3-phenyl-benzofuran-2-one derivatives containing phosphorus as stabilizers

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:
• YP, YO and YM are oxygen or represent a covalent bond;
• when YP, YO and YM are oxygen,
• R1P represents one of the subformulae II-P, II-O or II-M:
• R1O represents one of the subformulae II-O or II-M,
• R1M represents the subformulae II-M, or
• R1P together with R2P, R1O together with R2O and R1M together with R2M represent one of the subformulae III IV or V:
• or
• R1P, R1O and R1M are C6-C10-aryl, which is unsubstituted or substituted by C1-C8-alkyl, C1-C8-alkoxy, halogen or one phenyl, C1-C18-alkyl, C3-C16-cycloalkyl, C7-C13-aralkyl, C2-C18-alkenyl, C2-C30-alkyl, which is interrupted by one or more oxygen atoms, or C2-C16-alkyl, which is interrupted by one sulfur atom,
• R2P represents one of the subformulae II-P, II-O or II-M,
• R2O represents one of the subformulae II-O or II-M,
• R2M represents the subformulae II-M, or
• R2P together with R1P, R2O together with R1O and R2M together with R1M represent one of the subformulae III, IV or V, or
• R2P, R2O and R2M are C6-C10-aryl, which is unsubstituted or substituted by C1-C8-alkyl, C1-C8-alkoxy, halogen or one phenyl, C1-C18-alkyl, C3-C16-cycloalkyl, C7-C13-aralkyl, C2-C18-alkenyl C2-C30-alkyl which is interrupted by one or more oxygen atoms or C2-C16-alkyl which is interrupted by one sulfur atom;
• when YP, YO and YM represent a covalent bond,
• R1P represents one of the subformulae II-P, II-O or II-M,
• R1O represents one of the subformulae II-O or II-M,
• R1M represents the subformulae II-M, or
• R1P, R1O and R1M are C6-C10-aryl, which is unsubstituted or substituted by C1-C8-alkyl, C1-C8-alkoxy, halogen or one phenyl, C1-C18-alkyl, C3-C16-cycloalkyl, C7-C13-aralkyl C2-C18-alkenyl C2-C30-alkyl which is interrupted by one or more oxygen atoms or C2-C16-alkyl, which is interrupted by one sulfur atom,
• R2P, R2O and R2M are C6-C10-aryl, which is unsubstituted or substituted by C1-C8-alkyl, C1-C8-alkoxy, halogen or one phenyl, or halogen;
• R4, R5, R6 and R7 are independently from each other hydrogen or C1-C8-alkyl,
• RP2, RP3, RP5 and RP6 are independently from each other hydrogen or C1-C8-alkyl,
• RO1, RO2, RO5 and RO6 are independently from each other hydrogen or C1-C8-alkyl,
• RM1, RM3, RM5 and RM6 are independently from each other hydrogen or C1-C8-alkyl,
• Ra1, Ra2, Ra3 and Ra4 are independently from each other hydrogen or C1-C8-alkyl,
• Rb1, Rb2, Rb3, Rb4, Rb5 and Rb6 are independently from each other hydrogen or C1-C8-alkyl, and
• Rc1, Rc2, Rc3 and Rc4 are independently from each other hydrogen or C1-C8-alkyl.

A compound of formula I-P, I-O or I-M:

• wherein:
• YP, YO and YM are oxygen or represent a covalent bond;
• when YP, YO and YM are oxygen,
• R1P represents one of the subformulae II-P, II-O or II-M:
• R1O represents one of the subformulae II-O or II-M,
• R1M represents the subformulae II-M,
• R1P together with R2P, R1O together with R2O and R1M together with R2M represent one of the subformulae III, IV or V:
• or
• R1P, R1O and R1M are C6-C10-aryl, which is unsubstituted or substituted by C1-C8-alkyl, C1-C8-alkoxy, halogen or one phenyl, C1-C18-alkyl, C3-C16-cycloalkyl, C7-C13-aralkyl, C2-C18-alkenyl, C2-C30-alkyl, which is interrupted by one or more oxygen atoms, or C2-C16-alkyl, which is interrupted by one sulfur atom,
• R2P represents one of the subformulae II-P, II-O or II-M,
• R2O represents one of the subformulae II-O or II-M,
• R2M represents the subformulae II-M, or
• R2P together with R1P, R2O together with R1O and R2M together with R1M represent one of the subformulae III, IV or V, or
• R2P, R2O and R2M are C6-C10-aryl, which is unsubstituted or substituted by C1-C8-alkyl, C1-C8-alkoxy, halogen or one phenyl, C1-C18-alkyl, C3-C16-cycloalkyl, C7-C13-aralkyl, C2-C18-alkenyl, C2-C30-alkyl, which is interrupted by one or more oxygen atoms, or C2-C16-alkyl, which is interrupted by one sulfur atom;
• when YP, YO and YM represent a covalent bond,
• R1P represents one of the subformulae II-P, II-O or II-M,
• R1O represents one of the subformulae II-O or II-M,
• R1M represents the subformulae II-M, or
• R1O and R1M are C6-C10-aryl, which is unsubstituted or substituted by C1-C8-alkyl, C1-C8-alkoxy, halogen or one phenyl, C1-C18-alkyl, C3-C16-cycloalkyl, C7-C13-aralkyl, C2-C18-alkenyl, C2-C30-alkyl, which is interrupted by one or more oxygen atoms, or C2-C16-alkyl, which is interrupted by one sulfur atom,
• R2P, R2O and R2M are C6-C10-aryl, which is unsubstituted or substituted by C1-C8-alkyl, C1-C8-alkoxy, halogen or one phenyl, or halogen;
• R4, R5, R6 and R7 are independently from each other hydrogen or C1-C8-alkyl,
• RP2, RP3, RP5 and RP6 are independently from each other hydrogen or C1-C8-alkyl,
• RO1, RO2, RO5 and RO6 are independently from each other hydrogen or C1-C8-alkyl,
• RM1, RM3, RM5 and RM6 are independently from each other hydrogen or C1-C8-alkyl,
• Ra1, Ra2, Ra3 and Ra4 are independently from each other hydrogen or C1-C8-alkyl,
• Rb1, Rb2, Rb3, Rb4, Rb5 and Rb6 are independently from each other hydrogen or C1-C8-alkyl, and
• Rc1, Rc2, Rc3 and Rc4 are independently from each other hydrogen or C1-C8-alkyl.

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:
• YP, YO and YM are oxygen or represent a covalent bond;
• when YP, YO and YM are oxygen,
• R1P represents one of the subformulae II-P, II-O or II-M:
• R1O represents one of the subformulae II-O or II-M,
• R1M represents the subformulae II-M, or
• R1P together with R2P, R1O together with R2O and R1M together with R2M represent one of the subformulae III IV or V:
• or
• R1P, R1O and R1M are C6-C10-aryl, which is unsubstituted or substituted by C1-C8-alkyl, C1-C8-alkoxy, halogen or one phenyl, C1-C18-alkyl, C3-C16-cycloalkyl, C7-C13-aralkyl, C2-C18-alkenyl, C7-C30-alkyl, which is interrupted by one or more oxygen atoms, or C2-C16-alkyl, which is interrupted by one sulfur atom,
• R2P represents one of the subformulae II-P, II-O or II-M,
• R2O represents one of the subformulae II-O or II-M,
• R2M represents the subformulae II-M, or
• R2P together with R1P, R2O together with R1O and R2M together with R1M represent one of the subformulae III IV or V, or
• R2P, R2O and R2M are C6-C10-aryl, which is unsubstituted or substituted by C1-C8-alkyl, C1-C8-alkoxy, halogen or one phenyl, C1-C18-alkyl, C3-C16-cycloalkyl, C7-C13-aralkyl, C2-C18-alkenyl, C2-C30-alkyl, which is interrupted by one or more oxygen atoms, or C2-C16-alkyl, which is interrupted by one sulfur atom;
• when YP, YO and YM represent a covalent bond,
• R1P represents one of the subformulae II-P, II-O or II-M,
• R1O represents one of the subformulae II-O or II-M,
• R1M represents the subformulae II-M, or
• R1P, R1O and R1M are C6-C10-aryl, which is unsubstituted or substituted by C1-C8-alkyl, C1-C8-alkoxy, halogen or one phenyl, C1-C18-alkyl, C3-C16-cycloalkyl, C7-C13-aralkyl C2-C18-alkenyl C2-C30-alkyl which is interrupted by one or more oxygen atoms or C2-C16-alkyl, which is interrupted by one sulfur atom,
• R2P, R2O and R2M are C6-C10-aryl, which is unsubstituted or substituted by C1-C8-alkyl, C1-C8-alkoxy, halogen or one phenyl, or halogen;
• R4, R5, R6 and R7 are independently from each other hydrogen or C1-C8-alkyl,
• RP2, RP3, RP5 and RP6 are independently from each other hydrogen or C1-C8-alkyl,
• RO1, RO2, RO5 and RO6 are independently from each other hydrogen or C1-C8-alkyl,
• RM1, RM3, RM5 and RM6 are independently from each other hydrogen or C1-C8-alkyl,
• Ra1, Ra2, Ra3 and Ra4 are independently from each other hydrogen or C1-C8-alkyl,
• Rb1, Rb2, Rb3, Rb4, Rb5 and Rb6 are independently from each other hydrogen or C1-C8-alkyl, and
• Rc1, Rc2, Rc3 and Rc4 are independently from each other hydrogen or C1-C8-alkyl.

An intermediate compound of formula IN-P, IN-O or IN-M:

• wherein:
• Z1P-IN, Z2P-IN, Z1O-IN, Z2O-IN, Z1M-IN and Z2M-IN are independently from each other and represent a halogen atom,
• R4, R5, R6 and R7 are independently from each other hydrogen or C1-C8-alkyl,
• RP2, RP3, RP5 and RP6 are independently from each other hydrogen or C1-C8-alkyl,
• RO1, RO2, RO5 and RO6 are independently from each other hydrogen or C1-C8-alkyl, and
• RM1, RM3, RM5 and RM6 are independently from each other hydrogen or C1-C8-alkyl.