3-phenyl-benzofuran-2-one diphosphate derivatives as stabilizers

Patent metadata

Field	Value
Publication number	US-11767338-B2
Application number	US-201916973473-A
Country	US
Kind code	B2
Filing date	Jun 17, 2019
Priority date	Jun 21, 2018
Publication date	Sep 26, 2023
Grant date	Sep 26, 2023

Abstract

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 against degradation of the organic material, an additive composition comprising the compound, processes for manufacturing the compound and an intermediate involved therein.

First claim

What is claimed is:

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
R IP represents one of the subformulae II-P, II-O or II-M

R 1O represents one of the subformulae II-0 or II-M, or
R IM represents the subformula II-M;
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,
wherein the composition has a change in yellowness index of 5.0 to 19.7 when pellets of the composition are passed five times through a single screw extruder under air at 240° C.

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, a polyether, which is obtainable by the polymerization of an epoxide, an oxetane or a 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 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
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, and
R M6 is hydrogen or C 1 -C 8 -alkyl.

5. The composition according to claim 1 , wherein the compound is of formula I-P or I-0,
R 1P represents one of the subformulae II-P or II-O, and
R 1O represents the subformula II-O.

6. The composition according to claim 1 , further comprising
a) a polymer, which is a polyolefine or a copolymer thereof or a polystyrene or a copolymer thereof, and
b) the compound is of formula I-P or I-O, wherein
R 1P represents subformula II-P,
R 1O represents subformula II-O,
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 O1 is hydrogen or C 1 -C 8 -alkyl,
R O2 , R O5 and R O6 are hydrogen,
R P2 and R P6 are hydrogen, and
R P3 and R P5 are independently from each other hydrogen or C 1 -C 4 -alkyl.

7. The composition according to claim 1 , comprising component b) in an amount of 0.0005% to 10% based on the weight of component a).

8. The composition according to claim 1 , comprising as component c) a further additive.

9. The composition according to claim 8 , comprising as component c) a further additive, which is a phosphite or phosphonite different to component b), an acid scavenger, a phenolic antioxidant or an aminic antioxidant.

10. The composition according to claim 9 , comprising as component c) a phenolic antioxidant, which is an ester of p-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid.

11. The composition according to claim 8 , comprising 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 compound than component c).

12. A process for protection of an organic material susceptible to oxidative, thermal or light-induced degradation, comprising:
providing the organic material, and
incorporating into or applying onto the provided organic material a compound of formula I-P, I-O or I-M as defined in claim 1 , wherein the composition has a change in yellowness index of 5.0 to 19.7 when pellets of the composition are passed five times through a single screw extruder under air at 240° C.

13. The process according to claim 12 , wherein the organic material is a polymer, wherein the incorporating into the polymer takes place and a part or the complete incorporating takes place at a temperature between 135° C. to 350° C.

14. A method of using a compound of formula I-P, I-O or I-M as defined in claim 1 for stabilizing an organic material susceptible to oxidative, thermal or light-induced degradation against degradation by oxidation, heat or light, the method comprising:
combining the compound of formula I-P, I-O or I-M with the organic material.

Assignees

• Basf Se

Inventors

• Hoelzl Werner
• King Iii Roswell E
• Pauquet Jean-Roch

Classifications

• C07F9/65746 Primary

  the molecule containing more than one cyclic phosphorus atom · CPC title

• C08K5/51

  Phosphorus bound to oxygen · CPC title

• C08K5/527 Primary

  Cyclic esters · CPC title

• C07F9/65517

  condensed with carbocyclic rings or carbocyclic ring systems · CPC title

• C09K15/322

  containing only phosphorus · CPC title