Stabilizer Compositions Containing Substituted Chroman Compounds and Methods of Use
First Claim
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1. A stabilizer composition comprising a stabilizing amount of a chroman-based compound according to Formula (V):
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Abstract
Stabilizer compositions having a chroman-based compound according to Formula (V):
and their use in processes for stabilizing organic materials subject to degradation and/or discoloration due to the effects from light, oxygen and heat, and in processes for producing articles from organic materials blended therewith, are provided herein.
18 Citations
35 Claims
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1. A stabilizer composition comprising a stabilizing amount of a chroman-based compound according to Formula (V):
- View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35)
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2. A stabilizer composition according to claim 1 further comprising at least one compound chosen from the group of organic phosphites or phosphonites.
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3. A stabilizer composition according to claim 2, wherein the at least one organic phosphite or phosphonite is chosen from a compound according to Formulas 1-7:
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4. A stabilizer 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);
- triphenyl phosphite;
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5. A stabilizer 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); and
tetrakis(2,4-di-tert-butylphenyl)4,4′
-biphenylene-diphosphonite (IRGAFOS®
P-EPQ).
- 168);
-
6. A stabilizer composition according to claim 1 further comprising at least one hindered phenol compound.
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7. A stabilizer 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):
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8. A stabilizer composition according to claim 7, wherein each of R18 and R37 is independently chosen from methyl or t-butyl.
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9. A stabilizer composition according to claim 6, wherein the at least one hindered phenol compound is chosen from a member 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; and
octadecyl 3,5-di-(tert)-butyl-4-hydroxyhydrocinnamate.
- 1,1,3-Tris(2′
-
10. A stabilizer composition according to claim 1, wherein R22 is present in at least one instance and is methyl.
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11. A stabilizer composition according to claim 1, wherein R24 is a C1-C18 hydrocarbyl.
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12. A stabilizer composition according to claim 1, wherein the chroman-based compound is vitamin E acetate according to Formula (Va)
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13. A stabilizer 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.
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14. A stabilizer 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 stabilizer composition.
-
15. A stabilizer 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 stabilizer composition.
-
16. A stabilizer composition according to claim 1 further comprising an effective amount of a light stabilizer chosen from a member selected from the group consisting of hindered amine light stabilizers, hindered hydroxyl benzoates, nickel phenolates, ultraviolet light stabilizers, and combinations thereof.
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17. A stabilizer composition according to claim 16, wherein the light stabilizer is a hindered amine light stabilizer compound comprising a molecular fragment according to Formula (VI):
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18. A stabilizer composition according to claim 16, wherein the hindered amine light stabilizer is chosen from a member 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-piperidinyl 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-piperidinyl 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-piperidinyl ester;
bis(1-undecanoxy-2,2,6,6-tetramethylpiperidin-4-yl)carbonate;
1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethyl-4-piperidinol;
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-piperidinol;
a reaction product of 1-(2-hydroxyethyl)-2,2,6,6-tetramethyl-4-piperidinol 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 C20 to C24 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);
N1-(β
-hydroxyethyl)3,3-pentamethylene-5,5-dimethylpiperazin-2-one;
N1-tert-octyl-3,3,5,5-tetramethyl-diazepin-2-one;
N1-tert-octyl-3,3-pentamethylene-5,5-hexamethylene-diazepin-2-one;
N1-tert-octyl-3,3-pentamethylene-5,5-dimethylpiperazin-2-one;
trans-1,2-cyclohexane-bis-(N1-5,5-dimethyl-3,3-pentamethylene-2-piperazinone;
trans-1,2-cyclohexane-bis-(N1-3,3,5,5-dispiropentamethylene-2-piperazinone);
N1-isopropyl-1,4-diazadispiro-(3,3,5,5)pentamethylene-2-piperazinone;
N1-isopropyl-1,4-diazadispiro-3,3-pentamethylene-5,5-tetramethylene-2-piperazinone;
N1-isopropyl-5,5-dimethyl-3,3-pentamethylene-2-piperazinone;
trans-1,2-cyclohexane-bis-N1-(dimethyl-3,3-pentamethylene-2-piperazinone);
N1-octyl-5,5-dimethyl-3,3-pentamethylene-1,4-diazepin-2-one; and
N1-octyl-1,4-diazadispiro-(3,3,5,5)pentamethylene-1,5-diazepin-2-one.
- bis(2,2,6,6-tetramethylpiperidin-4-yl)succinate;
-
19. A stabilizer composition according to claim 16, wherein the light stabilizer is an ultraviolet light absorber chosen from a member 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.
- -hydroxyphenyl)benzotriazole compound, a 2-(2′
-
20. A stabilizer composition according to claim 19, wherein the ultraviolet light absorber is a 2-(2′
- -hydroxyphenyl)-1,3,5-triazine compound according to Formula (VII);
- -hydroxyphenyl)-1,3,5-triazine compound according to Formula (VII);
-
21. A stabilizer composition according to claim 19, wherein the 2-(2′
- -hydroxyphenyl)-1,3,5-triazine compound is chosen from a member 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-a-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.
- -hydroxyphenyl)-1,3,5-triazine compound is chosen from a member selected from the group consisting of 4,6-bis-(2,4-dimethylphenyl)-2-(2-hydroxy-4-octyloxyphenyl)-s-triazine (Cyasorb®
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22. A stabilizer composition according to claim 16, wherein the light stabilizer comprises a hindered amine light stabilizer and an ultraviolet light absorber.
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23. A stabilizer composition according to claim 1 further comprising at least one compound chosen from a member selected from the group consisting of:
a hydroxylamine compound according to Formula (VIII);
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24. A stabilizer composition according to claim 23, wherein the compound according to Formula (VIII) is a N,N-dihydrocarbylhydroxylamine wherein each of T1 and T2 is independently chosen from a member selected from the group consisting of benzyl, ethyl, octyl, lauryl, dodecyl, tetradecyl, hexadecyl, heptadecyl and octadecyl;
- or wherein each of T1 and T2 is the alkyl mixture found in hydrogenated tallow amine.
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25. A stabilizer composition according to claim 23, wherein the compound according to Formula (VIII) is a N,N-dihydrocarbylhydroxylamine chosen from a member 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.
- N,N-diethylhydroxylamine;
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26. A stabilizer composition according to claim 1 further comprising at least one compound chosen from a member selected from the group consisting of co-additives;
- tocopherol compounds;
nucleating agents;
fillers;
reinforcing agents;
polymer additives; and
combinations thereof.
- tocopherol compounds;
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27. A stabilizer composition according to claim 26, wherein the tocopherol compound is chosen from a member selected from the group consisting of α
- -tocopherol, β
-tocopherol, γ
-tocopherol, δ
-tocopherol, isomers thereof, related tocotrienols, and mixtures thereof.
- -tocopherol, β
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28. A masterbatch composition comprising a stabilizer composition as defined by claim 1, and an organic material identical to or compatible with an organic material to be stabilized.
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29. A process for producing a molded article, the process comprising adding a polymeric organic material and a polymer-stabilizing amount of a stabilizer composition as defined by claim 1 to a device or process for performing industrial molding;
- and cycling the stabilized polymeric organic material through the industrial molding process.
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30. A process according to claim 29, wherein the industrial molding process or device is chosen from injection molding, rotomolding, blow molding, reel-to-reel molding, metal injection molding, compression molding, transfer molding, dip molding, gas assist molding, insert injection molding, micro molding, reaction injection molding, and two shot injection molding.
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31. A process according to claim 29, wherein the stabilizer composition is present from 0.001 to 65.0% by weight of the total weight of the organic material to be stabilized.
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32. A process according to claim 31, wherein the stabilizer composition is present from 0.01 to 25% by weight of the total weight of the organic material to be stabilized.
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33. A process according to claim 32, wherein the stabilizer composition is present from 0.01 to 10% by weight of the total weight of the organic material to be stabilized.
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34. A process according to claim 29, wherein the organic material to be stabilized is chosen from a member selected from the group consisting of polyolefins, polyesters, polyethers, polyketones, polyamides, natural and synthetic rubbers, polyurethanes, polystyrenes, high-impact polystyrenes, polyacrylates, polymethacrylates, polyacetals, polyacrylonitriles, polybutadienes, polystyrenes, acrylonitrile-butadiene-styrene, styrene acrylonitrile, acrylate styrene acrylonitrile, cellulosic acetate butyrate, cellulosic polymers, polyimides, polyamideimides, polyetherimides, polyphenylsulfides, polyphenyloxidepolysulfones, polyethersulfones, polyvinylchlorides, polycarbonates, polyketones, aliphatic polyketones, thermoplastic olefins, aminoresin cross-linked polyacrylates and polyesters, polyisocyanate cross-linked polyesters and polyacrylates, phenol/formaldehyde, urea/formaldehyde and melamine/formaldehyde resins, drying and non-drying alkyd resins, alkyd resins, polyester resins, acrylate resins cross-linked with melamine resins, urea resins, isocyanates, isocyanurates, carbamates, epoxy resins, cross-linked epoxy resins derived from aliphatic, cycloaliphatic, heterocyclic and aromatic glycidyl compounds, which are cross-linked with anhydrides or amines, polysiloxanes, Michael addition polymers, amines, blocked amines with activated unsaturated and methylene compounds, ketimines with activated unsaturated and methylene compounds, polyketimines in combination with unsaturated acrylic polyacetoacetate resins, polyketimines in combination with unsaturated acrylic resins, radiation curable compositions, epoxymelamine resins, organic dyes, cosmetic products, cellulose-based paper formulations, photographic film paper, fibers, waxes, and inks.
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35. A process according to claim 34, wherein the organic material to be stabilized is a polyolefin polymer chosen from a member selected from the group consisting of i) polymers of monoolefins chosen from polypropylene, polyisobutylene, polybut-1-ene, poly-4-methylpent-1-ene;
- ii) polymers of diolefins chosen from polyisoprene or polybutadiene;
iii) polymers of cycloolefins chosen from cyclopentene, and 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), and ultralow density polyethylene (ULDPE);
v) copolymers thereof; and
vi) mixtures thereof.
- ii) polymers of diolefins chosen from polyisoprene or polybutadiene;
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2. A stabilizer composition according to claim 1 further comprising at least one compound chosen from the group of organic phosphites or phosphonites.
Specification
- Resources
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Current AssigneeCytec Technology Corp.
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Original AssigneeCytec Technology Corp.
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InventorsGUPTA, Ram, SAMUELS, Sari-Beth, ENG, J. Mon Hei, STEELE, Thomas
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Granted Patent
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Time in Patent OfficeDays
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Field of Search
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US Class Current106/287.21
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CPC Class CodesB29C 41/04 Rotational or centrifugal c...B29K 2023/00 Use of polyalkenes or deriv...B29K 2023/12 PP, i.e. polypropyleneC07D 311/72 3,4-Dihydro derivatives hav...C08K 5/00 Use of organic ingredientsC08K 5/005 Stabilisers against oxidati...C08K 5/098 Metal salts of carboxylic a...C08K 5/13 Phenols; PhenolatesC08K 5/1545 Six-membered ringsC08K 5/34 Heterocyclic compounds havi...C08K 5/3492 TriazinesC08K 5/51 Phosphorus bound to oxygenC08L 23/02 not modified by chemical af...C08L 23/0815 Copolymers of ethene with a...C08L 23/10 Homopolymers or copolymers ...C08L 23/12 Polypropene