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

Patent metadata

Field	Value
Publication number	US-10072136-B2
Application number	US-201515501655-A
Country	US
Kind code	B2
Filing date	Aug 3, 2015
Priority date	Aug 5, 2014
Publication date	Sep 11, 2018
Grant date	Sep 11, 2018

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, a process for manufacturing the compound and an intermediate involved therein.

First claim

The invention claimed is:

1. A composition, which comprises
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 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, or
R 1M 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.

2. The composition according to claim 1 , wherein the organic material selected from the group consisting of 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 selected from the group consisting of
a polyolefin or a copolymer thereof,
a polystyrene or a copolymer thereof,
a polyurethane or a copolymer thereof,
a polyether, which is obtained 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, and
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-O,
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 , which comprises:
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 , wherein component b) is contained in an amount of 0.0005% to 10% based on the weight of component a).

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

9. The composition according to claim 8 , wherein component c) 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 , wherein component c) is an ester of β-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid.

11. The composition according to claim 8 , which further comprises, as component d), a second additive, which is selected from the group consisting of a phosphite or phosphonite different to component b), an acid scavenger, a phenolic antioxidant and 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, which comprises:
incorporating into or applying onto an organic material a compound of formula I-P, I-O or I-M as defined in claim 1 .

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

14. A compound of formula I-P, I-O or I-M

wherein
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, or
R 1M 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.

15. An additive composition, which comprises:
b) a compound of formula I-P, I-O or I-M as defined in claim 1 , and
c) a first additive, which is selected from the group consisting of a phosphite or phosphonite different to component b), an acid scavenger, a phenolic antioxidant or an aminic antioxidant.

16. The additive composition according to claim 15 , which comprises as component c) a phenolic antioxidant, which is an ester of β-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid.

17. The additive composition according to claim 15 , which further comprises, as component d), a second additive, which is selected from the group consisting of a phosphite or phosphonite different to component b), an acid scavenger, a phenolic antioxidant, and an aminic antioxidant;
with the proviso that component d) is a different compound than component c).

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

wherein
Z 1P-1N , Z 1O-1N and Z 1M-1N are independently from each other 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, and
R M1 , R M3 , R M5 and R M6 are independently from each other hydrogen or C 1 -C 8 -alkyl.

Assignees

• Basf Se

Inventors

• Hoelzl Werner
• Rotzinger Bruno
• Schoening Kai-Uwe
• King Iii Rick

Classifications

• C08K5/101

  of monocarboxylic acids · CPC title

• C08K5/527 Primary

  Cyclic esters · CPC title

• C08K5/529 Primary

  Esters containing heterocyclic rings not representing cyclic esters of phosphoric or phosphorous acids · CPC title

• C09K15/322

  containing only phosphorus · CPC title

• C07F9/65746 Primary

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