not represent the subformulae II-M.
7. The composition according to claim 1 , wherein:
the compound of component b) is a compound of formula I-P or I-O;
Y P and Y O are oxygen,
R 1P together with R 2P and R 1O together with R 2O represent one of the subformulae III, IV or V,
R 2P together with R 1P and R 2O together with R 1O represent one of the subformulae III, IV or V,
R 4 , R 5 , R 6 and R 7 are independently from each other hydrogen or C 1 -C 8 -alkyl,
R a1 , R a2 , R a3 and R a4 are independently from each other hydrogen or C 1 -C 8 -alkyl,
R b1 , R b2 , R b3 , R b4 , R b5 and R b6 are independently from each other hydrogen or C 1 -C 8 -alkyl, and
R c1 , R c2 , R c3 and R c4 are independently from each other hydrogen or C 1 -C 8 -alkyl.
8. 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).
9. The composition according to claim 1 , which comprises, as component c), a first further additive.
10. The composition according to claim 9 , wherein said first further additive comprises at least one member selected from the group consisting of a phosphite or phosphonite different to component b), an acid scavenger, a phenolic antioxidant, and an aminic antioxidant.
11. The composition according to claim 10 , wherein said first further additive comprises a phenolic antioxidant, which is an ester of β-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid.
12. The composition according to claim 10 , which further comprises, as 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).
13. A process for protecting protection of an organic material susceptible to oxidative, thermal or light-induced degradation, the process comprising:
incorporating or applying a compound of formula I-P, I-O or I-M into or onto the organic material:
wherein:
Y P , Y O and Y M are oxygen or represent a covalent bond;
when Y P , Y O and Y M are oxygen,
R 1P represents one of the subformulae II-P, II-O or II-M:
R 1O represents one of the subformulae II-O or II-M,
R 1M represents the subformulae II-M, or
R 1P together with R 2P , R 1O together with R 2O and R 1M together with R 2M represent one of the subformulae III IV or V:
or
R 1P , R 1O and R 1M are C 6 -C 10 -aryl, which is unsubstituted or substituted by C 1 -C 8 -alkyl, C 1 -C 8 -alkoxy, halogen or one phenyl, C 1 -C 18 -alkyl, C 3 -C 16 -cycloalkyl, C 7 -C 13 -aralkyl, C 2 -C 18 -alkenyl, C 2 -C 30 -alkyl, which is interrupted by one or more oxygen atoms, or C 2 -C 16 -alkyl, which is interrupted by one sulfur atom,
R 2P represents one of the subformulae II-P, II-O or II-M,
R 2O represents one of the subformulae II-O or II-M,
R 2M represents the subformulae II-M, or
R 2P together with R 1P , R 2O together with R 1O and R 2M together with R 1M represent one of the subformulae III, IV or V, or
R 2P , R 2O and R 2M are C 6 -C 10 -aryl, which is unsubstituted or substituted by C 1 -C 8 -alkyl, C 1 -C 8 -alkoxy, halogen or one phenyl, C 1 -C 18 -alkyl, C 3 -C 16 -cycloalkyl, C 7 -C 13 -aralkyl, C 2 -C 18 -alkenyl C 2 -C 30 -alkyl which is interrupted by one or more oxygen atoms or C 2 -C 16 -alkyl which is interrupted by one sulfur atom;
when Y P , Y O and Y M represent a covalent bond,
R 1P represents one of the subformulae II-P, II-O or II-M,
R 1O represents one of the subformulae II-O or II-M,
R 1M represents the subformulae II-M, or
R 1P , R 1O and R 1M are C 6 -C 10 -aryl, which is unsubstituted or substituted by C 1 -C 8 -alkyl, C 1 -C 8 -alkoxy, halogen or one phenyl, C 1 -C 18 -alkyl, C 3 -C 16 -cycloalkyl, C 7 -C 13 -aralkyl C 2 -C 18 -alkenyl C 2 -C 30 -alkyl which is interrupted by one or more oxygen atoms or C 2 -C 16 -alkyl, which is interrupted by one sulfur atom,
R 2P , R 2O and R 2M are C 6 -C 10 -aryl, which is unsubstituted or substituted by C 1 -C 8 -alkyl, C 1 -C 8 -alkoxy, halogen or one phenyl, or halogen;
R 4 , R 5 , R 6 and R 7 are independently from each other hydrogen or C 1 -C 8 -alkyl,
R P2 , R P3 , R P5 and R P6 are independently from each other hydrogen or C 1 -C 8 -alkyl,
R O1 , R O2 , R O5 and R O6 are independently from each other hydrogen or C 1 -C 8 -alkyl,
R M1 , R M3 , R M5 and R M6 are independently from each other hydrogen or C 1 -C 8 -alkyl,
R a1 , R a2 , R a3 and R a4 are independently from each other hydrogen or C 1 -C 8 -alkyl,
R b1 , R b2 , R b3 , R b4 , R b5 and R b6 are independently from each other hydrogen or C 1 -C 8 -alkyl, and
R c1 , R c2 , R c3 and R c4 are independently from each other hydrogen or C 1 -C 8 -alkyl.
14. The process according to claim 13 , wherein the organic material is a polymer, wherein:
said incorporating is carried out and comprises incorporating said compound of formula I-P, I-O or I-M into the polymer;
at least a part of said incorporating or the entire incorporating 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.
15. A compound of formula I-P, I-O or I-M:
wherein:
Y P , Y O and Y M are oxygen or represent a covalent bond;
when Y P , Y O and Y M are oxygen,
R 1P represents one of the subformulae II-P, II-O or II-M:
R 1O represents one of the subformulae II-O or II-M,
R 1M represents the subformulae II-M,
R 1P together with R 2P , R 1O together with R 2O and R 1M together with R 2M represent one of the subformulae III, IV or V:
or
R 1P , R 1O and R 1M are C 6 -C 10 -aryl, which is unsubstituted or substituted by C 1 -C 8 -alkyl, C 1 -C 8 -alkoxy, halogen or one phenyl, C 1 -C 18 -alkyl, C 3 -C 16 -cycloalkyl, C 7 -C 13 -aralkyl, C 2 -C 18 -alkenyl, C 2 -C 30 -alkyl, which is interrupted by one or more oxygen atoms, or C 2 -C 16 -alkyl, which is interrupted by one sulfur atom,
R 2P represents one of the subformulae II-P, II-O or II-M,
R 2O represents one of the subformulae II-O or II-M,
R 2M represents the subformulae II-M, or
R 2P together with R 1P , R 2O together with R 1O and R 2M together with R 1M represent one of the subformulae III, IV or V, or
R 2P , R 2O and R 2M are C 6 -C 10 -aryl, which is unsubstituted or substituted by C 1 -C 8 -alkyl, C 1 -C 8 -alkoxy, halogen or one phenyl, C 1 -C 18 -alkyl, C 3 -C 16 -cycloalkyl, C 7 -C 13 -aralkyl, C 2 -C 18 -alkenyl, C 2 -C 30 -alkyl, which is interrupted by one or more oxygen atoms, or C 2 -C 16 -alkyl, which is interrupted by one sulfur atom;
when Y P , Y O and Y M represent a covalent bond,
R 1P represents one of the subformulae II-P, II-O or II-M,
R 1O represents one of the subformulae II-O or II-M,
R 1M represents the subformulae II-M, or
R 1O and R 1M are C 6 -C 10 -aryl, which is unsubstituted or substituted by C 1 -C 8 -alkyl, C 1 -C 8 -alkoxy, halogen or one phenyl, C 1 -C 18 -alkyl, C 3 -C 16 -cycloalkyl, C 7 -C 13 -aralkyl, C 2 -C 18 -alkenyl, C 2 -C 30 -alkyl, which is interrupted by one or more oxygen atoms, or C 2 -C 16 -alkyl, which is interrupted by one sulfur atom,
R 2P , R 2O and R 2M are C 6 -C 10 -aryl, which is unsubstituted or substituted by C 1 -C 8 -alkyl, C 1 -C 8 -alkoxy, halogen or one phenyl, or halogen;
R 4 , R 5 , R 6 and R 7 are independently from each other hydrogen or C 1 -C 8 -alkyl,
R P2 , R P3 , R P5 and R P6 are independently from each other hydrogen or C 1 -C 8 -alkyl,
R O1 , R O2 , R O5 and R O6 are independently from each other hydrogen or C 1 -C 8 -alkyl,
R M1 , R M3 , R M5 and R M6 are independently from each other hydrogen or C 1 -C 8 -alkyl,
R a1 , R a2 , R a3 and R a4 are independently from each other hydrogen or C 1 -C 8 -alkyl,
R b1 , R b2 , R b3 , R b4 , R b5 and R b6 are independently from each other hydrogen or C 1 -C 8 -alkyl, and
R c1 , R c2 , R c3 and R c4 are independently from each other hydrogen or C 1 -C 8 -alkyl.
16. An additive composition, comprising:
b) a compound of formula I-P, I-O or I-M; and
c) a first further additive, which is a phosphite or phosphonite different to component b), an acid scavenger, a phenolic antioxidant or an aminic antioxidant:
wherein:
Y P , Y O and Y M are oxygen or represent a covalent bond;
when Y P , Y O and Y M are oxygen,
R 1P represents one of the subformulae II-P, II-O or II-M:
R 1O represents one of the subformulae II-O or II-M,
R 1M represents the subformulae II-M, or
R 1P together with R 2P , R 1O together with R 2O and R 1M together with R 2M represent one of the subformulae III IV or V:
or
R 1P , R 1O and R 1M are C 6 -C 10 -aryl, which is unsubstituted or substituted by C 1 -C 8 -alkyl, C 1 -C 8 -alkoxy, halogen or one phenyl, C 1 -C 18 -alkyl, C 3 -C 16 -cycloalkyl, C 7 -C 13 -aralkyl, C 2 -C 18 -alkenyl, C 7 -C 30 -alkyl, which is interrupted by one or more oxygen atoms, or C 2 -C 16 -alkyl, which is interrupted by one sulfur atom,
R 2P represents one of the subformulae II-P, II-O or II-M,
R 2O represents one of the subformulae II-O or II-M,
R 2M represents the subformulae II-M, or
R 2P together with R 1P , R 2O together with R 1O and R 2M together with R 1M represent one of the subformulae III IV or V, or
R 2P , R 2O and R 2M are C 6 -C 10 -aryl, which is unsubstituted or substituted by C 1 -C 8 -alkyl, C 1 -C 8 -alkoxy, halogen or one phenyl, C 1 -C 18 -alkyl, C 3 -C 16 -cycloalkyl, C 7 -C 13 -aralkyl, C 2 -C 18 -alkenyl, C 2 -C 30 -alkyl, which is interrupted by one or more oxygen atoms, or C 2 -C 16 -alkyl, which is interrupted by one sulfur atom;
when Y P , Y O and Y M represent a covalent bond,
R 1P represents one of the subformulae II-P, II-O or II-M,
R 1O represents one of the subformulae II-O or II-M,
R 1M represents the subformulae II-M, or
R 1P , R 1O and R 1M are C 6 -C 10 -aryl, which is unsubstituted or substituted by C 1 -C 8 -alkyl, C 1 -C 8 -alkoxy, halogen or one phenyl, C 1 -C 18 -alkyl, C 3 -C 16 -cycloalkyl, C 7 -C 13 -aralkyl C 2 -C 18 -alkenyl C 2 -C 30 -alkyl which is interrupted by one or more oxygen atoms or C 2 -C 16 -alkyl, which is interrupted by one sulfur atom,
R 2P , R 2O and R 2M are C 6 -C 10 -aryl, which is unsubstituted or substituted by C 1 -C 8 -alkyl, C 1 -C 8 -alkoxy, halogen or one phenyl, or halogen;
R 4 , R 5 , R 6 and R 7 are independently from each other hydrogen or C 1 -C 8 -alkyl,
R P2 , R P3 , R P5 and R P6 are independently from each other hydrogen or C 1 -C 8 -alkyl,
R O1 , R O2 , R O5 and R O6 are independently from each other hydrogen or C 1 -C 8 -alkyl,
R M1 , R M3 , R M5 and R M6 are independently from each other hydrogen or C 1 -C 8 -alkyl,
R a1 , R a2 , R a3 and R a4 are independently from each other hydrogen or C 1 -C 8 -alkyl,
R b1 , R b2 , R b3 , R b4 , R b5 and R b6 are independently from each other hydrogen or C 1 -C 8 -alkyl, and
R c1 , R c2 , R c3 and R c4 are independently from each other hydrogen or C 1 -C 8 -alkyl.
17. The additive composition according to claim 16 , comprising, as the first further additive, a phenolic antioxidant, which is an ester of β-(3,5-di-tert-butyl-4-hydroxy phenyl)propionic acid.
18. The additive composition according to claim 16 , further comprising:
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 the second further additive d) is a different substance than the first further additive c).
19. An intermediate compound of formula IN-P, IN-O or IN-M:
wherein:
Z 1P-IN , Z 2P-IN , Z 1O-IN , Z 2O-IN , Z 1M-IN and Z 2M-IN are independently from each other and represent a halogen atom,
R 4 , R 5 , R 6 and R 7 are independently from each other hydrogen or C 1 -C 8 -alkyl,
R P2 , R P3 , R P5 and R P6 are independently from each other hydrogen or C 1 -C 8 -alkyl,
R O1 , R O2 , R O5 and R O6 are independently from each other hydrogen or C 1 -C 8 -alkyl, and
R M1 , R M3 , R M5 and R M6 are independently from each other hydrogen or C 1 -C 8 -alkyl.
20. The composition according to claim 11 , wherein said first further additive comprises 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.
21. The composition according to claim 10 , wherein said first further additive comprises a phosphite, which is tris-(2,4-di-tert-butylphenyl) phosphite.
22. The composition according to claim 12 , wherein:
said first further additive comprises 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; and
said second further additive comprises a phosphite, which is tris-(2,4-di-tert-butylphenyl) phosphite.
23. The additive composition according to claim 17 , comprising, as the first further additive, 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.
24. The additive composition according to claim 16 , comprising, as the first further additive, a phosphite, which is tris-(2,4-di-tert-butylphenyl) phosphite.
25. The additive composition according to claim 18 , comprising, as the first further additive, 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, and which comprises, as component d), a second further additive, which is tris-(2,4-di-tert-butylphenyl) phosphite.