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

Patent metadata

Field	Value
Publication number	US-10590263-B2
Application number	US-201615751497-A
Country	US
Kind code	B2
Filing date	Aug 4, 2016
Priority date	Aug 10, 2015
Publication date	Mar 17, 2020
Grant date	Mar 17, 2020

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 for stabilizing the organic material, an additive composition comprising the compound and a process for manufacturing the compound. The organic material is for example a polymer.

First claim

The invention 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
Y P , Y O and Y M are oxygen or a covalent bond;
when Y P , Y O and Y M are oxygen,
R 1P is a group represented by formula II-P, II-O or II-M

R 1O is a group represented by formula II-O or II-M,
R 1M is a group represented by the formula II-M, or
R 1P together with R 2P , R 1O together with R 2O , and R 1M together with R 2M represent a group of formula III, IV or V

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 is a group represented by the formula II-P, II-O or II-M,
R 2O is a group represented by the formula II-O or II-M,
R 2M is a group represented by the formula II-M, or
R 2P together with R 1P , R 2O together with R 1O , and R 2M together with R 1M represent a group of the formula 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 are a covalent bond,
R 1P is a group represented by the formula II-P, II-O or II-M,
R 1O is a group represented by the formula II-O or II-M,
R 1M is a group represented by the formula 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;

R 4 , R 5 , R 6 and R 7 are independently hydrogen or C 1 -C 8 -alkyl,
R P2 , R P3 , R P5 and R P6 are independently hydrogen or C 1 -C 8 -alkyl,
R O1 , R O2 , R O5 and R O6 are independently hydrogen or C 1 -C 8 -alkyl,
R M1 , R M3 , R M5 and R M6 are independently hydrogen or C 1 -C 8 -alkyl,
R a1 , R a2 , R a3 and R a4 are independently hydrogen or C 1 -C 8 -alkyl,
R b1 , R b2 , R b3 , R b4 , R b5 and R b6 are independently hydrogen or C 1 -C 8 -alkyl, and
R c1 , R c2 , R c3 and R c4 are independently 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,
a polyether obtained by 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
R 4 and R 6 are hydrogen,
R 5 and R 7 are independently hydrogen or C 1 -C 8 -alkyl,
R P2 and R P6 are independently hydrogen or C 1 -alkyl,
R P3 and R P5 are independently hydrogen or C 1 -C 4 -alkyl,
R O1 and R O6 are independently 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 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 hydrogen or C 1 -C 4 -alkyl,
R b1 , R b2 , R b3 , R b4 , R b5 and R b6 are independently hydrogen or C 1 -C 4 -alkyl, and
R c1 , R c2 , R c3 and R c4 are independently hydrogen or C 1 -C 4 -alkyl.

5. The composition according to claim 1 , wherein
when Y P , Y O and Y M are oxygen,
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 15 -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, C 1 -C 18 -alkyl or C 3 -C 16 -cycloalkyl;

when Y P , Y O and Y M are a covalent bond,
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.

6. The composition according to claim 1 , wherein the compound is one of the formula I-P or I-O, wherein
when Y P and Y O are oxygen,
R 1P , R 2P , R 1O or R 2O is not a group represented by the formula II-M;

when Y P and Y O are a covalent bond,
R 1P or R 1O is not a group represented by the formula II-M.

7. The composition according to claim 1 , wherein the compound is one of the formula I-P or I-O, wherein
Y P and Y O are oxygen,
R 1P together with R 2P and R 1O together with R 2O represent a group represented by the formula III, IV or V, and
R 2P together with R 1P and R 2O together with R 1O represent a group represented by the formula III, IV or V.

8. 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).

9. The composition according to claim 1 , further comprising
c) an additive.

10. The composition according to claim 9 , wherein the additive is a phosphite or phosphonite, an acid scavenger, a phenolic antioxidant or an aminic antioxidant.

11. The composition according to claim 10 , wherein the additive is a phosphite or phosphonite or a phenolic antioxidant.

12. The composition according to claim 10 , wherein the additive is a phenolic antioxidant, which is an ester of β-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid.

13. The composition according to claim 9 , further comprising
d) a second additive, which is different from component c) and is a phosphite or phosphonite, an acid scavenger, a phenolic antioxidant or an aminic antioxidant.

14. A process for protecting an organic material susceptible to oxidative, thermal or light-induced degradation, the process comprising
incorporating into or applying onto the organic material a compound of formula I-P, I-O or I-M

Assignees

• Basf Se

Inventors

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

Classifications

• C08K5/5333

  Esters of phosphonic acids · CPC title

• C08K5/5317

  Phosphonic compounds, e.g. R—P(:O)(OR')2 · CPC title

• C08K5/53

  bound to oxygen and to carbon only · CPC title

• C07F9/65517

  condensed with carbocyclic rings or carbocyclic ring systems · CPC title

• C08L69/00

  Compositions of polycarbonates; Compositions of derivatives of polycarbonates · CPC title