Polyolefin compositions containing substituted chroman compounds and molded articles produced therefrom
Abstract
Polyolefin compositions of a polyolefin, a chroman-based compound according to Formula (V):and a basic co-additive selected from alkali metal or alkaline metal salts of higher fatty acids are disclosed. Amounts of the chroman-based compound and the basic co-additive are selected to enhance processing stability of the polyolefin composition when subjected to extrusion, even in the absence of antistatic agents and organic phosphites and phosphonites. Masterbatch compositions of a first polyolefin, the chroman-based compound and the basic co-additive can be blended with a second polyolefin, identical to, or compatible with, the first polyolefin to form a stabilized polyolefin composition. Molded articles produced by molding the polyolefin compositions are also disclosed. R21, R22, R23, R24, R25, R26, and R27 are also described.
Claims
exact text as granted — not AI-modifiedWhat is claimed is:
1 . A polyolefin composition comprising:
(i) a polyolefin; (ii) a chroman-based compound according to Formula (V):
wherein
R 21 is chosen from —COR 28 or —Si(R 29 ) 3 , wherein R 28 is a C 1 -C 20 hydrocarbyl; and R 29 is chosen from C 1 -C 12 hydrocarbyl or alkoxy;
R 22 is a substituent that is present at from n=0 to 3 instances of the aromatic portion of Formula V and in each instance is independently chosen from H or a C 1 -C 12 hydrocarbyl;
R 23 is chosen from H or a C 1 -C 12 hydrocarbyl;
R 24 is chosen from H or a C 1 -C 20 hydrocarbyl; and
each of R 25 -R 26 is independently chosen from H, a C 1 -C 12 hydrocarbyl, and —OR 30 , wherein R 30 is chosen from H or a C 1 -C 12 hydrocarbyl; and
R 27 is H, or a bond which together with R 26 forms ═O; and
(iii) a basic co-additive selected from alkali metal or alkaline metal salts of higher fatty acids;
wherein amounts of the chroman-based compound and the basic co-additive are selected to enhance processing stability of the polyolefin composition when subjected to extrusion, even in the absence of antistatic agents and organic phosphites and phosphonites, as measured by at least one of the following properties:
improved retention of melt index (MI) after multi-pass extrusion, as measured according to ASTM D1238-10;
improved retention of percent elongation at break after single-pass extrusion; or
lower Yellowness Index after multi-pass extrusion, as measured according to ASTM E313.
2 . The polyolefin composition according to claim 1 further comprising at least one compound chosen from organic phosphites or phosphonites.
3 . A polyolefin composition according to claim 2 , wherein the at least one organic phosphite or phosphonite is chosen from:
(i) a compound according to Formulas (1)-(7):
in which the indices are integral and
n is 2, 3 or 4; p is 1 or 2; q is 2 or 3; y is 1, 2 or 3; and z is 1 to 6;
A 1 , if n or q is 2, is C 2 -C 18 alkylene; C 2 -C 12 alkylene interrupted by oxygen, sulfur or —NR 4 —; a radical of the formula
or phenylene;
A 1 , if n or q is 3, is a trivalent radical of the formula C r H 2r-1 ; wherein r is an integer from 4 to 12;
A 1 , if n is 4, is
B is a direct bond, —CH 2 —, —CHR 4 —, —CR 1 R 4 —, sulfur, C 5 -C 7 cycloalkylidene, or cyclohexylidene which is substituted by from 1 to 4 C 1 -C 4 alkyl radicals in position 3, 4 and/or 5;
D 1 , if p is 1, is C 1 -C 4 alkyl and, if p is 2, is —CH 2 OCH 2 —;
D 2 , if p is 1, is C 1 -C 4 alkyl;
E, if y is 1, is C 1 -C 18 alkyl, —OR 1 or halogen;
E, if y is 2, is —O-A 2 -O—, wherein A 2 is as defined for A 1 when n is 2;
E, if y is 3, is a radical of the formula R 4 C(CH 2 O—) 3 or N(CH 2 CH 2 O—) 3 ;
Q is the radical of an at least z-valent mono- or poly-alcohol or phenol, this radical being attached via the oxygen atom of the OH group of the mono- or poly-alcohol or phenol to the phosphorus atom;
R 1 , R 2 and R 3 independently of one another are C 1 -C 18 alkyl which is unsubstituted or substituted by halogen, —COOR 4 , —CN or —CONR 4 R 4 ; C 2 -C 18 alkyl interrupted by oxygen, sulfur or —NR 4 —; C 7 -C 9 phenylalkyl; C 5 -C 12 cycloalkyl, phenyl or naphthyl; naphthyl or phenyl substituted by halogen, 1 to 3 alkyl radicals or alkoxy radicals having a total of 1 to 18 carbon atoms or by C 7 -C 9 phenylalkyl; or a radical of the formula
in which m is an integer from the range 3 to 6;
R 4 is hydrogen, C 1 -C 8 alkyl, C 5 -C 12 cycloalkyl or C 7 -C 9 phenylalkyl,
R 5 and R 6 independently of one another are hydrogen, C 1 -C 8 alkyl or C 5 -C 6 cycloalkyl,
R 7 and R 8 , if q is 2, independently of one another are C 1 -C 4 alkyl or together are a 2,3-dehydropentamethylene radical;
R 7 and R 8 , if q is 3, are methyl;
each instance of R 14 is independently hydrogen, C 1 -C 9 alkyl or cyclohexyl;
each instance of R 15 is independently hydrogen or methyl;
X and Y are each a direct bond or oxygen;
Z is a direct bond, methylene, —C(R 16 ) 2 — or sulfur, and
R 16 is C 1 -C 8 alkyl;
(ii) a trisarylphosphite according to Formula 8:
wherein R 17 is a substituent that is present at from 0 to 5 positions of the aromatic portion of Formula 8 and in each instance is independently selected from the group consisting of C 1 -C 20 alkyl, C 3 -C 20 cycloalkyl, C 4 -C 20 alkyl cycloalkyl, C 6 -C 10 aryl, and C 7 -C 20 alkylaryl; and
(iii) combinations of (i) and (ii).
4 . A polyolefin composition according to claim 3 , wherein the organic phosphite or phosphonite is chosen from: triphenyl phosphite; diphenyl alkyl phosphites; phenyl dialkyl phosphites; trilauryl phosphite; trioctadecyl phosphite; distearyl pentaerythritol phosphite; tris(2,4-di-tert-butylphenyl) phosphite; tris(nonylphenyl) phosphite; a compound of formulae (A), (B), (C), (D), (E), (F), (G), (H), (J), (K) and (L):
2-butyl-2-ethyl-1,3-propanediol 2,4,6-tri-t-butylphenol phosphite, bis-(2,6-di-t-butyl-4-methlphenyl) pentaerythritol diphosphite, 2-butyl-2-ethyl-1,3-propanediol 2,4-di-cumylphenol phosphite, 2-butyl-2-ethyl-1,3-propanediol 4-methyl-2,6-di-t-butylphenol phosphite, or bis-(2,4,6-tri-t-butyl-phenyl) pentaerythritol diphosphite.
5 . A polyolefin composition according to claim 3 , wherein the at least one organic phosphite or phosphonite is chosen from tris(2,4-di-tert-butylphenyl)phosphite (IRGAFOS®168); bis(2,4-dicumylphenyl)pentaerythritol diphosphite (DOVERPHOS® S9228); or tetrakis(2,4-di-tert-butylphenyl)4,4′-biphenylene-diphosphonite (IRGAFOS® P-EPQ).
6 . A polyolefin composition according to claim 1 further comprising at least one hindered phenol compound.
7 . A polyolefin composition according to claim 6 , wherein the at least one hindered phenol compound comprises a molecular fragment according to one or more of Formula (IVa), (IVb), or (IVc):
wherein
R 18 of Formula (IVa), (IVb), or (IVc) is independently chosen from hydrogen or a C 1-4 hydrocarbyl;
each of R 19 and R 20 of Formula (IVa), (IVb), or (IVc) is independently chosen from hydrogen or a C 1 -C 20 hydrocarbyl; and
R 37 of Formula (IVa), (IVb), or (IVc) is independently chosen from a C 1 -C 12 hydrocarbyl.
8 . A polyolefin composition according to claim 7 , wherein each of R 18 and R 37 of Formula (IVa), (IVb), or (IVc) is independently chosen from methyl or t-butyl.
9 . A polyolefin composition according to claim 6 , wherein the at least one hindered phenol compound is selected from the group consisting of (1,3,5-tris(4-t-butyl-3-hydroxy-2,6-dimethylbenzyl)-1,3,5-triazine-2,4,6-(1H,3H,5H)-trione; 1,1,3-tris(2′-methyl-4′-hydroxy-5′-t-butylphenyl)butane; triethylene glycol bis[3-(3-t-butyl-4-hydroxy-5-methylphenyl)propionate]; 4,4′-thiobis(2-t-butyl-5-methylphenol); 2,2′-thiodiethylene bis[3-(3-t-butyl-4-hydroxyl-5-methylphenyl)propionate]; octadecyl 3-(3′-t-butyl-4′-hydroxy-5′-methylphenyl)propionate; tetrakismethylene(3-t-butyl-4-hydroxy-5-methylhydrocinnamate)methane; N,N′-hexamethylene bis[3-(3-t-butyl-4-hydroxy-5-methylphenyl)propionamide]; di(4-tertiarybutyl-3-hydroxy-2,6-dimethyl benzyl) thiodipropionate; octadecyl 3,5-di-(tert)-butyl-4-hydroxyhydrocinnamate; and mixtures thereof.
10 . A polyolefin composition according to claim 1 , wherein R 22 is present in at least one instance and is methyl.
11 . A polyolefin composition according to claim 1 , wherein R 24 is a C 1 -C 18 hydrocarbyl.
12 . A polyolefin composition according to claim 1 , wherein the chroman-based compound is vitamin E acetate according to Formula (Va)
or isomers and/or mixtures thereof.
13 . A polyolefin composition according to claim 1 , wherein the chroman-based compound is a blend of compounds comprising a chroman-based compound according to Formula (V) and another chroman-based compound.
14 . A stabilizer polyolefin composition according to claim 1 , wherein the chroman-based compound is present from 0.001 to 5.0% by weight of the total weight of the polyolefin composition.
15 . A stabilizer polyolefin composition according to claim 14 , wherein the chroman-based compound is present from 0.01 to 1.0% by weight of the total weight of the polyolefin composition.
16 . A polyolefin composition according to claim 1 further comprising an effective amount of a light stabilizer selected from the group consisting of hindered amine light stabilizers, hindered hydroxyl benzoates, nickel phenolates, ultraviolet light stabilizers, and combinations thereof.
17 . A polyolefin composition according to claim 16 , wherein the light stabilizer is a hindered amine light stabilizer compound comprising a molecular fragment according to:
(i) Formula (VI):
wherein
R 62 is selected from the group consisting of hydrogen; OH; C 1 -C 20 hydrocarbyl; —CH 2 CN; C 1 -C 12 acyl; and C 1 -C 18 alkoxy;
R 65 is selected from the group consisting of hydrogen; and C 1 -C 8 hydrocarbyl; and
each of R 60 , R 61 , R 63 , and R 64 is independently chosen from a C 1 -C 20 hydrocarbyl, or R 60 and R 61 and/or R 63 and R 64 taken together with the carbon to which they are attached form a C 5 -C 10 cycloalkyl; or
(ii) Formula (VIa)
wherein
m is an integer from 1 to 2;
R 39 is selected from the group consisting of hydrogen; OH; C 1 -C 20 hydrocarbyl; —CH 2 CN; C 1 -C 12 acyl; and C 1 -C 18 alkoxy; and
each of G 1 -G 4 is independently chosen from a C 1 -C 20 hydrocarbyl.
18 . A polyolefin composition according to claim 17 , wherein the hindered amine light stabilizer is selected from the group consisting of bis(2,2,6,6-tetramethylpiperidin-4-yl) sebacate; bis(2,2,6,6-tetramethylpiperidin-4-yl)succinate; bis(1,2,2,6,6-pentamethylpiperidin-4-yl)sebacate; bis(1-octyloxy-2,2,6,6-tetramethylpiperidin-4-yl)sebacate; bis(1,2,2,6,6-pentamethylpiperidin-4-yl) n-butyl 3,5-di-tert-butyl-4-hydroxybenzylmalonate; a condensate of 1-(2-hydroxyethyl)-2,2,6,6-tetramethyl-4-hydroxypiperidine and succinic acid; 2,2,6,6-tetramethylpiperidin-4-yl stearate; 2,2,6,6-tetramethylpiperidin-4-yl dodecanate; 1,2,2,6,6-pentamethylpiperidin-4-yl stearate; 1,2,2,6,6-pentamethylpiperidin-4-yl dodecanate; a condensate of N,N′-bis(2,2,6,6-tetramethylpiperidin-4-yl)hexamethylenediamine and 4-tert-octylamino-2,6-dichloro-1,3,5-triazine; tris(2,2,6,6-tetramethylpiperidin-4-yl) nitrilotriacetate; tetrakis(2,2,6,6-tetramethylpiperidin-4-yl)-1,2,3,4-butanetetracarboxylate; 4-benzoyl-2,2,6,6-tetramethylpiperidine; 4-stearyloxy-2,2,6,6-tetramethylpiperidine; bis(1,2,2,6,6-pentamethylpiperidyl)-2-n-butyl-2-(2-hydroxy-3,5-di-tert-butylbenzyl)malonate; 3-n-octyl-7,7,9,9-tetramethyl-1,3,8-triazaspiro[4.5]decan-2,4-dione; bis(1-octyloxy-2,2,6,6-tetramethylpiperidyl)sebacate; bis(1-octyloxy-2,2,6,6-tetramethylpiperidyl)succinate; a condensate of N,N′-bis(2,2,6,6-tetramethylpiperidin-4-yl)hexamethylenediamine and 4-morpholino-2,6-dichloro-1,3,5-triazine; 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; a condensate of 2-chloro-4,6-bis(4-n-butylamino-1,2,2,6,6-pentamethylpiperidyl)-1,3,5-triazine and 1,2-bis-(3-aminopropylamino)ethane; 8-acetyl-3-dodecyl-7,7,9,9-tetramethyl-1,3,8-triazaspiro[4.5]decane-2,4-dione; 3-dodecyl-1-(2,2,6,6-tetramethylpiperidin-4-yl)pyrrolidin-2,5-dione; 3-dodecyl-1-(1-ethanoyl-2,2,6,6-tetramethylpiperidin-4-yl)pyrrolidin-2,5-dione; 3-dodecyl-1-(1,2,2,6,6-pentamethylpiperidin-4-yl)pyrrolidine-2,5-dione; a mixture of 4-hexadecyloxy- and 4-stearyloxy-2,2,6,6-tetramethylpiperidine; a condensate of N,N′-bis(2,2,6,6-tetramethylpiperidin-4-yl)hexamethylenediamine and 4-cyclohexylamino-2,6-dichloro-1,3,5-triazine; a condensate of 1,2-bis(3-aminopropylamino)ethane, 2,4,6-trichloro-1,3,5-triazine and 4-butylamino-2,2,6,6-tetramethylpiperidine; 2-undecyl-7,7,9,9-tetramethyl-1-oxa-3,8-diaza-4-oxospiro[4.5]decane; oxo-piperanzinyl-triazines; a reaction product of 7,7,9,9-tetramethyl-2-cycloundecyl-1-oxa-3,8-diaza-4-oxospiro[4.5]decane and epichlorohydrin; tetrakis(2,2,6,6-tetramethyl-4-piperidyl) butane-1,2,3,4-tetracarboxylate; 1,2,3,4-butanetetracarboxylic acid, tetrakis(1,2,2,6,6-pentamethyl-4-piperidinyl)ester, 1,2,3,4-butanetetracarboxylic acid, 1,2,2,6,6-pentamethyl-4-piperdinyl tridecyl ester, 1,2,3,4-butanetetracarboxylic acid, 2,2,6,6-tetramethyl-4-piperidinyl tridecyl ester; 1,2,3,4-butanetetracarboxylic acid, polymer with 2,2,6,6-tetramethyl-2,4,8,10-tetraoxaspiro[5.5]-undecane-3,9-diethanol,1,2,2,6,6-pentamethyl-4-piperdinyl ester, 1,2,3,4-butanetetracarboxylic acid, polymer with 2,2,6,6-tetramethyl-2,4,8,10-tetraoxaspiro[5.5]-undecane-3,9-diethanol, 2,2,6,6-tetramethyl-4-piperdinyl ester, bis(1-undecanoxy-2,2,6,6-tetramethylpiperidin-4-yl)carbonate; 1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethyl-4-piperdinol; 1-(2-hydroxy-2-methylpropoxy)-4-octadecanoyloxy-2,2,6,6-tetramethylpiperidine; 1-(4-octadecanoyloxy-2,2,6,6-tetramethylpiperidin-1-yloxy)-2-octadecanoyloxy-2-methylpropane; 1-(2-hydroxyethyl)-2,2,6,6-tetramethyl-4-piperdinol; a reaction product of 1-(2-hydroxyethyl)-2,2,6,6-tetramethyl-4-piperdinol and dimethylsuccinate; 2,2,4,4-tetramethyl-7-oxa-3,20-diazadispiro[5.1.11.2]heneicosan-21-one; the ester of 2,2,6,6-tetramethyl-4-piperidinol with higher fatty acids; 3-dodecyl-1-(2,2,6,6-tetramethyl-4-piperidyl)pyrrolidine-2,5-dione; 1H-Pyrrole-2,5-dione, 1-octadecyl-, polymer with (1-methylethenyl)benzene and 1-(2,2,6,6-tetramethyl-4-piperidinyl)-1H-pyrrole-2,5-dione; piperazinone, 1,1′,1″-[1,3,5-triazine-2,4,6-triyltris[(cyclohexylimino)-2,1-ethanediyl]]tris[3,3,5,5-tetramethyl-; piperazinone, 1,1′,1″-[1,3,5-triazine-2,4,6-triyltris[(cyclohexylimino)-2,1-ethanediyl]]tris[3,3,4,5,5-pentamethyl-; the reaction product of 7,7,9,9-tetramethyl-2-cycloundecyl-1-oxa-3,8-diaza-4-oxospiro[4.5]decane and epichlorohydrin; the condensate of N,N′-bis(2,2,6,6-tetramethylpiperidin-4-yl)hexamethylenediamine and 4-cyclohexylamino-2,6-dichloro-1,3,5-triazine; the condensate of 1,2-bis(3-aminopropylamino)ethane, 2,4,6-trichloro-1,3,5-triazine and 4-butylamino-2,2,6,6-tetramethylpiperidine; the condensate of N,N′-bis(2,2,6,6-tetramethylpiperidin-4-yl)hexamethylenediamine and 4-morpholino-2,6-dichloro-1,3,5-triazine; the 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; the condensate of 2-chloro-4,6-bis(4-n-butylamino-1,2,2,6,6-pentamethylpiperidyl)-1,3,5-triazine and 1,2-bis-(3-aminopropylamino)ethane; 2-[(2-hydroxyethyl)amino]-4,6-bis[N-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)butylamino-1,3,5-triazine; propanedioic acid, [(4-methoxyphenyl)-methylene]-bis-(1,2,2,6,6-pentamethyl-4-piperidinyl) ester, tetrakis(2,2,6,6-tetramethylpiperidin-4-yl)-1,2,3,4-butanetetracarboxylate; benzenepropanoic acid, 3,5-bis(1,1-dimethylethyl)-4-hydroxy-, 1-[2-[3-[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]-1-oxopropoxy]ethyl]-2,2,6,6-tetramethyl-4-piperidinyl ester; N-(1-octyloxy-2,2,6,6-tetramethylpiperidin-4-yl)-N′-dodecyloxalamide; tris(2,2,6,6-tetramethylpiperidin-4-yl) nitrilotriacetate; 1,5-dioxaspiro{5,5}undecane-3,3-dicarboxylic acid, bis(1,2,2,6,6-pentamethyl-4-piperidinyl): 1,5-dioxaspiro{5,5}undecane-3,3-dicarboxylic acid, bis(2,2,6,6-tetramethyl-4-piperidinyl); the condensate of 1-(2-hydroxyethyl)-2,2,6,6-tetramethyl-4-hydroxypiperidine and succinic acid; the condensate of N,N′-bis(2,2,6,6-tetramethylpiperidin-4-yl)hexamethylenediamine and 4-tert-octylamino-2,6-dichloro-1,3,5-triazine; 1,2,3,4-butanetetracarboxylic acid, 1,2,2,6,6-pentamethyl-4-piperidinyl tridecyl ester, tetrakis(2,2,6,6-tetramethylpiperidin-4-yl)-1,2,3,4-butanetetracarboxylate; 1,2,3,4-butanetetracarboxylic acid, 2,2,6,6-tetramethyl-4-piperidinyl tridecyl ester, tetrakis(1,2,2,6,6-pentamethylpiperidin-4-yl)-1,2,3,4-butanetetracarboxylate; mixture of 2,2,4,4-tetramethyl-21-oxo-7-oxa-3.20-diazaspiro(5.1.11.2)-heneicosane-20-propanoic acid-dodecylester and 2,2,4,4-tetramethyl-21-oxo-7-oxa-3.20-diazaspiro(5.1.11.2)-heneicosane-20-propanoic acid-tetradecylester; 1H,4H,5H,8H-2,3a,4a,6,7a,8a-hexaazacyclopenta[def]fluorene-4,8-dione, hexahydro-2,6-bis(2,2,6,6-tetramethyl-4-piperidinyl)-; polymethyl[propyl-3-oxy(2′,2′,6′,6′-tetramethyl-4,4′-piperidinyl)]siloxane; polymethyl[propyl-3-oxy(1′,2′,2′,6′,6′-pentamethyl-4,4′-piperidinyl)]siloxane; copolymer of methylmethacrylate with ethyl acrylate and 2,2,6,6-tetramethylpiperidin-4-yl acrylate; copolymer of mixed C 20 to C 24 alpha-olefins and (2,2,6,6-tetramethylpiperidin-4-yl)succinimide; 1,2,3,4-butanetetracarboxylic acid, polymer with β,β,β′,β′-tetramethyl-2,4,8,10-tetraoxaspiro[5.5]undecane-3,9-diethanol, 1,2,2,6,6-pentamethyl-4-piperidinyl ester, 1,2,3,4-butanetetracarboxylic acid, polymer with β,β,β′,β′-tetramethyl-2,4,8,10-tetraoxaspiro[5.5]undecane-3,9-diethanol, 2,2,6,6-tetramethyl-4-piperidinyl ester copolymer, 1,3-benzenedicarboxamide, N,N′-bis(2,2,6,6-tetramethyl-4-piperidinyl; 1,1′-(1,10-dioxo-1,10-decanediyl)-bis(hexahydro-2,2,4,4,6-pentamethylpyrimidine; ethane diamide, N-(1-acetyl-2,2,6,6-tetramethylpiperidinyl)-N′-dodecyl; formamide, N,N′-1,6-hexanediylbis[N-(2,2,6,6-tetramethyl-4-piperidinyl); D-glucitol, 1,3:2,4-bis-O-(2,2,6,6-tetramethyl-4-piperidinylidene)-; 2,2,4,4-tetramethyl-7-oxa-3,20-diaza-21-oxo-dispiro[5.1.11.2]heneicosane; propanamide, 2-methyl-N-(2,2,6,6-tetramethyl-4-piperidinyl)-2-[(2,2,6,6-tetramethyl-4-piperidinyl)amino]-; 7-oxa-3,20-diazadispiro[5.1.11.2]heneicosane-20-propanoic acid, 2,2,4,4-tetramethyl-21-oxo-, dodecyl ester, N-(2,2,6,6-tetramethylpiperidin-4-yl)-β-aminopropionic acid dodecyl ester, N-(2,2,6,6-tetramethylpiperidin-4-yl)-N′-aminooxalamide; propanamide, N-(2,2,6,6-tetramethyl-4-piperidinyl)-3-[(2,2,6,6-tetramethyl-4-piperidinyl)amino]-; mixture of 4-hexadecyloxy- and 4-stearyloxy-2,2,6,6-tetramethylpiperidine; 3-dodecyl-1-(1,2,2,6,6-pentamethylpiperidin-4-yl)pyrrolidine-2,5-dione; 3-dodecyl-1-(1-ethanoyl-2,2,6,6-pentamethylpiperidin-4-yl)pyrrolidine-2,5-dione; bis(2,2,6,6-tetramethylpiperidin-4-yl)succinate; bis(1,2,2,6,6-pentamethylpiperidin-4-yl) n-butyl 3,5-di-tert-butyl-4-hydroxybenzylmalonate; tris(2,2,6,6-tetramethylpiperidin-4-yl) nitrilotriacetate; 1,1′-(1,2-ethanediyl)bis(3,3,5,5-tetramethylpiperazinone); 4-benzoyl-2,2,6,6-tetramethylpiperidine; 4-stearyloxy-2,2,6,6-tetramethylpiperidine; bis(1,2,2,6,6-pentamethylpiperidyl)-2-n-butyl-2-(2-hydroxy-3,5-di-tert-butylbenzyl)malonate; 3-n-octyl-7,7,9,9-tetramethyl-1,3,8-triazaspiro[4.5]decan-2,4-dione; bis(1-octyloxy-2,2,6,6-tetramethylpiperidyl)sebacate; bis(1-octyloxy-2,2,6,6-tetramethylpiperidyl)succinate; 8-acetyl-3-dodecyl-7,7,9,9-tetramethyl-1,3,8-triazaspiro[4.5]decane-2,4-dione; 3-dodecyl-1-(2,2,6,6-tetramethylpiperidin-4-yl)pyrrolidin-2,5-dione; 3-dodecyl-1-(1-ethanoyl-2,2,6,6-tetramethylpiperidin-4-yl)pyrrolidin-2,5-dione; 3-dodecyl-1-(1,2,2,6,6-pentamethylpiperidin-4-yl)pyrrolidine-2,5-dione; a mixture of 4-hexadecyloxy- and 4-stearyloxy-2,2,6,6-tetramethylpiperidine; 2-undecyl-7,7,9,9-tetramethyl-1-oxa-3,8-diaza-4-oxospiro[4.5]decane; 1,5-dioxaspiro{5,5}undecane-3,3-dicarboxylic acid, bis(2,2,6,6-tetramethyl-4-piperidinyl) and 1,5-dioxaspiro{5,5}undecane-3,3-dicarboxylic acid, bis(1,2,2,6,6-pentamethyl-4-piperidinyl); N 1 -(β-hydroxyethyl)3,3-pentamethylene-5,5-dimethylpiperazin-2-one; N 1 -tert-octyl-3,3,5,5-tetramethyl-diazepin-2-one; N 1 -tert-octyl-3,3-pentamethylene-5,5-hexamethylene-diazepin-2-one; N 1 -tert-octyl-3,3-pentamethylene-5,5-dimethylpiperazin-2-one; trans-1,2-cyclohexane-bis-(N 1 -5,5-dimethyl-3,3-pentamethylene-2-piperazinone; trans-1,2-cyclohexane-bis-(N 1 -3,3,5,5-dispiropentamethylene-2-piperazinone); N 1 -isopropyl-1,4-diazadispiro-(3,3,5,5)pentamethylene-2-piperazinone; N 1 -isopropyl-1,4-diazadispiro-3,3-pentamethylene-5,5-tetramethylene-2-piperazinone; N 1 -isopropyl-5,5-dimethyl-3,3-pentamethylene-2-piperazinone; trans-1,2-cyclohexane-bis-N 1 -(dimethyl-3,3-pentamethylene-2-piperazinone); N 1 -octyl-5,5-dimethyl-3,3-pentamethylene-1,4-diazepin-2-one; and N 1 -octyl-1,4-diazadispiro-(3,3,5,5)pentamethylene-1,5-diazepin-2-one.
19 . A polyolefin composition according to claim 16 , wherein the light stabilizer is an ultraviolet light absorber selected from the group consisting of a 2-hydroxybenzophenone compound, a 2-(2′-hydroxyphenyl)benzotriazole compound, a 2-(2′-hydroxyphenyl)-1,3,5-triazine compound, and combinations thereof.
20 . A polyolefin composition according to claim 19 , wherein the ultraviolet light absorber is a 2-(2′-hydroxyphenyl)-1,3,5-triazine compound according to Formula (VII):
wherein
each of R 34 and R 35 is independently selected from the group consisting of an optionally substituted C 6 -C 10 aryl group, a C 1 -C 10 hydrocarbyl-substituted amino, a C 1 -C 10 acyl and a C 1 -C 10 alkoxyl; and
R 36 is a substituent that is present at from 0 to 4 instances of the phenoxy portion of Formula VII and in each instance is independently selected from the group consisting of hydroxyl, a C 1 -C 12 hydrocarbyl, a C 1 -C 12 alkoxyl, a C 1 -C 12 alkoxyester, and a C 1 -C 12 acyl.
21 . A polyolefin composition according to claim 19 , wherein the 2-(2′-hydroxyphenyl)-1,3,5-triazine compound is selected from the group consisting of 4,6-bis-(2,4-dimethylphenyl)-2-(2-hydroxy-4-octyloxyphenyl)-s-triazine (Cyasorb® 1164 available from Cytec Industries Inc.); 4,6-bis-(2,4-dimethylphenyl)-2-(2,4-dihydroxyphenyl)-s-triazine; 2,4-bis(2,4-dihydroxyphenyl)-6-(4-chlorophenyl)-s-triazine; 2,4-bis[2-hydroxy-4-(2-hydroxy-ethoxy)phenyl]-6-(4-chlorophenyl)-s-triazine; 2,4-bis[2-hydroxy-4-(2-hydroxy-4-(2-hydroxy-ethoxy)phenyl]-6-(2,4-dimethylphenyl)-s-triazine; 2,4-bis[2-hydroxy-4-(2-hydroxyethoxy)phenyl]-6-(4-bromophenyl)-s-triazine; 2,4-bis[2-hydroxy-4-(2-acetoxyethoxy)phenyl]-6-(4-chlorophenyl)-s-triazine; 2,4-bis(2,4-dihydroxyphenyl)-6-(2,4-dimethylphenyl)-s-triazine; 2,4-bis(4-biphenylyl)-6-[2-hydroxy-4-[(octyloxycarbonyl)ethylideneoxy]phenyl]-s-triazine; 2,4-bis(4-biphenylyl)-6-[2-hydroxy-4-(2-ethylhexyloxy)phenyl]-s-triazine; 2-phenyl-4-[2-hydroxy-4-(3-sec-butyloxy-2-hydroxypropyloxy)phenyl]-6-[2-hydroxy-4-(3-sec-amyloxy-2-hydroxypropyloxy)phenyl]-s-triazine; 2,4-bis(2,4-dimethylphenyl)-6-[2-hydroxy-4(-3-benzyloxy-2-hydroxypropyloxy)phenyl]-s-triazine; 2,4-bis(2-hydroxy-4-n-butyloxyphenyl)-6-(2,4-di-n-butyloxyphenyl)-s-triazine; 2,4-bis(2,4-dimethylphenyl)-6-[2-hydroxy-4-(3-nonyloxy-2-hydroxypropylox-y)-5-α-cumylphenyl]-s-triazine; methylenebis-{2,4-bis(2,4-dimethylphenyl)-6-[2-hydroxy-4-(3-butyloxy-2-hydroxypropoxy)phenyl]-s-triazine}; methylene bridged dimer mixture bridged in the 3:5′, 5:5′ and 3:3′ positions in a 5:4:1 ratio; 2,4,6-tris(2-hydroxy-4-isooctyloxycarbonyliso-propylideneoxy-phenyl)-s-triazine; 2,4-bis(2,4-dimethylphenyl)-6-(2-hydroxy-4-hexyloxy-5-α-cumylphenyl)-s-triazine; 2-(2,4,6-trimethylphenyl)-4,6-bis[2-hydroxy-4-(3-butyloxy-2-hydroxypropyloxy)phenyl]-s-triazine; 2,4,6-tris[2-hydroxy-4-(3-sec-butyloxy-2-hydroxypropyloxy)-phenyl]-s-triazine; mixture of 4,6-bis-(2,4-dimethylphenyl)-2-(2-hydroxy-4-(3-dodecyloxy-2-hydroxypropoxy)phenyl)-s-triazine and 4,6-bis-(2,4-dimethylphenyl)-2-(2-hydroxy-4-(3-tridecyloxy-2-hydroxypropoxy)phenyl)-s-triazine (Tinuvin® 400 available from Ciba Specialty Chemicals Corp.); 4,6-bis-(2,4-dimethylphenyl)-2-(2-hydroxy-4(3-(2-ethylhexyloxy)-2-hydroxypropoxy)-phenyl)-s-triazine; 4,6-diphenyl-2-(4-hexyloxy-2-hydroxyphenyl)-s-triazine; and combinations thereof.
22 . A polyolefin composition according to claim 16 , wherein the light stabilizer is a hindered amine light stabilizer as defined by claim 18 , and an ultraviolet light absorber as defined by claim 21 .
23 . A polyolefin composition according to claim 1 further comprising at least one compound selected from the group consisting of:
(i) a hydroxylamine compound according to Formula (VIII):
wherein
T 1 is selected from the group consisting of an optionally substituted C 1 -C 36 hydrocarbyl, an optionally substituted C 5 -C 12 cycloalkyl, and an optionally substituted C 7 -C 9 aralkyl; and
T 2 is chosen from hydrogen or T 1 ; and
(ii) a tertiary amine oxide compound according to Formula (IX):
wherein
each of W 1 and W 2 is independently chosen from a C 6 -C 36 hydrocarbyl selected from the group consisting of a straight or branched chain C 6 -C 36 alkyl, a C 6 -C 12 aryl, a C 7 -C 36 aralkyl, a C 7 -C 36 alkaryl, a C 6 -C 36 cycloalkyl, a C 6 -C 36 alkcycloalkyl; and a C 6 -C 36 cycloalkylalkyl;
W 3 is chosen from a C 1 -C 36 hydrocarbyl selected from the group consisting of a straight or branched chain C 1 -C 36 alkyl, a C 6 -C 12 aryl, a C 7 -C 36 aralkyl, a C 7 -C 36 alkaryl, a C 5 -C 36 cycloalkyl, a C 6 -C 36 alkcycloalkyl; and a C 6 -C 36 cycloalkylalkyl;
with the proviso that at least one of W 1 , W 2 and W 3 contains a β carbon-hydrogen bond; and
wherein said alkyl, aralkyl, alkaryl, cycloalkyl, alkcycloalkyl and cycloalkylalkyl groups of W 1 , W 2 and W 3 may be interrupted by from one to sixteen groups selected from the group consisting of —O—, —S—, —SO—, —SO 2 —, —COO—, —OCO—, —CO—, —NW 4 —, —CONW 4 — and —NW 4 CO—, or wherein said alkyl, aralkyl, alkaryl, cycloalkyl, alkcycloalkyl and cycloalkylalkyl groups of W 1 , W 2 and W 3 may be substituted with from one to sixteen groups selected from the group consisting of —OW 4 , —SW 4 , —COOW 4 , —OCOW 4 , —COW 4 , —N(W 4 ) 2 , —CON(W 4 ) 2 , —NW 4 COW 4 and 5- and 6-membered rings containing the group —C(CH 3 )(CH 2 R x )NL(CH 2 R x )(CH 3 )C—; and
wherein
W 4 is chosen from hydrogen or a C 1 -C 8 alkyl;
R x is chosen from hydrogen or methyl; and
L is chosen from a C 1 -C 30 alkyl; a —C(O)R moiety, or a —OR moiety, wherein R is a C 1 -C 30 straight or branched chain alkyl group; or
wherein said alkyl, aralkyl, alkaryl, cycloalkyl, alkcycloalkyl and cycloalkylalkyl groups of W 1 , W 2 and W 3 are both interrupted and substituted by any of the groups mentioned above; and
wherein said aryl groups of W 1 , W 2 and W 3 may be substituted with from one to three substituents independently selected from the group consisting of: halogen groups, a C 1 -C 8 alkyl group, a C 1 -C 8 alkoxy group, and combinations thereof.
24 . A polyolefin composition according to claim 23 , wherein the compound according to Formula (VIII) is a N,N-dihydrocarbylhydroxylamine wherein each of T 1 and T 2 is independently selected from the group consisting of benzyl, ethyl, octyl, lauryl, dodecyl, tetradecyl, hexadecyl, heptadecyl and octadecyl; or wherein each of T 1 and T 2 is the alkyl mixture found in hydrogenated tallow amine.
25 . A polyolefin composition according to claim 24 , wherein the compound according to Formula (VIII) is a N,N-dihydrocarbylhydroxylamine selected from the group consisting of: N,N-dibenzylhydroxylamine; N,N-diethylhydroxylamine; N,N-dioctylhydroxylamine; N,N-dilaurylhydroxylamine; N,N-didodecylhydroxylamine; N,N-ditetradecylhydroxylaamine; N,N-dihexadecylhydroxylamine; N,N-dioctadecylhydroxylamine; N-hexadecyl-N-tetradecylhydroxylamine; N-hexadecyl-N-heptadecylhydroxylamine; N-hexadecyl-N-octadecylhydroxylamine; N-heptadecyl-N-octadecylhydroxylamine; and N,N-di(hydrogenated tallow)hydroxylamine.
26 . A polyolefin composition according to claim 1 further comprising at least one compound selected from the group consisting of co-additives; tocopherol compounds; nucleating agents; fillers; reinforcing agents; and polymer additives.
27 . A polyolefin composition according to claim 26 , wherein the tocopherol compound is selected from the group consisting of α-tocopherol, β-tocopherol, γ-tocopherol, δ-tocopherol, isomers thereof, related tocotrienols, and mixtures thereof.
28 . A polyolefin composition according to claim 1 , wherein a stabilizer composition comprising the chroman-based compound and the basic co-additive is present from 0.01 to 10% by weight of the total weight of the polyolefin.
29 . A polyolefin composition according to claim 1 , wherein the polyolefin is selected from the group consisting of:
i) polymers of monoolefins chosen from polypropylene, polyisobutylene, polybut-1-ene, or poly-4-methylpent-1-ene; ii) polymers of diolefins chosen from polyisoprene or polybutadiene; iii) polymers of cycloolefins chosen from cyclopentene or norbornene; iv) polyethylene chosen from optionally crosslinked polyethylene, high density polyethylene (HDPE), high density and high molecular weight polyethylene (HDPE-HMW), high density and ultrahigh molecular weight polyethylene (HDPE-UHMW), medium density polyethylene (MDPE), low density polyethylene (LDPE), linear low density polyethylene (LLDPE), very low density polyethylene (VLDPE), or ultralow density polyethylene (ULDPE); v) copolymers of the monoolefins, diolefins, or cycloolefins of any of (i) to (iv); and vi) mixtures of any of (i) to (v).
30 . A masterbatch composition comprising:
(i) a first polyolefin; (ii) a chroman-based compound according to Formula (V):
wherein:
R 21 is chosen from —COR 28 or —Si(R 29 ) 3 , wherein R 28 is a C 1 -C 20 hydrocarbyl; and R 29 is chosen from C 1 -C 12 hydrocarbyl or alkoxy;
R 22 is a substituent that is present at from n=0 to 3 instances of the aromatic portion of Formula V and in each instance is independently chosen from H or a C 1 -C 12 hydrocarbyl;
R 23 is chosen from H or a C 1 -C 12 hydrocarbyl;
R 24 is chosen from H or a C 1 -C 20 hydrocarbyl; and
each of R 25 -R 26 is independently chosen from H, a C 1 -C 12 hydrocarbyl, or —OR 30 , wherein R 30 is chosen from H or a C 1 -C 12 hydrocarbyl; and
R 27 is H, or a bond which together with R 26 forms ═O; and
(iii) a basic co-additive selected from alkali metal or alkaline metal salts of higher fatty acids;
wherein the masterbatch composition can be blended with a second polyolefin, identical to, or compatible with, the first polyolefin to form a stabilized polyolefin composition;
wherein final concentrations of the chroman-based compound and the basic co-additive in the stabilized polyolefin composition enhance processing stability of the stabilized polyolefin composition when subjected to extrusion, even in the absence of antistatic agents and organic phosphites and phosphonites, as measured by at least one of the following properties:
improved retention of melt index (MI) after multi-pass extrusion, as measured according to ASTM D1238-10;
improved retention of percent elongation at break after single-pass extrusion; or
lower Yellowness Index after multi-pass extrusion, as measured according to ASTM E313.
31 . A molded article produced by molding the polyolefin composition of claim 1 .
32 . The molded article of claim 31 , wherein the molding is performed by any of injection molding, blow molding, reel-to-reel molding, compression molding, transfer molding, dip molding, or gas assist molding.Join the waitlist — get patent alerts
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