CN111051322A - Stabilized polyolefin compositions comprising benzofuranones and organophosphorus stabilizers - Google Patents

Abstract

The present invention provides polyolefin compositions comprising i) a polyolefin, ii) one or more phosphorus-containing benzofuranone compounds and iii) one or more organophosphorus stabilizers, which compositions have excellent protection against discoloration and improved thermal stability during melt processing, which is manifested by improved molecular weight retention and retention of polymer molecular structure.

Description

Stabilized polyolefin compositions comprising benzofuranones and organophosphorus stabilizers

The present invention relates to polyolefin compositions comprising phosphorus-containing 3-phenyl-benzofuran-2-one compounds and specific organophosphorus stabilizers. The polyolefin compositions exhibit excellent color properties and improved thermal stability during melt processing.

For decades, traditional phenolic/phosphite antioxidant mixtures have been successfully used to provide good melt flow control and acceptable color retention properties to polyolefins. However, there is an increasing need to reduce the color of polyolefin articles and to improve color retention.

SUMMARY

Accordingly, disclosed herein are polyolefin compositions comprising i) a polyolefin, ii) one or more phosphorus-containing benzofuranone compounds, and iii) one or more organophosphorus stabilizers. The phosphorus-containing benzofuranone compounds can have the formula I-p1, I-p2, I-o1, I-o2, I-m1, or I-m2, as described in detail below. Also disclosed herein are additive compositions comprising a phosphorus-containing benzofuranone compound and an organophosphorus stabilizer.

Also disclosed herein is a method of stabilizing a polyolefin against the adverse effects of heat, light, and oxygen, which comprises incorporating into the polyolefin ii) one or more benzofuranone compounds selected from the group consisting of formula I-p1, I-p2, I-o1, I-o2, I-m1, and I-m2, and iii) one or more organophosphorus stabilizers. The adverse effects of heat, light and oxygen can lead to undesirable color.

Detailed description of the invention

The phosphorus-containing 3-phenyl-benzofuran-2-one compound may have the formula I-p1, I-p2, I-o1, I-o2, I-m1, or I-m2 (also referred to herein as a "benzofuran-2-one" or "benzofuranone" compound).

Wherein

X and Z are independently P or P ═ O; y is^p、Y^oAnd Y^mIs oxygen or represents a covalent bond;

when Y is^p、Y^oAnd Y^mWhen is oxygen, R^1pRepresents one of the sub-formulae II-p, II-o or II-m:

R^1orepresents one of the sub-formulae II-o or II-m, R^1mRepresents the sub-formula II-m, or

R^1pAnd R^2pTogether, R^1oAnd R^2oTogether with R^1mAnd R^2mTogether represent one of the sub-formulae III, IV or V:

or R^1p、R^1oAnd R^1mIs unsubstituted or substituted by C₁-C₈Alkyl radical, C₁-C₈Alkoxy, halogen or C substituted by one phenyl group₆-C₁₀Aryl radical, C₁-C₁₈Alkyl radical, C₃-C₁₆Cycloalkyl radical, C₇-C₁₃Aralkyl radical, C₂-C₁₈Alkenyl, C interrupted by one or more oxygen atoms₂-C₃₀Alkyl, or C interrupted by a sulfur atom₂-C₁₆Alkyl radical, R^2pRepresents one of the sub-formulae II-p, II-o or II-m, R^2oRepresents one of the sub-formulae II-o or II-m, R^2mRepresents the sub-formula II-m, or R^2pAnd R^1pTogether, R^2oAnd R^1oTogether with R^2mAnd R^1mTogether represent one of the sub-formulae III, IV or V, or R^2p、R^2oAnd R^2mIs unsubstituted or substituted by C₁-C₈Alkyl radical, C₁-C₈Alkoxy radicalHalogen or C substituted by one phenyl group₆-C₁₀Aryl radical, C₁-C₁₈Alkyl radical, C₃-C₁₆Cycloalkyl radical, C₇-C₁₃Aralkyl radical, C₂-C₁₈Alkenyl, C interrupted by one or more oxygen atoms₂-C₃₀Alkyl, or C interrupted by a sulfur atom₂-C₁₆An alkyl group; when Y is^p、Y^oAnd Y^mWhen represents a covalent bond, R^1pRepresents one of the sub-formulae II-p, II-o or II-m, R^1oRepresents one of the sub-formulae II-o or II-m, R^1mRepresents the sub-formula II-m, or R^1p、R^1oAnd R^1mIs unsubstituted or substituted by C₁-C₈Alkyl radical, C₁-C₈Alkoxy, halogen or C substituted by one phenyl group₆-C₁₀Aryl radical, C₁-C₁₈Alkyl radical, C₃-C₁₆Cycloalkyl radical, C₇-C₁₃Aralkyl radical, C₂-C₁₈Alkenyl, C interrupted by one or more oxygen atoms₂-C₃₀Alkyl, or C interrupted by a sulfur atom₂-C₁₆Alkyl radical, R^2p、R^2oAnd R^2mIs unsubstituted or substituted by C₁-C₈Alkyl radical, C₁-C₈Alkoxy, halogen or C substituted by one phenyl group₆-C₁₀Aryl, or halogen; r⁴、R⁵、R⁶And R⁷Each independently is hydrogen or C₁-C₈Alkyl radical, R^p2、R^p3、R^p5And R^p6Each independently is hydrogen or C₁-C₈Alkyl radical, R^o1、R^o2、R^o5And R^o6Each independently is hydrogen or C₁-C₈An alkyl group, a carboxyl group,

R^m1、R^m3、R^m5and R^m6Each independently is hydrogen or C₁-C₈Alkyl radical, R^a1、R^a2、R^a3And R^a4Each independently is hydrogen or C₁-C₈Alkyl radical, R^b1、R^b2、R^b3、R^b4、R^b5And R^b6Each independently is hydrogen or C₁-C₈Alkyl, and R^c1、R^c2、R^c3And R^c4Each independently is hydrogen or C₁-C₈An alkyl group.

A point of attachment on the subformulae II-p, II-o or II-m is indicated by the end of the line, which end has no property and is blank. The two connection points on subformulae III, IV or V are each represented by the ends of the respective lines, which have no characteristic and are blank. When R is^1pAnd R^2pTogether, R^1oAnd R^2oTogether with R^1mAnd R^2mWhen together represent one of the sub-formulae III, IV or V, R^2pAnd R^1pTogether, R^2oAnd R^1oTogether with R^2mAnd R^1mTogether represent the same sub-formula.

Compounds of the formulae I-p1, I-p2, I-o1, I-o2, I-m1 or 1-m2 have at least one asymmetric carbon atom, i.e. the carbon atom located in the 3-position of the benzofuran-2-one structural unit. Other asymmetric carbon atoms may be present in an alkyl substituent having at least four carbon atoms. Phosphorus atoms substituted with three different substituents may show steric inversion, which may result in an asymmetric phosphorus atom that is temperature dependent. The present invention relates to any of these enantiomers, resulting diastereomers, or mixtures thereof.

Unsubstituted or substituted by C₁-C₈Alkyl radical, C₁-C₈Alkoxy, halogen or C substituted by one phenyl group₆-C₁₀Aryl is for example phenyl, 2-methyl-phenyl, 3-methyl-phenyl, 4-methyl-phenyl, 2, 4-dimethyl-phenyl, 3, 5-dimethyl-phenyl, 4- (1, 1-dimethylethyl) -phenyl, 4- (1,1,3, 3-tetramethylpentyl) -phenyl, naphthalen-1-yl, naphthalen-2-yl, 6-methylnaphthalen-2-yl, 4-phenyl, 2-methoxy-phenyl, 3-methoxy-phenyl, 4-methoxy-phenyl, 2-ethoxyphenyl, 3-ethoxy-phenyl, 3- (n-propoxy) -phenyl, 4- (1, 1-dimethylethoxy) -phenyl, 2-chloro-phenyl, 3-chlorophenyl, 4-chlorophenyl, 2-chloro-4-methylphenyl. In some embodiments, C₆-C₁₀Aryl radicalsIs unsubstituted or substituted by C₁-C₈Alkyl or C₁-C₈Alkoxy substitution. In a particular embodiment, aryl is unsubstituted or substituted with C₁-C₈Alkyl-substituted phenyl. In other embodiments, aryl is phenyl.

C₁-C₈Alkyl is straight-chain or branched, and is, for example, methyl, ethyl, n-propyl, 1-methyl-ethyl, n-butyl, 1-methyl-propyl, 2-methyl-propyl, 1, 1-dimethyl-ethyl, n-pentyl, 1-methyl-butyl, 3-methyl-butyl, n-hexyl, 1-methyl-pentyl, 2-methyl-pentyl, 4-methyl-pentyl, 2-ethyl-butyl, n-heptyl, 1-methyl-hexyl, n-octyl, 1-methyl-heptyl, 2-ethyl-hexyl, 5, 5-dimethyl-hexyl or 1,1,3, 3-tetramethyl-butyl. In some embodiments, alkyl is C₁-C₄Alkyl or C₈Alkyl, such as methyl, ethyl, 1-methyl-propyl, 1-dimethyl-ethyl or 1,1,3, 3-tetramethyl-butyl. In a particular embodiment, alkyl is C₁-C₄Alkyl groups such as methyl, ethyl, 1-methyl-propyl, 1-dimethyl-ethyl, and in other particular embodiments methyl, 1-methyl-propyl or 1, 1-dimethyl-ethyl.

C₁-C₈Alkoxy is straight-chain or branched and is, for example, methoxy, ethoxy, n-propoxy, 1-methyl-ethoxy, n-butoxy, 1-methyl-propoxy, 1, 1-dimethyl-ethoxy, n-pentoxy, 2-methyl-pentoxy, 2-ethyl-butoxy, 1-methyl-hexoxy, n-octoxy, 1-methyl-heptoxy, 2-ethyl-hexoxy, 1,1,3, 3-tetramethyl-butoxy. In some embodiments, alkoxy is C₁-C₄Alkoxy groups, such as methoxy.

Halogen is, for example, a fluorine atom (fluoro), a chlorine atom (chloro), a bromine atom (bromo) or an iodine atom (iodo). In particular embodiments, halogen is a chlorine atom or a fluorine atom; in some embodiments, the halogen is a fluorine atom.

C₁-C₁₈Alkyl being straight-chain or branched, e.g. methyl, ethyl, n-propyl, 1-methyl-ethylN-butyl, 1-methyl-propyl, 2-methyl-propyl, 1, 1-dimethyl-ethyl, n-pentyl, 1-methyl-butyl, 3-methyl-butyl, n-hexyl, 1-methyl-pentyl, 2-methyl-pentyl, 4-methyl-pentyl, 2-ethyl-butyl, n-heptyl, 1-methyl-hexyl, n-octyl, 1-methyl-heptyl, 2-ethyl-hexyl, 5, 5-dimethyl-hexyl, 1,1,3, 3-tetramethyl-butyl, n-nonyl, 2-ethyl-heptyl, n-decyl, undecyl, n-dodecyl, tridecyl, tetradecyl, pentadecyl, n-hexadecyl or n-octadecyl. In some embodiments, C₁-C₁₈Alkyl being straight-chain or branched C₁-C₁₂An alkyl group.

C₃-C₁₆Cycloalkyl being unsubstituted or substituted by C₁-C₄Alkyl substituents are, for example, cyclobutyl, cyclopentyl, 3, 4-dimethyl-cyclopentyl, cyclohexyl, 4-methyl-cyclohexyl, 4- (1-methylethyl) -cyclohexyl, 4- (1, 1-dimethylethyl) -cyclohexyl, 3, 5-dimethyl-cyclohexyl, 5-methyl-2- (1-methyl-ethyl) -cyclohexyl, cycloheptyl, cyclooctyl or cyclododecyl. In a particular embodiment, C₃-C₁₆Cycloalkyl is C₅-C₇Cycloalkyl radicals, such as cyclohexyl.

C₇-C₁₃Aralkyl is, for example, benzyl, 4-methyl-benzyl, 2-phenyl-ethyl, 3, 5-dimethylbenzyl, 1-phenyl-1, 1-dimethyl-methyl, 3-phenyl-propyl, 3-phenyl-2-methyl-propyl, 3, 5-di-tert-butyl-benzyl or 4-phenyl-methyl. In a particular embodiment, the aralkyl group is benzyl. C₂-C₁₈Alkenyl is straight-chain or branched, for example vinyl, allyl, Z-or E-but-2-en-yl, or E-but-3-en-yl, Z-or E-pent-2-en-yl, pent-4-en-yl, Z-or E-2-methyl-but-2-en-yl, Z-or E-3-methyl-but-3-en-yl, Z-or E-hex-1-en-yl, Z-or E-hexadec-9-en-yl or Z-or E-octadec-9-en-yl, (9Z,12Z) -octadeca-9, 12-dienyl or (9Z,12Z,15Z) -octadeca-9, 12, 15-triene-yl. In a particular embodiment, alkenyl is allyl.

C interrupted by one or more oxygen atoms₂-C₃₀The alkyl group is either straight-chain or branched,examples are methoxy-methyl, 2-methoxy-ethyl, 2-ethoxy-ethyl, 2- (2-methoxy-ethoxy) -ethyl, 2-n-butoxy-ethyl, 2- [2- (2-methoxy-ethoxy) -ethoxy]-ethyl, 2- [2- [2- (2-methoxy-ethoxy) -ethoxy ] -ethyl]-ethoxy radical]-ethyl, 2- (2-methoxy-1-methyl-ethoxy) -1-methyl-ethyl, 3- (n-propoxy) -propyl, 2- [2- [2- (2-n-butoxy-ethoxy) -ethoxy ] -ethoxy]-ethoxy radical]-ethyl, 2- [2- (2-n-butoxy-2-methyl-ethoxy) -2-methyl-ethoxy]-2-methyl-ethyl or 2- [ (2-n-lauryl) -ethoxy]-ethyl. In some embodiments, the alkyl group interrupted by one or more oxygen atoms is a 2-methoxy-ethyl or 2-ethoxy-ethyl group.

C interrupted by a sulfur atom₂-C₁₆Alkyl is straight-chain or branched, and is, for example, 2- (methyl-sulfanyl) -ethyl, 3-thiaundecyl or 3-thiapentadecyl.

In some embodiments, the benzofuranone is a compound of formula I-p1, I-p2, I-o1, I-o2, I-m1, or I-m2, wherein R⁴And R⁶Is hydrogen, and R⁵And R⁷Each independently is hydrogen or C₁-C₈Alkyl radicals, e.g. hydrogen or C₁-C₄An alkyl group. In certain embodiments, R⁴、R⁶And R⁷Is hydrogen, and R⁵Is hydrogen or C₁-C₈Alkyl radicals, e.g. hydrogen or C₁-C₄An alkyl group. In some embodiments, R^p2And R^p6Each independently is hydrogen or C₁Alkyl radical, R^p3And R^p5Each independently is hydrogen or C₁-C₄Alkyl radical, R^o1And R^o6Each independently is hydrogen or C₁-C₈Alkyl radical, R^o2Is hydrogen or C₁Alkyl, and R^o5Is hydrogen or C₁-C₄Alkyl radical, R^m1Is hydrogen or C₁Alkyl radical, R^m3And R^m5Each independently is hydrogen or C₁-C₄Alkyl, and R^m6Is hydrogen or C₁-C₈An alkyl group.

In particular embodiments, the benzofuranones are of the formula I-p1, I-p2, I-o1, I-o2, I-m1 or I-m2, wherein R^p2And R^p6Is hydrogen, and R^p3And R^p5Each independently is hydrogen or C₁-C₄Alkyl radical, R^o1Is hydrogen or C₁-C₈Alkyl radical, R^o2Is hydrogen, R^o5And R^o6Each independently is hydrogen or C₁-C₄Alkyl radical, R^m1And R^m3Is hydrogen or C₁Alkyl radical, R^m5Is hydrogen or C₁-C₃Alkyl, and R^m6Is hydrogen or C₁-C₈An alkyl group. In other embodiments, R^p2And R^p6Is hydrogen, and R^p3And R^p5Each independently is hydrogen or C₁-C₄Alkyl radical, wherein R^p3And R^p5One is not C₄Alkyl radical, R^o1Is hydrogen or C₁-C₈Alkyl radical, R^o2Is hydrogen, R^o5Is hydrogen or C₁-C₃Alkyl, and

R^o6is hydrogen or C₁-C₄Alkyl, and R^m1And R^m3Is hydrogen or C₁Alkyl radical, R^m5Is hydrogen or C₁-C₃Alkyl, and R^m6Is hydrogen or C₁-C₈An alkyl group.

In some embodiments, R^p2And R^p6Is hydrogen, and R^p3And R^p5One being hydrogen and the other being hydrogen or C₁-C₄Alkyl radical, R^o1Is hydrogen or C₁-C₈Alkyl radical, R^o2Is hydrogen, R^o5Is hydrogen or C₁Alkyl radical, R^o6Is hydrogen or C₁-C₄Alkyl radical, R^m1、R^m3And R^m5Is hydrogen, and R^m6Is hydrogen or C₁-C₈An alkyl group. In certain embodiments, R^a1、R^a2、R^a3And R^a4Each independently is hydrogen or C₁-C₄Alkyl radical, R^b1、R^b2、R^b3、R^b4、R^b5And R^b6Each independently is hydrogen or C₁-C₄Alkyl, and R^c1、R^c2、R^c3And R^c4Each independently is hydrogen or C₁-C₄An alkyl group.

In some embodiments, R^a1、R^a2、R^a3And R^a4Each independently is hydrogen or C₁-C₄Alkyl radical, R^b1、R^b2、R^b3、R^b4Each independently is hydrogen or C₁-C₄Alkyl, and R^b5And R^b6One is C₁-C₄Alkyl, and the other is hydrogen, and R^c1、R^c2、R^c3And R^c4Each independently is hydrogen or C₁-C₄An alkyl group. In particular embodiments, Y^p、Y^oAnd Y^mIs oxygen or represents a covalent bond; when Y is^p、Y^oAnd Y^mWhen is oxygen, R^1pRepresents one of the sub-formulae II-p, II-o or II-m, R^1oRepresents one of the sub-formulae II-o or II-m, R^1mRepresents the sub-formula II-m, or R^1pAnd R^2pTogether, R^1oAnd R^2oTogether with R^1mAnd R^2mTogether represent one of the sub-formulae III, IV or V, or R^1p、R^1oAnd R^1mIs unsubstituted or substituted by C₁-C₈Alkyl substituted C₆-C₁₀Aryl radical, C₁-C₁₈Alkyl radical, C₃-C₁₆Cycloalkyl radicals, or C₂-C₁₈Alkenyl radical, R^2pRepresents one of the sub-formulae II-p, II-o or II-m, R^2oRepresents one of the sub-formulae II-o or II-m, R^2mRepresents the sub-formula II-m, or R^2pAnd R^1pTogether, R^2oAnd R^1oTogether with R^2mAnd R^1mTogether represent one of the sub-formulae III, IV or V, or R^2p、R^2oAnd R^2mIs unsubstituted or substituted by C₁-C₆Alkyl substituted C₆-C₁₀Aryl radical, C₁-C₁₈Alkyl radical, C₃-C₁₆Cycloalkyl radicals, or C₂-C₁₈An alkenyl group; when Y is^p、Y^oAnd Y^mWhen represents a covalent bond, R^1pIs represented by the sub-formula IIOne of-p, II-o or II-m, R^1oRepresents one of the sub-formulae II-o or II-m, R^1mRepresents the sub-formula II-m, or R^1p、R^1oAnd R^1mIs unsubstituted or substituted by C₁-C₈Alkyl substituted C₆-C₁₂Aryl radical, C₁-C₁₈Alkyl radical, C₃-C₁₆Cycloalkyl radicals, or C₂-C₁₈Alkenyl, and R^2p、R^2oAnd R^2mIs unsubstituted or substituted by C₁-C₈Alkyl substituted C₆-C₁₀Aryl, or halogen, wherein halogen is chloro or fluoro.

In some embodiments, Y is^p、Y^oAnd Y^mIs oxygen or represents a covalent bond; when Y is^p、Y^oAnd Y^mWhen is oxygen, R^1pRepresents the sub-formula II-p, R^1oRepresents formula II-o, R^1mRepresents the sub-formula II-m, or R^1pAnd R^2pTogether, R^1oAnd R^2oTogether with R^1mAnd R^2mTogether represent one of the sub-formulae III, IV or V, or R^1p、R^1oAnd R^1mIs unsubstituted or substituted by C₁-C₈Alkyl substituted C₆-C₁₀Aryl radical, C₁-C₁₈Alkyl radical, C₃-C₁₆Cycloalkyl radicals, or C₂-C₁₈Alkenyl, and R^2pRepresents the sub-formula II-p, R^2oRepresents the sub-formula II-o, R^2mRepresents the sub-formula II-m, or R^2pAnd R^1pTogether, R^2oAnd R^1oTogether with R^2mAnd R^1mTogether represent one of the sub-formulae III, IV or V, or R^2p、R^2oAnd R^2mIs unsubstituted or substituted by C₁-C₈Alkyl substituted C₆-C₁₀Aryl radical, C₁-C₁₈Alkyl radical, C₃-C₁₆Cycloalkyl radicals, or C₂-C₁₈An alkenyl group; when Y is^p、Y^oAnd Y^mWhen represents a covalent bond, R^1pRepresents the sub-formula II-p, R^1oRepresents the sub-formula II-o, R^1mRepresents the sub-formula II-m, or R^1p、R^1oAnd R^1mIs unsubstituted or substituted by C₁-C₈Alkyl substituted C₆-C₁₀Aryl radical, C₁-C₁₈Alkyl radical, C₃-C₁₆Cycloalkyl radicals, or C₂-C₁₈Alkenyl, and R^2p、R^2oAnd R^2mIs unsubstituted or substituted by C₁-C₈Alkyl substituted C₆-C₁₀Aryl, or halogen, wherein halogen is chloro or fluoro.

In some embodiments, the benzofuranone is a compound of formula I-p1, I-p2, I-o1, I-o2, I-m1, or I-m2, wherein Y is^p、Y^oAnd Y^mIs oxygen or represents a covalent bond; when Y is^p、Y^oAnd Y^mWhen is oxygen, R^1pRepresents the sub-formula II-p, R^1oRepresents formula II-o, R^1mRepresents the sub-formula II-m, or R^1pAnd R^2pTogether, R^1oAnd R^2oTogether with R^1mAnd R^2mTogether represent one of the sub-formulae III, IV or V, or R^1p、R^1oAnd R^1mIs unsubstituted or substituted by C₁-C₈Alkyl substituted C₆-C₁₀Aryl radical, C₁-C₁₈Alkyl radical, C₃-C₁₆Cycloalkyl radicals, or C₂-C₁₈Alkenyl, and R^2pIs R^1p，R^2oIs R^1o，R^2mIs R^1mOr R is^2pAnd R^1pTogether, R^2oAnd R^1oTogether with R^2mAnd R^1mTogether represent one of the sub-formulae III, IV or V; when Y is^p、Y^oAnd Y^mWhen represents a covalent bond, R^1pRepresents the sub-formula II-p, R^1oRepresents the sub-formula II-o, R^1mRepresents the sub-formula II-m, and R^2p、R^2oAnd R^2mIs unsubstituted or substituted by C₁-C₈Alkyl substituted C₆-C₁₀Aryl, or halogen, wherein halogen is chloro or fluoro.

In some embodiments, the benzofuranone is a compound of formula I-p1, I-p2, I-o1, I-o2, I-m1, or I-m2, wherein Y is^p、Y^oAnd Y^mIs oxygenOr represents a covalent bond; when Y is^p、Y^oAnd Y^mWhen is oxygen, R^1pRepresents one of the sub-formulae II-p, II-o or II-m, R^1oRepresents one of the sub-formulae II-o or II-m, R^1mRepresents the sub-formula II-m, or R^1pAnd R^2pTogether, R^1oAnd R^2oTogether with R^1mAnd R^2mTogether represent one of the sub-formulae III, IV or V, or R^1p、R^1oAnd R^1mIs unsubstituted or substituted by C₁-C₈Alkyl substituted C₆-C₁₀Aryl radical, C₁-C₁₈Alkyl, or C₃-C₁₆Cycloalkyl radical, and R^2pRepresents one of the sub-formulae II-p, II-o or II-m, R^2oRepresents one of the sub-formulae II-o or II-m, R^2mRepresents the sub-formula II-m, or R^2pAnd R^1pTogether, R^2oAnd R^1oTogether with R^2mAnd R^1mTogether represent one of the sub-formulae III, IV or V, or R^2p、R^2oAnd R^2mIs unsubstituted or substituted by C₁-C₈Alkyl substituted C₆-C₁₀Aryl radical, C₁-C₁₈Alkyl or C₃-C₁₆A cycloalkyl group; when Y is^p、Y^oAnd Y^mWhen represents a covalent bond, R^1pRepresents one of the sub-formulae II-p, II-o or II-m, R^1oRepresents one of the sub-formulae II-o or II-m, R^1mRepresents the sub-formula II-m, or R^1p、R^1oAnd R^1mIs unsubstituted or substituted by C₁-C₈Alkyl substituted C₆-C₁₀Aryl radical, C₁-C₁₈Alkyl, or C₃-C₁₆Cycloalkyl radical, and R^2p、R^2oAnd R^2mIs unsubstituted or substituted by C₁-C₈Alkyl substituted C₆-C₁₀Aryl, or fluoro.

In particular embodiments, Y^p、Y^oAnd Y^mIs oxygen or represents a covalent bond; when Y is^p、Y^oAnd Y^mWhen is oxygen, R^1pRepresents one of the sub-formulae II-p, II-o or II-m, R^1oRepresents one of the sub-formulae II-o or II-m, R^1mRepresents a compound of the sub-formula II-m,or R^1pAnd R^2pTogether, R^1oAnd R^2oTogether with R^1mAnd R^2mTogether represent sub-formula III, or R^1p、R^1oAnd R^1mIs unsubstituted or substituted by C₁-C₈Alkyl substituted C₆-C₁₀Aryl, or C₁-C₁₈Alkyl, and R^2pRepresents one of the sub-formulae II-p, II-o or II-m, R^2oRepresents one of the sub-formulae II-o or II-m, R^2mRepresents the sub-formula II-m, or R^2pAnd R^1pTogether, R^2oAnd R^1oTogether with R^2mAnd R^1mTogether represent sub-formula III, or R^2p、R^2oAnd R^2mIs unsubstituted or substituted by C₁-C₈Alkyl substituted C₆-C₁₀Aryl, or C₁-C₁₈An alkyl group; when Y is^p、Y^oAnd Y^mWhen represents a covalent bond, R^1pRepresents one of the sub-formulae II-p, II-o or II-m, R^1oRepresents one of the sub-formulae II-o or II-m, R^1mRepresents the sub-formula II-m, or R^1p、R^1oAnd R^1mIs unsubstituted or substituted by C₁-C₈Alkyl substituted C₆-C₁₀Aryl, or C₁-C₁₈Alkyl, and R^2p、R^2oAnd R^2mIs unsubstituted or substituted by C₁-C₈Alkyl substituted C₆-C₁₀Aryl, or fluoro.

In some embodiments, the benzofuranone is a compound of formula I-p1, I-p2, I-o1, or I-o2, wherein Y is^pAnd Y^oIs oxygen or represents a covalent bond; when Y is^pAnd Y^oWhen is oxygen, R^1p、R^2p、R^1oOr R^2oDoes not represent sub-formula II-m; when Y is^pAnd Y^oWhen represents a covalent bond, R^1pOr R^1oDoes not represent sub-formula II-m. In certain embodiments, in the compounds of formula I-p1 or I-p2, Y is^pIs oxygen or represents a covalent bond; when Y is^pWhen is oxygen, R^1pOr R^2pDoes not represent sub-formula II-o or II-m; when Y is^pWhen represents a covalent bond, R^1pDo not represent sub-formula II-o orII-m。

In some embodiments, the benzofuranone is a compound of formula I-p1, I-p2, I-o1, I-o2, I-m1, or I-m2, wherein Y is^p、Y^oAnd Y^mIs oxygen or represents a covalent bond; when Y is^p、Y^oAnd Y^mWhen is oxygen, R^1pRepresents one of the sub-formulae II-p, II-o or II-m, R^1oRepresents one of the sub-formulae II-o or II-m, R^1mRepresents the sub-formula II-m, or R^1p、R^1oAnd R^1mIs unsubstituted or substituted by C₁-C₈Alkyl radical, C₁-C₈Alkoxy, halogen or C substituted by one phenyl group₆-C₁₀Aryl radical, C₁-C₁₈Alkyl radical, C₃-C₁₆Cycloalkyl radical, C₇-C₁₃Aralkyl radical, C₂-C₁₈Alkenyl, C interrupted by one or more oxygen atoms₂-C₃₀Alkyl, or C interrupted by a sulfur atom₂-C₁₆An alkyl group; r^2pRepresents one of the sub-formulae II-p, II-o or II-m, R^2oRepresents one of the sub-formulae II-o or II-m, R^2mRepresents the sub-formula II-m, or R^2p、R^2oAnd R^2mIs unsubstituted or substituted by C₁-C₈Alkyl radical, C₁-C₈Alkoxy, halogen or C substituted by one phenyl group₆-C₁₀Aryl radical, C₁-C₁₈Alkyl radical, C₃-C₁₆Cycloalkyl radical, C₇-C₁₃Aralkyl radical, C₂-C₁₈Alkenyl, C interrupted by one or more oxygen atoms₂-C₃₀Alkyl, or C interrupted by a sulfur atom₂-C₁₆An alkyl group; when Y is^p、Y^oAnd Y^mWhen represents a covalent bond, R^1pRepresents one of the sub-formulae II-p, II-o or II-m, R^1oRepresents one of the sub-formulae II-o or II-m, R^1mRepresents the sub-formula II-m, or R^1p、R^1oAnd R^1mIs unsubstituted or substituted by C₁-C₈Alkyl radical, C₁-C₈Alkoxy, halogen or C substituted by one phenyl group₆-C₁₀Aryl radical, C₁-C₁₈Alkyl radical, C₃-C₁₆Cycloalkyl radical, C₇-C₁₃Aralkyl radical, C₂-C₁₈Alkenyl, C interrupted by one or more oxygen atoms₂-C₃₀Alkyl, or C interrupted by a sulfur atom₂-C₁₆An alkyl group; r^2p、R^2oAnd R^2mIs unsubstituted or substituted by C₁-C₈Alkyl radical, C₁-C₈Alkoxy, halogen or C substituted by one phenyl group₆-C₁₀Aryl, or halogen.

In particular embodiments, the benzofuranone is a compound of formula I-p1, I-p2, I-o1, I-o2, I-m1, or I-m2, wherein Y is^p、Y^oAnd Y^mIs oxygen. In some embodiments, the benzofuranone is a compound of formula I-p or I-o, wherein Y is^pAnd Y^oIs oxygen, and R^1p、R^2p、R^1oOr R^2oDoes not represent sub-formula II-m. In other embodiments, the benzofuranone is a compound of formula I-p1, I-p2, I-o1, I-o2, I-m1, or I-m2, wherein Y is^p、Y^oAnd Y^mIs oxygen, R^1pAnd R^2pTogether, R^1oAnd R^2oTogether with R^1mAnd R^2mTogether represent one of the sub-formulae III, IV or V, and R^2pAnd R^1pTogether, R^2oAnd R^1oTogether with R^2mAnd R^1mTogether represent one of the sub-formulae III, IV or V.

In some embodiments, the benzofuranone is a compound of formula I-p1, I-p2, I-o1, or I-o2, wherein Y is^pAnd Y^oIs oxygen, R^1pAnd R^2pTogether with R^1oAnd R^2oTogether represent one of the sub-formulae III, IV or V, and R^2pAnd R^1pTogether with R^2oAnd R^1oTogether represent one of the sub-formulae III, IV or V. In certain embodiments, the benzofuranone is a compound of formula I-p1 or I-p2, wherein Yp is oxygen, and R is^1pAnd R^2pTogether represent one of the sub-formulae III, IV or V. In some embodiments, the benzofuranone is a compound of formula I-p, wherein Yp is oxygen, and R is^1pAnd R^2pTogether represent sub-formula IV.

The above embodiments for compounds of the formulae I-p1, I-p2, I-o1, I-o2, I-m1 or I-m2 each represent a structural unit having the formula I-p1, I-p2, I-o1, I-o2, I-m1 or I-m 2. These structural units comprise benzofuran-2-one units including R⁴、R⁵、R⁶And R⁷(ii) a A phenylene linking unit comprising R^p2、R^p3、R^p5、R^p6、R^o1、R^o2、R^o5、R^o6、R^m1、R^m3、R^m5And R^m6(ii) a And other units adjacent to the phosphorus atom comprising R^1p、R^2p、R^1o、R^2o、R^1mAnd R^2mHaving substituents of sub-formula III, IV or V, i.e. R^a1、R^a1、R^a3、R^a4、R^b1、R^b2、R^b3、R^b4、R^b5、R^b6、R^c1、R^c2、R^c3And R^c4. The above-described embodiments with respect to these three building blocks can be combined. Examples of which are described below.

In some embodiments, the benzofuranone is a compound of formula I-p1, I-p2, I-o1, I-o2, I-m1, or I-m2, wherein Y is^p、Y^oAnd Y^mIs oxygen or represents a covalent bond; when Y is^p、Y^oAnd Y^mWhen is oxygen, R^1pRepresents one of the sub-formulae II-p, II-o or II-m, R^1oRepresents one of the sub-formulae II-o or II-m, R^1mRepresents the sub-formula II-m, or R^1pAnd R^2pTogether, R^1oAnd R^2oTogether with R^1mAnd R^2mTogether represent one of the sub-formulae III, IV or V, or R^1p、R^1oAnd R^1mIs unsubstituted or substituted by C₁-C₈Alkyl radical, C₁-C₈Alkoxy, halogen or C substituted by one phenyl group₆-C₁₀Aryl radical, C₁-C₁₈Alkyl radical, C₃-C₁₆Cycloalkyl radical, C₇-C₁₃Aralkyl radical, C₂-C₁₈Alkenyl radicals bound by one or more oxygen atomsSpaced C₂-C₃₀Alkyl, or C interrupted by a sulfur atom₂-C₁₆Alkyl radical, R^2pRepresents one of the sub-formulae II-p, II-o or II-m, R^2oRepresents one of the sub-formulae II-o or II-m, R^2mRepresents the sub-formula II-m, or R^2pAnd R^1pTogether, R^2oAnd R^1oTogether with R^2mAnd R^1mTogether represent one of the sub-formulae III, IV or V, or R^2p、R^2oAnd R^2mIs unsubstituted or substituted by C₁-C₈Alkyl radical, C₁-C₈Alkoxy, halogen or C substituted by one phenyl group₆-C₁₀Aryl radical, C₁-C₁₈Alkyl radical, C₃-C₁₆Cycloalkyl radical, C₇-C₁₃Aralkyl radical, C₂-C₁₈Alkenyl, C interrupted by one or more oxygen atoms₂-C₃₀Alkyl, or C interrupted by a sulfur atom₂-C₁₆An alkyl group; when Y is^p、Y^oAnd Y^mWhen represents a covalent bond, R^1pRepresents one of the sub-formulae II-p, II-o or II-m, R^1oRepresents one of the sub-formulae II-o or II-m, R^1mRepresents the sub-formula II-m, or R^1p、R^1oAnd R^1mIs unsubstituted or substituted by C₁-C₈Alkyl radical, C₁-C₈Alkoxy, halogen or C substituted by one phenyl group₆-C₁₀Aryl radical, C₁-C₁₈Alkyl radical, C₃-C₁₆Cycloalkyl radical, C₇-C₁₃Aralkyl radical, C₂-C₁₈Alkenyl, C interrupted by one or more oxygen atoms₂-C₃₀Alkyl, or C interrupted by a sulfur atom₂-C₁₆Alkyl radical, R^2p、R^2oAnd R^2mIs unsubstituted or substituted by C₁-C₈Alkyl radical, C₁-C₈Alkoxy, halogen or C substituted by one phenyl group₆-C₁₀Aryl, or halogen; r⁴And R⁶Is hydrogen, R⁵And R⁷Each independently is hydrogen or C₁-C₈Alkyl radical, R^p2And R^p6Each independently is hydrogen or C₁Alkyl radical, R^p3And R^p5Each independently is hydrogen or C₁-C₄Alkyl radical, R^o1And R^o6Each independently is hydrogen or C₁-C₈Alkyl radical, R^o2Is hydrogen or C₁Alkyl radical, R^o5Is hydrogen or C₁-C₄Alkyl radical, R^m1Is hydrogen or C₁Alkyl radical, R^m3And R^m5Each independently is hydrogen or C₁-C₄Alkyl radical, R^m6Is hydrogen or C₁-C₈Alkyl radical, R^a1、R^a2、R^a3And R^a4Each independently is hydrogen or C₁-C₄Alkyl radical, R^b1、R^b2、R^b3、R^b4、R^b5And R^b6Each independently is hydrogen or C₁-C₄Alkyl, and R^c1、R^c2、R^c3And R^c4Each independently is hydrogen or C₁-C₄An alkyl group.

In some embodiments, the benzofuranone is a compound of formula I-p1, I-p2, I-o1, I-o2, I-m1, or I-m2, wherein Y is^p、Y^oAnd Y^mIs oxygen or represents a covalent bond; when Y is^p、Y^oAnd Y^mWhen is oxygen, R^1pRepresents one of the sub-formulae II-p, II-o or II-m, R^1oRepresents one of the sub-formulae II-o or II-m, R^1mRepresents the sub-formula II-m, or R^1pAnd R^2pTogether, R^1oAnd R^2oTogether with R^1mAnd R^2mTogether represent one of the sub-formulae III, IV or V, or R^1p、R^1oAnd R^1mIs unsubstituted or substituted by C₁-C₈Alkyl substituted C₆-C₁₀Aryl radical, C₁-C₁₈Alkyl, or C₃-C₁₆Cycloalkyl radical, and R^2pRepresents one of the sub-formulae II-p, II-o or II-m, R^2oRepresents one of the sub-formulae II-o or II-m, R^2mRepresents the sub-formula II-m, or R^2pAnd R^1pTogether, R^2oAnd R^1oTogether with R^2mAnd R^1mTogether represent one of the sub-formulae III, IV or V, or R^2p、R^2oAnd R^2mIs unsubstituted or substituted by C₁-C₈Alkyl substituted C₆-C₁₀Aryl radical, C₁-C₁₈Alkyl or C₃-C₁₆A cycloalkyl group; when Y is^p、Y^oAnd Y^mWhen represents a covalent bond, R^1pRepresents one of the sub-formulae II-p, II-o or II-m, R^1oRepresents one of the sub-formulae II-o or II-m, R^1mRepresents the sub-formula II-m, or R^1p、R^1oAnd R^1mIs unsubstituted or substituted by C₁-C₈Alkyl substituted C₆-C₁₀Aryl radical, C₁-C₁₈Alkyl or C₃-C₁₆Cycloalkyl radical, and R^2p、R^2oAnd R^2mIs unsubstituted or substituted by C₁-C₈Alkyl substituted C₆-C₁₀Aryl, or fluoro; r⁴、R⁵、R⁶And R⁷Each independently is hydrogen or C₁-C₈Alkyl radical, R^p2、R^p3、R^p5And R^p6Each independently is hydrogen or C₁-C₈Alkyl radical, R^o1、R^o2、R^o5And R^o6Each independently is hydrogen or C₁-C₈Alkyl radical, R^m1、R^m3、R^m5And R^m6Each independently is hydrogen or C₁-C₈Alkyl radical, R^a1、R^a2、R^a3And R^a4Each independently is hydrogen or C₁-C₈Alkyl radical, R^b1、R^b2、R^b3、R^b4、R^b5And R^b6Each independently is hydrogen or C₁-C₈Alkyl, and R^o1、R^c2、R^c3And R^c4Each independently is hydrogen or C₁-C₈An alkyl group.

In particular embodiments, the benzofuranone is a compound of formula I-p1, I-p2, I-o1, or I-o2, wherein Y is^pAnd Y^oIs oxygen or represents a covalent bond; when Y is^pAnd Y^oWhen is oxygen, R^1pRepresents one of the sub-formulae II-p or II-o, R^1oRepresents the sub-formula II-o, or R^1pAnd R^2pTogether with R^1oAnd R^2oTogether represent one of the sub-formulae III, IV or V, or R^1pAnd R^1oIs unsubstituted or substituted by C₁-C₈Alkyl radical, C₁-C₈Alkoxy, halogen or C substituted by one phenyl group₆-C₁₀Aryl radical, C₁-C₁₈Alkyl radical, C₃-C₁₆Cycloalkyl radical, C₇-C₁₃Aralkyl radical, C₂-C₁₈Alkenyl, C interrupted by one or more oxygen atoms₂-C₃₀Alkyl, or C interrupted by a sulfur atom₂-C₁₆Alkyl radical, R^2pRepresents one of the sub-formulae II-p or 11-0, R^2oRepresents the sub-formula II-o, or R^2pAnd R^1pTogether with R^2oAnd R^1oTogether represent one of the sub-formulae III, IV or V, or R^2pAnd R^2oIs unsubstituted or substituted by C₁-C₈Alkyl radical, C₁-C₈Alkoxy, halogen or C substituted by one phenyl group₆-C₁₀Aryl radical, C₁-C₁₈Alkyl radical, C₃-C₁₆Cycloalkyl radical, C₇-C₁₃Aralkyl radical, C₂-C₁₈Alkenyl, C interrupted by one or more oxygen atoms₂-C₃₀Alkyl, or C interrupted by a sulfur atom₂-C₁₆An alkyl group; when Y is^pAnd Y^oWhen represents a covalent bond, R^1pRepresents one of the sub-formulae II-p or II-o, R^1oRepresents the sub-formula II-o, or R^1pAnd R^1oIs unsubstituted or substituted by C₁-C₈Alkyl radical, C₁-C₈Alkoxy, halogen or C substituted by one phenyl group₆-C₁₀Aryl radical, C₁-C₁₈Alkyl radical, C₃-C₁₆Cycloalkyl radical, C₇-C₁₃Aralkyl radical, C₂-C₁₈Alkenyl, C interrupted by one or more oxygen atoms₂-C₃₀Alkyl, or C interrupted by a sulfur atom₂-C₁₆Alkyl radical, R^2pAnd R^2oIs unsubstituted or substituted by C₁-C₈Alkyl radical, C₁-C₆Alkoxy, halogen or C substituted by one phenyl group₆-C₁₀Aryl, or halogen; r⁴、R⁵、R⁶And R⁷Each independently is hydrogen or C₁-C₆Alkyl radical, R^p2、R^p3、R^p5And R^p6Each independently is hydrogen or C₁-C₈Alkyl radical, R^o1、R^o2、R^o5And R^o6Each independently is hydrogen or C₁-C₈Alkyl radical, R^a1、R^a2、R^a3And R^a4Each independently is hydrogen or C₁-C₈Alkyl radical, R^b1、R^b2、R^b3、R^b4、R^b5And R^b6Each independently is hydrogen or C₁-C₈Alkyl, and R^c1、R^c2、R^c3And R^c4Each independently is hydrogen or C₁-C₈An alkyl group.

In some embodiments, the benzofuranone is a compound of formula I-p1, I-p2, I-o1, or I-o2, wherein Y is^pAnd Y^oIs oxygen or represents a covalent bond; when Y is^pAnd Y^oWhen is oxygen, R^1pRepresents one of the sub-formulae II-p or II-o, R^1oRepresents the sub-formula II-o, or R^1pAnd R^2pTogether with R^1oAnd R^2oTogether represent sub-formula III, or R^1pAnd R^1oIs unsubstituted or substituted by C₁-C₈Alkyl substituted C₆-C₁₀Aryl, or C₁-C₁₈Alkyl radical, R^2pRepresents one of the sub-formulae II-p or II-o, R^2oRepresents the sub-formula II-o, or R^2pAnd R^1pTogether with R^2oAnd R^1oTogether represent sub-formula III, or R^2pAnd R^2oIs unsubstituted or substituted by C₁-C₈Alkyl substituted C₆-C₁₀Aryl, or C₁-C₁₈An alkyl group; when Y is^pAnd Y^oWhen represents a covalent bond, R^1pRepresents one of the sub-formulae II-p or II-o, R^1oRepresents the sub-formula II-o, or R^1pAnd R^1oIs unsubstituted or substituted by C₁-C₈Alkyl substituted C₆-C₁₀Aryl, or C₁-C₁₈Alkyl radical, R^2pAnd R^2oIs unsubstituted or substituted by C₁-C₈Alkyl substituted C₆-C₁₀Aryl, or fluoro; r⁴And R⁶Is hydrogen, R⁵And R⁷Each independently is hydrogen or C₁-C₈Alkyl radical, R^p2And R^p6Is hydrogen, R^p3And R^p5Each independently is hydrogen or C₁-C₄Alkyl radical, wherein R^p3And R^p5One is not C_aAlkyl radical, R^o1Is hydrogen or C₁-C₈Alkyl radical, R^o2Is hydrogen, R^o5Is hydrogen or C₁-C₃Alkyl radical, R^o6Is hydrogen or C₁-C₄Alkyl radical, R^a1、Rae、R^a3And R^a4Each independently is hydrogen or C₁-C₄Alkyl radical, R^b1、R^b2、R^b3、R^b4、R^b5And R^b6Each independently is hydrogen or C₁-C₄Alkyl, and R^c1、R^c2、R^c3And R^c4Each independently is hydrogen or C₁-C₄An alkyl group.

In other embodiments, the benzofuranone is a compound of formula I-p1, I-p2, I-o1, I-o2, I-m1, or I-m2, wherein Y is^p、Y^oAnd Y^mIs oxygen or represents a covalent bond; when Y is^p、Y^oAnd Y^mWhen is oxygen, R^1pRepresents one of the sub-formulae II-p, II-o or II-m, R^1oRepresents one of the sub-formulae II-o or II-m, R^1mRepresents the sub-formula II-m, or R^1p、R^1oAnd R^1mIs unsubstituted or substituted by C₁-C₈Alkyl radical, C₁-C₈Alkoxy, halogen or C substituted by one phenyl group₆-C₁₀Aryl radical, C₁-C₁₈Alkyl radical, C₃-C₁₆Cycloalkyl radical, C₇-C₁₃Aralkyl radical, C₂-C₁₈Alkenyl, C interrupted by one or more oxygen atoms₂-C₃₀Alkyl, or C interrupted by a sulfur atom₂-C₁₆Alkyl radical, R^2pRepresents the sub-formulae II-p, IIOne of-o or II-m, R^2oRepresents one of the sub-formulae II-o or II-m, R^2mRepresents the sub-formula II-m, or R^2p、R^2oAnd R^2mIs unsubstituted or substituted by C₁-C₈Alkyl radical, C₁-C₈Alkoxy, halogen or C substituted by one phenyl group₆-C₁₀Aryl radical, C₁-C₁₈Alkyl radical, C₃-C₁₆Cycloalkyl radical, C₇-C₁₃Aralkyl radical, C₂-C₁₈Alkenyl, C interrupted by one or more oxygen atoms₂-C₃₀Alkyl, or C interrupted by a sulfur atom₂-C₁₆An alkyl group; when Y is^p、Y^oAnd Y^mWhen represents a covalent bond, R^1pRepresents one of the sub-formulae II-p, II-o or II-m, R^1oRepresents one of the sub-formulae II-o or II-m, R^1mRepresents the sub-formula II-m, or R^1p、R^1oAnd R^1mIs unsubstituted or substituted by C₁-C₈Alkyl radical, C₁-C₈Alkoxy, halogen or C substituted by one phenyl group₆-C₁₀Aryl radical, C₁-C₁₈Alkyl radical, C₃-C₁₆Cycloalkyl radical, C₇-C₁₃Aralkyl radical, C₂-C₁₈Alkenyl, C interrupted by one or more oxygen atoms₂-C₃₀Alkyl, or C interrupted by a sulfur atom₂-C₁₆Alkyl radical, R^2p、R^2oAnd R^2mIs unsubstituted or substituted by C₁-C₈Alkyl radical, C₁-C₈Alkoxy, halogen or C substituted by one phenyl group₆-C₁₀Aryl, or halogen; r⁴、R⁵、R⁶And R⁷Each independently is hydrogen or C₁-C₈Alkyl radical, R^p2、R^p3、R^p5And R^p6Each independently is hydrogen or C₁-C₈Alkyl radical, R^o1、R^o2、R^o5And R^o6Each independently is hydrogen or C₁-C₈Alkyl, and R^m1、R^m3、R^m5And R^m6Each independently is hydrogen or C₁-C₈An alkyl group.

In some embodiments, the benzofuranone is a compound of formula I-p1, I-p2, I-o1, I-o2, I-m1, or I-m2, wherein Y is^p、Y^oAnd Y^mIs oxygen, R^1pAnd R^2pTogether, R^1oAnd R^2oTogether with R^1mAnd R^2mTogether represent one of the sub-formulae III, IV or V, R^2pAnd R^1pTogether, R^2oAnd R^1oTogether with R^2mAnd R^1mTogether represent one of the sub-formulae III, IV or V, R⁴、R⁵、R⁶And R⁷Each independently is hydrogen or C₁-C₈Alkyl radical, R^p2、R^p3、R^p5And R^p6Each independently is hydrogen or C₁-C₈Alkyl radical, R^o1、R^o2、R^o5And R^o6Each independently is hydrogen or C₁-C₈Alkyl radical, R^m1、R^m3、R^m5And R^m6Each independently is hydrogen or C₁-C₈Alkyl radical, R^a1、R^a2、R^a3And R^a4Each independently is hydrogen or C₁-C₈Alkyl radical, R^b1、R^b2、R^b3、R^b4、R^b5And R^b6Each independently is hydrogen or C₁-C₈Alkyl, and R^c1、R^c2、R^c3And R^c4Each independently is hydrogen or C₁-C₈An alkyl group.

In particular embodiments, the benzofuranone is a compound of formula I-p1, I-p2, I-o1, or I-o2, wherein Y is^pAnd Y^oIs oxygen, R^1pAnd R^2pTogether with R^1oAnd R^2oTogether represent one of the sub-formulae III, IV or V, R^2pAnd R^1pTogether with R^2oAnd R^1oTogether represent one of the sub-formulae III, IV or V, R⁴、R⁵、R⁶And R⁷Each independently is hydrogen or C₁-C₈Alkyl radical, R^p2、R^p3、R^p5And R^p6Each independently is hydrogen or C₁-C₈Alkyl radical，R^o1、R^o2、R^o5And R^o6Each independently is hydrogen or C₁-C₈Alkyl radical, R^a1、R^a2、R^a3And R^a4Each independently is hydrogen or C₁-C₈Alkyl radical, R^b1、R^b2、R^b3、R^b4、R^b5And R^b6Each independently is hydrogen or C₁-C₈Alkyl, and R^c1、R^c2、R^c3And R^c4Each independently is hydrogen or C₁-C₈An alkyl group.

In some embodiments, the benzofuranone is a compound of formula I-p1 or I-p2, wherein Y is^pIs oxygen, R^1pAnd R^2pTogether represent one of the sub-formulae III, IV or V, R⁴、R⁵、R⁶And R⁷Each independently is hydrogen or C₁-C₈Alkyl radical, R^p2、R^p3、R^p5And R^p6Each independently is hydrogen or C₁-C₈Alkyl radical, R^a1、R^a2、R^a3And R^a4Each independently is hydrogen or C₁-C₈Alkyl radical, R^b1、R^b2、R^b3、R^b4、R^b5And R^b6Each independently is hydrogen or C₁-C₈Alkyl, and R^c1、R^c2、R^c3And R^c4Each independently is hydrogen or C₁-C₈An alkyl group.

In some embodiments, in the benzofuranone compounds of formula I-p1 or I-p2, Y is^pIs oxygen, R^1pAnd R^2pTogether represent sub-formula IV, R⁴、R⁵、R⁶And R⁷Each independently is hydrogen or C₁-C₈Alkyl radical, R^p2、R^p3、R^p5And R^p6Each independently is hydrogen or C₁-C₈Alkyl, and R^b1、R^b2、R^b3、R^b4、R^b5And R^b6Each independently is hydrogen or C₁-C₈An alkyl group.

In some embodiments, the benzofuranone is a compound selected from formulas (101) to (133):

benzofuranones of the invention can be prepared as described in US2017/0226323, US2017/0066905 and US application No.15/751497, published as WO 2017/025431.

Organic phosphorus stabilizers include organic phosphite and organic phosphonite stabilizers, including for example triphenyl phosphite, diphenylalkyl phosphites, phenyl dialkyl phosphites, tris (nonylphenyl) phosphite, trilauryl phosphite, trioctadecyl phosphite, tris (2, 4-di-tert-butylphenyl) phosphite, tris- (2-sec-butylphenyl) phosphite (O), distearyl pentaerythritol diphosphite (F), bis (2, 4-di- α -cumylphenyl) pentaerythritol diphosphite (K), diisodecyl pentaerythritol diphosphite, bis (2, 4-di-tert-butylphenyl) pentaerythritol diphosphite (D), bis (2, 6-di-tert-butyl-4-methylphenyl) pentaerythritol diphosphite (E), diisodecyloxy-pentaerythritol diphosphite, bis (2, 4-di-tert-butyl-6-methylphenyl) pentaerythritol diphosphite, bis (2,4, 6-tri-tert-butylphenyl) pentaerythritol diphosphite, tristearyl sorbitol triphosphite, tetrakis (2, 4-di-tert-butylphenyl) 4,4' -dioctadene-biphenyl-8, 8-tetra-tert-butyl-O-diphenyl phosphite, dibenzo [4, 8-tert-butyl-4-diphenyl-O-diphenyl-O ] diphenyl phosphite, 4, 8-tert-butyl-4-diphenyl-O-di-tert-butyl-4-diphenyl][1,3,2]Dioxaphosphepin (C), 6-fluoro-2, 4,8, 10-tetra-tert-butyl-12-methyl-dibenzo [ d, g][1,3,2]Dioxaphosphocyclooctane (A), bis (2, 4-di-tert-butyl-6-methylphenyl) methyl phosphite, bis (2, 4-di-tert-butyl-6-methylphenyl) ethyl phosphite (G), 2,2', 2 "-nitrilo [ triethyltris (3, 3', 5' -tetra-tert-butyl-1, 1' -biphenyl-2, 2' -diyl) phosphite](B) Bis (2, 4-di-tert-butylphenyl) octylphosphite, poly (4,4' - {2,2' dimethyl-5, 5' -di-tert-butylphenyl thio- } octylphosphite), poly (4,4' { -isopropylidenediphenol } -octylphosphite), poly (4,4' - { isopropylidenedi [2, 6-dibromophenol ] o]Octyl phosphite), poly (4,4' - {2,2' -dimethyl-5, 5' -di-tert-butylphenyl-thio } -pentaerythrityl tetrakisAlcohol diphosphite), phosphorous acid, mixed 2, 4-bis (1, 1-dimethylpropyl) phenyl and 4- (1, 1-dimethylpropyl) phenyl triester (CAS No.939402-02-5), phosphorous acid, triphenyl ester, having α -hydro-omega-hydroxypoly [ oxy (methyl-1, 2-ethanediyl)]Polymer of (2), C_10-16Alkyl esters (CAS No.1227937-46-3),

in some embodiments, a combination of one or more organophosphorus stabilizers may be used.

In a particular embodiment, the organophosphorus stabilizer is selected from the group consisting of tris (nonylphenyl) phosphite, bis (2, 4-di-tert-butylphenyl) pentaerythritol diphosphite, bis (2, 4-di-tert-butyl-6-methylphenyl) ethyl phosphite, 2,2', 2 "-nitrilo [ triethyltris (3, 3', 5' -tetra-tert-butyl-1, 1' -biphenyl-2, 2' -diyl) phosphite ], bis (2, 4-di- α -cumylphenyl) pentaerythritol diphosphite, tris (2, 4-di-tert-butylphenyl) phosphite, and combinations thereof.

The benzofuranone stabilizer may be used in an amount ranging from any of about 20ppm, about 30ppm, about 40ppm, about 50ppm, about 60ppm, about 70ppm, about 80ppm, about 90ppm, about 100ppm, about 110ppm, about 120ppm, about 130ppm, about 140ppm, about 150ppm, about 160ppm, about 170ppm, about 180ppm, about 190ppm, about 200ppm, about 250ppm, about 300ppm, about 350ppm, about 400ppm, about 450ppm or about 500ppm by weight to any of about 550ppm, about 600ppm, about 650ppm, about 700ppm, about 750ppm, about 800ppm, about 850ppm, about 900ppm, about 950ppm, about 1250ppm, about 1050ppm, about 1100ppm, about 1150ppm, about 1200ppm, about 1250ppm, about 1300ppm, about 1350ppm or about 1400ppm by weight based on the weight of the polyolefin.

In other embodiments, the benzofuranone stabilizer can be used in an amount ranging from about 0.05 wt% (weight percent), about 0.07 wt%, about 0.09 wt%, about 0.10 wt%, about 0.15 wt%, about 0.20 wt%, about 0.25 wt%, about 0.30 wt%, about 0.35 wt%, about 0.40 wt%, about 0.50 wt%, about 0.60 wt%, about 0.65 wt%, about 0.70 wt%, about 0.75 wt%, about 0.80 wt%, about 0.90 wt%, about 1.0 wt%, about 1.3 wt%, about 1.5 wt%, about 1.7 wt%, about 2.0 wt%, about 2.5 wt%, about 3.0 wt%, about 3.5 wt%, about 4.0 wt%, about 4.5 wt%, about 5.0 wt%, or about 5 wt%, about 0.5 wt%, about 6.5 wt%, about 0.5 wt%, about 5.5 wt%, about 0.5 wt%, about 6.5 wt%, about 0.5 wt%, about 5 wt%, about 0.5 wt%, about 6.5 wt%, about 0.5 wt%, about 0 wt%, about 0.5 wt%, about 8.5 wt%, about 6 wt%, about 0.5 wt%, about 0 wt%, about 0.5 wt%, about 8.5 wt, Within a range of any of about 9.5 wt% or about 10.0 wt%, based on the weight of the polyolefin.

In other embodiments, the benzofuranone stabilizer can be used in an amount ranging from any of about 1 weight percent, about 5 weight percent, about 10 weight percent, about 15 weight percent, about 20 weight percent, about 25 weight percent, or about 30 weight percent to any of about 35 weight percent, about 40 weight percent, about 45 weight percent, or about 50 weight percent, based on the weight of the polyolefin.

The organophosphorus stabilizer may be used in an amount ranging from any of about 20ppm, about 30ppm, about 40ppm, about 50ppm, about 60ppm, about 70ppm, about 80ppm, about 90ppm, about 100ppm, about 110ppm, about 120ppm, about 130ppm, about 140ppm, about 150ppm, about 160ppm, about 170ppm, about 180ppm, about 190ppm, about 200ppm, about 250ppm, about 300ppm, about 350ppm, about 400ppm, about 450ppm, or about 500ppm to any of about 550ppm, about 600ppm, about 650ppm, about 700ppm, about 750ppm, about 800ppm, about 850ppm, about 900ppm, about 950ppm, about 1000ppm, about 1250ppm, about 1100ppm, about 1150ppm, about 1200ppm, about 1300ppm, about 1350ppm, or about 1400ppm by weight, based on the weight of the polyolefin.

In other embodiments, the organic phosphorus stabilizer may be used in an amount ranging from about 0.05 wt% (weight percent), about 0.07 wt%, about 0.09 wt%, about 0.10 wt%, about 0.15 wt%, about 0.20 wt%, about 0.35 wt%, about 0.50 wt%, about 0.75 wt%, about 0.1 wt%, about 0.2 wt%, about 0.3 wt%, about 0.4 wt%, about 0.5 wt%, about 0.6 wt%, about 0.7 wt%, about 0.8 wt%, about 0.9 wt%, about 1.0 wt%, about 1.3 wt%, about 1.5 wt%, about 1.7 wt%, about 2.0 wt%, about 2.5 wt%, about 3.0 wt%, about 3.5 wt%, about 4.0 wt%, about 4.5 wt%, about 5.0 wt%, about 5.5 wt%, about 0.5 wt%, about 5.5 wt%, about 0 wt%, about 0.5 wt%, about 8 wt%, about 0 wt%, about 0.5 wt%, about 0 wt%, about 0.5 wt%, about 5 wt%, about 0.5 wt%, about 0 wt%, about 5 wt%, about 0.5 wt%, about 8 wt%, about 0.5 wt%, about 0 wt%, about 0.5 wt%, about 8 wt%, about, Within a range of any of about 9.0 wt%, about 9.5 wt%, or about 10.0 wt%, based on the weight of the polyolefin.

In some embodiments, the weight/weight ratio between the one or more benzofuranones and the one or more organophosphorus stabilizers can be from any one of about 1/99, about 1/90, about 1/80, about 1/70, about 1/60, about 1/50, about 1/40, about 1/30, about 1/20, about 1/10, about 1/9, about 1/8, about 1/7, about 1/6, about 1/5, about 1/4, about 1/3, about 1/2, or about 1/1 to about 2/1, about 3/1, about 4/1, about 5/1, about 6/1, about 7/1, about 8/1, about 9/1, about 10/1, about 20/1, about 30/1, about 6384, About 40/1, about 50/1, about 60/1, about 70/1, about 80/1, about 90/1, or about 99/1.

In some embodiments, the organophosphorus stabilizer may be used in an amount by weight equal to or greater than the amount by weight of the one or more benzofuranones. For example, in some embodiments, the weight/weight ratio between the one or more benzofuranones and the one or more organophosphorus stabilizers can range from any one of about 0.05, about 0.10, about 0.15, about 0.20, about 0.25, about 0.30, about 0.35, about 0.40, about 0.45, or about 0.50 to any one of about 0.55, about 0.60, about 0.65, about 0.70, about 0.75, about 0.80, about 0.85, about 0.90, about 0.95, or about 1.0.

Also disclosed herein are additive compositions comprising one or more of the benzofuranone compounds and one or more organophosphorus stabilizers. The weight/weight ratio between the benzofuranone and the organophosphorus stabilizer can be set as described above.

In some embodiments, the composition may further comprise one or more additional additives selected from the group consisting of: antioxidants, ultraviolet light absorbers, hindered amine light stabilizers, acid scavengers, metal deactivators, hydroxylamines, nitrones, amine N-oxides, thiosynergists, peroxide scavengers, nucleating agents, fillers, flame retardants and antistatic agents.

In some embodiments, the additional additives may include plasticizers, lubricants, emulsifiers, pigments, dyes, optical brighteners, rheological additives, catalysts, flow control agents, slip agents, crosslinking promoters, halogen scavengers, smoke suppressants, antistatic agents, or clarifying agents, such as substituted and unsubstituted dibenzylidene sorbitol.

The additional additives, used alone or in combination, may range from any of about 20ppm, about 30ppm, about 40ppm, about 50ppm, about 60ppm, about 70ppm, about 80ppm, about 90ppm, about 100ppm, about 110ppm, about 120ppm, about 130ppm, about 140ppm, about 150ppm, about 160ppm, about 170ppm, about 180ppm, about 190ppm, about 200ppm, about 250ppm, about 300ppm, about 350ppm, about 400ppm, about 450ppm, or about 500ppm to any of about 550ppm, about 600ppm, about 650ppm, about 700ppm, about 750ppm, about 800ppm, about 850ppm, about 900ppm, about 950ppm, about 1000ppm, about 1250ppm, about 1100ppm, about 1150ppm, about 1200ppm, about 1300ppm, about 1350ppm, or about 1400ppm by weight based on the weight of the polyolefin.

In other embodiments, the additional additives, used alone or in combination, may be present in an amount ranging from about 0.05 wt% (weight percent), about 0.07 wt%, about 0.09 wt%, about 0.10 wt%, about 0.15 wt%, about 0.20 wt%, about 0.35 wt%, about 0.50 wt%, about 0.75 wt%, about 0.1 wt%, about 0.2 wt%, about 0.3 wt%, about 0.4 wt%, about 0.5 wt%, about 0.6 wt%, about 0.7 wt%, about 0.8 wt%, about 0.9 wt%, about 1.0 wt%, about 1.3 wt%, about 1.5 wt%, about 1.7 wt%, about 2.0 wt%, about 2.5 wt%, about 3.0 wt%, about 3.5 wt%, about 4.0 wt%, about 4.5 wt%, about 5.0 wt%, about 5.5 wt%, about 0.5 wt%, about 6.5 wt%, about 0.5 wt%, about 0 wt%, about 0.5 wt%, about 6 wt%, about 0.7 wt%, about 0.5 wt%, about 6 wt%, about 0.5 wt%, about 0 wt%, about 0.5 wt%, about 6 wt%, about 0.5 wt%, about 0 wt%, about 0.5 wt%, about 6, Within a range of any of about 8.5 wt%, about 9.0 wt%, about 9.5 wt%, or about 10.0 wt%, based on the weight of the polyolefin.

In some embodiments, the hindered amine light stabilizer is a compound containing one or more moieties of the formula:

wherein R is₁、R₂、R₃And R₄Independently methyl or ethyl, and wherein R is H, methyl, hydroxy, propoxy, octyloxy, cyclohexyloxy, acyloxy or N- (2-hydroxy-2-methylpropyloxy).

Suitable hindered amine light stabilizers are, for example:

(1) 1-cyclohexyloxy-2, 2,6, 6-tetramethyl-4-octadecylaminopiperidine,

(2) bis (2,2,6, 6-tetramethylpiperidin-4-yl) sebacate,

(3) bis (1-acetoxy-2, 2,6, 6-tetramethylpiperidin-4-yl) sebacate,

(4) bis (1,2,2,6, 6-pentamethylpiperidin-4-yl) sebacate,

(5) bis (1-cyclohexyloxy-2, 2,6, 6-tetramethylpiperidin-4-yl) sebacate,

(6) bis (1-octyloxy-2, 2,6, 6-tetramethylpiperidin-4-yl) sebacate;

(7) bis (1-acyl-2, 2,6, 6-tetramethylpiperidin-4-yl) sebacate,

(8) bis (1,2,2,6, 6-pentamethyl-4-piperidinyl) -n-butyl-3, 5-di-tert-butyl-4-hydroxybenzylmalonate

(9)2, 4-bis [ (1-cyclohexyloxy-2, 2,6, 6-tetramethylpiperidin-4-yl) butylamino ] -6- (2-hydroxyethylamino-s-triazine,

(10) bis (1-cyclohexyloxy-2, 2,6, 6-tetramethylpiperidin-4-yl) adipate,

(11)2, 4-bis [ (1-cyclohexyloxy-2, 2,6, 6-piperidin-4-yl) butylamino ] -6-chloro-s-triazine,

(12)1- (2-hydroxy-2-methylpropoxy) -4-hydroxy-2, 2,6, 6-tetramethylpiperidine,

(13)1- (2-hydroxy-2-methylpropoxy) -4-oxo-2, 2,6, 6-tetramethylpiperidine,

(14)1- (2-hydroxy-2-methylpropoxy) -4-octadecanoyloxy-2, 2,6, 6-tetramethylpiperidine,

(15) bis (1- (2-hydroxy-2-methylpropoxy) -2,2,6, 6-tetramethylpiperidin-4-yl) sebacate,

(16) bis (1- (2-hydroxy-2-methylpropoxy) -2,2,6, 6-tetramethylpiperidin-4-yl) adipate,

(17)2, 4-bis { N- [1- (2-hydroxy-2-methylpropoxy) -2,2,6, 6-tetramethylpiperidin-4-yl ] -N-butylamino } -6- (2-hydroxyethylamino) -s-triazine,

(18) 4-benzoyl-2, 2,6, 6-tetramethylpiperidine,

(19) bis- (1,2,2,6, 6-pentamethylpiperidin-4-yl) -p-methoxybenzylidene malonate,

(20)2,2,6, 6-tetramethylpiperidin-4-yl octadecanoate,

(21) bis (1-octyloxy-2, 2,6, 6-tetramethylpiperidyl) succinate,

(22)1,2,2,6, 6-pentamethyl-4-aminopiperidine,

(23) 2-undecyl-7, 7,9, 9-tetramethyl-1-oxa-3, 8-diaza-4-oxo-spiro [4,5] decane,

(24) tris (2,2,6, 6-tetramethyl-4-piperidyl) nitrilotriacetate,

(25) tris (2-hydroxy-3- (amino- (2,2,6, 6-tetramethylpiperidin-4-yl) propyl) nitrilotriacetate,

(26) tetrakis (2,2,6, 6-tetramethyl-4-piperidyl) -1,2,3, 4-butane-tetracarboxylate,

(27) tetrakis (1,2,2,6, 6-pentamethyl-4-piperidinyl) -1,2,3, 4-butane-tetracarboxylate,

(28)1,1' - (1, 2-ethanediyl) -bis (3,3,5, 5-tetramethylpiperazinone),

(29) 3-n-octyl-7, 7,9, 9-tetramethyl-1, 3, 8-triazaspiro [4.5] decane-2, 4-dione,

(30) 8-acetyl-3-dodecyl-7, 7,9, 9-tetramethyl-1, 3, 8-triazaspiro [4.5] decane-2, 4-dione,

(31) 3-dodecyl-1- (2,2,6, 6-tetramethyl-4-piperidyl) pyrrolidine-2, 5-dione,

(32) 3-dodecyl-1- (1,2,2,6, 6-pentamethyl-4-piperidyl) pyrrolidine-2, 5-dione,

(33) n, N '-di-formyl-N, N' -di (2,2,6, 6-tetramethyl-4-piperidyl) hexamethylenediamine,

(33a) bis (1-undecanoyl-2, 2,6, 6-tetramethylpiperidin-4-yl) carbonate,

(34) the reaction product of 2, 4-bis [ (1-cyclohexyloxy-2, 2,6, 6-piperidin-4-yl) butylamino ] -6-chloro-s-triazine with N, N' -bis (3-aminopropyl) ethylenediamine),

(35) a condensate of 1- (2-hydroxyethyl) -2,2,6, 6-tetramethyl-4-hydroxypiperidine and succinic acid,

(36) the condensate of N, N' -bis (2,2,6, 6-tetramethyl-4-piperidyl) -hexamethylenediamine and 4-tert-octylamino-2, 6-dichloro-1, 3, 5-triazine,

(37) the condensate of N, N' -bis (2,2,6, 6-tetramethyl-4-piperidyl) -hexamethylenediamine and 4-cyclohexylamino-2, 6-dichloro-1, 3, 5-triazine,

(38) a condensate of N, N' -bis- (2,2,6, 6-tetramethyl-4-piperidyl) hexamethylenediamine and 4-morpholino-2, 6-dichloro-1, 3, 5-triazine,

(39) a condensate of N, N' -bis- (1,2,2,6, 6-pentamethyl-4-piperidyl) hexamethylenediamine and 4-morpholino-2, 6-dichloro-1, 3, 5-triazine,

(40) a condensate of 2-chloro-4, 6-bis (4-n-butylamino-2, 2,6, 6-tetramethylpiperidyl) -1,3, 5-triazine and 1, 2-bis (3-aminopropylamino) ethane,

(41) a condensate of 2-chloro-4, 6-bis- (4-n-butylamino-1, 2,2,6, 6-pentamethylpiperidyl) -1,3, 5-triazine with 1, 2-bis- (3-aminopropylamino) ethane,

(42) a reaction product of 7,7,9, 9-tetramethyl-2-cycloundecyl-1-oxa-3, 8-diaza-4-oxospiro [4,5] decane and epichlorohydrin,

(43) poly [ methyl, (3-oxy- (2,2,6, 6-tetramethylpiperidin-4-yl) propyl) ] siloxane, CAS #182635-99-0,

(44) maleic anhydride-C₁₈-C₂₂- α -the reaction product of an olefin copolymer with 2,2,6, 6-tetramethyl-4-aminopiperidine,

(45) oligomeric condensates of 4,4' -hexamethylenebis (amino-2, 2,6, 6-tetramethylpiperidine) with 2, 4-dichloro-6- [ (2,2,6, 6-tetramethylpiperidin-4-yl) butylamino ] -s-triazine, terminated with 2-chloro-4, 6-bis (dibutylamino) -s-triazine,

(46) oligomeric condensates of 4,4' -hexamethylenebis (amino-1, 2,2,6, 6-pentamethylpiperidine) with 2, 4-dichloro-6- [ (1,2,2,6, 6-pentamethylpiperidin-4-yl) butylamino ] -s-triazine, which are end-capped with 2-chloro-4, 6-bis (dibutylamino) -s-triazine,

(47) oligomeric condensates of 4,4' -hexamethylenebis (amino-1-propoxy-2, 2,6, 6-tetramethylpiperidine) with 2, 4-dichloro-6- [ (1-propoxy-2, 2,6, 6-tetramethylpiperidin-4-yl) butylamino ] -s-triazine, terminated with 2-chloro-4, 6-bis (dibutylamino) -s-triazine,

(48) oligomeric condensates of 4,4' -hexamethylenebis (amino-1-acyloxy-2, 2,6, 6-tetramethylpiperidine) with 2, 4-dichloro-6- [ (1-acetoxy-2, 2,6, 6-tetramethylpiperidin-4-yl) butylamino ] -s-triazine, terminated with 2-chloro-4, 6-bis (dibutylamino) -s-triazine,

(49) a product obtained by reacting (a) a product obtained by reacting 1, 2-bis (3-aminopropylamino) ethane with cyanuric chloride and (b) a product obtained by reacting (2,2,6, 6-tetramethylpiperidin-4-yl) butylamine,

(50) (4-piperidinol, 2,2,6, 6-tetramethyl-1- (undecyloxy)) -,4,4' -carbonate, and

(51)1,3, 5-triazine-2, 4, 6-triamine, N2, N2' -1, 6-hexanediylbis [ N4, N6-dibutyl-N2, N4, N6-tris (2,2,6, 6-tetramethyl-4-piperidinyl) -, N-propoxy.

Also included are the sterically hindered N-H, N-methyl, N-methoxy, N-hydroxy, N-propoxy, N-octyloxy, N-cyclohexyloxy, N-acyloxy and N- (2-hydroxy-2-methylpropyloxy) analogs of any of the foregoing compounds. For example, in the case of replacing the N-H hindered amine with an N-methyl hindered amine, the N-methyl analog would be used in place of N-H.

For illustrative purposes, some structures of the above compounds are shown below.

(6)

(8)

(9)

(12)

(19)

(23)

(25)

(26)

(28)

(29)

(31)

(33)

(34)

(35)

(36)

(38)

(41)

(42)

(43)

(44)

(45)

(49)

Wherein R '═ R' or H,

n is 2 or 3, and n is 2 or 3,

and wherein

In particular embodiments, the composition may further comprise a hindered phenolic antioxidant, such as β - (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate, for example an ester of a mono-or polyhydric alcohol, for example with methanol, ethanol, n-octanol, isooctanol, linear and branched C₇-C₉Mixture of alkanols, stearyl alcohol, straight-chain and branched C₁₃-C₁₅Mixtures of alkanols, 1, 6-hexanediol, 1, 9-nonanediol, ethylene glycol, 1, 2-propanediol, 1, 3-propanediol, neopentyl glycol, 1, 4-cyclohexanedimethanol, glycerol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris (hydroxyethyl) isocyanurate, N, N' -bis- (hydroxy-ethyl) oxamide, 3-thiaundecanol, 3-thiapentadecanol, trimethylhexanediol, trimethylolpropane, 4-hydroxymethyl-1-phospha-2, 6, 7-trioxabicyclo [2.2.2 ] trioxabicyclo [2.2]Octane.

In other embodiments, the hindered phenolic antioxidant comprises tris (3, 5-di-tert-butyl-4-hydroxybenzyl) isocyanurate, 1,3, 5-tris- (3, 5-di-tert-butyl-4-hydroxybenzyl) -2,4, 6-trimethylbenzene, the calcium salt of the monoethyl ester of 3, 5-di-tert-butyl-4-hydroxybenzylphosphonic acid, 1, 2-bis (3, 5-di-tert-butyl-4-hydroxyhydrocinnamoyl) hydrazine, pentaerythrityl tetrakis [3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate ], octadecyl 3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate, N '-hexamethylenebis (3, 5-di-tert-butyl-4-hydroxyhydrocinnamide), 1,3, 5-tris- (4-tert-butyl-3-hydroxy-2, 6-dimethylbenzyl) -1,3, 5-triazine-2, 4,6- (1H,3H,5H) -trione, 2,2' -methylenebis (4-methyl-6-t-butylphenol) α or tocopheryl mono-acrylate.

In some embodiments, the composition is substantially free or free of hindered phenol antioxidants. "substantially free" means unintentionally added in which there are only incidental amounts or trace amounts, such as less than or equal to 500ppm (parts per million) by weight, less than or equal to 400ppm, less than or equal to 300ppm, less than or equal to 200ppm, less than or equal to 150ppm, less than or equal to 100ppm, less than or equal to 75ppm, less than or equal to 50ppm, less than or equal to 25ppm, less than or equal to 20ppm, less than or equal to 15ppm, less than or equal to 10ppm, less than or equal to 5ppm, less than or equal to 4ppm, less than or equal to 3ppm, less than or equal to 2ppm or less than 1ppm, based on the weight of the polyolefin.

Thiosynergists include, for example, dilauryl thiodipropionate or distearyl thiodipropionate.

Acid scavengers include hydrotalcite and amorphous basic aluminum magnesium carbonate, see, for example, U.S. patent nos.4,427,816, 5,106,898 and 5,234,981. Hydrotalcite is also known as hycite, DHT4A, DHT4V, DHT4Z, DHT4a2 or DHT 4C. Hydrotalcites are natural or synthetic, and may contain a coating. Natural hydrotalcite is believed to have the structure Mg₆Al₂(OH)₁₆CO_3.4H₂And O. A typical empirical formula for the synthetic hydrotalcite is Al₂Mg_4.35OH_11.36CO_3(1.67).xH₂And O. Examples of synthetic products include Mg_0.7Al_0.3(OH)₂(CO₃)_0.15.0.54H₂O、Mg_4.5Al₂(OH)₁₃CO₃.3.5H₂O and Mg_4.2Al(OH)_12.4CO₃。

In some embodiments, the acid scavenger comprises a metal salt of a fatty acid, such as an alkali metal salt or an alkaline earth metal salt of a fatty acid. In some embodiments, the acid scavenger comprises a calcium, magnesium, zinc, sodium, potassium, or aluminum salt of a fatty acid. In some embodiments, the acid scavenger comprises a stearate, behenate, ricinoleate, or palmitate salt of calcium, magnesium, zinc, sodium, potassium, or aluminum. In particular embodiments, the acid scavenger comprises calcium stearate, zinc stearate, magnesium behenate, magnesium stearate, sodium ricinoleate, and potassium palmitate. In other embodiments, the acid scavenger comprises zinc oxide.

In some embodiments, a combination of one or more acid scavengers may be used.

The Ultraviolet (UV) light absorber may be selected from the group consisting of hydroxyphenylbenzotriazoles, triaryl-s-triazines, hydroxybenzoates, 2-hydroxybenzophenones and cyanoacrylate ultraviolet light absorbers (UVAs).

Hydroxyphenyl benzotriazole UVA may include those disclosed in U.S. Pat. Nos.3,004,896;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;. 5,607,987,5,977,219, and 6,166,218; -such as 2- (2-hydroxy-5-methylphenyl) -2H-benzotriazole, 2- (3, 5-di-tert-butyl-2-hydroxyphenyl) -2H-benzotriazole, 2- (2-hydroxy-5-tert-butylphenyl) -2H-benzotriazole, 2- (2-hydroxy-5-tert-butylphenyl) -2H-benzotriazole, 2- (3, 5-di-tert-butyl-2-octyloxy) -2H-benzotriazole, 5-chloro-2- (3, 5-di-tert-butyl-2-hydroxyphenyl) -2H-benzotriazole, 5-2- (2-t-octylphenyl) -2H-benzotriazolyl) -2H-benzotriazole, 5-2-octyloxy-2- (2, 2-tert-butyl-2-hydroxyphenyl) -2H-benzotriazolyl) -2H-benzotriazole, 5- (2-2H-phenyloctyl-2H-triazolyl) -2H-2, 5- (2H-2-octyloxy-2, 5-2H-tert-2-tert-octyloxy) -2H-2, 5-tert-2-tert-phenyl) -2H-benzotriazolyl) -2H-2-octyloxy-2, 2H-2H-2-tert-octyloxy-2, 2-2H-2, 2-2H-2-tert-2, 5-2-octyloxy-2H-2-octyloxy-2, 5-2, 5-2H-2, 5-2H-2H-tert-2-octyloxy-2H-2, 5-tert-2H-2-octyloxy-2H-2H-2, 5-2H-2, 5-2H-2H-2, 5-2H-2-phenyl) -2, 5-2H-2H-2-phenyl-2H-2-.

Triaryl-s-triazine UVA may include those disclosed in U.S. Pat. No. 3,843,371; 4,619,956; 4,740,542; 5,096,489; 5,106,891; 5,298,067; 5,300,414; 5,354,794; 5,461,151; 5,476,937; 5,489,503; 5,543,518; 5,556,973; 5,597,854; 5,681,955; 5,726,309; 5,736,597; 5,942,626; 5,942,626; 5,942,626; and U.S. applications disclose those disclosed in U.S. Pat. No. 5/5,942,626 and U.S. application Nos.2, 4, 6-tris (2-hydroxy-3-methyl-4-hexyloxyphenyl) -1,3, 5-triazine, dodecanedioic acid, 1, 12-bis [2- [4- (4, 6-diphenyl-1, 3, 5-triazine-2-yl) -3-hydroxyphenoxy ] ethyl ] ester, 4, 6-bis- (2, 4-dimethylphenyl) -2- (2-hydroxy-4-octyloxyphenyl) -s-triazine-s-2- (2-hydroxy-propoxy) -2, 6-propyloxy) -2, 6-bis- (2-octyloxy) -2-phenyl) -2-hydroxy-propyloxy) -1,3, 6-bis- (2-phenyl) -4-propyloxy) -2-bis- (2-hydroxy-propyloxy) -2, 6-bis- (2-phenyl) -2-4-hydroxy-propyloxy) -1, 6-bis- (2-phenyl) -6-bis- (2-bis- (4-octyloxy) -2-hydroxy-propyloxy) -1, 6-phenyl) -6-bis- (2-phenyl) -2-bis- (2-hydroxy-phenyl) -4-propyloxy) -6-bis- (2-hydroxy-propyloxy) -6-phenyl) -6-bis- (2-hydroxy-phenyl) -6-bis- (2-propyloxy-bis- (2-phenyl) -6-4-propyloxy-4-phenyl) -6-bis- (2-phenyl) -6-phenyl) -4-bis- (2-phenyl) -6-bis- (2-hydroxy-phenyl) -1, 6-hydroxy-propyloxy-phenyl) -6-bis- (2-phenyl) -1, 6-phenyl) -6-bis- (2-propyloxy-4-phenyl) -6-bis- (2-hydroxy-phenyl) -4-hydroxy-propyloxy-phenyl) -6-bis- (2-phenyl) -1, 6-phenyl) -4-bis- (2-propyloxy-phenyl) -4-propyloxy-phenyl) -1, 6-hydroxy-4-propyloxy-phenyl) -6-hydroxy-phenyl) -6-hydroxy-phenyl) -1, 6-phenyl) -6-bis- (2-phenyl) -4-phenyl) -1, 6-phenyl) -6-bis- (2-4-phenyl) -6-phenyl) -1, 6-phenyl) -4-phenyl) -6-bis- (2-phenyl) -6-phenyl) -4-bis- (2-hydroxy-phenyl) -1, 6-phenyl) -4-bis- (2-phenyl) -4-phenyl) -1, 6-bis- (2-propyloxy-phenyl) -6-phenyl) -4-propyloxy-phenyl) -1, 6-phenyl) -6-bis- (2-propyloxy-phenyl) -6-bis- (2-phenyl) -6-propyloxy-phenyl) -6-bis- (2-phenyl) -1, 6-bis- (2-phenyl) -6-bis- (2-phenyl) -6-bis- (2-phenyl) -6-bis- (.

Hydroxybenzoate UV absorbers may include, for example, esters of substituted and unsubstituted benzoic acids, such as 4-tert-butylphenyl salicylate, phenyl salicylate, octylphenyl salicylate, dibenzoyl resorcinol, bis (4-tert-butylbenzoyl) resorcinol, benzoyl resorcinol, 2, 4-di-tert-butylphenyl 3, 5-di-tert-butyl-4-hydroxybenzoate, hexadecyl 3, 5-di-tert-butyl-4-hydroxybenzoate, octadecyl 3, 5-di-tert-butyl-4-hydroxybenzoate, 2-methyl-4, 6-di-tert-butylphenyl 3, 5-di-tert-butyl-4-hydroxybenzoate.

2-hydroxybenzophenone UV absorbers include, for example, the 4-hydroxy, 4-methoxy, 4-octyloxy, 4-decyloxy, 4-dodecyloxy, 4-benzyloxy, 4,2',4' -trihydroxy and 2 '-hydroxy-4, 4' -dimethoxy derivatives.

Cyanoacrylate UV absorbers include, for example, pentaerythritol tetrakis (2-cyano-3, 3-diphenylacrylate), ethyl or isooctyl α -cyano- β -diphenylacrylate, and α -cyano- β -methyl-p-methoxy-cinnamic acid methyl or butyl ester.

In some embodiments, the UVA may include 5-chloro-2- (3-tert-butyl-2-hydroxy-5-methylphenyl) -2H-benzotriazole, 2- (3, 5-bis- α -cumyl-2-hydroxyphenyl) -2H-benzotriazole, 4, 6-diphenyl-2- (4-hexyloxy-2-hydroxyphenyl) -s-triazine, 4, 6-bis- (2, 4-dimethylphenyl) -2- (2-hydroxy-4-octyloxyphenyl) -s-triazine, hexadecyl 3, 5-di-tert-butyl-4-hydroxybenzoate or 4-octyloxy-2-hydroxybenzophenone.

Many UVAs are commercially available, such as TINUVIN 326, TINUVIN 234, TINUVIN 1577, TINUVIN1600, CYASORB UV 1164, CYASORB THT, CYASORB UV 2908, CHIMASSORB 81, UVINUL 3030, ADK LA-F70, ADK LA-1000, TINUVIN 400, and the like.

Hydroxylamine stabilizers may include, for example: n, N-dibenzylhydroxylamine, N, N-diethylhydroxylamine, N, N-dioctylhydroxylamine, N, N-dilaurylhydroxylamine, N, N-didodecylhydroxylamine, N, N-ditetradecylhydroxylamine, N, N-dihexadecylhydroxylamine, N, N-dioctadecylhydroxylamine, N-hexadecyl-N-tetradecylhydroxylamine, N-hexadecyl-N-heptadecylhydroxylamine, N-hexadecyl-N-decadecylhydroxylamineOctaalkylhydroxylamine, N-heptadecyl-N-octadecylhydroxylamine, N-methyl-N-octadecylhydroxylamine, or in particular embodiments N, N-di (C)₁₆-C₁₈Alkyl) hydroxylamine.

In particular embodiments, the polyolefin comprises a Polyethylene (PE) homopolymer, a polyethylene random or block copolymer, a polypropylene (PP) homopolymer, a polypropylene random or block copolymer, an ethylene/propylene copolymer, a mixture of polypropylene and polyethylene, or a mixture of different types of polyethylene. In a particular embodiment, the polyolefin is polypropylene. In some embodiments, the polyethylene is Linear Low Density (LLDPE), Low Density (LDPE), Medium Density (MDPE), or High Density (HDPE). Such mixtures are, for example, PP/HDPE, PP/LDPE and LDPE/HDPE. Ternary mixtures, such as PP/HDPE/LLDPE, are also included. The polyolefins may be formulated with or without crosslinking.

The polyolefin composition contains, for example, greater than or equal to about 10 weight percent (wt.%) of a polyolefin, such as greater than or equal to about 15 wt.%, > or equal to about 20 wt.%, > or equal to about 25 wt.%, > or equal to about 30 wt.%, > or equal to about 35 wt.%, > or equal to about 40 wt.%, > or equal to about 45 wt.%, > or equal to about 50 wt.%, > or equal to about 55 wt.%, > or equal to about 60 wt.%, > or equal to about 65 wt.%, > or equal to about 70 wt.%, > or equal to about 75 wt.%, > or equal to about 80 wt.% or greater than or equal to about 85 wt.% of the polyolefin, based on the weight of the composition.

The polypropylene may be a polypropylene homopolymer, polypropylene random copolymer, alternating or segmented copolymer or block copolymer containing one or more comonomers selected from the group consisting of: ethylene, C₄-C₃₀- α -olefin, vinylcyclohexane, vinylcyclohexene, C₄-C₂₀Alkadienes of C₅-C₁₂Cycloalkadienes and norbornene derivatives; the total amount of propylene and one or more comonomers is 100%.

Polypropylene copolymers also include long chain branched polypropylene copolymers.

Suitable C₄-C₃₀α examples of olefins are 1-butene, 1-pentene, 1-hexene, 1-heptene, 1-octene, 1-nonene, 1-decene, 1-undecene, 1-dodecene1-tetradecene, 1-hexadecene, 1-octadecene, 1-eicosene, 4-methyl-1-pentene, 1-eicosene, 1-docosene, 1-tetracosene, 1-hexacosene, 1-octacosene, and 1-triacontene.

Suitable C₄-C₂₀Examples of the alkadienes include hexadiene and octadiene. Suitable C₅-C₁₂Examples of the cycloalkane diene include cyclopentadiene, cyclohexadiene and cyclooctadiene. Examples of suitable norbornene derivatives include 5-ethylidene-2-norbornene (ENB), Dicyclopentadiene (DCP) and methylene-endomethylene-hexahydronaphthalene (MEN).

The propylene/ethylene copolymer contains, for example, from about 50 to 99.9%, in some embodiments from about 80 to 99.9%, and in other embodiments, from about 90 to 99.9% by weight propylene.

Propylene copolymer wherein the comonomer is C₉-C₂₀α -alkenes, for example 1-nonene, 1-decene, 1-undecene, 1-dodecene, 1-tetradecene, 1-hexadecene, 1-octadecene or 1-eicosene, C₉-C₂₀Alkadienes of C₉-C₁₂Cycloalkadienes or norbornene derivatives, such as 5-ethylidene-2-norbornene (ENB) or methylene-endomethylene-hexahydronaphthalene (MEN), such propylene copolymers may contain greater than about 90 mole%, from about 90 mole% to about 99.9 mole%, or from about 90 mole% to about 99 mole% propylene.

Propylene copolymer wherein the comonomer is C₄-C₈α -olefins, e.g. 1-butene, 1-pentene, 1-hexene, 1-heptene, 1-octene or 4-methyl-1-pentene, vinylcyclohexane, vinylcyclohexene, C₄-C₈Alkadienes or C₅-C₈Naphthenic dienes such propylene copolymers may contain greater than 80 mole percent, from about 80 to about 99.9 mole percent, or from about 80 to about 99 mole percent propylene.

Other examples of polypropylene are propylene/isobutylene copolymers, propylene/butadiene copolymers, propylene/cycloolefin copolymers, terpolymers of propylene with ethylene and a diene, such as hexadiene, dicyclopentadiene or ethylidene-norbornene; propylene/1-olefin copolymers wherein the 1-olefin is produced in situ; and propylene/carbon monoxide copolymers.

Allyl or vinyl terminated oligomers of ethylene or propylene can be used as branches in polymerization reactions with propylene to produce branched polypropylene with high melt strength, see, for example, U.S. patent No.8,399,725 and U.S. application publication nos.2013/0274425,2013/0274425,2013/0030135 and 2013/0137829.

The linear chain structure of polypropylene allows the polymer to exhibit low melt strength and lack strain hardening. This can lead to processing problems where the polymer is required to have extensibility. In contrast, polypropylene exhibiting high melt strength is valuable in industrial converting operations, such as blow molding, thermoforming, or foaming of polypropylene sheets. The polypropylene-based compositions of the present invention exhibit acceptable melt strength, ductility and strain hardening to produce extruded profiles and siding.

Advantageously, the polyolefin comprises a polypropylene homopolymer or copolymer, optionally blended with a polyethylene homopolymer or copolymer, having suitably high melt strength. The blend may further contain a third polymer suitable for promoting compatibility, partial miscibility or miscibility of the different polyolefins. Such materials are known as interfacial tension reducers or compatibilizers.

Suitable compatibilizers are generally polymers containing two or more different segments that are miscible or compatible with the components to be blended. Compatibilized polymer blends need not be completely miscible, nor need all mixing thermodynamics (e.g., resulting in a single phase, or a single glass transition temperature) be satisfied. But such a blend of different polymer structures will show improved properties compared to the individual components.

One compatibilizer used to blend PP and PE is a segmented "olefin block copolymer" or "OBC" containing propylene, ethylene and optionally additional α -olefin sequences, such as those produced by Dow Global Technologies, and see U.S. application publication nos.2011/032621,2011/060103,2010/298515,2011/054121 and 2011/015354, which includes therein the Dow product under the trade name INFUSE and the VISTAMAXX product of ExxonMobil, these block copolymers are made with a bulk molecular weight distribution and a segment molecular weight distribution such that Mw/Mn >1.4, with two or more blocks of ethylene and α -olefins per chain and a low molecular weight (Mw <200,000g/mol), these alternating block copolymers are characterized by a crystallizable tough 'hard block' segment and an amorphous elastomeric 'soft block' content, the hard block content in these c is 12-84 wt%, and the total 1-octene content (i.e., the branched HDPE) is 3-14 wt%, where the blend can achieve increased tensile strength and elongation compared to long chain compatibilized OBC blends and obps.

Polypropylene homopolymers or copolymers or blends with polyethylene, optionally compatibilized, can be chemically crosslinked to introduce Long Chain Branching (LCB) outside the polypropylene backbone, resulting in higher melt strength and elongation and lower melt flow rates than conventional products.

Chemical crosslinking of a polypropylene homopolymer or copolymer with another polypropylene or with a polyethylene homopolymer or copolymer and/or with a compatibilizing material is advantageous. This crosslinking process can impart beneficial increases in melt strength, melt extensibility, mechanical strength, and tensile strength in the extrusion process to the polyolefin blend. Crosslinking on polypropylene can produce Long Chain Branching (LCB) in the polypropylene backbone and increased amounts of polymer chain entanglement to achieve higher polymer melt strength.

Crosslinking may be carried out with reagents such as organic peroxides, or by treatment with a radiation source, such as ultraviolet light, electron beam or gamma radiation. Irradiation may be accomplished in a reduced oxygen environment or an oxygen-free environment. For example, polypropylene having high melt strength and melt extensibility can be obtained by blending linear polypropylene with branched polypropylene (b-PP) in an extruder. b-PP is obtained by reacting a peroxide with an unmodified polypropylene and optionally a difunctional unsaturated monomer capable of grafting onto the unmodified polypropylene, resulting in long chain branching, see US 2015175789. In another example, U.S. Pat. Nos.5,508,318, 5,731,362, 5,591,785, 5,554,668, and 4,916,198 disclose mixing blends of irradiated and unirradiated olefin polymer materials suitable for extrusion.

The formation of long chain branches on polyolefins may be performed upstream during the production of the polymer, as compared to downstream extrusion or the case where the polymer is chemically modified to form crosslinks or long chain branches to improve melt strength. For example, polyethylene can be modified in the polymerization unit via exposure to low levels of oxygen, a so-called 'oxygen engineering', which results in the formation of long branches and improved melt strength, see U.S. application publication No. 2012/100357.

The polyolefin may contain additives that promote a higher degree of crystallization when the polymer is melt converted into a shaped article. Such additives are known as nucleating agents.

The crystallinity of polypropylene is an important parameter that can affect properties such as modulus, yield stress, strength, and the like. It is within the scope of the present invention to use nucleating agents that can favorably influence the degree of crystallinity formed, which improves the melt strength of the polymer during extrusion processing and improves the mechanical properties of the final article. Suitable nucleating agents are, for example, sodium benzoate, 2,2' -methylene-bis (4, 6-di-tert-butylphenyl) phosphate, zinc glycerolate, the calcium salt of cyclohexane-1, 2-dicarboxylate, the aromatic triamide compound, the disodium salt of cis-bridged-bicyclo [2.2.1] heptane-2, 3-dicarboxylic acid, aluminum hydroxy-bis [4- (tert-butyl) benzoate ], and sorbitol, for example 1,3:2, 4-bis (3, 4-dimethylbenzylidene) sorbitol, 1,3:2, 4-bis (4-methylbenzylidene) sorbitol or 1,3:2, 4-bis (3, 4-dimethylbenzylidene) sorbitol, see U.S. Pat. Nos.7,423,088, 7,790,793 and 8,183,312 and U.S. application publication No. 2012/0190797.

The nucleating agent may be present in an amount of, for example, from about 10 parts per million (ppm) to about 10,000ppm, from about 12ppm to about 1,000ppm, from about 12ppm to about 500ppm, or from about 12ppm to about 300ppm or about 400ppm by weight based on the weight of the polyolefin.

The polyolefin advantageously contains inorganic (mineral) fillers to balance melt strength and extensibility or stretchability, allowing extrusion to produce profiles and siding. The filler is described in more detail below.

The polyolefin comprises a polypropylene homopolymer or copolymer optionally blended with a polyethylene homopolymer or copolymer, wherein the blend may further contain a compatibilizer that can exhibit high melt strength. The polyolefin may have a melt strength of at least about 4 centinewtons (cN) at 210 ℃. For example, the polyolefin has a melt strength of about 4, about 5, about 6, about 7, about 8, about 9, about 10, about 11, about 12, about 13, about 14, about 15, about 16, about 17, about 18, about 19, about 20, about 21, about 22, about 23, about 24, or about 25 centinewtons at 210 ℃. For example, a melt strength of greater than or equal to about 5, greater than or equal to about 7, greater than or equal to about 9, greater than or equal to about 11, greater than or equal to about 13, greater than or equal to about 15, greater than or equal to about 17, greater than or equal to about 19, greater than or equal to about 21, or greater than or equal to about 23 centiNewtons at 210 ℃.

Polyolefins may be prepared by the following process:

a) free radical polymerization (usually carried out under high pressure and high temperature), or

b) Catalytic polymerisation using a catalyst which typically contains one or more metals of groups IVb, Vb, VIb or VIII of the periodic Table. These metals typically have one or more ligands, typically oxides, halides, alkoxides, esters, ethers, amines, alkyls, alkenyls, and/or aryls, which may be pi-or sigma-coordinated. These metal complexes may be in the free form or fixed on substrates, usually on activated magnesium chloride, titanium (III) chloride, alumina or silicon oxide. These catalysts may be soluble or insoluble in the polymerization medium. The catalyst may be used as such in the polymerization, or other activators may be used, typically metal alkyls, metal hydrides, metal alkyl halides, metal alkyl oxides or metal alkoxides, the metals being elements of groups Ia, IIa and/or IIIa of the periodic Table. The activators may be modified conveniently with further ester, ether, amine or silyl ether groups. These catalyst systems are generally known as Phillips, Standard OilIngiana, Ziegler (-Natta), TNZ (DuPont), metallocene or Single Site Catalysts (SSC).

Polypropylene is prepared by a process described in the literature including: kissin, Y.V, (2008), olefin polymerization using transition metal catalysts, Elsevier, pp.207-. ISBN 978-0-444-; hoff, Ray and Mathers, Robert T. (2010), handbook of transition metal polymerization catalysts, John Wiley & Sons, pp.158-ISBN 978-0-470-; moore, E.P, (1996) polypropylene handbook, polymerization, characterization, performance, processing, applications, hanser publishers: new York, ISBN 1569902089; benedikt, g.m. and Goodall, B.L. (ed) (1998) metallocene-catalyzed polymers, ChemTech Publishing: toronto, ISBN 978-1-884207-59-4; malpass, d.b., introduction to industrial polyethylene, properties, catalysts, processes, Wiley publ., (2010); and Malpass, d.b., introduction to industrial polyethylene, properties, catalysts, processes, Wiley publ., (2012).

In some embodiments, the polyolefin comprises a base polyolefin, a polyolefin recycle, or a mixture thereof. The polyolefin recycle may be collected from household, commercial or industrial waste or from usable materials. The recycled material may come from packaging materials such as films, bags, bottles and other containers or foam materials. It is also possible to stabilize polyolefins which have previously been damaged by use, storage or processing. These materials come, for example, from the collection or recycling duties of usable materials, for example from the automotive industry, the electronics/electrical industry, the construction, agriculture or textile industry.

The introduction of the benzofuranones and the organophosphorus stabilizers into the polyolefin is carried out by known methods, for example before or after moulding, or by applying the dissolved or dispersed additive mixture to the polyolefin, with or without subsequent evaporation of the solvent. The benzofuranone and organophosphorus stabilizer can also be added to the polyolefin in the form of a masterbatch, which contains the additive in a concentration of, for example, about 2 to 40 weight percent, based on the total weight of the masterbatch. In the case of a masterbatch form, the polymer in the masterbatch need not be the same as the polyolefin. The molding can be carried out using known mixers, such as mixers, kneaders or extruders.

The benzofuranone and the organophosphorus stabilizer may be premixed or added separately. The benzofuranones and organophosphorus stabilizers can also be added before or during polymerization or before crosslinking. The benzofuranones and organophosphorus stabilizers can be incorporated into the polyolefin in pure form or encapsulated in waxes, oils or polymers.

Benzofuranones and organophosphorus stabilizers can also be sprayed onto polyolefins. They are capable of diluting other additives or their melts so that they can also be sprayed onto the polyolefin together with these additives.

In a particular embodiment, the benzofuranone additive and the organophosphorus stabilizer are incorporated into the polyolefin by melt blending them in an extruder. The benzofuranone and the organophosphorus stabilizer can be added together or separately.

In some embodiments, the process for preparing the polyolefin composition comprises detecting the weight of the raw materials and then dry blending the raw material components. This mixture can be fed into a screw extruder at a constant feed rate to extrude the material into the desired form, followed by water cooling and drying.

Another subject of the invention is an article, for example a shaped article, comprising the polyolefin composition of the invention. Examples of the shaped article include, but are not limited to, those listed in the following items I-1) to IIV-8).

I-1) flotation devices, marine applications, pontoons, buoys, plastics or composites for bridges or piers, boats, kayaks, oars and beach reinforcements.

I-2) automotive applications, interior trim applications, exterior trim applications, such as bumpers, instrument panels, batteries, rear and front linings, molded parts under hoods, trunk linings, inner liners, airbag covers, electronic moldings for fittings (lamps), panels for instrument panels, headlamp lenses, instrument panels, exterior linings, cushions, automotive lamps, headlamps, parking lamps, tail lamps, parking lamps, interior panels and exterior panels; a door panel; a gas tank; a glass front; a rear windshield; a chair back; exterior panels, wire insulation, profile extrusions for sealing, cladding, lamp frames, chassis components, exhaust systems, fuel filters/fillers, fuel pumps, fuel tanks, body side moldings, convertible tops, rear view mirrors, exterior trim panels, fasteners/accessories, front end modules, glass, hinges, locking systems, luggage/roof racks, stamped/pressed parts, seals, side impact protection, silencers/sound insulators and awnings.

I-3) road traffic equipment, such as signs, posters for road marking, vehicle accessories, warning triangle, medical kit, helmets, tires.

I-4) installations, including interior furnishings, for aircraft, railways, motor vehicles (cars, motorcycles, trucks).

I-5) devices for space applications, such as rockets and satellites, for example reentry guards.

I-6) devices for construction and related, mining applications, sound insulation systems, street shelters and coverings.

II-1) devices, housings and covers in conventional and electronic/electrical appliances (personal computers, telephones, cell phones, printers, television sets, video equipment), flowerpots, satellite TV transmitting and receiving equipment.

II-2) sheaths for other materials such as iron or textiles.

II-3) devices for the electronics industry, such as insulation for plugs, in particular computer plugs, housings for electronic and electrical components, printing plates, and materials for electronic data storage, such as chips, check cards and credit cards.

II-4) electrical appliances, such as washing machines, vacuum cups, ovens (microwave ovens), dishwashers, mixers and irons.

II-5) covers for lamps (e.g. street lamps, lamp covers).

II-6) applications in wires and cables (semi-conductors, insulation and cable sheathing).

II-7) foils for condensers, refrigerators, heating devices, air conditioners, encapsulated electronics, semiconductors, coffee makers and vacuum cleaners.

III-1) technical articles, such as cogwheels (gears), sliding fittings, gaskets, screws, bolts, handles and grips.

III-2) rotating vanes, ventilators and windmill vanes, solar plants, swimming pools, pool covers, pool liners, closets, wardrobes, partition walls, slat walls, folding walls, roofs, shutters (e.g., roller blinds), fittings, connections between pipes, sleeves, and conveyor belts.

III-3) sanitary articles, such as tridimensional bathrooms, toilet seats, lids and sinks.

III-4) hygiene articles, such as diapers (babies, adults), feminine hygiene articles, shower curtains, brushes, mats, basins, portable toilets, toothbrushes and bed boards.

III-5) pipes for water, waste water and chemicals (crosslinked or uncrosslinked), pipes for protecting electric wires and cables, pipes for gas, oil and sewage, materials for drainage systems, sewer pipes and drainage systems.

III-6) profiles (window panes) and wall panels with any geometry.

III-7) glass substitutes, such as extruded or coextruded sheets, glazes for buildings (monolithic, double-walled or multi-walled), for aircraft, schools, extruded sheets, window films for architectural glazing, trains, transportation, sanitary and greenhouse.

III-8) boards (walls, cutting boards), extrusion-coatings (photographic paper, tetra pack and pipe coatings), basements, wood substitutes, plastic panels, wood composites, walls, surfaces, furniture, decorative foils, floor coverings (interior and exterior applications), floors, sailboards and tiles.

III-9) inlet and outlet manifolds.

III-10) applications of cement, concrete, composite materials, and coverings, siding and cladding, handrails, balustrades, kitchen worktops, roofing sheets, bricks, and rubberized canvas.

IV-1) boards (walls and cutting boards), trays, artificial turf, synthetic materials (e.g. Astro-

) Artificial coverings for sports tracks (sports), artificial floors for sports tracks (sports) and adhesive tapes.

IV-2) woven fabrics, continuous staple fibers (carpet/hygiene article/agrotextiles/monofilaments; a filter material; rags/curtains (shades)/medical applications), body fibers (applications such as gowns/protective clothing), nets, ropes, cables, strings, threads, safety seat belts, outerwear, underwear, gloves; a boot; rubber boots, underwear, clothing, swimwear, sportswear, umbrellas (parasol, canopy), parachutes, paragliders, sails, "balloon silk fabrics", camping supplies, tents, air beds, sun beds, flexible freight bags and bags. Non-woven fabrics, such as medical and related apparel, industrial apparel, outdoor fabrics, upholstery and structural fabrics.

IV-3) membranes, barriers, coverings and sealing materials for roofs, tunnels, storehouses, ponds, warehouses, wall covering membranes, agricultural membranes, swimming pools, curtains (shades)/sun-shading goods, awnings, canopies, wallpaper, food packaging and packaging (flexible and solid), medical packaging (flexible & solid), airbags/safety belts, arm-rests and head rests, carpets, center consoles, instrument panels, cockpit, doors, roof control modules, door frames, headcables, interior lighting, interior mirrors, storage panels, trunk lids, seats, steering columns, steering devices, fabrics and rear cabin trim panels.

V) films (packaging, warehouse, laminating, agriculture and horticulture (greenhouse covering, tunnels, low walk-in tunnels, high tunnels, pavement coverings, storage, silo bags, silo stretchings, fumigation, air bubbles, tent strips, sun-packs, heat packs, care products, film tubes), greenhouses, pavement coverings, tunnels, storage), wrappings, swimming pools, waste bags, wallpaper, stretch film, Raffia, desalination films, batteries and connectors. The film may have a single layer structure or a multilayer structure, for example, 3,5 or 7 layers. Examples include the film structure represented by A-B-A, A-B-C, A-B-C-B-A, A-B-C-B-D, A-B-C-D-C-B-A, A-A-B-C-B-A-A, wherein A, B, C and D represent different polymers or tackifiers. These layers may also be arranged to provide a film with an even number of layers, i.e. 2,4 or 6 layers, for example A-A-B-A, A-A-B-B, A-A-B-A-A, A-B-B-A-A, A-A-B-C-B, A-A-B-C-A-A, etc.

VI-1) food packaging and wrapping (flexible and solid), bottles.

VI-2) storage systems, such as boxes (feedboxes), luggage, cases, household cases, cots, shelves, rails, screw boxes, bags and cans.

VI-3) kits, syringes, medical devices, containers for any transport, waste baskets and waste buckets, waste bags, bins, trash cans, bin liners, wheel hoppers, conventional containers, tanks for water/waste water/chemicals/gas/oil/gasoline/diesel; can liners, boxes, feedboxes, battery boxes, sinks, medical devices such as pistons, ophthalmic applications, diagnostic devices, and blister packs for pharmaceuticals.

VII-1) extrusion coating (photographic paper, tetra pack, tube coating), any type of household item (e.g. household appliance, thermos bottle/hanger), fastening systems, such as plugs, wire and cable clamps, zippers, partitions, locks and closure snaps.

VII-2) support devices, leisure articles, such as sports and health devices, gymnastic mats, ski shoes, ice skates, skis, sports shoes, remote surfaces (for example badminton grounds); screw caps, caps and stoppers for bottles and cans.

VII-3) conventional furniture, foamed articles (cushions, impact absorbers), foams, sponges, dishcloths, mats, garden chairs, gym chairs, tables, couches, toys, assembly kits (boards/pictures/balls), playhouses, siding and playcars.

VII-4) materials for optical and magnetic data storage.

VII-5) kitchen utensils (eating, drinking, cooking, storing).

VII-6) boxes for CDs, cassettes and video tapes; DVD electronics, office supplies of any kind (ball-point pens, stamp pads, mice, shelves, music tracks), bottles of any volume and content (beverages, detergents, cosmetics, including perfumes) and adhesive tapes.

VII-7) footwear (shoes/soles), insoles, overshoes, adhesives, structural adhesives, food boxes (fruits, vegetables, meat, fish), synthetic paper, bottle labels, couches, artificial joints (human body), printing plates (offset printing), printed circuit boards and display technology.

VII-8) use in filled polymers (talc, chalk)Clay (kaolin), wollastonite, pigment, carbon black and TiO₂Mica, nanocomposite, dolomite, silicate, glass, asbestos).

In particular embodiments, the shaped article is a film, tube, profile, bottle, can, container, or fiber. Shaped articles may be prepared by molding, for example injection molding, blow molding, compression molding, rotational molding, slush molding or extrusion molding.

The methods and compositions of the present invention can provide excellent color properties and improved thermal stability of polyolefins during melt processing. Melt processing stability can be manifested in improved molecular weight retention and retention of polymer molecular structure.

The articles "a" and "an" herein mean one or more than one (e.g., at least one) of the grammatical subject matter. Any ranges mentioned herein are inclusive. The term "about" is used herein to describe and account for small fluctuations. For example, "about" can indicate that the value can be modified by 5%, ± 4%, ± 3%, ± 2%, ± 1%, ± 0.5%, ± 0.4%, ± 0.3%, ± 0.2%, ± 0.1% or ± 0.05%. All numerical values are modified by the term "about," whether or not explicitly indicated. A value modified by the term "about" includes the explicitly stated value. For example, "about 5.0" includes 5.0.

The U.S. patents, U.S. patent applications, and published U.S. patent applications referred to in this discussion are incorporated herein by reference.

All parts and percentages are by weight unless otherwise indicated. Weight percent (wt%) is based on the entire composition without any volatiles, unless otherwise specified.

Examples

The following additives AO1 is a sterically hindered phenolic antioxidant, pentaerythritol tetrakis (3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate), AO2 is octadecyl 3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate, which is a sterically hindered phenolic antioxidant, Phos1-Phos6 is an organophosphorus stabilizer, tris (2, 4-di-tert-butylphenyl) phosphite (Phos1), tris (nonylphenyl) phosphite (Phos2), bis (2, 4-di-tert-butylphenyl) pentaerythritol diphosphite (Phos3), bis (2, 4-di-tert-butyl-6-methylphenyl) ethyl phosphite (Phos4), 2' -nitrilo [ triethyltris (3, 3', 5', tetra-tert-butyl-1, 1' -biphenyl-2, 2' -diyl) phosphite ] (Phos5), bis (2, 4-di- α -cumylphenyl) pentaerythritol diphosphite (Phos4, 4-propyl) phosphite (Phos7), a mixture of dimethyl-phenyl phosphites (Phos4, 4-propyl) and Phos7 are used in the examples.

The unit of additive loading is ppm by weight (parts per million), based on the weight of the polymer. When the total amount of phosphorus (P) is listed in the formulation, the unit of this amount is also reported as ppm by weight, based on the weight of the polymer.

The color change of the polymer sheet was measured according to ASTM-313 using a DCI SF600 spectrometer with a large area viewing angle; comprises a spectrum component; 2 degree observer. The color is expressed by the Yellowness Index (YI).

Melt flow rate retention was measured from the zero pass polymer sample and the 5 th pass extrudate. The melt flow rate was measured according to ASTM-1238 on a Tinius-Olsen extrusion plastograph at 190 ℃ under 2.16 kg; the units are grams of polymer flowing from a given die in 10 minutes.

Oxidative Induction Time (OIT) is a measure of the oxidative stability of a polymer. OIT was detected with a Differential Scanning Calorimeter (DSC). Scans were collected from 50 ℃ to 190 ℃ under nitrogen using a heating rate of 10 ℃/min, switched to oxygen, and held under isothermal conditions until catastrophic oxidation occurred. The time until catastrophic oxidation began to occur was reported (as observed as a strong exotherm) in minutes.

Example 1 m-LLDPE

Cast film grade metallocene linear low density polyethylene (m-LLDPE) was formulated with the following additives.

1)500ppm of Phos 1; 24ppm of P

2)1000ppm of Phos 1; 48ppm of P

3)400ppm of Phos 1; 100ppm of benzofuranone (109); 23ppm of P

4)375ppm of Phos 1; 125ppm of benzofuranone (109); 23ppm of P

5)425ppm of Phos 1; 125ppm of benzofuranone (109); 25ppm of P

6)450ppm of Phos 2; 100ppm of benzofuranone (109); 23ppm of P

7)187ppm of Phos 3; 100ppm of benzofuranone (109); 23ppm of P

8)304ppm of Phos 4; 100ppm of benzofuranone (109); 23ppm of P

9)187ppm of Phos 5; 100ppm of benzofuranone (109); 23ppm of P

10)264ppm of Phos 6; 100ppm of benzofuranone (109); 23ppm of P

These additives are blended with the particulate polymer without any stabilizing additives. In addition to the additives listed, all formulations were blended with 250ppm AO2 and 200ppm AO 1. The fully blended formulation was melt mixed in a twin screw extruder at 210 ℃ under nitrogen. The mixed formulation was extruded several times in a single-screw extruder equipped with a Maddock mixing section at 260 ℃ with aeration. The pelletized sample of extrudate from the third pass was compression molded into a 3.2mm plaque. The results are shown below.

Example 2 blow Molding grade HMW Cr-HDPE

Blow molding grade chromium catalyzed high molecular weight high density polyethylene (HMW Cr-HDPE) with a High Load Melt Index (HLMI) of 5.5 was formulated with the following additives.

1)620ppm of Phos1

2)1250ppm of Phos1

3)375ppm of Phos 1; 125ppm of benzofuranone (109)

4)450ppm of Phos 1; 150ppm of benzofuranone (109)

5)375ppm of a 1:1 weight mixture of Phos1/Phos 6; 125ppm of benzofuranone (109)

6)375ppm of a 1:1 weight mixture of Phos1/Phos 3; 125ppm of benzofuranone (109)

These additives are blended with the particulate polymer without any stabilizing additives. All formulations were blended with 500ppm AO1 in addition to the listed additives. The fully blended formulation was melt mixed in a twin screw extruder at 210 ℃ under nitrogen. The granulated sample was compression molded into 3.2mm plaques. The results are shown below.

Example 3m-LLDPE

Blown film grade metallocene linear low density polyethylene (m-LLDPE) was formulated with the following additives.

1)500ppm of Phos 1; 24ppm of P

2)1000ppm of Phos 1; 48ppm of P

3)375ppm of Phos 1; 125ppm of benzofuranone (109); 23ppm of P

4)500ppm of Phos 2; 21ppm of P

5)1000ppm of Phos 2; 43ppm of P

6)375ppm of Phos 2; 125ppm of benzofuranone (109); 21ppm of P

7)500ppm of Phos 7; 24ppm of P

8)1000ppm of Phos 7; 48ppm of P

9)375ppm of Phos 7; 125ppm of benzofuranone (109); 22ppm of P

10)500ppm of Phos 8; 27ppm of P

11)1000ppm of Phos 8; 53ppm of P

12)375ppm of Phos 8; 125ppm benzofuranone (109); 25ppm of P

These additives are blended with the particulate polymer without any stabilizing additives. In addition to the additives listed, all formulations were blended with 500ppm zinc stearate and 500ppm AO 2. The fully blended formulation was melt mixed in a twin screw extruder at 210 ℃ under nitrogen. The mixed formulation was extruded several times in a single-screw extruder equipped with a Maddock mixing section at 260 ℃ with aeration. The pelletized sample of extrudate from the third pass was compression molded into a 3.2mm plaque. The results are shown below.

Example 4 blown film grade m-LLDPE

Blown film grade metallocene linear low density polyethylene (m-LLDPE) was formulated with the following additives.

1)500ppm AO 2; 0ppm of P

2)500ppm of Phos 1; 500ppm AO 2; 24ppm of P

3)1000ppm of Phos 1; 500ppm AO 2; 48ppm of P

4)375ppm of Phos 1; 500ppm AO 2; 125ppm of benzofuranone (109); 23ppm of P

5)450ppm of Phos 1; 500ppm AO 2; 150ppm of benzofuranone (109); 27ppm of P

6)600ppm of Phos 1; 150ppm of benzofuranone (109); 34ppm of P

7)800ppm of Phos 1; 200ppm of benzofuranone (109); 46ppm of P

These additives are blended with the particulate polymer without any stabilizing additives. All formulations were blended with 500ppm of zinc stearate in addition to the additives listed. The fully blended formulation was melt mixed in a twin screw extruder at 210 ℃ under nitrogen. The mixed formulation was extruded several times in a single-screw extruder equipped with a Maddock mixing section at 260 ℃ with aeration. The pelletized sample of extrudate from the third pass was compression molded into a 3.2mm plaque. The results are shown below.

Example 5zn-LLDPE

Blown film grade Ziegler-Natta linear low density polyethylene (zn-LLDPE) was formulated with the following additives.

1) - - - - -; 0ppm of P

2)500ppm of Phos 1; 24ppm of P

3)1000ppm of Phos 1; 48ppm of P

4)300ppm of Phos 1; 100ppm of benzofuranone (109); 18ppm of P

5)375ppm of Phos 1; 125ppm of benzofuranone (109); 23ppm of P

6)450ppm of Phos 1; 150ppm of benzofuranone (109); 27ppm of P

7)400ppm of benzofuranone (109); 15ppm of P

8)500ppm of benzofuranone (109); 19ppm of P

9)600ppm of benzofuranone (109); 22ppm of P

These additives are blended with the particulate polymer without any stabilizing additives. In addition to the additives listed, all formulations were blended with 450ppm of the 4/5 weight mixture of AO1/AO2 and 800ppm of zinc oxide. The fully blended formulation was melt mixed in a twin screw extruder at 210 ℃ under nitrogen. The mixed formulation was extruded several times in a single-screw extruder equipped with a Maddock mixing section at 260 ℃ with aeration. The pelletized sample of extrudate from the third pass was compression molded into a 3.2mm plaque. The results are shown below.

Example 6m-LLDPE

Cast film grade metallocene linear low density polyethylene (m-LLDPE) was formulated with the following additives.

1) - - - - -; 0ppm of P

2)500ppm of Phos 1; 24ppm of P

3)1000ppm of Phos 1; 48ppm of P

4)300ppm of Phos 1; 100ppm of benzofuranone (109); 18ppm of P

5)375ppm of Phos 1; 125ppm of benzofuranone (109); 23ppm of P

6)450ppm of Phos 1; 150ppm of benzofuranone (109); 27ppm of P

7)400ppm of benzofuranone (109); 15ppm of P

8)500ppm of benzofuranone (109); 19ppm of P

9)600ppm of benzofuranone (109); 22ppm of P

These additives are blended with the particulate polymer without any stabilizing additives. In addition to the additives listed, all formulations were blended with 450ppm of a 4/5 weight mixture of AO1/AO2, 300ppm of calcium stearate and 500ppm of hydrotalcite. The fully blended formulation was melt mixed in a twin screw extruder at 210 ℃ under nitrogen. The mixed formulation was extruded several times in a single-screw extruder equipped with a Maddock mixing section at 260 ℃ with aeration. The pelletized sample of extrudate from the third pass was compression molded into a 3.2mm plaque. The results are shown below.

。

Claims (24)

1. A composition, comprising:

i) a polyolefin,

ii) one or more benzofuranone compounds selected from the group consisting of formula I-p1, I-p2, I-o1, I-o2, I-m1, and I-m 2:

wherein

X and Z are independently P or P ═ O; y is^p、Y^oAnd Y^mIs oxygen or represents a covalent bond;

when Y is^p、Y^oAnd Y^mWhen is oxygen, R^1pRepresents one of the sub-formulae II-p, II-o or II-m:

R^1orepresents one of the sub-formulae II-o or II-m, R^1mRepresents the sub-formula II-m, or

R^1pAnd R^2pTogether, R^1oAnd R^2oTogether with R^1mAnd R^2mTogether represent one of the sub-formulae III, IV or V:

or R^1p、R^1oAnd R^1mIs unsubstituted or substituted by C₁-C₈Alkyl radical, C₁-C₈Alkoxy, halogen or C substituted by one phenyl group₆-C₁₀Aryl radical, C₁-C₁₈Alkyl radical, C₃-C₁₆Cycloalkyl radical, C₇-C₁₃Aralkyl radical, C₂-C₁₈Alkenyl, C interrupted by one or more oxygen atoms₂-C₃₀Alkyl, or C interrupted by a sulfur atom₂-C₁₆Alkyl radical, R^2pRepresents one of the sub-formulae II-p, II-o or II-m, R^2oRepresents one of the sub-formulae II-o or II-m, R^2mRepresents the sub-formula II-m, or R^2pAnd R^1pTogether, R^2oAnd R^1oTogether with R^2mAnd R^1mTogether represent one of the sub-formulae III, IV or V, or R^2p、R^2oAnd R^2mIs unsubstituted or substituted by C₁-C₈Alkyl radical, C₁-C₈Alkoxy, halogen or C substituted by one phenyl group₆-C₁₀Aryl radical, C₁-C₁₈Alkyl radical, C₃-C₁₆Cycloalkyl radical, C₇-C₁₃Aralkyl radical, C₂-C₁₈Alkenyl, C interrupted by one or more oxygen atoms₂-C₃₀Alkyl, or C interrupted by a sulfur atom₂-C₁₆An alkyl group; when Y is^p、Y^oAnd Y^mWhen represents a covalent bond, R^1pRepresents one of the sub-formulae II-p, II-o or II-m, R^1oRepresents one of the sub-formulae II-o or II-m, R^1mRepresents the sub-formula II-m, or R^1p、R^1oAnd R^1mIs unsubstituted or substituted by C₁-C₈Alkyl radical, C₁-C₈Alkoxy, halogen or C substituted by one phenyl group₆-C₁₀Aryl radical, C₁-C₁₈Alkyl radical, C₃-C₁₆Cycloalkyl radical, C₇-C₁₃Aralkyl radical, C₂-C₁₈Alkenyl, C interrupted by one or more oxygen atoms₂-C₃₀Alkyl, or C interrupted by a sulfur atom₂-C₁₆Alkyl radical, R^2p、R^2oAnd R^2mIs unsubstituted or substituted by C₁-C₈Alkyl radical, C₁-C₈Alkoxy, halogen or C substituted by one phenyl group₆-C₁₀Aryl, or halogen; r⁴、R⁵、R⁶And R⁷Each independently is hydrogen or C₁-C₈Alkyl radical, R^p2、R^p3、R^p5And R^p6Each independently is hydrogen or C₁-C₈Alkyl radical, R^o1、R^o2、R^o5And R^o6Each independently is hydrogen or C₁-C₈An alkyl group, a carboxyl group,

R^m1、R^m3、R^m5and R^m6Each independently is hydrogen or C₁-C₈Alkyl radical, R^a1、R^a2、R^a3And R^a4Each independently is hydrogen or C₁-C₈Alkyl radical, R^b1、R^b2、R^b3、R^b4、R^b5And R^b6Each independently is hydrogen or C₁-C₈Alkyl, and R^c1、R^c2、R^c3And R^c4Each independently is hydrogen or C₁-C₈An alkyl group, a carboxyl group,

and

iii) one or more organophosphorus stabilizers.

2. The composition of claim 1, wherein the polyolefin comprises polypropylene.

3. The composition of claim 1, wherein the polyolefin comprises polyethylene.

4. The composition of claim 1, wherein the organophosphorus stabilizer is selected from the group consisting of triphenylphosphite, diphenylalkylphosphite, phenyldialkylphosphite, tris (2, 4-di-tert-butylphenyl) phosphite, tris- (sec-butylphenyl) phosphite, tris (nonylphenyl) phosphite, trilauryl phosphite, trioctadecyl phosphite, distearylpentaerythritol diphosphite, bis (2, 4-di- α -cumylphenyl) pentaerythritol diphosphite, diisodecyl pentaerythritol diphosphite, bis (2, 4-di-tert-butylphenyl) pentaerythritol diphosphite, bis (2, 6-di-tert-butyl-4-methylphenyl) pentaerythritol diphosphite, diisodecyloxy-pentaerythritol diphosphite, bis (2, 4-di-tert-butyl-6-methylphenyl) pentaerythritol diphosphite, bis (2,4, 6-tri-tert-butylphenyl) pentaerythritol diphosphite, tristearyl sorbitol phosphate, tetrakis (2, 4-di-tert-butylphenyl) 4,4' -diphenylene-diphosphonite, 6-isooctyloxy-2, 4,8, 10-tetra-tert-butylphenyl) pentaerythritol diphosphite, tris (2, 4' -di-tert-butyl-4 ' -dimethyl-3, 5' -di-octyl) phosphite, 2, 4' -di-tert-butyl-4 ' -dimethyl-4 ' -phenyl-4 ' -dimethyl-phenyl-phosphite, 3' -di-octyl-4 ' -tetra-3 ' -dimethyl-3-o-1, 5' -phenyl-di-dimethyl-1, 4' -tetra-butyl-4 ' -dimethyl-o-phosphite, 5' -phenyl-diphenyl-4 ' -dimethyl-1, 4' -dimethyl-o-1, 4' -phenyl-diphenyl-o-2, 4' -dimethyl-1, 4' -phenyl-diphenyl-dimethyl-phosphite, 4' -dimethyl-phenyl-1, 4' -dimethyl-o-1, 4' -phenyl-dimethyl-o-phenyl-1, 4' -phenyl-diphenyl-1, 4' -dimethyl-phosphite, 4' -phenyl-o-dimethyl-o-1 ' -phenyl-1, 4' -diphenyl-phosphite, 4' -dimethyl-diphenyl-o-1, 4' -diphenyl-1, 4' -phenyl-1, 4' -dimethyl-phenyl-1, 4' -diphenyl-dimethyl-diphenyl-phenyl-diphenyl-,

5. the composition of claim 1 wherein the organophosphorus stabilizer is selected from the group consisting of tris (2, 4-di-tert-butylphenyl) phosphite, tris (nonylphenyl) phosphite, bis (2, 4-di-tert-butylphenyl) pentaerythritol diphosphite, bis (2, 4-di-tert-butyl-6-methylphenyl) ethyl phosphite, 2,2', 2 "-nitrilo [ triethyltris (3, 3', 5' -tetra-tert-butyl-1, 1' -biphenyl-2, 2' -diyl) phosphite ] and bis (2, 4-di- α -cumylphenyl) pentaerythritol diphosphite.

6. The composition of claim 1 comprising tris- (2, 4-di-tert-butylphenyl) phosphite.

7. The composition according to any one of claims 1-6, further comprising one or more compounds selected from the group consisting of sterically hindered phenolic antioxidants.

8. The composition of any one of claims 1-6, further comprising one or more hindered phenolic antioxidants selected from β - (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate.

9. The composition of any one of claims 1-6, wherein the composition is substantially free of hindered phenol antioxidants.

10. The composition of any of claims 1-6, wherein the one or more benzofuranone compounds are present in an amount of about 20 to 1000ppm by weight, based on the weight of the polyolefin.

11. The composition of any of claims 1-6, wherein the one or more organophosphorus stabilizers are present in an amount of about 20 to 1000ppm by weight, based on the weight of the polyolefin.

12. The composition of any of claims 1-6, wherein the weight/weight ratio between one or more benzofuranone compounds and one or more organophosphorus stabilizers is from about 0.05 to about 1.0.

13. The composition of any one of claims 1-6, wherein the benzofuranone compound is selected from the group consisting of formula I-p1, I-p2, and I-o 1.

14. The composition of any one of claims 1-6, wherein in the benzofuranone compound, X and Z are P, and Y is O.

15. The composition of any one of claims 1-6, wherein the benzofuranone compound is a compound of formula I-p1, I-p2, I-o1, I-o2, I-m1, or I-m2, wherein Y is^p、Y^oAnd Y^mIs oxygen or represents a covalent bond; when Y is^p、Y^oAnd Y^mWhen is oxygen, R^1pRepresents one of the sub-formulae II-p, II-o or II-m, R^1oRepresents one of the sub-formulae II-o or II-m, R^1mRepresents the sub-formula II-m, or R^1pAnd R^2pTogether, R^1oAnd R^2oTogether with R^1mAnd R^2mTogether represent one of the sub-formulae III, IV or V, or R^1p、R^1oAnd R^1mIs unsubstituted or substituted by C₁-C₈Alkyl radical, C₁-C₈Alkoxy, halogen or C substituted by one phenyl group₆-C₁₀Aryl radical, C₁-C₁₈Alkyl radical, C₃-C₁₆Cycloalkyl radical, C₇-C₁₃Aralkyl radical, C₂-Cis alkenyl, C interrupted by one or more oxygen atoms₂-C₃₀Alkyl, or C interrupted by a sulfur atom₂-C₁₆Alkyl radical, R^2pRepresents one of the sub-formulae II-p, II-o or II-m, R^2oRepresents one of the sub-formulae II-o or II-m, R^2mRepresents the sub-formula II-m, or R^2pAnd R^1pTogether, R^2oAnd R^1oTogether with R^2mAnd R^1mTogether represent one of the sub-formulae III, IV or V, or R^2p、R^2oAnd R^2mIs unsubstituted or substituted by C₁-C₈Alkyl radical, C₁-C₈Alkoxy, halogen or C substituted by one phenyl group₆-C₁₀Aryl radical, C₁-C₁₈Alkyl radical, C₃-C₁₆Cycloalkyl radical, C₇-C₁₃Aralkyl radical, C₂-C₁₈Alkenyl, C interrupted by one or more oxygen atoms₂-C₃₀Alkyl, or C interrupted by a sulfur atom₂-C₁₆An alkyl group; when Y is^p、Y^oAnd Y^mWhen represents a covalent bond, R^1pRepresents one of the sub-formulae II-p, II-o or II-m, R^1oRepresents one of the sub-formulae II-o or II-m, R^1mRepresents the sub-formula II-m, or R^1p、R^1oAnd R^1mIs unsubstituted or substituted by C₁-C₈Alkyl radical, C₁-C₈Alkoxy, halogen or C substituted by one phenyl group₆-C₁₀Aryl radical, C₁-C₁₈Alkyl radical, C₃-C₁₆Cycloalkyl radical, C₇-C₁₃Aralkyl radical, C₂-C₁₈Alkenyl, C interrupted by one or more oxygen atoms₂-C₃₀Alkyl, or C interrupted by a sulfur atom₂-C₁₆Alkyl radical, R^2p、R^2oAnd R^2mIs unsubstituted or substituted by C₁-C₈Alkyl radical, C₁-C₈Alkoxy, halogen or C substituted by one phenyl group₆-C₁₀Aryl, or halogen; r⁴And R⁶Is hydrogen, R⁵And R⁷Each independently is hydrogen or C₁-C₈Alkyl radical, R^p2And R^p6Each independently is hydrogen or C₁Alkyl radical, R^p3And R^p5Are each independently hydrogen or C₁-C₄Alkyl radical, R^o1And R^o6Each independently is hydrogen or C₁-C₈Alkyl radical, R^o2Is hydrogen or C₁Alkyl radical, R^o5Is hydrogen or C₁-C₄Alkyl radical, R^m1Is hydrogen or C₁Alkyl radical, R^m3And R^m5Each independently is hydrogen or C₁-C₄Alkyl radical, R^m6Is hydrogen or C₁-C₈Alkyl radical, R^a1、R^a2、R^a3And R^a4Each independently is hydrogen or C₁-C₄Alkyl radical, R^b1、R^b2、R^b3、R^b4、R^b5And R^b6Each independently is hydrogen or C₁-C₄Alkyl, and R^c1、R^c2、R^c3And R^c4Each independently is hydrogen or C₁-C₄An alkyl group.

16. The composition of any one of claims 1-6, wherein benzofuranone is a compound of formula I-p1, I-p2, I-o1, I-o2, I-m1, or I-m2, wherein Y^p、Y^oAnd Y^mIs oxygen or represents a covalent bond; when Y is^p、Y^oAnd Y^mWhen is oxygen, R^1pRepresents one of the sub-formulae II-p, II-o or II-m, R^1oRepresents one of the sub-formulae II-o or II-m, R^1mRepresents the sub-formula II-m, or R^1pAnd R^2pTogether, R^1oAnd R^2oTogether with R^1mAnd R^2mTogether represent one of the sub-formulae III, IV or V, or R^1p、R^1oAnd R^1mIs unsubstituted or substituted by C₁-C₈Alkyl substituted C₆-C₁₀Aryl radical, C₁-C₁₈Alkyl or C₃-C₁₆Cycloalkyl radical, and R^2pRepresents one of the sub-formulae II-p, II-o or II-m, R^2oRepresents one of the sub-formulae II-o or II-m, R^2mRepresents the sub-formula II-m, or R^2pAnd R^1pTogether, R^2oAnd R^1oTogether with R^2mAnd R^1mTogether represent one of the sub-formulae III, IV or V, or R^2p、R^2oAnd R^2mIs unsubstituted or substituted by C₁-C₈Alkyl substituted C₆-C₁₀Aryl radical, C₁-C₁₈Alkyl or C₃-C₁₆A cycloalkyl group; when Y is^p、Y^oAnd Y^mWhen represents a covalent bond, R^1pRepresents one of the sub-formulae II-p, II-o or II-m, R^1oRepresentsOne of the sub-formulae II-o or II-m, R^1mRepresents the sub-formula II-m, or R^1p、R^1oAnd R^1mIs unsubstituted or substituted by C₁-C₈Alkyl substituted C₆-C₁₀Aryl radical, C₁-C₁₈Alkyl or C₃-C₁₆Cycloalkyl radical, and R^2p、R^2oAnd R^2mIs unsubstituted or substituted by C₁-C₈Alkyl substituted C₆-C₁₀Aryl, or fluoro.

17. The composition of any one of claims 1-6, wherein benzofuranone is a compound of formula I-p1, I-p2, I-o1, or I-o2, wherein Y^pAnd Y^oIs oxygen or represents a covalent bond; when Y is^pAnd Y^oWhen is oxygen, R^1p、R^2p、R^1oOr R^2oDoes not represent sub-formula II-m; when Y is^pAnd Y^oWhen represents a covalent bond, R^1pOr R^1oDoes not represent sub-formula II-m.

18. The composition of any one of claims 1-6, wherein benzofuranone is a compound of formula I-p1, I-p2, I-o1, or I-o2, wherein Y^pAnd Y^oIs oxygen, R^1pAnd R^2pTogether with R^1oAnd R^2oTogether represent one of the sub-formulae III, IV or V, R^2pAnd R^1pTogether with R^2oAnd R^1oTogether represent one of the sub-formulae III, IV or V, R⁴、R⁵、R⁶And R⁷Each independently is hydrogen or C₁-C₈Alkyl radical, R^p2、R^p3、R^p5And R^p6Each independently is hydrogen or C₁-C₈Alkyl radical, R^o1、R^o2、R^o5And R^o6Each independently is hydrogen or C₁-C₈Alkyl radical, R^a1、R^a2、R^a3And R^a4Each independently is hydrogen or C₁-C₈Alkyl radical, R^b1、R^b2、R^b3、R^b4、R^b5And R^b6Each independently of the otherGround is hydrogen or C₁-C₈Alkyl, and R^c1、R^c2、R^c3And R^c4Each independently is hydrogen or C₁-C₈An alkyl group.

19. The composition of any one of claims 1-6, wherein benzofuranone is a compound selected from formulas (101) to (133):

20. a shaped article comprising the composition of any one of claims 1-6.

21. A method of making the shaped article of claim 20, comprising melt blending the composition.

22. An additive composition comprising ii) one or more benzofuranone compounds selected from the group consisting of formula I-p1, I-p2, I-o1, I-o2, I-m1, and I-m2 according to claim 1 and iii) one or more organophosphorus stabilizers.

23. The additive composition of claim 22, wherein the weight/weight ratio between one or more benzofuranone compounds and one or more organophosphorus stabilizers is from about 0.05 to about 1.0.

24. A method of stabilizing polyolefins against the adverse effects of heat, light and oxygen, which comprises incorporating into the polyolefin ii) one or more benzofuranone compounds of formula I-p1, I-p2, I-o1, I-o2, I-m1 and I-m2 according to claim 1 and iii) one or more organophosphorus stabilizers.