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

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. ##STR00001##

Claims

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 ##STR00031## wherein Y.sup.P, Y.sup.O and Y.sup.M are oxygen or a covalent bond; when Y.sup.P, Y.sup.O and Y.sup.M are oxygen, R.sup.1P is a group represented by formula II-P, II-O or II-M ##STR00032## R.sup.1O is a group represented by formula II-O or II-M, R.sup.1M is a group represented by the formula II-M, or R.sup.1P together with R.sup.2P, R.sup.1O together with R.sup.2O, and R.sup.1M together with R.sup.2M represent a group of formula III, IV or V ##STR00033## R.sup.1P, R.sup.1O and R.sup.1M are C.sub.6-C.sub.10-aryl, which is unsubstituted or substituted by C.sub.1-C.sub.8-alkyl, C.sub.1-C.sub.8-alkoxy, halogen or one phenyl, C.sub.1-C.sub.18-alkyl, C.sub.3-C.sub.16-cycloalkyl, C.sub.7-C.sub.13-aralkyl, C.sub.2-C.sub.18-alkenyl, C.sub.2-C.sub.30-alkyl, which is interrupted by one or more oxygen atoms, or C.sub.2-C.sub.16-alkyl, which is interrupted by one sulfur atom, R.sup.2P is a group represented by the formula II-P, II-O or II-M, R.sup.2O is a group represented by the formula II-O or II-M, R.sup.2M is a group represented by the formula II-M, or R.sup.2P together with R.sup.1P, R.sup.2O together with R.sup.1O, and R.sup.2M together with R.sup.1M represent a group of the formula III, IV or V, or R.sup.2P, R.sup.2O and R.sup.2M are C.sub.6-C.sub.10-aryl, which is unsubstituted or substituted by C.sub.1-C.sub.8-alkyl, C.sub.1-C.sub.8-alkoxy, halogen or one phenyl, C.sub.1-C.sub.18-alkyl, C.sub.3-C.sub.16-cycloalkyl, C.sub.7-C.sub.13-aralkyl, C.sub.2-C.sub.18-alkenyl, C.sub.2-C.sub.30-alkyl, which is interrupted by one or more oxygen atoms, or C.sub.2-C.sub.16-alkyl, which is interrupted by one sulfur atom; when Y.sup.P, Y.sup.O and Y.sup.M are a covalent bond, R.sup.1P is a group represented by the formula II-P, II-O or II-M, R.sup.1O is a group represented by the formula II-O or II-M, R.sup.1M is a group represented by the formula II-M, or R.sup.1P, R.sup.1O and R.sup.1M are C.sub.6-C.sub.10-aryl, which is unsubstituted or substituted by C.sub.1-C.sub.8-alkyl, C.sub.1-C.sub.8-alkoxy, halogen or one phenyl, C.sub.1-C.sub.18-alkyl, C.sub.3-C.sub.16-cycloalkyl, C.sub.7-C.sub.13-aralkyl, C.sub.2-C.sub.18-alkenyl, C.sub.2-C.sub.30-alkyl, which is interrupted by one or more oxygen atoms, or C.sub.2-C.sub.16-alkyl, which is interrupted by one sulfur atom, R.sup.2P, R.sup.2O and R.sup.2M are C.sub.6-C.sub.10-aryl, which is unsubstituted or substituted by C.sub.1-C.sub.8-alkyl, C.sub.1-C.sub.8-alkoxy, halogen or one phenyl; R.sup.4, R.sup.5, R.sup.6 and R.sup.7 are independently hydrogen or C.sub.1-C.sub.8-alkyl, R.sup.P2, R.sup.P3, R.sup.P5 and R.sup.P6 are independently hydrogen or C.sub.1-C.sub.8-alkyl, R.sup.O1, R.sup.O2, R.sup.O5 and R.sup.O6 are independently hydrogen or C.sub.1-C.sub.8-alkyl, R.sup.M1, R.sup.M3, R.sup.M5 and R.sup.M6 are independently hydrogen or C.sub.1-C.sub.8-alkyl, R.sup.a1, R.sup.a2, R.sup.a3 and R.sup.a4 are independently hydrogen or C.sub.1-C.sub.8-alkyl, R.sup.b1, R.sup.b2, R.sup.b3, R.sup.b4, R.sup.b5 and R.sup.b6 are independently hydrogen or C.sub.1-C.sub.8-alkyl, and R.sup.c1, R.sup.c2, R.sup.c3 and R.sup.c4 are independently hydrogen or C.sub.1-C.sub.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.sup.4 and R.sup.6 are hydrogen, R.sup.5 and R.sup.7 are independently hydrogen or C.sub.1-C.sub.8-alkyl, R.sup.P2 and R.sup.P6 are independently hydrogen or C.sub.1-alkyl, R.sup.P3 and R.sup.P5 are independently hydrogen or C.sub.1-C.sub.4-alkyl, R.sup.O1 and R.sup.O6 are independently hydrogen or C.sub.1-C.sub.8-alkyl, R.sup.O2 is hydrogen or C.sub.1-alkyl, R.sup.O5 is hydrogen or C.sub.1-C.sub.4-alkyl, R.sup.M1 is hydrogen or C.sub.1-alkyl, R.sup.M3 and R.sup.M5 are independently hydrogen or C.sub.1-C.sub.4-alkyl, R.sup.M6 is hydrogen or C.sub.1-C.sub.8-alkyl, R.sup.a1, R.sup.a2, R.sup.a3 and R.sup.a4 are independently hydrogen or C.sub.1-C.sub.4-alkyl, R.sup.b1, R.sup.b2, R.sup.b3, R.sup.b4, R.sup.b5 and R.sup.b6 are independently hydrogen or C.sub.1-C.sub.4-alkyl, and R.sup.c1, R.sup.c2, R.sup.c3 and R.sup.c4 are independently hydrogen or C.sub.1-C.sub.4-alkyl.

5. The composition according to claim 1, wherein when Y.sup.P, Y.sup.O and Y.sup.M are oxygen, R.sup.1P, R.sup.1O and R.sup.1M are C.sub.6-C.sub.10-aryl, which is unsubstituted or substituted by C.sub.1-C.sub.8-alkyl, C.sub.1-C.sub.15-alkyl or C.sub.3-C.sub.16-cycloalkyl, and R.sup.2P, R.sup.2O and R.sup.2M are C.sub.6-C.sub.10-aryl, which is unsubstituted or substituted by C.sub.1-C.sub.8-alkyl, C.sub.1-C.sub.18-alkyl or C.sub.3-C.sub.16-cycloalkyl; when Y.sup.P, Y.sup.O and Y.sup.M are a covalent bond, R.sup.1P, R.sup.1O and R.sup.1M are C.sub.6-C.sub.12-aryl, which is unsubstituted or substituted by C.sub.1-C.sub.8-alkyl, C.sub.1-C.sub.18-alkyl or C.sub.3-C.sub.16-cycloalkyl, and R.sup.2P, R.sup.2O and R.sup.2M are C.sub.6-C.sub.10-aryl, which is unsubstituted or substituted by C.sub.1-C.sub.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.sup.P and Y.sup.O are oxygen, R.sup.1P, R.sup.2P, R.sup.1O or R.sup.2O is not a group represented by the formula II-M; when Y.sup.P and Y.sup.O are a covalent bond, R.sup.1P or R.sup.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.sup.P and Y.sup.O are oxygen, R.sup.1P together with R.sup.2P and R.sup.1O together with R.sup.2O represent a group represented by the formula III, IV or V, and R.sup.2P together with R.sup.1P and R.sup.2O together with R.sup.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 -(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 ##STR00034## wherein Y.sup.P, Y.sup.O and Y.sup.M are oxygen or a covalent bond; when Y.sup.P, Y.sup.O and Y.sup.M are oxygen, R.sup.1P is a group represented by formula II-P, II-O or II-M ##STR00035## R.sup.1O is a group represented by formula II-O or II-M, R.sup.1M is a group represented by the formula II-M, or R.sup.1P together with R.sup.2P, R.sup.1O together with R.sup.2O, and Rim together with R.sup.2M represent a group of formula III, IV or V ##STR00036## R.sup.1P, R.sup.1O and R.sup.1M are C.sub.6-C.sub.10-aryl, which is unsubstituted or substituted by C.sub.1-C.sub.8-alkyl, C.sub.1-C.sub.8-alkoxy, halogen or one phenyl, C.sub.1-C.sub.18-alkyl, C.sub.3-C.sub.16-cycloalkyl, C.sub.7-C.sub.13-aralkyl, C.sub.2-C.sub.18-alkenyl, C.sub.2-C.sub.30-alkyl, which is interrupted by one or more oxygen atoms, or C.sub.2-C.sub.16-alkyl, which is interrupted by one sulfur atom, R.sup.2P is a group represented by the formula II-P, II-O or II-M, R.sup.2O is a group represented by the formula II-O or II-M, R.sup.2M is a group represented by the formula II-M, or R.sup.2P together with R.sup.1P, R.sup.2O together with R.sup.1O, and R.sup.2M together with R.sup.1M represent a group of the formula III, IV or V, or R.sup.2P, R.sup.2O and R.sup.2M are C.sub.6-C.sub.10-aryl, which is unsubstituted or substituted by C.sub.1-C.sub.8-alkyl, C.sub.1-C.sub.8-alkoxy, halogen or one phenyl, C.sub.1-C.sub.18-alkyl, C.sub.3-C.sub.16-cycloalkyl, C.sub.7-C.sub.13-aralkyl, C.sub.2-C.sub.18-alkenyl, C.sub.2-C.sub.30-alkyl, which is interrupted by one or more oxygen atoms, or C.sub.2-C.sub.16-alkyl, which is interrupted by one sulfur atom; when Y.sup.P, Y.sup.O and Y.sup.M are a covalent bond, R.sup.1P is a group represented by the formula II-P, II-O or II-M, R.sup.1O is a group represented by the formula II-O or II-M, R.sup.1M is a group represented by the formula II-M, or R.sup.1P, R.sup.1O and R.sup.1M are C.sub.6-C.sub.10-aryl, which is unsubstituted or substituted by C.sub.1-C.sub.8-alkyl, C.sub.1-C.sub.8-alkoxy, halogen or one phenyl, C.sub.1-C.sub.18-alkyl, C.sub.3-C.sub.16-cycloalkyl, C.sub.7-C.sub.13-aralkyl, C.sub.2-C.sub.18-alkenyl, C.sub.2-C.sub.30-alkyl, which is interrupted by one or more oxygen atoms, or C.sub.2-C.sub.16-alkyl, which is interrupted by one sulfur atom, R.sup.2P, R.sup.2O and R.sup.2M are C.sub.6-C.sub.10-aryl, which is unsubstituted or substituted by C.sub.1-C.sub.8-alkyl, C.sub.1-C.sub.8-alkoxy, halogen or one phenyl; R.sup.4, R.sup.5, R.sup.6 and R.sup.7 are independently hydrogen or C.sub.1-C.sub.8-alkyl, R.sup.P2, R.sup.P3, R.sup.P5 and R.sup.P6 are independently hydrogen or C.sub.1-C.sub.8-alkyl, R.sup.O1, R.sup.O2, R.sup.O5 and R.sup.O6 are independently hydrogen or C.sub.1-C.sub.8-alkyl, R.sup.M1, R.sup.M3, R.sup.M5 and R.sup.M6 are independently hydrogen or C.sub.1-C.sub.8-alkyl, R.sup.a1, R.sup.a2, R.sup.a3 and R.sup.a4 are independently hydrogen or C.sub.1-C.sub.8-alkyl, R.sup.b1, R.sup.b2, R.sup.b3, R.sup.b4, R.sup.b5 and R.sup.b6 are independently hydrogen or C.sub.1-C.sub.8-alkyl, and R.sup.c1, R.sup.c2, R.sup.c3 and R.sup.c4 are independently hydrogen or C.sub.1-C.sub.8-alkyl.

15. The process according to claim 14, 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; and wherein the incorporating into the polymer takes place and a part or a complete incorporation takes place at a temperature ranging from 135 C. to 350 C.

16. A compound of formula I-P, I-O or I-M ##STR00037## wherein Y.sup.P, Y.sup.O and Y.sup.M are oxygen or a covalent bond; when Y.sup.P, Y.sup.O and Y.sup.M are oxygen, R.sup.1P is a group represented by formula II-P, II-O or II-M ##STR00038## R.sup.1O is a group represented by the formula II-O or II-M, R.sup.1M is a group represented by the formula II-M, R.sup.1P together with R.sup.2P, R.sup.1O together with R.sup.2O, and R.sup.1M together with R.sup.2M represent a group represented by formula III, IV or V ##STR00039## R.sup.1P, R.sup.1O and R.sup.1M are C.sub.6-C.sub.10-aryl, which is unsubstituted or substituted by C.sub.1-C.sub.8-alkyl, C.sub.1-C.sub.8-alkoxy, halogen or one phenyl, C.sub.1-C.sub.18-alkyl, C.sub.3-C.sub.16-cycloalkyl, C.sub.7-C.sub.13-aralkyl, C.sub.2-C.sub.18-alkenyl, C.sub.2-C.sub.30-alkyl, which is interrupted by one or more oxygen atoms, or C.sub.2-C.sub.16-alkyl, which is interrupted by one sulfur atom, R.sup.2P is a group represented by the formula II-P, II-O or II-M, R.sup.2O is a group represented by the formula II-O or II-M, R.sup.2M is a group represented by the formula II-M, or R.sup.2P together with R.sup.1P, R.sup.2O together with R.sup.1O and R.sup.2M together with R.sup.1M represent a group represented by the formula III, IV or V, or R.sup.2P, R.sup.2O and R.sup.2M are C.sub.6-C.sub.10-aryl, which is unsubstituted or substituted by C.sub.1-C.sub.8-alkyl, C.sub.1-C.sub.8-alkoxy, halogen or one phenyl, C.sub.1-C.sub.18-alkyl, C.sub.3-C.sub.16-cycloalkyl, C.sub.7-C.sub.13-aralkyl, C.sub.2-C.sub.18-alkenyl, C.sub.2-C.sub.30-alkyl, which is interrupted by one or more oxygen atoms, or C.sub.2-C.sub.16-alkyl, which is interrupted by one sulfur atom; when Y.sup.P, Y.sup.O and Y.sup.M are a covalent bond, R.sup.1P is a group represented by the formula II-P, II-O or II-M, R.sup.1O is a group represented by the formula II-O or II-M, R.sup.1M is a group represented by the formula II-M, or R.sup.1P, R.sup.1O and R.sup.1M are C.sub.6-C.sub.10-aryl, which is unsubstituted or substituted by C.sub.1-C.sub.8-alkyl, C.sub.1-C.sub.8-alkoxy, halogen or one phenyl, C.sub.1-C.sub.18-alkyl, C.sub.3-C.sub.16-cycloalkyl, C.sub.7-C.sub.13-aralkyl, C.sub.2-C.sub.18-alkenyl, C.sub.2-C.sub.30-alkyl, which is interrupted by one or more oxygen atoms, or C.sub.2-C.sub.16-alkyl, which is interrupted by one sulfur atom, R.sup.2P, R.sup.2O and R.sup.2M are C.sub.6-C.sub.10-aryl, which is unsubstituted or substituted by C.sub.1-C.sub.8-alkyl, C.sub.1-C.sub.8-alkoxy, halogen or one phenyl; R.sup.4, R.sup.5, R.sup.6 and R.sup.7 are independently hydrogen or C.sub.1-C.sub.8-alkyl, R.sup.P2, R.sup.P3, R.sup.P5 and R.sup.P6 are independently hydrogen or C.sub.1-C.sub.8-alkyl, R.sup.O1, R.sup.O2, R.sup.O5 and R.sup.O6 are independently hydrogen or C.sub.1-C.sub.8-alkyl, R.sup.M1, R.sup.M3, R.sup.M5 and R.sup.M6 are independently hydrogen or C.sub.1-C.sub.8-alkyl, R.sup.a1, R.sup.a2, R.sup.a3 and R.sup.a4 are independently hydrogen or C.sub.1-C.sub.8-alkyl, R.sup.b1, R.sup.b2, R.sup.b3, R.sup.b4, R.sup.b5 and R.sup.b6 are independently hydrogen or C.sub.1-C.sub.8-alkyl, and R.sup.c1, R.sup.c2, R.sup.c3 and R.sup.c4 are independently hydrogen or C.sub.1-C.sub.8-alkyl.

17. An additive composition, comprising b) a compound of formula I-P, I-O or I-M ##STR00040## wherein Y.sup.P, Y.sup.O and Y.sup.M are oxygen or a covalent bond; when Y.sup.P, Y.sup.O and Y.sup.M are oxygen, R.sup.1P is a group represented by formula II-P, II-O or II-M ##STR00041## R.sup.1O is a group represented by formula II-O or II-M, R.sup.1M is a group represented by the formula II-M, or R.sup.1P together with R.sup.2P, R.sup.1O together with R.sup.2O, and R.sup.1M together with R.sup.2M represent a group of formula III, IV or V ##STR00042## R.sup.1P, R.sup.1O and R.sup.1M are C.sub.6-C.sub.10-aryl, which is unsubstituted or substituted by C.sub.1-C.sub.8-alkyl, C.sub.1-C.sub.8-alkoxy, halogen or one phenyl, C.sub.1-C.sub.18-alkyl, C.sub.3-C.sub.16-cycloalkyl, C.sub.7-C.sub.13-aralkyl, C.sub.2-C.sub.18-alkenyl, C.sub.2-C.sub.30-alkyl, which is interrupted by one or more oxygen atoms, or C.sub.2-C.sub.16-alkyl, which is interrupted by one sulfur atom, R.sup.2P is a group represented by the formula II-P, II-O or II-M, R.sup.2O is a group represented by the formula II-O or II-M, R.sup.2M is a group represented by the formula II-M, or R.sup.2P together with R.sup.1P, R.sup.2O together with R.sup.1O, and R.sup.2M together with R.sup.1M represent a group of the formula III, IV or V, or R.sup.2P, R.sup.2O and R.sup.2M are C.sub.6-C.sub.10-aryl, which is unsubstituted or substituted by C.sub.1-C.sub.8-alkyl, C.sub.1-C.sub.8-alkoxy, halogen or one phenyl, C.sub.1-C.sub.18-alkyl, C.sub.3-C.sub.16-cycloalkyl, C.sub.7-C.sub.13-aralkyl, C.sub.2-C.sub.18-alkenyl, C.sub.2-C.sub.30-alkyl, which is interrupted by one or more oxygen atoms, or C.sub.2-C.sub.16-alkyl, which is interrupted by one sulfur atom; when Y.sup.P, Y.sup.O and Y.sup.M are a covalent bond, R.sup.1P is a group represented by the formula II-P, II-O or II-M, R.sup.1O is a group represented by the formula II-O or II-M, R.sup.1M is a group represented by the formula II-M, or R.sup.1P, R.sup.1O and R.sup.1M are C.sub.6-C.sub.10-aryl, which is unsubstituted or substituted by C.sub.1-C.sub.8-alkyl, C.sub.1-C.sub.8-alkoxy, halogen or one phenyl, C.sub.1-C.sub.18-alkyl, C.sub.3-C.sub.16-cycloalkyl, C.sub.7-C.sub.13-aralkyl, C.sub.2-C.sub.18-alkenyl, C.sub.2-C.sub.30-alkyl, which is interrupted by one or more oxygen atoms, or C.sub.2-C.sub.16-alkyl, which is interrupted by one sulfur atom, R.sup.2P, R.sup.2O and R.sup.2M are C.sub.6-C.sub.10-aryl, which is unsubstituted or substituted by C.sub.1-C.sub.8-alkyl, C.sub.1-C.sub.8-alkoxy, halogen or one phenyl; R.sup.4, R.sup.5, R.sup.6 and R.sup.7 are independently hydrogen or C.sub.1-C.sub.8-alkyl, R.sup.P2, R.sup.P3, R.sup.P5 and R.sup.P6 are independently hydrogen or C.sub.1-C.sub.8-alkyl, R.sup.O1, R.sup.O2, R.sup.O5 and R.sup.O6 are independently hydrogen or C.sub.1-C.sub.8-alkyl, R.sup.M1, R.sup.M3, R.sup.M5 and R.sup.M6 are independently hydrogen or C.sub.1-C.sub.8-alkyl, R.sup.a1, R.sup.a2, R.sup.a3 and R.sup.a4 are independently hydrogen or C.sub.1-C.sub.8-alkyl, R.sup.b1, R.sup.b2, R.sup.b3, R.sup.b4, R.sup.b5 and R.sup.b6 are independently hydrogen or C.sub.1-C.sub.8-alkyl, and R.sup.c1, R.sup.c2, R.sup.c3 and R.sup.c4 are independently hydrogen or C.sub.1-C.sub.8-alkyl, and c) an additive, which is a phosphite or phosphonite, an acid scavenger, a phenolic antioxidant or an aminic antioxidant.

18. The additive composition according to claim 17, wherein the additive c) is a phosphite or phosphonite or a phenolic antioxidant.

19. The additive composition according to claim 17, wherein the additive c) is a phenolic antioxidant, which is an ester of -(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid.

20. The additive composition according to claim 17, further comprising d) a second additive, which is different from the additive c) and is a phosphite or phosphonite, an acid scavenger, a phenolic antioxidant or an aminic antioxidant.

Description

SYNTHETIC EXAMPLES

(1) The synthetic procedures are conducted under a nitrogen atmosphere.

(2) If not otherwise stated, the starting materials are commercially available, for example from Sigma-Aldrich Corp.

Example S-1: Synthesis of Compound (101)

(3) ##STR00019##

(4) 18.6 g (55 mmol) of compound (201) (obtainable according to EP 2500341 A, page 8, example 1) are heated to 65 C. in 85 ml of dry 1,2-dichloroethane. 5.19 g (65 mmol) dry pyridine are added. 2.5 g (18 mmol) phosphorous-trichloride, which are dissolved in 2 mL of dry 1,2-dichloroethane, are added over 20 minutes. The reaction mass is stirred for 2 hours at 65 C. After cooling to ambient temperature, 120 mL cyclohexane are added and the white precipitate formed is filtrated and washed with another 120 mL cyclohexane. The combined cyclohexane portions are concentrated to dryness and the white residue is dried at 70 C. under vacuum for 3 hours. 15.0 g (80% of theory) of compound (101) as a white amorphous solid are obtained.

(5) .sup.31P-NMR (toluene-d.sub.8): 128 ppm

(6) .sup.1H-NMR (toluene-d.sub.8): 4.7 ppm (s, 3H, CH at lactone-ring)

(7) MS (LC/MS, ACPI positive mode): [M+1].sup.+=1044

Example S-2: Synthesis of Compound (102)

(8) ##STR00020##

(9) Compound (102) is prepared in analogy to example S-1 from compound (202) (obtainable according to EP 2500341 A, page 8, example 1 by using the corresponding 4-tert-octyl-phenol) and obtained in a yield of 71% of theory as an amorphous solid.

(10) .sup.31P-NMR (toluene-d.sub.8): 128 ppm

(11) .sup.1H-NMR (toluene-d.sub.8): 4.7 ppm (s, 3H, CH at lactone-ring)

(12) MS (LC/MS, ACPI positive mode): [M+1].sup.+=1381

Example S-3: Synthesis of Compound (103)

(13) ##STR00021##

(14) Compound (103) is prepared in analogy to example S-1 from compound (203) (obtainable according to EP 0648765 A, page 30, compound 115) and obtained in a yield of 89% of theory as an amorphous solid.

(15) .sup.31P-NMR (toluene-d.sub.8): 142 ppm

(16) .sup.1H-NMR (toluene-d.sub.8): 4.2 ppm (s, 3H, CH at lactone-ring)

(17) MS (LC/MS, ACPI positive mode): [M+1].sup.+=1128

Example S-4: Synthesis of Compound (104)

(18) ##STR00022##

(19) 20.0 g (55 mmol) of compound (203) are heated to 65 C. in 85 mL of dry 1,2-dichloroethane. 4.75 g (60 mmol) dry pyridine is added. 4.98 g (27 mmol) of compound (301) (=dichlorophenylphosphane) dissolved in 5 mL of dry 1,2-dichloroethane is added over 20 minutes. The reaction mass is stirred for 4 hours at reflux. After cooling to room temperature, the solvent is removed under vacuum and the solid residue is dried at 70 C. under vacuum for 3 hours. 15.4 g of compound (104) is obtained (67% of theory) as a white solid.

(20) .sup.31P-NMR (toluene-d.sub.8): 169 ppm

(21) .sup.1H-NMR (toluene-d.sub.8): 4.2 ppm (s, 2H, CH at lactone ring)

(22) MS (LC/MS, ACPI positive mode): [M+1].sup.+=840

Example S-5: Synthesis of Compound (105)

(23) ##STR00023##

(24) 2.0 g (5 mmol) of compound (203) are dissolved in 10 mL of dry dichloroethane at 65 C. To the solution are subsequently added 0.52 g (7 mmol) of dry pyridine and within 20 minutes 2.59 g (5 mmol) of compound (302) (=2,4,8,10-tetra-t-butyl-6-chlorobenzo[d][1,3,2]benzodioxaphosphepine, obtainable according to U.S. Pat. No. 5,858,905, page 2, example 1). The reaction mass is stirred under reflux for 6 hours, cooled to room temperature and 10 mL of pentane are added. The suspension is filtrated, the residue is washed with 2 portions of 10 mL dichloroethane and the combined solvent fractions are evaporated to dryness under vacuum. The glassy solid residue is further dried at 70 C. in vacuum. 2.92 g of compound (105) are obtained (66% of theory) as a white glassy solid.

(25) .sup.31P-NMR (toluene-d.sub.8): 141 ppm

(26) .sup.1H-NMR (toluene-d.sub.8): 4.2 ppm (s, 1H, CH at lactone ring)

(27) MS (LC/MS, ACPI positive mode): [M+1].sup.+=806

Example S-6: Synthesis of Compound (106)

(28) ##STR00024##

(29) Compound (106) is prepared in analogy to example S-5 from compound (201) and compound (302) and obtained in a yield of 82% of theory as a solid.

(30) .sup.31P-NMR (toluene-d.sub.8): 143 ppm

(31) .sup.1H-NMR (toluene-d.sub.8): 4.8 ppm (s, 1H, CH at lactone ring)

(32) MS (LC/MS, ACPI positive mode): [M+1].sup.+=778

Example S-7: Synthesis of Compound (107)

(33) ##STR00025##

(34) Compound (107) is prepared in analogy to example S-5 from compound (203) and compound (303) (=1,3,7,9-tetratert-butyl-11-chloro-5H-benzo[d][1,3,2]benzodioxaphosphocine, obtainable according to U.S. Pat. No. 5,858,905, page 2, example 1) and is obtained in a yield of 87% of theory as a solid.

(35) .sup.31P-NMR (toluene-d.sub.8): 137 ppm

(36) .sup.1H-NMR (toluene-d.sub.8): 4.3 ppm (s, 1H, CH at lactone ring)

(37) MS (LC/MS, ACPI positive mode): [M+1].sup.+=820

Example S-8: Synthesis of Compound (108)

(38) ##STR00026##

(39) Compound (108) is prepared in analogy to example S-5 from compound (203) and compound (304) (=1,3,7,9-tetratert-butyl-11-chloro-5-methyl-5H-benzo[d][1,3,2]benzodioxaphosphocine, obtainable according to U.S. Pat. No. 5,858,905, page 2, example 1) and is obtained in a yield of 90% of theory as a solid.

(40) .sup.31P-NMR (toluene-d.sub.8): 138 ppm

(41) .sup.1H-NMR (toluene-d.sub.8): 4.3 ppm (s, 1H, CH at lactone ring)

(42) MS (LC/MS, ACPI positive mode): [M+1].sup.+=834

Example S-9: Synthesis of Compound (109)

(43) ##STR00027##

(44) Compound (109) is prepared in analogy to example S-5 from compound (204) (obtainable according to EP 0648765 A, page 30, compound 115) and compound (304) and is obtained in a yield of 75% of theory as a solid.

(45) .sup.31P-NMR (toluene-d.sub.8): 137 ppm

(46) .sup.1H-NMR (toluene-d.sub.8): 4.9 ppm (s, 1H, CH at lactone ring)

(47) MS (LC/MS, ACPI positive mode): [M+1].sup.+=87

Example P-1: Synthesis of Compound (401)

(48) ##STR00028##

(49) 15.2 g (13 mmol) of compound (103) are dissolved in 50 mL dry dichloromethane and the solution is cooled to 5 C. 3.29 g of 70% m-chloroperbenzoic acid (13 mmol) are added in 5 portions. A colorless precipitate is formed, the suspension is stirred for 3 h at 5 C. The precipitate is filtered off and washed with additional 100 mL of dichloromethane. The combined filtrates are evaporated to dryness and the solid residue is purified by flash chromatography (SiO.sub.2, heptane/ethyl acetate 9:1). 6.6 g of a colourless amorphous solid is obtained (43% of theory).

(50) .sup.31P-NMR (CD.sub.2Cl.sub.2): 16.5 ppm

(51) .sup.1H-NMR (CD.sub.2Cl.sub.2): 4.82 ppm (s, 3H, CH at lactone ring)

(52) MS (LC/MS, ACPI positive mode): [M+1].sup.+=1144

Example P-2: Synthesis of Compound (402)

(53) ##STR00029##

(54) 1.0 g (1.12 mmol) of compound (108) are dissolved in 7 mL dichloroethane at 35 C. 0.32 g (1.31 mmol) m-chloroperbenzoic acid dissolved in 3 mL dichloroethane are added within 5 min. The reaction mass is cooled to room temperature and stirred for 30 min. After removing the solvent, the solid product is dissolved in 10 mL pentane. The solution is extracted twice with 30 mL of a saturated aqueous solution of NaHCO.sub.3 and once with 20 mL water. After drying with sodium sulfate, the solvent is removed. The obtained solid material is triturated with 10 mL acetonitrile, filtrated and dried. 0.64 g of a colorless, amorphous solid is obtained (63% of theory).

(55) .sup.31P-NMR (CD.sub.2CO.sub.2): 18.1 ppm

(56) .sup.1H-NMR (CD.sub.2CO.sub.2): 4.82 ppm (s, 1H, CH at lactone ring)

(57) MS (LC/MS, ACPI positive mode): [M+1].sup.+=850

APPLICATION EXAMPLES

(58) The following known stabilizers are partly employed in addition to the inventive compounds:

(59) AO-1 is Irganox 1010 (RTM BASF), which contains pentaerythritol tetrakis(3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate).

(60) AO-2 is Irganox 1076 (RTM BASF), which contains octadecyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl) propionate.

(61) Phos-1 is Irgafos 168 (RTM BASF), which contains tris(2,4-di-tert-butylphenyl) phosphite.

(62) CaSt is commercially available calcium stearate, which acts as acid scavenger.

(63) ZnSt is commercially available zinc stearate, which acts as acid scavenger.

Polymer Processing Experimental for Examples A-1 to A-4

(64) The various additives are blended with the stated applied granular polymer, which is essentially free of any stabilization additives, in a composition according to the respective tables A-1-1 to A-4-1. The blending is carried out using a Henschel, a Turbula or a Kitchen-Aid mixer.

(65) The thoroughly blended formulations are melt compounded in a twin screw extruder at a lower temperature of 210 C. (410 F.) under nitrogen, which is denoted in the tables as the zero pass extrusion. This ensures good melt mixing with minimal damage to the polymer due to oxidative degradation.

(66) The resultant zero pass extrudate is then extruded multiple times a single screw extruder, fitted with a Maddock mixing section, at a higher temperature of 260 C. (500 F.) and open to air. Extrusion at higher temperatures in combination with the presence of oxygen (air) enhances the rate of polymer degradation. Pelletized samples of zero, first, third and fifth pass extrudate are collected and stored in sealed plastic bags at room temperature in storage boxes in the dark.

(67) Melt Flow Rates: The samples are tested for retention of molecular mass (weight). This is measured by melt flow rate retention according to ASTM-1238 on a Tinius-Olsen Extrusion Plastometer. For polypropylene type polymer samples, the test conditions are 230 C. and 2.16 kg. For polyethylene type polymer samples, the test conditions are 190 C. and 2.16 kg or 21.6 kg. The melt flow ratio is calculated as the melt flow rate at 21.6 kg divided by the melt flow rate at 2.16 kg. Melt flow rates are measured in grams of polymer that flow out of a defined orifice in 10 minutes and are stated as grams/10 minutes (decigrams per minute).

(68) Yellowness Index: The yellowness index of some samples is tested for color development observed during the multiple extrusion and is measured according to ASTM-313 on compression molded plaques of 3.2 mm (125 mil). Color is measured on a DCI SF600 spectrophotometer with large area view, spectral component included, C illuminant and 2 degree observer. Color in these measurements is expressed as Yellowness Index.

(69) Oven Aging: Some samples are tested for oxidative stability below the melting point of the polymer using oven aging to accelerate polymer degradation. A general approach is described in ASTM D3045-92. One specific approach is to simulate inventory or transportation storage stability at 60 C. (140 F.) to evaluate the resistance to discoloration. Oven ageing at 60 C. (open to air) simulates storage in railcars in hot weather. Oven ageing in the presence of oxides of nitrogen simulates pollution in warehouse storage. Compression molded plaques of 0.25 mm (10 mil) are put into a forced draft oven equipped with a rotating carousel. The resistance to discoloration, measured by yellowness index of the samples, is measured in intervals of 7 days. Another specific approach for testing for oxidative stability below the melting point of the polymer is to put compression molded plaques of 1 mm (40 mil) in a Blue M forced draft oven equipped with a rotating carousel at an elevated temperature of 135 C. (275 F.). In this approach, failure is measured by days to embrittlement by bending the plaque every 3 to 4 days until the plaque snapped due to oxidative degradation.

(70) Oxidative Induction Time: Some samples are tested for oxidative stability above the melting point of the polymer using oxidative induction time (OIT) as a means of measuring the activity of the stabilizer in the polymer melt at a high temperature of 190 C. in an oxidative environment (oxygen). The experiments are run on compression molded 0.25 mm (10 mil) films using a differential scanning calorimeter (DSC). Scans are collected using a heating rate of 10 C./min under nitrogen from 50 C. to 190 C., then switching to oxygen and holding at isothermal conditions until catastrophic oxidation. Time to onset of catastrophic oxidation (observed as an exotherm) is stated in minutes.

Example A-1: Stabilization of a Molding Grade Ziegler-Natta Polypropylene Homopolymer

(71) A molding grade Ziegler-Natta polypropylene homopolymer (zn-PP-homopolymer) with a nominal melt flow rate of 20 dg/min from a bulk/slurry phase polymerization process is evaluated.

(72) TABLE-US-00001 TABLE A-1-1 composition No. 1 .sup.a) 2 .sup.a) 3 .sup.a) 4 .sup.b) zn-PP-homopoly- 99.890 99.840 99.790 99.840 mer CaSt 0.060 0.060 0.060 0.060 AO-1 0.050 0.050 0.050 0.050 Phos-1 0.050 0.100 0.0375 compound (401) 0.0125 total additives 0.110 0.160 0.210 0.160 content 260 C. (500 F.) melt processing melt flow rates zero pass 24.41 23.10 22.22 22.11 1.sup.st pass 36.72 34.95 32.63 30.78 3.sup.rd pass 46.51 43.18 41.33 36.12 5.sup.th pass 56.40 49.56 46.16 44.94 yellowness index zero pass 5.50 5.20 5.60 5.60 1.sup.st pass 7.30 7.40 7.90 6.80 3.sup.rd pass 9.60 10.00 10.30 8.50 5.sup.th pass 11.60 12.10 12.60 8.70 oven ageing at 60 C. and yellowness index 0 days .sup.2.60 .sup.c), d) .sup.2.50 .sup.c) .sup.2.50 .sup.c), d) .sup.2.50 .sup.c) 7 days 3.00 2.90 2.80 2.90 14 days 3.10 3.00 3.00 2.90 21 days 3.20 3.20 3.20 3.10 28 days 3.40 3.40 3.40 3.30 oven ageing at 60 C. with oxides of nitrogen and yellowness index 0 days .sup.2.80 .sup.c), d) .sup.2.50 .sup.c) .sup.2.60 .sup.c), d) .sup.2.50 .sup.c) 7 days 4.60 4.60 4.90 4.30 14 days 5.50 5.50 5.70 5.20 21 days 6.20 6.30 6.40 5.90 28 days 6.60 6.80 7.10 6.40 Footnotes: .sup.a) reference .sup.b) inventive .sup.c) differences in yellowness after zero pass at extrusion and zero day at oven ageing are mainly caused by the difference of the thickness of the tested molded plaques (plaques with 3.2 mm (125 mil) at extrusion versus plaques with 0.25 mm (10 mil) at oven ageing) .sup.d) small differences in yellowness at the two oven ageing tests at the initial molded plaques are due to measurement differences (+/5%) as well as the molded plaques have small differences originating from their molding (+/5%)

(73) The composition comprised of a low concentration of an inventive compound (125 ppm), a phenolic antioxidant (500 ppm) and a traditional phosphite melt processing stabilizer (375 ppm) provide good performance as measured by retention of melt flow rates in comparison to a common binary blend of the phenolic antioxidant (500 ppm) and the traditional phosphite melt processing stabilizer (500 or 1000 ppm). The ternary blend comprising an inventive compound provides as good or better performance at the same or even at a lower concentration (1600 ppm) in comparison to the common binary blends (1600 ppm or 2100 ppm). There are no deleterious effects to discoloration resistance as measured by oven ageing at 60 C. under two different exposure conditions.

Example A-2: Stabilization of a Molding Grade Ziegler-Natta Polypropylene Copolymer

(74) A molding grade Ziegler-Natta polypropylene copolymer (zn-PP-copolymer; ethylene as random comonomer in around 2% by weight) with a melt flow rate of 3 dg/min from a bulk/slurry phase polymerization process is evaluated.

(75) TABLE-US-00002 TABLE A-2-1 composition No. 1 .sup.a) 2 .sup.a) 3 .sup.a) 4 .sup.b) zn-PP-copolymer 99.890 99.840 99.790 99.840 CaSt 0.060 0.060 0.060 0.060 AO-1 0.050 0.050 0.050 0.050 Phos-1 0.050 0.100 0.0375 compound (401) 0.0125 total additives content 0.110 0.160 0.210 0.160 260 C. (500 F.) melt processing melt flow rates zero pass 3.29 2.95 2.66 2.67 1.sup.st pass 6.26 4.10 3.27 3.21 3.sup.rd pass 10.66 5.73 4.30 3.65 5.sup.th pass 15.09 8.27 5.49 4.87 oven ageing at 60 C. and yellowness index 0 days 2.80 2.70 2.60 2.60 7 days 3.20 2.90 2.90 2.80 14 days 3.30 3.20 3.20 3.00 21 days 3.50 3.30 3.30 3.20 28 days 3.60 3.40 3.40 3.30 oven ageing at 135 C. days to embrittlement 27 24 27 37 oxidative induction time (10 mil films/onset at 190 C.) minutes to exotherm 10 11 12 23 Footnotes: .sup.a) reference; .sup.b) inventive

(76) The composition comprised of a low concentration of an inventive compound (125 ppm), a phenolic antioxidant (500 ppm) and a traditional phosphite melt processing stabilizer (375 ppm) provides good performance as measured by retention of melt flow rates in comparison to a common binary blend of the phenolic antioxidant (500 ppm) and the traditional phosphite melt processing stabilizer (500 or 1000 ppm). The ternary blend comprising an inventive compound provides as good or better performance at the same or even at a lower concentration (1600 ppm) in comparison to the common binary blends (1600 ppm or 2100 ppm). There is no deleterious effects to discoloration resistance as measured by oven ageing at 60 C. There is an advantageous effect under oven ageing at 135 C. as a high temperature and at oxidative induction time.

Example A-3: Stabilization of a Film Grade Metallocene Catalyzed Linear Low Density Polyethylene Copolymer

(77) A film grade metallocene catalyzed low density polyethylene copolymer (m-LLDPE-copolymer; hexene as comonomer, density 0.92 g/cm.sup.3) with a melt flow rate of 1 dg/min at 190 C. and 2.16 kg from a gas phase polymerization process is evaluated.

(78) TABLE-US-00003 TABLE A-3-1 composition No. 1 .sup.a) 2 .sup.a) 3 .sup.a) 4.sup.b) m-LLDPE-copolymer 99.900 99.850 99.800 99.850 ZnSt 0.050 0.050 0.050 0.050 AO-2 0.050 0.050 0.050 0.050 Phos-1 0.050 0.100 0.0375 compound (103) 0.0125 compound (104) total additives content 0.100 0.150 0.200 0.150 260 C. (500 F.) melt processing melt flow rates (190 C./2.16 kg) zero pass 0.85 0.89 0.94 0.94 1.sup.st pass 0.70 0.76 0.84 0.81 3.sup.rd pass 0.50 0.58 0.69 0.64 5.sup.th pass 0.38 0.46 0.57 0.54 melt flow ratio (190 C.; melt flow at 21.6 kg/melt flow at 2.16 kg) zero pass 16.02 15.10 15.09 15.07 1.sup.st pass 17.61 17.43 16.39 16.80 3.sup.rd pass 24.10 21.69 18.96 19.83 5.sup.th pass 30.21 26.26 22.26 22.52 oven ageing at 60 C. and yellowness index 0 days 1.80 1.80 1.80 2.00 7 days 2.10 2.00 2.00 2.00 14 days 2.30 2.20 2.10 2.10 21 days 2.50 2.40 2.30 2.30 28 days 2.50 2.50 2.40 2.30 oxidative induction time (10 mil films/onset at 190 C.) minutes to exotherm 10 11 12 23 Footnotes: .sup.a) reference; .sup.b) inventive

(79) The composition comprised of a low concentration of an inventive compound (125 ppm), in combination with a phenolic antioxidant (500 ppm) and a common phosphite melt processing stabilizer (375 ppm), provides good performance as measured by retention of melt flow rates in comparison to a traditional binary blend of the phenolic antioxidant (500 ppm) and a common phosphite melt processing stabilizer (500 or 1000 ppm). The ternary blend comprising an inventive compound provides as good or better performance at the same or even at a lower concentration (1500 ppm) in comparison to the common binary blends (1500 ppm or 2000 ppm). There is no deleterious effects to discoloration resistance as measured by oven ageing at 60 C. There is an advantageous effect at oxidative induction time.

Example A-4: Stabilization of a Blown Film Grade Ziegler-Natta Catalyzed High Density Polyethylene

(80) A blown film grade Ziegler-Natta catalyzed high density polyethylene (zn-HDPE; density 0.960 g/cm.sup.3) with a melt flow rate of 0.7 dg/min at 190 C. and 2.16 kg from a solution phase polymerization process is evaluated.

(81) TABLE-US-00004 TABLE A-4-1 composition No. 1 .sup.a) 2 .sup.a) 3 .sup.a) 4 .sup.b) zn-HDPE-polymer 99.970 99.920 99.870 99.920 AO-1 0.030 0.030 0.030 0.030 Phos-1 0.050 0.100 0.040 compound (401) 0.010 total additives content 0.030 0.080 0.130 0.080 260 C. (500 F.) melt processing melt flow rates (190 C./2.16 kg) zero pass 0.76 0.81 0.81 0.76 1.sup.st pass 0.63 0.69 0.72 0.67 3.sup.rd pass 0.52 0.60 0.64 0.63 5.sup.th pass 0.46 0.52 0.55 0.60 melt flow ratio (190 C.; melt flow at 21.6 kg/melt flow at 2.16 kg) zero pass 98.6 94.8 94.4 95.8 1.sup.st pass 111.2 105.2 102.7 102.7 3.sup.rd pass 133.4 118.3 111.9 109.4 5.sup.th pass 148.0 134.3 125.8 114.0 oven ageing at 60 C. and yellowness index 0 days 2.10 2.00 2.00 2.30 7 days 2.30 2.00 2.20 2.30 14 days 2.30 2.30 2.30 2.30 21 days 2.40 2.40 2.40 2.40 28 days 2.60 2.50 2.60 2.60 oxidative induction time (10 mil films/onset at 190 C.) minutes to exotherm 38 58 80 62 Footnotes: .sup.a) reference; .sup.b) inventive

(82) The composition comprised of a low concentration of an inventive compound (100 ppm), in combination with a phenolic antioxidant (300 ppm) and a common phosphite melt processing stabilizer (400 ppm), provides good performance as measured by retention of melt flow rates in comparison to a traditional binary blend of the phenolic antioxidant (300 ppm) and a common phosphite melt processing stabilizer (500 or 1000 ppm). The ternary blend comprising an inventive compound provides as good or better performance at the same or even at a lower concentration (800 ppm) in comparison to the common binary blends (800 ppm or 1300 ppm). There is no deleterious effects to discoloration resistance as measured by oven ageing at 60 C. There is an advantageous effect at oxidative induction time in comparison to a common binary blend at the same concentration (800 ppm).

Example H-1: Hydrolytic Stability of Compound (401)

(83) Hydrolysis testing: A sample is tested for hydrolytic stability using a forced draft humidity oven with the proper adjustments to maintain 50 C. (122 F.) and 80% relative humidity. The test method involves putting 0.5 grams of the material to be tested in properly labeled glass vials, uncapped. For the present testing, 3 sets of vials are provided and the samples are removed from the humidity oven once a week. The exposed sample is then tested for the extent of hydrolysis by High Pressure Liquid Chromatography (HPLC), which measures the retention of intact starting material as well as transformation chemistry. The increase of the presence of a hydrolysis product is used as an indicator for loss of intact starting material.

(84) Compound (401) and compound (103) are tested for hydrolysis by observation of the content of compound (203).

(85) ##STR00030##

(86) Sample H-1-I: compound (103) in the form of a white powder

(87) Sample H-1-II: a composition comprising 100 parts of compound (103) and 0.6 parts of triisopropanolamine (at the synthesis of compound (103) as described in example S-3, 0.6% by weight of triisopropanolamine based on the expected yield of compound (103) is added to the combined cyclohexane portions prior to their concentration to dryness, the composition is obtained as an amorphous solid) in the form of a white powder

(88) Sample H-1-III: compound (401) in the form of a white powder

(89) TABLE-US-00005 TABLE H-1-1 content of compound (203) in % by weight after days of exposure sample No. 0 7 14 21 H-1-I 0.4 85 H-1-II 0.4 74 H-1-III 0.3 0.2 0.2 0.3

(90) All tested samples start out intact with less than 1% of compound (203). After 7 days, compound (103) as well as the composition comprising 100 parts of compound (103) and 0.6 parts of triisopropanolamine as a common hydrolysis inhibitor are failed. It is noted that the composition is less hydrolyzed than compound (103) after 7 days. In comparison, after 21 days, there is virtually no hydrolysis of compound (403). This illustrates the advantage of a compound of formula I-P, formula I-O or formula I-M as a class of powerful melt processing stabilizers with remarkable hydrolytic stability.