US4590231A
Expired / Lapsed
US
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Polyolefin compositions stabilized against degradation using hydroxylamine derivatives
Assignee: BASF Corp
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Filing: 1984-07-23
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Granted: 1986-05-20
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Expires: 2004-07-23
Abstract
Abstract N,N-Dibenzylhydroxylamine and other selected hydroxylamine derivatives are effective in stabilizing polyolefin compositions containing a stabilizer or mixture of stabilizers selected from the group consisting of the phenolic antioxidants, the hindered amine light stabilizers, the ultraviolet light absorbers, the organic phosphorus compounds, the alkaline metal salts of fatty acids and the thiosynergists, against degradation upon high temperature extrusion, exposure to the combustion products of natural gas, gamma irradiation or upon storage for extended periods.
Inventors
- 👤 Raymond Seltzer
- 👤 Ambelal R. Patel
- 👤 Peter W. Stewart
- 👤 Charlene White
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 03:56
CPC Classifications
C; C08; C08K; C08K5/00; C08K5/16; C08K5/34; C08K5/3412; C08K5/3432; C08K5/3435; C08K5/32; C08K5/3442; C08K5/3462
Claims Analysis
Total Claims: 18
Claim 1
Independent Claim
168 words
A composition, stabilized against discoloration, which comprises (a) a saturated polyolefin or mixture thereof, (b) a stabilizing amount of an alkaline metal salt of a fatty acid, or mixture thereof, (c) a stabilizing amount of a phenolic antioxidant, or mixture thereof, selected from the group consisting of n-octadecyl 3,5-di-tert-butyl-4-hydroxyhydrocinnamate, neopentanetetrayl tetrakis(3,5-di-tert-butyl-4-hydroxyhydrocinnamate), di-n-octadecyl 3,5-di-tert-butyl-4-hydroxybenzylphosphonate, 1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)isocyanurate, thiodiethylene bis(3,5-di-tert-butyl-4-hydroxyhydrocinnamate), 1,3,5-trimethyy-2,4-6-tris(3,5-di-tert-butyl-4-hydroxybenzyl)benzene, 3,6-di-oxaoctamethylene bis(3-methyl-5-tert-butyl-4-hydroxyhydrocinnamate), 2,6-di-tert-butyl-p-cresol, 2,2'-ethylidene-bis(4,6-di-tert-butylphenol), 1,3,5-tris(2,6-dimethyl-4-tert-butyl-3-hydroxybenzyl)isocyanurate, 1,1,3-tris (2-methyl-4-hydroxy-5-tert-butylphenyl)butane, 1,3,5-tris[2-(3,5-di-tert-butyl-4-hydroxyhydrocinnamoyloxy)-ethyl]-isocyanurate, 3,5-di-(3,5-di-tert-butyl-4-hydroxybenzyl)-mesitol, hexamethylene bis(3,5-di-tert-butyl-4-hydroxyhydrocinnamate), 1-(3,5-di-tert-butyl-4-hydroxyanilion)-3,-5-di(octylthio)-s-triaxine, N,N'-hexamethylene-bis(3,5-di-tert-buty-4-hydroxyhydrocinnamamide), calcium bis(ethyl 3,5-di-tert-butyl-4-hydroxybenzylphosphonate), ethylene bis[3,3-di(3-tert-butyl-4-hydroxyphenyl)butyrate], octyl 3,5-di-tert-butyl-4-hydroxybenzylmercaptoacetate, bis(3,5-di-tert-butyl-4-hydroxyhydrocinnamoyl)hydrazide, and N,N'-bis[2-(3,5-tert-butyl-4-hydroxyhydroxocinnamoyloxy)ethyl[oxamide, and (d) a stabilizing amount of a hydroxylamine derivative of the formula ##STR14## wherein T 1 is alkyl of 1 to 36 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, aralkyl of 7 to 9 carbon atoms, or said aralkyl substituted by alkyl of 1 to 4 carbon atoms or by one or two halogen atoms, T 2 is hydrogen, or independently has the same meaning as T 1 ; and the carbon content of T 1 and T 2 together is 6 to 36 carbon atoms.
Claim 2
Dependent Claim
168 words
A composition, stabilized against discoloration, which comprises (a) a saturated polyolefin or mixture thereof, (b) a stabilizing amount of an alkaline metal salt of a fatty acid, or mixture thereof, (c) a stabilizing amount of a phenolic antioxidant, or mixture thereof, selected from the group consisting of n-octadecyl 3,5-di-tert-butyl-4-hydroxyhydrocinnamate, neopentanetetrayl tetrakis(3,5-di-tert-butyl-4-hydroxyhydrocinnamate), di-n-octadecyl 3,5-di-tert-butyl-4-hydroxybenzylphosphonate, 1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)isocyanurate, thiodiethylene bis(3,5-di-tert-butyl-4-hydroxyhydrocinnamate), 1,3,5-trimethyy-2,4-6-tris(3,5-di-tert-butyl-4-hydroxybenzyl)benzene, 3,6-di-oxaoctamethylene bis(3-methyl-5-tert-butyl-4-hydroxyhydrocinnamate), 2,6-di-tert-butyl-p-cresol, 2,2'-ethylidene-bis(4,6-di-tert-butylphenol), 1,3,5-tris(2,6-dimethyl-4-tert-butyl-3-hydroxybenzyl)isocyanurate, 1,1,3-tris (2-methyl-4-hydroxy-5-tert-butylphenyl)butane, 1,3,5-tris[2-(3,5-di-tert-butyl-4-hydroxyhydrocinnamoyloxy)-ethyl]-isocyanurate, 3,5-di-(3,5-di-tert-butyl-4-hydroxybenzyl)-mesitol, hexamethylene bis(3,5-di-tert-butyl-4-hydroxyhydrocinnamate), 1-(3,5-di-tert-butyl-4-hydroxyanilion)-3,-5-di(octylthio)-s-triaxine, N,N'-hexamethylene-bis(3,5-di-tert-buty-4-hydroxyhydrocinnamamide), calcium bis(ethyl 3,5-di-tert-butyl-4-hydroxybenzylphosphonate), ethylene bis[3,3-di(3-tert-butyl-4-hydroxyphenyl)butyrate], octyl 3,5-di-tert-butyl-4-hydroxybenzylmercaptoacetate, bis(3,5-di-tert-butyl-4-hydroxyhydrocinnamoyl)hydrazide, and N,N'-bis[2-(3,5-tert-butyl-4-hydroxyhydroxocinnamoyloxy)ethyl[oxamide, and (d) a stabilizing amount of a hydroxylamine derivative of the formula ##STR14## wherein T 1 is alkyl of 1 to 36 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, aralkyl of 7 to 9 carbon atoms, or said aralkyl substituted by alkyl of 1 to 4 carbon atoms or by one or two halogen atoms, T 2 is hydrogen, or independently has the same meaning as T 1 ; and the carbon content of T 1 and T 2 together is 6 to 36 carbon atoms.
Claim 3
Dependent Claim
21 words
A composition according to claim 1 wherein component (a) is a polyolefin which is a homopolymer or copolymer of an alpha-olefin.
Claim 4
Dependent Claim
46 words
A composition according to claim 2 wherein the polyolefin is selected from the group consisting of polypropylene, low density polyethylene, medium density polyethylene, high density polyethylene, linear low density polyethylene, poly(butene-1), ethylene/vinyl acetate copolymer, ethylene/propylene copolymer, and copolymers of ethylene or of propylene with other alpha-olefins.
Claim 5
Dependent Claim
27 words
A composition according to claim 3 wherein the polyolefin is polypropylene, high density polyethylene, ethylene/propylene copolymer or a copolymer of ethylene or of propylene with another alpha-olefin.
Claim 6
Dependent Claim
44 words
A composition according to claim 1 wherein T 2 is hydrogen and T 1 is cycloalkyl of 6 to 12 carbon atoms; or T 1 and T 2 are the same and each are alkyl of 4 to 18 carbon atoms, cyclohexyl or benzyl.
Claim 7
Dependent Claim
24 words
A composition according to claim 5 wherein the hydroxyamine of formula I is N,N-di-tert-butylhydroxylamine, N,N-di-n-octylhydroxylamine, N-cyclohexylhydroxylamine, N-cyclododecylhydroxylamine, N,N-dicyclohexylhydroxylamine or N,N-dibenzylhydroxylamine, or a mixture thereof.
Claim 8
Dependent Claim
20 words
A composition according to claim 1 wherein the phenolic antioxidant is neopentanetetrayl tetrakis(3,5-di-tert-butyl-4-hydroxyhydrocinnamate), n-octadecyl 3,5-di-tert-butyl-4-hydroxyhydrocinnamate, 1,3,5-trimethyl-2,4,6-tris(3,5-di-tert-butyl-4-hydroxybenzyl)benzene, 1,3,5-tris-(3,5-di-tert-butyl-4-hydroxybenzyl)isocyanurate, 2,6-di-tert-butyl-p-cresol or 2,2'-ethylidene-bis(4,6-di-tert-butylphenol).
Claim 9
Dependent Claim
23 words
A composition according to claim 1 wherein the alkaline metal salt is calcium stearate, zinc stearate, magnesium behenate, sodium ricinoleate or potassium palmitate.
Claim 10
Dependent Claim
14 words
A composition according to claim 8 wherein the alkaline metal salt is calcium stearate.
Claim 11
Dependent Claim
41 words
A stabilized composition according to claim 1 which additionally contains (e) a stabilizing amount of an organic phosphorus compound, or mixture thereof, selected from the group consisting of tris(2,4-di-tert-butylphenyl) phosphite, 3,9-di(2,4-di-tert-butylphenoxy)-2,4,8,10-tetraoxa-3,9-diphospha [5.5]undecane, tris(p-nonylphenyl) phosphite, 3,9-distearyloxy-2,4,8,10-tetraoxa-3,9-diphospha[5.5]-undecane, dilauryl phosphite, 3,9-di[2,6-di-tert-buty-4-(2-(n-octadecyloxycarbonyl)ethyl)-phenoxyl]-2,4,8,10-tetraoxa-3,9-diphospha[5.5]undecane and tetrakis(2,4-di-tert-butylphenyl) 4,4'-bis(diphenylene)phosphonite.
Claim 12
Dependent Claim
14 words
A composition according to claim 10 wherein the organic phosphate compound is tris(2,4-di-tert-butyl-phenyl) phosphite.
Claim 13
Dependent Claim
33 words
A stabilized composition according to claim 1 which additionally contains (e) a stabilizing amount of a thiosynergist, or mixture thereof, selected from the group consisiting of dilauryl thiodipropionate, distearyl thiodiproprionate and neopentanetetrayl tetrakis(3-dodecylthiopropionate).
Claim 14
Dependent Claim
15 words
A composition according to claim 12 wherein the thiosynergist is dilauryl thiopropionate or distearyl thiodipropionate.
Claim 15
Dependent Claim
70 words
A stabilized composition according to claim 1 which additionally contains (e) a stabilizing amount of a hindered amine light stabilizer, or mixture thereof, selected from the group consisting of bis(2,2,6,6-tetramethylpiperidin-4-yl) sebacate, bis(1,2,2,6,6-pentamethylpiperidin-4-yl) sebacate, di(1,2,2,6,6-pentamethylpiperidin-4-yl) (3,5-di-tert-butyl-4-hydroxybenzyl)-butylmalonate, tris-(2,2,6,6-tetramethylpiperidin-4-yl) nitrilotriacetate, 1,2-bis(2,2,6,6-tetramethyl-3-oxopiperazin-4-yl)ethane, 2,2,4,4-tetramethyl-7-oxa-3,20-diaza-21-oxodispiro- [5.1.11.2]-heneicosane, polycondensation product of 2,4-dichloro-6-tert-octylamino-s-triazine and 4,4'-hexamethylenebis(amino-2,2,6,6-tetramethylpiperidine), polycondensation product of 1-(2-hydroxyethyl)-2,2,6,6-tetramethyl-4-hydroxypiperidine and succinic acid, polycondensation product of 4,4'-hexamethylene-bis(amino-2,2,-6,6-tetramethylpiperidine) and 1,2-dibromoethane, polycondensation product of 2,4-dichloro-6-moropholino-s-triazine and 4,4'-hexamethylenebis(amino-2,2,6,6-tetramethylpiperidine) N,N',N",N"'-tetrakis[(4,6-bis(butyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino)-s-triaxine-2-yl]-1,10-diamino-4,7-diazadecane, octamethylene bis(2,2,6,6-tetramethylpiperidin-4-carbosylate) and 4,4'-ethylenebis(2,2,6,-6-tetramethylpiperazine-3-one).
Claim 16
Dependent Claim
32 words
A composition according to claim 14 wherein the hindered amine light stabilizer is bis(2,2,6,6-tetramethylpiperidin-4-yl) sebacate, the polycondensation product of 1-(2-hydroxyethyl)-2,2,6,6-tetramethyl-4-hydroxypiperidine and succinic acid, the polycondensation product of 2,4-dichloro-6-tert-octylamino-s-triazine and 4,4'-hexamethylenebis(amino-2,2,6,6-tetramethylpiperidine) or N,N',N",N"'-tetrakis[4,6-bis(butyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino)-s-triazin-2-yl]-1,10-diamino-4,7-diazadecane.
Claim 17
Dependent Claim
40 words
A stabilized composition according to claim 14 which additionally contains (f) a stabilizing amount of an organic phosphorus compound, or mixture thereof, selected from the group consisting of tris(2,4-di-tert-butylphenyl) phosphite, 3,9-di(2,4-di-tert-butylphenoxy)-2,4,8,10-tetraoxa-3,9-diphospha[5.5]undecane, tris(p-nonylphenyl) phosphite, 3,9-distearyloxy-2,4,8,10-tetraoxa-3,9-diphospha[5.5]undecane, dilauryl phosphite, 3,9-di[2,6-di-tert-butyl-4-(2-(n-octadecyloxycarbonyl)ethyl)-phenosyl]-2,4,8,10-tetraoxa-3,9,-diphospha[5.5]undecane and tetrakis(2,4-di-tert-butylphenyl) 4,4'-bis(diphenylene)phosphonite.
Claim 18
Dependent Claim
15 words
A composition according to claim 16 which additionally contains the organic phosphorus compound tris(2,4-di-tert-butylphenyl) phosphite.
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