Stabilized polyolefin composition

Claim 2

A compound selected from the group consisting of (a) a dimethyl sulfoxide complex of a compound having the structural formula: ##STR8## wherein Z is a bivalent radical having at least one C--C double bond and is selected from the group consisting of phenylene, vinylene, cyclohexenylene, cyclohexenylene substituted by a methyl group and norbornenylene; (b) a tertiary amide complex of the compound of the structural formula (I) wherein Z is a bivalent radical having at least one C--C double bond and is selected from the group consisting of phenylene, vinylene, cyclohexenylene, cyclohexenylene substituted by a methyl group and norbornenylene; (c) a compound having the structural formula: ##STR9## (d) a tertiary amide complex of the compound of structural formula (II); (e) the hydrated enol form of the compound of the structural formula (I) wherein Z is phenylene; (f) a compound having the structural formula: ##STR10## and mixtures thereof.

Claim 3

The compound according to claim 1 in which the tertiary amide forming the complex is selected from the group consisting of N-methyl-2-pyrrolidone, dimethylformamide and dimethylacetamide.

Claim 4

The compound according to claim 1 which is ##STR11##

Claim 5

The compound according to claim 1 which is N,N'-bis(phthalimido)oxamide-N-methyl-2-pyrrolidone complex.

Claim 6

The compound according to claim 1 which is N,N'-bis(4-cyclohexene-1,2-carboximido)oxamide-N-methyl-2-pyrrolidone complex.

Claim 7

The compound according to claim 1 which is N,N'-bis(phthalimido)oxamide-dimethyl sulfoxide complex.

Claim 8

The compound according to claim 1 which is N,N'-bis(phthalimido)oxamide-dimethylformamide complex.

Claim 9

The compound according to claim 1 which is N,N'-bis(phthalimido)oxamide-dimethylacetamide complex.

Claim 10

The compound according to claim 1 which is oxalic acid bis[2-(2'-carboxybenzoyl)hydrazide]-N-methyl-2-pyrrolidone complex.

Claim 11

The compound according to claim 1 which is oxalic acid bis[2-(2'-carboxybenzoyl)hydrazide].

Claim 12

The compound according to claim 1 which is N,N'-bis(isophthalimido)oxamide.

Claim 13

A process for preparing a tertiary amide complex of a compound of the formula ##STR12## wherein Z is a bivalent radical having at least one C--C double bond and is selected from the group consisting of phenylene, vinylene, cyclohexenylene, cyclohexenylene substituted by a methyl group and norbornenylene, which comprises reacting oxalic acid dihydrazide and a cyclic dicarboxylic anhydride of the formula ##STR13## wherein Z is a bivalent radical as defined above, in a molar ratio of one part oxalic acid dihydrazide to two parts cyclic dicarboxylic anhydride in the presence of a hydrocarbon/tertiary amide solvent, wherein the tertiary amide is selected from the group consisting of N-methyl-2-pyrrolidone, N,N-dimethylformamide, N,N-dimethylacetamide and N-methyl piperidone, to form a reaction mixture containing an intermediate of the formula ##STR14## wherein Z is defined as above; refluxing the reaction mixture to dehydrocyclize the intermediate of formula (V) and form the tertiary amide complex of the compound of formula (I); filtering the reaction mixture to isolate a residue which is the tertiary amide complex of the compound of formula (I) and drying the residue.

Claim 14

A process for preparing a tertiary amide complex of a compound of the formula ##STR12## wherein Z is a bivalent radical having at least one C--C double bond and is selected from the group consisting of phenylene, vinylene, cyclohexenylene, cyclohexenylene substituted by a methyl group and norbornenylene, which comprises reacting oxalic acid dihydrazide and a cyclic dicarboxylic anhydride of the formula ##STR13## wherein Z is a bivalent radical as defined above, in a molar ratio of one part oxalic acid dihydrazide to two parts cyclic dicarboxylic anhydride in the presence of a hydrocarbon/tertiary amide solvent, wherein the tertiary amide is selected from the group consisting of N-methyl-2-pyrrolidone, N,N-dimethylformamide, N,N-dimethylacetamide and N-methyl piperidone, to form a reaction mixture containing an intermediate of the formula ##STR14## wherein Z is defined as above; refluxing the reaction mixture to dehydrocyclize the intermediate of formula (V) and form the tertiary amide complex of the compound of formula (I); filtering the reaction mixture to isolate a residue which is the tertiary amide complex of the compound of formula (I) and drying the residue.

Claim 15

A process for preparing a compound of the formula ##STR15## which comprises reacting oxalic dihydrazide and phthalic anhydride in a molar ratio of 1 to 2 at about 80° C. to about 100° C. in a solvent system selected from the group consisting of glacial acetic acid and a hydrocarbon and isolating the compound of the formula (II).

Claim 16

A process for preparing a compound of the formula ##STR15## which comprises reacting oxalic dihydrazide and phthalic anhydride in a molar ratio of 1 to 2 at about 80° C. to about 100° C. in a solvent system selected from the group consisting of glacial acetic acid and a hydrocarbon and isolating the compound of the formula (II).

Claim 17

A process for preparing a tertiary amide complex of a compound of the formula ##STR16## which comprises reacting oxalic dihydrazide and phthalic anhydride in a molar ratio of 1 to 2 at about 80° c. to about 100° C. in the presence of a hydrocarbon/tertiary amide solvent and isolating the tertiary amide complex of the compound of the formula (II).

Claim 18

A process for preparing a tertiary amide complex of a compound of the formula ##STR16## which comprises reacting oxalic dihydrazide and phthalic anhydride in a molar ratio of 1 to 2 at about 80° c. to about 100° C. in the presence of a hydrocarbon/tertiary amide solvent and isolating the tertiary amide complex of the compound of the formula (II).

Claim 19

A process for preparing a compound of the formula ##STR17## which comprises hydrolyzing a tertiary amide or dimethyl sulfoxide complex of a compound of the formula ##STR18## and isolating the compound of formula (VI).

Claim 20

A process for preparing a compound of the formula ##STR17## which comprises hydrolyzing a tertiary amide or dimethyl sulfoxide complex of a compound of the formula ##STR18## and isolating the compound of formula (VI).

Claim 21

A process for preparing N,N'-bis(isophthalimido)oxamide which comprises reacting oxalic dihydrazide and phthalic anhydride in a molar ratio of 1 to 2 in a solvent system comprising a hydrocarbon and a tertiary amide at about 80° C. to about 100° C., isolating the tertiary amide complex of the intermediate of the formula: ##STR19## and dehydrocyclizing said tertiary amide complex of the intermediate at a temperature above about 200° C.

Claim 22

A process for preparing N,N'-bis(isophthalimido)oxamide which comprises reacting oxalic dihydrazide and phthalic anhydride in a molar ratio of 1 to 2 in a solvent system comprising a hydrocarbon and a tertiary amide at about 80° C. to about 100° C., isolating the tertiary amide complex of the intermediate of the formula: ##STR19## and dehydrocyclizing said tertiary amide complex of the intermediate at a temperature above about 200° C.

Claim 23

The process of claim 16, wherein the tertiary amide is N-methyl-2-pyrrolidone.

Claim 24

A composition having enhanced resistance to metal-catalyzed oxidation comprising a polyolefin having 2 to 10 carbon atoms in each olefin unit and an amount effective to impart resistance to metal-catalyzed oxidation of at least one product selected from the group consisting of (a) a dimethyl sulfoxide complex of the compound having the structural formula ##STR20## wherein Z is a bivalent radical having at least one C--C double bond and is selected from the group consisting of phenylene, vinylene, cyclohexenylene, cyclohexenylene substituted by a methyl group and norbornenylene; (b) a tertiary amide complex of the compound of the structural formula (I) wherein Z is a bivalent radical having at least one C--C double bond and is selected from the group consisting of phenylene, vinylene, cyclohexenylene, cyclohexenylene substituted by a methyl group and norbornenylene; (c) the hydrated enol form of the compound of the structural formula (I) wherein Z is phenylene; and (d) a compound having the structural formula: ##STR21## and mixtures thereof.

Claim 25

A composition having enhanced resistance to metal-catalyzed oxidation comprising a polyolefin having 2 to 10 carbon atoms in each olefin unit and an amount effective to impart resistance to metal-catalyzed oxidation of at least one product selected from the group consisting of (a) a dimethyl sulfoxide complex of the compound having the structural formula ##STR20## wherein Z is a bivalent radical having at least one C--C double bond and is selected from the group consisting of phenylene, vinylene, cyclohexenylene, cyclohexenylene substituted by a methyl group and norbornenylene; (b) a tertiary amide complex of the compound of the structural formula (I) wherein Z is a bivalent radical having at least one C--C double bond and is selected from the group consisting of phenylene, vinylene, cyclohexenylene, cyclohexenylene substituted by a methyl group and norbornenylene; (c) the hydrated enol form of the compound of the structural formula (I) wherein Z is phenylene; and (d) a compound having the structural formula: ##STR21## and mixtures thereof.

Claim 26

The composition according to claim 18 in which the product is present in the amount of from about 0.01 to about 5.0 parts per hundred parts polyolefin.

Claim 27

The composition according to claim 18 in which the polyolefin is polyethylene.

Claim 28

The composition according to claim 18 in which the polyolefin is polypropylene.

Claim 29

The composition according to claim 18 in which the polyolefin is ethylene-propylene copolymer.

Claim 30

The composition according to claim 18 which further comprises an antioxidant.

Claim 31

The composition according to claim 23 in which the antioxidant is tetrakis[methylene-3-(3',5'-di-t-butyl-4'-hydroxyphenyl)propionate]methane

Claim 32

The composition according to claim 18 which further comprises a filler.

Claim 33

The composition according to claim 25 in which the filler is selected from the group consisting of asbestos and talc.

Claim 34

A process for stabilizing polyolefins against metal-catalyzed oxidation comprising compounding a polyolefin having 2 to 10 carbon atoms in each olefin unit and an amount effective to impart resistance to metal-catalyzed oxidation of at least one product selected from the group consisting of (a) a dimethyl sulfoxide complex of the compound having the structural formula ##STR22## wherein Z is a bivalent radical having at least one C--C double bond and is selected from the group consisting of phenylene, vinylene, cyclohexenylene, cyclohexenylene substituted by a methyl group and norbornenylene; (b) a tertiary amide complex of the compound of the structural formula (I) wherein Z is a bivalent radical having at least one C--C double bond and is selected from the group consisting of phenylene, vinylene, cyclohexenylene, cyclohexenylene substituted by a methyl group and norbornenylene; (c) the hydrated enol form of the compound of the structural formula (I) wherein Z is phenylene; and (d) a compound having the structural formula: ##STR23## and mixtures thereof.

Claim 35

A process for stabilizing polyolefins against metal-catalyzed oxidation comprising compounding a polyolefin having 2 to 10 carbon atoms in each olefin unit and an amount effective to impart resistance to metal-catalyzed oxidation of at least one product selected from the group consisting of (a) a dimethyl sulfoxide complex of the compound having the structural formula ##STR22## wherein Z is a bivalent radical having at least one C--C double bond and is selected from the group consisting of phenylene, vinylene, cyclohexenylene, cyclohexenylene substituted by a methyl group and norbornenylene; (b) a tertiary amide complex of the compound of the structural formula (I) wherein Z is a bivalent radical having at least one C--C double bond and is selected from the group consisting of phenylene, vinylene, cyclohexenylene, cyclohexenylene substituted by a methyl group and norbornenylene; (c) the hydrated enol form of the compound of the structural formula (I) wherein Z is phenylene; and (d) a compound having the structural formula: ##STR23## and mixtures thereof.

Claim 36

A process for preparing N,N'-bis(isophthalimido)-oxamide which comprises reacting oxalic dihydrazide and phthalic anhydride in a molar ratio of 1 to 2 in a hydrocarbon solvent at about 80° to about 100° C., isolating the intermediate having the formula: ##STR24## and dehydrocyclizing said intermediate at a temperature above about 200° C.

Claim 37

A process for preparing N,N'-bis(isophthalimido)-oxamide which comprises reacting oxalic dihydrazide and phthalic anhydride in a molar ratio of 1 to 2 in a hydrocarbon solvent at about 80° to about 100° C., isolating the intermediate having the formula: ##STR24## and dehydrocyclizing said intermediate at a temperature above about 200° C.