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

Patent metadata

Field	Value
Publication number	US-9951207-B2
Application number	US-201515119317-A
Country	US
Kind code	B2
Filing date	Feb 13, 2015
Priority date	Feb 17, 2014
Publication date	Apr 24, 2018
Grant date	Apr 24, 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 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.

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 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.

Assignees

• Basf Se

Inventors

• Hoelzl Werner
• Rotzinger Bruno
• Schoening Kai-Uwe
• King Roswell Easton

Classifications

• C08K5/04

  Oxygen-containing compounds {(C08K5/0091 takes precedence)} · CPC title

• C08K5/098

  Metal salts of carboxylic acids · CPC title

• C08K5/523 Primary

  with hydroxyaryl compounds · CPC title

• C08K5/5377

  Phosphinous compounds, e.g. R2=P—OR' · CPC title

• C08K5/1535

  Five-membered rings · CPC title