Stabilized Polyolefin Compositions Comprising Benzofuranones and Hindered Amine Light Stabilizers

Abstract

Polyolefin compositions comprising i) a polyolefin, ii) one or more phosphorus-containing benzofuranone compounds and iii) one or more hindered amine light stabilizers are provided excellent protection against discoloration and enhanced thermal stability during melt processing as exhibited by improved retention of molecular weight and maintenance of polymer molecular architecture.

Claims

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-m2 ##STR00021## ##STR00022## wherein X and Z are independently P or P?O; Y.sup.p, Y.sup.o and Y.sup.m are oxygen or represent a covalent bond; when Y.sup.p, Y.sup.o and Y.sup.m are oxygen, R.sup.1p represents one of subformulae II-p, II-o or II-m ##STR00023## R.sup.1o represents one of subformulae II-o or II-m, R.sup.1m represents subformula II-m, or R.sup.1p together with R.sup.2p, R.sup.1o together with R.sup.2o and R.sup.1m together with R.sup.2m represent one of subformulae III, IV or V ##STR00024## or R.sup.1p, R.sup.1o and R.sup.1m are C.sub.6-C.sub.10-aryl, which is unsubstituted or substituted by C.sub.1-C.sub.8-alkyl, C.sub.1-C.sub.8-alkoxy, halogen or one phenyl, C.sub.1-C.sub.18-alkyl, C.sub.3-C.sub.16-cycloalkyl, C.sub.7-C.sub.13-aralkyl, C.sub.2-C.sub.18-alkenyl, C.sub.2-C.sub.30-alkyl, which is interrupted by one or more oxygen atoms, or C.sub.2-C.sub.16-alkyl, which is interrupted by one sulfur atom, R.sup.2p represents one of subformulae II-p, II-o or II-m, R.sup.2o represents one of subformulae II-o or II-m, R.sup.2m represents subformula II-m, or R.sup.2p together with R.sup.1p, R.sup.2o together with R.sup.1o and R.sup.2m together with R.sup.1m represent one of subformulae III, IV or V, or R.sup.2p, R.sup.2o and R.sup.2m are C.sub.6-C.sub.10-aryl, which is unsubstituted or substituted by C.sub.1-C.sub.8-alkyl, C.sub.1-C.sub.8-alkoxy, halogen or one phenyl, C.sub.1-C.sub.18-alkyl, C.sub.3-C.sub.16-cycloalkyl, C.sub.7-C.sub.13-aralkyl, C.sub.2-C.sub.18-alkenyl, C.sub.2-C.sub.30-alkyl, which is interrupted by one or more oxygen atoms, or C.sub.2-C.sub.16-alkyl, which is interrupted by one sulfur atom; when Y.sup.p, Y.sup.o and Y.sup.m represent a covalent bond, R.sup.1p represents one of subformulae II-p, II-o or II-m, R.sup.1o represents one of subformulae II-o or II-m, R.sup.1m represents subformula II-m, or R.sup.1p, R.sup.1o and R.sup.1m are C.sub.6-C.sub.10-aryl, which is unsubstituted or substituted by C.sub.1-C.sub.8-alkyl, C.sub.1-C.sub.8-alkoxy, halogen or one phenyl, C.sub.1-C.sub.18-alkyl, C.sub.3-C.sub.16-cycloalkyl, C.sub.7-C.sub.13-aralkyl, C.sub.2-C.sub.18-alkenyl, C.sub.2-C.sub.30-alkyl, which is interrupted by one or more oxygen atoms, or C.sub.2-C.sub.16-alkyl, which is interrupted by one sulfur atom, R.sup.2p, R.sup.2o and R.sup.2m are C.sub.6-C.sub.10-aryl, which is unsubstituted or substituted by C.sub.1-C.sub.8-alkyl, C.sub.1-C.sub.8-alkoxy, halogen or one phenyl, or halogen; R.sup.4, R.sup.5, R.sup.6 and R.sup.7 are each independently hydrogen or C.sub.1-C.sub.8-alkyl, R.sup.p2, R.sup.p3, R.sup.p5 and R.sup.p6 are each independently hydrogen or C.sub.1-C.sub.8-alkyl, R.sup.o1, R.sup.o2, R.sup.o5 and R.sup.o6 are each independently hydrogen or C.sub.1-C.sub.8-alkyl, R.sup.m1, R.sup.m3, R.sup.m5 and R.sup.m6 are each independently hydrogen or C.sub.1-C.sub.8-alkyl, R.sup.a1, R.sup.a2, R.sup.a3 and R.sup.a4 are each independently hydrogen or C.sub.1-C.sub.8-alkyl, R.sup.b1, R.sup.b2, R.sup.b3, R.sup.b4, R.sup.b5 and R.sup.b6 are each independently hydrogen or C.sub.1-C.sub.8-alkyl and R.sup.c1, R.sup.c2, R.sup.c3 and R.sup.c4 are each independently hydrogen or C.sub.1-C.sub.8-alkyl and iii) one or more hindered amine light stabilizers.

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

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

4. The composition according to claim 1, wherein the hindered amine light stabilizers are selected from the group consisting of (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-piperidyl) 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-hydroxyethyl amino-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) di-(1,2,2,6,6-pentamethylpiperidin-4-yl) p-methoxybenzylidenemalonate, (20) 2,2,6,6-tetramethylpiperidin-4-yloctadecanoate, (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-piperidyl)-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]decan-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)pyrrolidin-2,5-dione, (32) 3-dodecyl-1-(1,2,2,6,6-pentamethyl-4-piperidyl)pyrrolidine-2,5-dione, (33) N,N-bis-formyl-N,N-bis(2,2,6,6-tetramethyl-4-piperidyl)hexamethylenediamine, (33a) bis(1-undecanyloxy-2,2,6,6-tetramethylpiperidin-4-yl)carbonate, (34) 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) condensate of 1-(2-hydroxyethyl)-2,2,6,6-tetramethyl-4-hydroxypiperidine and succinic acid, (36) 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) condensate of N,N-bis(2,2,6,6-tetramethyl-4-piperidyl)-hexamethylenediamine and 4-cyclohexylamino-2,6-dichloro-1,3,5-triazine, (38) condensate of N,N-bis-(2,2,6,6-tetramethyl-4-piperidyl)hexamethylenediamine and 4-morpholino-2,6-dichloro-1,3,5-triazine, (39) 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) 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) condensate of 2-chloro-4,6-di-(4-n-butylamino-1,2,2,6,6-pentamethylpiperidyl)-1,3,5-triazine and 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) reaction product of maleic acid anhydride-C.sub.18-C.sub.22-?-olefin-copolymer with 2,2,6,6-tetramethyl-4-aminopiperidine, (45) oligomeric condensate of 4,4-hexamethylenebis(amino-2,2,6,6-tetramethylpiperidine) and 2,4-dichloro-6-[(2,2,6,6-tetramethylpiperidin-4-yl)butylamino]-s-triazine end-capped with 2-chloro-4,6-bis(dibutylamino)-s-triazine, (46) oligomeric condensate of 4,4-hexamethylenebis(amino-1,2,2,6,6-pentaamethylpiperidine) and 2,4-dichloro-6-[(1,2,2,6,6-pentaamethylpiperidin-4-yl)butylamino]-s-triazine end-capped with 2-chloro-4,6-bis(dibutylamino)-s-triazine, (47) oligomeric condensate of 4,4-hexamethylenebis(amino-1-propoxy-2,2,6,6-tetramethyl piperidine) and 2,4-dichloro-6-[(1-propoxy-2,2,6,6-tetramethylpiperidin-4-yl)butylamino]-s-triazine end-capped with 2-chloro-4,6-bis(dibutylamino)-s-triazine, (48) oligomeric condensate of 4,4-hexamethylenebis(amino-1-acyloxy-2,2,6,6-tetramethyl piperidine) and 2,4-dichloro-6-[(1-acyloxy-2,2,6,6-tetramethylpiperidin-4-yl)butylamino]-s-triazine end-capped with 2-chloro-4,6-bis(dibutylamino)-s-triazine (49) product obtained by reacting (a) with (b) where (a) is product obtained by reacting 1,2-bis(3-aminopropylamino)ethane with cyanuric chloride and (b) is (2,2,6,6-tetramethyl piperidin-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.

5. The composition according to claim 1, comprising one or more hindered amine light stabilizers selected from the group consisting of (2) bis(2,2,6,6-tetramethylpiperidin-4-yl) sebacate, (20) 2,2,6,6-tetramethylpiperidin-4-yloctadecanoate, (14) 1-(2-hydroxy-2-methylpropoxy)-4-octadecanoyloxy-2,2,6,6-tetramethylpiperidine, (33) N,N-bis-formyl-N,N-bis(2,2,6,6-tetramethyl-4-piperidyl)hexamethylenediamine, (34) 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) condensate of 1-(2-hydroxyethyl)-2,2,6,6-tetramethyl-4-hydroxypiperidine and succinic acid, (36) condensate of N,N-bis(2,2,6,6-tetramethyl-4-piperidyl)-hexamethylenediamine and 4-tert-octylamino-2,6-dichloro-1,3,5-triazine, (38) condensate of N,N-bis-(2,2,6,6-tetramethyl-4-piperidyl)hexamethylenediamine and 4-morpholino-2,6-dichloro-1,3,5-triazine, (39) condensate of N,N-bis-(1,2,2,6,6-pentamethyl-4-piperidyl)hexamethylenediamine and 4-morpholino-2,6-dichloro-1,3,5-triazine, (41) condensate of 2-chloro-4,6-di-(4-n-butylamino-1,2,2,6,6-pentamethylpiperidyI)-1,3,5-triazine and 1,2-bis-(3-aminopropylamino)ethane, (44) reaction product of maleic acid anhydride-C.sub.18-C.sub.22-?-olefin-copolymer with 2,2,6,6-tetramethyl-4-aminopiperidine, (45) oligomeric compound condensate of 4,4-hexamethylenebis(amino-2,2,6,6-tetramethyl piperidine) and 2,4-dichloro-6-[(2,2,6,6-tetramethylpiperidin-4-yl)butylamino]-s-triazine end-capped with 2-chloro-4,6-bis(dibutylamino)-s-triazine and (47) oligomeric compound condensate of 4,4-hexamethylenebis(amino-1-propoxy-2,2,6,6-tetramethylpiperidine) and 2,4-dichloro-6-[(1-propoxy-2,2,6,6-tetramethylpiperidin-4-yl)butylamino]-s-triazine end-capped with 2-chloro-4,6-bis(dibutylamino)-s-triazine and binary or ternary combinations thereof.

6. The composition according to claim 1, comprising one or more hindered amine light stabilizers selected from the group consisting of (14) 1-(2-hydroxy-2-methylpropoxy)-4-octadecanoyloxy-2,2,6,6-tetramethylpiperidine, (34) 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) condensate of 1-(2-hydroxyethyl)-2,2,6,6-tetramethyl-4-hydroxypiperidine and succinic acid, (36) condensate of N,N-bis(2,2,6,6-tetramethyl-4-piperidyl)-hexamethylenediamine and 4-tert-octylamino-2,6-dichloro-1,3,5-triazine, (41) condensate of 2-chloro-4,6-di-(4-n-butylamino-1,2,2,6,6-pentamethylpiperidyI)-1,3,5-triazine and 1,2-bis-(3-aminopropylamino)ethane, (45) oligomeric compound condensate of 4,4-hexamethylenebis(amino-2,2,6,6-tetramethyl piperidine) and 2,4-dichloro-6-[(2,2,6,6-tetramethylpiperidin-4-yl)butylamino]-s-triazine end-capped with 2-chloro-4,6-bis(dibutylamino)-s-triazine and (47) oligomeric compound condensate of 4,4-hexamethylenebis(amino-1-propoxy-2,2,6,6-tetramethylpiperidine) and 2,4-dichloro-6-[(1-propoxy-2,2,6,6-tetramethylpiperidin-4-yl)butylamino]-s-triazine end-capped with 2-chloro-4,6-bis(dibutylamino)-s-triazine and binary or ternary combinations thereof.

7. The composition according to claim 1, wherein the composition comprises essentially no hindered phenolic antioxidants.

8. The composition according to claim 1, further comprising one or more compounds selected from the group consisting of organophosphorus stabilizers.

9. The composition according to claim 1, wherein the one or more benzofuranone compounds are present from about 20 ppm to about 1000 ppm by weight, based on the weight of the polyolefin.

10. The composition according to claim 1, wherein the one or more hindered amine light stabilizers are present from about 20 ppm to about 1000 ppm by weight, based on the weight of the polyolefin.

11. The composition according to claim 1, wherein a weight/weight ratio of the one or more benzofuranone compounds to the one or more hindered amine light stabilizers is from about 0.05 to about 1.0.

12. The composition according to claim 1, wherein the benzofuranone compounds are selected from the group consisting of formula I-p1, I-p2 and I-01.

13. The composition according to claim 1, wherein in the benzofuranone compounds, X and Z are P and Y is O.

14. The composition according to claim 1, wherein the benzofuranone compounds are formula I-p1, I-p2, I-o1, I-o2, I-m1 or I-m2, wherein YP, rand Ym are oxygen or represent a covalent bond; when Y.sup.p, Y.sup.o and Y.sup.m are oxygen, R.sup.1p represents one of subformulae II-p, II-o or II-m, R.sup.1o represents one of subformulae II-o or II-m, R.sup.1m represents subformula II-m, or R.sup.1p together with R.sup.2p, R.sup.1o together with R.sup.2o and R.sup.1m together with R.sup.2m represent one of subformulae III, IV or V, or R.sup.1p, R.sup.1o and R.sup.1m are C.sub.6-C.sub.10-aryl, which is unsubstituted or substituted by C.sub.1-C.sub.8-alkyl, C.sub.1-C.sub.8-alkoxy, halogen or one phenyl, C.sub.l-C.sub.18-alkyl, C.sub.3-C.sub.16-cycloalkyl, C.sub.7-C.sub.13-aralkyl, C.sub.2-Cis-alkenyl, C.sub.2-C.sub.30-alkyl, which is interrupted by one or more oxygen atoms, or C.sub.2-C.sub.16-alkyl, which is interrupted by one sulfur atom, R.sup.2p represents one of subformulae II-p, II-o or II-m, R.sup.2o represents one of subformulae II-o or II-m, R.sup.2m represents subformula II-m, or R.sup.2p together with R.sup.1p, R.sup.2o together with R.sup.1o and R.sup.2m together with R.sup.1m represent one of subformulae III, IV or V, or R.sup.2p, R.sup.2o and R.sup.2m are C.sub.6-C.sub.10-aryl, which is unsubstituted or substituted by C.sub.1-C.sub.8-alkyl, C.sub.1-C.sub.8-alkoxy, halogen or one phenyl, C.sub.1-C.sub.18-alkyl, C.sub.3-C.sub.16-cycloalkyl, C.sub.7-C.sub.13-aralkyl, C.sub.2-C.sub.18-alkenyl, C.sub.2-C.sub.30-alkyl, which is interrupted by one or more oxygen atoms, or C.sub.2-C.sub.16-alkyl, which is interrupted by one sulfur atom; when Y.sup.p, Y.sup.o and Y.sup.m represent a covalent bond, R.sup.1p represents one of subformulae II-p, II-o or II-m, R.sup.1o represents one of subformulae II-o or II-m, R.sup.1m represents subformula II-m, or R.sup.1p, R.sup.1o and R.sup.1m are C.sub.6-C.sub.10-aryl, which is unsubstituted or substituted by C.sub.1-C.sub.8-alkyl, C.sub.1-C.sub.8-alkoxy, halogen or one phenyl, C.sub.1-C.sub.18-alkyl, C.sub.3-C.sub.16-cycloalkyl, C.sub.7-C.sub.13-aralkyl, C.sub.2-C.sub.18-alkenyl, C.sub.2-C.sub.30-alkyl, which is interrupted by one or more oxygen atoms, or C.sub.2-C.sub.16-alkyl, which is interrupted by one sulfur atom, R.sup.2p, R.sup.2o and R.sup.2m are C.sub.6-C.sub.10-aryl, which is unsubstituted or substituted by C.sub.1-C.sub.8-alkyl, C.sub.1-C.sub.8-alkoxy, halogen or one phenyl, or halogen; R.sup.4 and R.sup.6 are hydrogen, R.sup.5 and R.sup.7 are each independently hydrogen or C.sub.1-C.sub.8-alkyl, R.sup.p2 and R.sup.p6 are each independently hydrogen or C.sub.l-alkyl, R.sup.p3 and R.sup.p5 are each independently hydrogen or C.sub.1-C.sub.4-alkyl, R.sup.o1 and R.sup.o6 are each independently hydrogen or C.sub.1-C.sub.8-alkyl, R.sup.o2 is hydrogen or C.sub.l-alkyl, R.sup.o5 is hydrogen or C.sub.1-C.sub.4-alkyl, R.sup.m1 is hydrogen or C.sub.1-alkyl, R.sup.m3 and R.sup.m5 are each independently hydrogen or C.sub.1-C.sub.4-alkyl, R.sup.m6 is hydrogen or C.sub.1-C.sub.8-alkyl, R.sup.a1, R.sup.a2, R.sup.a3 and R.sup.a4 are each independently hydrogen or C.sub.1-C.sub.4-alkyl, R.sup.b1, R.sup.b2, R.sup.b3, R.sup.b4, R.sup.b5 and R.sup.b6 are each independently hydrogen or C.sub.1-C.sub.4-alkyl and R.sup.c1, R.sup.c2, R.sup.c3 and R.sup.c4 are each independently hydrogen or C.sub.1-C.sub.4-alkyl.

15. The composition according to claim 1, wherein the benzofuranones are of formula I-p1, I-p2, I-o1, I-o2, I-m1 or I-m2, wherein Y.sup.p, Y.sup.o and Y.sup.m are oxygen or represent a covalent bond; when Y.sup.p, Y.sup.o and Y.sup.m are oxygen, R.sup.1p represents one of subformulae II-p, II-o or II-m, R.sup.1o represents one of subformulae II-o or II-m, R.sup.1m represents subformula II-m, or R.sup.1p together with R.sup.2p, R.sup.1o together with R.sup.2o and R.sup.1m together with R.sup.2m represent one of subformulae III, IV or V, or R.sup.1p, R.sup.1o and R.sup.1m are C.sub.6-C.sub.10-aryl, which is unsubstituted or substituted by C.sub.1-C.sub.8-alkyl, C.sub.1-C.sub.18-alkyl or C.sub.3-C.sub.16-cycloalkyl and R.sup.2p represents one of subformulae II-p, II-o or II-m, R.sup.2o represents one of subformulae II-o or II-m, R.sup.2m represents subformula II-m, or R.sup.2p together with R.sup.1p, R.sup.2o together with R.sup.1o and R.sup.2m together with R.sup.1m represent one of subformulae III, IV or V, or R.sup.2p, R.sup.2o and R.sup.2m are C.sub.6-C.sub.10-aryl, which is unsubstituted or substituted by C.sub.1-C.sub.8-alkyl, C.sub.1-C.sub.18-alkyl or C.sub.3-C.sub.16-cycloalkyl; when Y.sup.p, Y.sup.o and Y.sup.m represent a covalent bond, R.sup.1p represents one of subformulae II-p, II-o or II-m, R.sup.1o represents one of subformulae II-o or II-m, R.sup.1m represents subformula II-m, or R.sup.1p, R.sup.1o and R.sup.1m are C.sub.6-C.sub.10-aryl, which is unsubstituted or substituted by C.sub.1-C.sub.8-alkyl, C.sub.1-C.sub.18-alkyl or C.sub.3-C.sub.16-cycloalkyl and R.sup.2p, R.sup.2o and R.sup.2m are C.sub.6-C.sub.10-aryl, which is unsubstituted or substituted by C.sub.1-C.sub.8-alkyl or fluoro.

16. The composition according to claim 1, wherein the benzofuranones are of formula I-p1, I-p2, I-o1 or I-o2, wherein Y.sup.p and Y.sup.o are oxygen or represent a covalent bond; when Y.sup.p and Y.sup.o are oxygen, R.sup.1p, R.sup.2p, R.sup.1o or R.sup.2o does not represent subformula II-m; when Y.sup.p and Y.sup.o represent a covalent bond, R.sup.1p or R.sup.1o does not represent subformula II-m.

17. The composition according to claim 1, wherein the benzofuranones are of formula I-p1, I-p2, I-o1 or I-o2, wherein Y.sup.p and Y.sup.o rare oxygen, R.sup.1p together with R.sup.2p and R.sup.1o together with R.sup.2o represent one of subformulae III, IV or V, R.sup.2p together with R.sup.1p and R.sup.2o together with R.sup.1o represent one of subformulae III, IV or V, R.sup.4, R.sup.5, R.sup.6 and R.sup.7 are each independently hydrogen or C.sub.1-C.sub.8-alkyl, R.sup.p2, R.sup.p3, R.sup.p5 and R.sup.p6 are each independently hydrogen or C.sub.1-C.sub.8-alkyl, R.sup.o1, R.sup.o2, R.sup.o5 and R.sup.o6 are each independently hydrogen or C.sub.1-C.sub.8-alkyl, R.sup.a1, R.sup.a2, R.sup.a3 and R.sup.a4 are each independently hydrogen or C.sub.1-C.sub.8-alkyl, R.sup.b1, R.sup.b2, R.sup.b3, R.sup.b4, R.sup.b5 and R.sup.b6 are each independently hydrogen or C.sub.1-C.sub.8-alkyl and R.sup.c1, R.sup.c2, R.sup.c3 and R.sup.c4 are each independently hydrogen or C.sub.1-C.sub.8-alkyl.

18. The composition according to claim 1, wherein the benzofuranones are selected from the group consisting of compounds of formula (101)-(133) ##STR00025## ##STR00026## ##STR00027## ##STR00028## ##STR00029## ##STR00030## ##STR00031## ##STR00032## ##STR00033##

19. The composition according to claim 1, comprising one or more additives selected from the group consisting of ultraviolet light absorbers.

20. A shaped article comprising the composition according to claim 1.

21. A method of preparing the shaped article according to claim 20, the method 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 of claim 1 and iii) one or more hindered amine light stabilizers.

23. The additive composition according to claim 22, wherein a weight/weight ratio of the one or more benzofuranone compounds to the one or more hindered amine light stabilizers is from about 0.05 to about 1.0.

24. A method of stabilizing a polyolefin against deleterious effects of heat, light and oxygen, the method comprising 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 of claim 1 and iii) one or more hindered amine light stabilizers.

Description

EXAMPLES

[0224] The following additives are employed in the Examples: AO1 is a hindered phenolic antioxidant, pentaerythritol tetrakis(3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate); AO2 is a hindered phenolic antioxidant, octadecyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propanoate; AO3 is a hindered phenolic antioxidant, the calcium salt of the monoethyl ester of 3,5-di-tert-butyl-4-hydroxybenzylphosphonic acid; Phos1 is an organophosphorus stabilizer tris(2,4-di-tert-butylphenyl) phosphite; the hindered amine light stabilizers (HALS) and the benzofuranone stabilizers are as labelled herein and above.

[0225] Additive loadings are in ppm (parts per million) by weight, based on the weight of the polymer. Where total amount of phosphorus (P) is listed with the formulations, this is also reported in ppm by weight, based on the weight of the polymer.

[0226] Polymer plaques are tested for color development according to ASTM-313 with a DCI SF600 spectrophotometer; large area view; spectral component included; 2 degree observer. Color is expressed as yellowness index (YI).

[0227] Melt flow rate retentions are determined for polymer samples from the zero pass and fifth pass extrudate. Melt flow rate is performed according to ASTM-1238 on a Tinius-Olsen Extrusion Plastometer at 190? C.; 2.16 kg; measured in grams of polymer that flow out of a defined orifice in 10 minutes.

[0228] Oxidative Induction Time (OIT) is a measure of oxidative stability of the polymer. OIT is measured with a differential scanning calorimeter (DSC). Scans are collected using a heating rate of 10? C./minute under nitrogen from 50? C. to 190? C., switching to oxygen and holding at isothermal conditions until catastrophic oxidation. Time to onset of catastrophic oxidation (observed as a strong exotherm) is reported in minutes.

Example 1

Fiber Grade zn-Polypropylene

[0229] Fiber grade Ziegler-Natta polypropylene homopolymer (zn-PP) is formulated with additives listed below.

[0230] 1) 500 ppm Phos1; 500 ppm AO1; 24 ppm P

[0231] 2) 1000 ppm Phos1; 500 ppm AO1; 48 ppm P

[0232] 3) 1000 ppm Phos1; 500 ppm HALS (45); 43 ppm P

[0233] 4) 625 ppm Phos1; 500 ppm HALS (45); 125 ppm benzofuranone (109); 21 ppm P

[0234] 5) 625 ppm Phos1; 500 ppm HALS (45); 125 ppm benzofuranone (113); 22 ppm P

[0235] 6) 625 ppm Phos1; 500 ppm HALS (45); 125 ppm benzofuranone (105); 23 ppm P

[0236] 7) 625 ppm Phos1; 500 ppm HALS (36); 125 ppm benzofuranone (109); 21 ppm P

[0237] 8) 625 ppm Phos1; 500 ppm HALS (41); 125 ppm benzofuranone (109); 21 ppm P

[0238] 9) 625 ppm Phos1; 500 ppm HALS (35); 125 ppm benzofuranone (109); 21 ppm P

[0239] 10) 625 ppm Phos1; 500 ppm HALS (14); 125 ppm benzofuranone (109); 22 ppm P

[0240] 11) 625 ppm Phos1; 500 ppm HALS (34); 125 ppm benzofuranone (109); 21 ppm P

[0241] 12) 625 ppm Phos1; 500 ppm HALS (47); 125 ppm benzofuranone (109); 22 ppm P

[0242] Additives are blended with granular polymer free of any stabilization additives. In addition to the additives listed, all formulations are blended with 600 ppm calcium stearate. Thoroughly blended formulations are melt compounded in a twin screw extruder at 210? C. under nitrogen. The compounded formulations are extruded multiple times in a single screw extruder fitted with a Maddock mixing section at 260? C., open to air. Pelletized samples of the third pass extrudate are compression molded into 3.2 mm plaques. Results are below.

TABLE-US-00001 melt flow melt flow formulation YI (zero pass) (fifth pass) OIT 1 7.1 14.76 25.48 13 2 6.6 14.15 21.50 19 3 4.8 15.46 37.32 6 4 6.7 14.65 21.53 7 5 13.3 14.51 19.96 6 6 16.0 15.21 19.79 6 7 5.5 15.38 28.94 6 8 5.4 15.61 26.45 8 9 6.1 14.70 23.84 3 10 8.8 15.04 25.24 4 11 8.0 15.17 22.95 4 12 10.3 13.95 18.98 7

Example 2

Blown Film Grade m-LLDPE

[0243] Blown film grade metallocene linear low density polyethylene (m-LLDPE) is formulated with additives listed below.

[0244] 1) 500 ppm AO2; 0 ppm P

[0245] 2) 500 ppm Phos1; 500 ppm AO2; 24 ppm P

[0246] 3) 1000 ppm Phos1; 500 ppm AO2; 48 ppm P

[0247] 4) 375 ppm Phos1; 500 ppm AO2; 125 ppm benzofuranone (109); 23 ppm P

[0248] 5) 450 ppm Phos1; 500 ppm AO2; 150 ppm benzofuranone (109); 27 ppm P

[0249] 6) 600 ppm Phos1; 150 ppm benzofuranone (109); 34 ppm P

[0250] 7) 800 ppm Phos1; 200 ppm benzofuranone (109); 46 ppm P

[0251] Additives are blended with granular polymer free of any stabilization additives. In addition to the additives listed, all formulations are blended with 500 ppm zinc stearate. Thoroughly blended formulations are melt compounded in a twin screw extruder at 210? C. under nitrogen. The compounded formulations are extruded multiple times in a single screw extruder fitted with a Maddock mixing section at 260? C., open to air. Pelletized samples of the third pass extrudate are compression molded into 3.2 mm plaques. Results are below.

TABLE-US-00002 formulation YI OIT 1 0.6 22 2 0.6 29 3 0.2 42 4 1.3 85 5 0.7 101 6 ?0.6 8 7 ?0.5 10

Example 3

Blown Film Grade m-LLDPE

[0252] Blown film grade metallocene linear low density polyethylene (m-LLDPE) is formulated with additives listed below.

[0253] 1) 500 ppm Phos1; 500 ppm AO1

[0254] 2) 500 ppm Phos1; 1000 ppm AO1

[0255] 3) 1000 ppm Phos1; 500 ppm HALS (45)

[0256] 4) 650 ppm Phos1; 500 ppm HALS (45); 125 ppm benzofuranone (109)

[0257] 5) 650 ppm Phos1; 500 ppm HALS (45); 125 ppm benzofuranone (113)

[0258] 6) 650 ppm Phos1; 500 ppm HALS (45); 125 ppm benzofuranone (105)

[0259] 7) 650 ppm Phos1; 500 ppm HALS (36); 125 ppm benzofuranone (109)

[0260] 8) 650 ppm Phos1; 500 ppm HALS (41); 125 ppm benzofuranone (109)

[0261] 9) 650 ppm Phos1; 500 ppm HALS (35); 125 ppm benzofuranone (109)

[0262] 10) 650 ppm Phos1; 500 ppm HALS (14); 125 ppm benzofuranone (109)

[0263] 11) 650 ppm Phos1; 500 ppm HALS (34); 125 ppm benzofuranone (109)

[0264] 12) 650 ppm Phos1; 500 ppm HALS (47); 125 ppm benzofuranone (109)

[0265] Additives are blended with granular polymer free of any stabilization additives. Thoroughly blended formulations are melt compounded in a twin screw extruder at 210? C. under nitrogen. The compounded formulations are extruded multiple times in a single screw extruder fitted with a Maddock mixing section at 260? C., open to air. Pelletized samples of the third pass extrudate are compression molded into 3.2 mm plaques. Results are below.

TABLE-US-00003 melt flow melt flow formulation YI (zero pass) (fifth pass) OIT 1 3.0 3.77 3.24 83 2 3.3 3.76 3.50 118 3 2.2 3.71 2.15 31 4 1.3 3.69 2.55 27 5 2.8 3.68 2.89 34 6 1.8 3.68 2.71 28 7 1.9 3.65 2.33 28 8 1.3 3.55 1.96 46 9 2.9 3.62 2.68 15 10 2.5 3.68 3.12 19 11 5.0 3.66 3.41 37 12 4.1 3.67 3.28 42

Example 4

Blown Film Grade zn-LLDPE

[0266] Blown film grade Ziegler-Natta linear low density polyethylene (zn-LLDPE) is formulated with additives listed below. [0267] 1) 500 ppm Phos1; 450 ppm of a 4/5 weight ratio of A01/AO2; 24 ppm P [0268] 2) 1000 ppm Phos1; 450 ppm of a 4/5 weight ratio of A01/AO2; 48 ppm P [0269] 3) 413 ppm Phos1; 450 ppm of a 4/5 weight ratio of A01/AO2; 138 ppm benzofuranone (109); 20 ppm P [0270] 4) 413 ppm Phos1; 450 ppm AO3; 138 ppm benzofuranone (109); 25 ppm P [0271] 5) 800 ppm Phos1; 200 ppm benzofuranone (109); 38 ppm P [0272] 6) 750 ppm Phos1; 250 ppm benzofuranone (109); 36 ppm P [0273] 7) 670 ppm Phos1; 330 ppm benzofuranone (109); 32 ppm P [0274] 8) 500 ppm Phos1; 500 ppm benzofuranone (109); 43 ppm P [0275] 9) 800 ppm Phos1; 200 ppm benzofuranone (109); 250 ppm HALS (35); 38 ppm P [0276] 10) 750 ppm Phos1; 250 ppm benzofuranone (109); 250 ppm HALS (35); 36 ppm P [0277] 11) 670 ppm Phos1; 330 ppm benzofuranone (109); 250 ppm HALS (35); 32 ppm P [0278] 12) 500 ppm Phos1; 500 ppm benzofuranone (109); 250 ppm HALS (35); 43 ppm P

[0279] Additives are blended with granular polymer free of any stabilization additives. In addition to the additives listed, all formulations are blended with 840 ppm zinc oxide. Thoroughly blended formulations are melt compounded in a twin screw extruder at 210? C. under nitrogen. The compounded formulations are extruded multiple times in a single screw extruder fitted with a Maddock mixing section at 260? C., open to air. Pelletized samples of the third pass extrudate are compression molded into 3.2 mm plaques. Results are below.

TABLE-US-00004 melt flow melt flow formulation YI (zero pass) (fifth pass) OIT 1 3.5 2.00 1.49 67 2 3.9 2.00 1.77 106 3 3.3 2.04 1.69 128 4 1.3 2.05 1.66 46 5 2.0 2.04 1.29 9 6 4.1 2.08 1.43 11 7 3.3 1.97 1.53 12 8 3.3 2.02 1.62 19 9 3.5 1.97 1.19 21 10 2.6 2.06 1.25 23 11 3.2 2.07 1.52 24 12 4.0 1.96 1.65 31