Claims
- 1. A stabilized composition which comprises (a) an organic material subject to oxidative, thermal or actinic degradation, and (b) an effective stabilizing amount of a poly-1,3,2-oxaza-phospholidine compound of formula I ##STR8## wherein n is an integer from 2 to 4,
- R.sub.1 is alkyl of 1 to 20 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, phenylalkyl of 7 to 15 carbon atoms, said phenylalkyl substituted on the phenyl ring by one or two alkyl groups of 1 to 12 carbon atoms, aryl of 6 to 10 carbon atoms or a radical of formula II ##STR9## R.sub.2, R.sub.3 and R.sub.4 are independently hydrogen, alkyl of 1 to 20 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, phenylalkyl of 7 to 15 carbon atoms, said phenylalkyl substituted on the phenyl ring by one or two alkyl groups of 1 to 12 carbon atoms, aryl of 6 to 10 carbon atoms or said aryl substituted by one or two alkyl groups of 1 to 12 carbon atoms, or
- R.sub.3 and R.sub.4 together are straight or branched chain alkylene of 3 to 6 carbon atoms so that, with the two ring carbon atoms to which they are attached, they form a cycloalkyl ring of 5 to 6 carbon atoms,
- R.sub.5 and R.sub.6 are independently hydrogen, alkyl of 1 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, phenylalkyl of 7 to 15 carbon atoms or said phenylalkyl substituted on the phenyl ring by one or two alkyl groups of 1 to 12 carbon atoms,
- R.sub.7 is hydrogen, alkyl of 1 to 18 carbon atoms or a group of the formula --(CH.sub.2).sub.k COOR.sub.8 where k is 0, 1 or 2, and R.sub.8 is hydrogen or alkyl of 1 to 20 carbon atoms, and
- when n is 2, T is a direct bond, --O--, --S--, --SO--, --SO.sub.2 --, --CO-- or --NR-- where R is alkyl of 1 to 8 carbon atoms, or
- when n is 2-4, T is an n-valent aliphatic hydrocarbon radical containing 1 to 20 carbon atoms, which radical is linear or branched, or which radical is interrupted by one or more moieties selected from the group consisting of --O--, --S--, --SO--, --SO.sub.2 --, --CO--, --NR--, phenylene and mixtures thereof, where R is alkyl of 1 to 8 carbon atoms.
- 2. A composition according to claim 1 wherein the organic material is a synthetic polymer.
- 3. A composition according to claim 2 wherein the polymer is a polyolefin.
- 4. A composition according to claim 3 wherein the polyolefin is polypropylene.
- 5. A composition according to claim 1 wherein the compound of component (b) is 1,6-bis[2-(2,6-di-tert-butyl-4-(2-(n-octadecyloxycarbonyl)-ethyl)phenoxy)-3-tert-butyl-1,3,2-oxazaphospholidin-5-yl]-2,5-dioxahexane.
- 6. A composition according to claim 1 which additionally contains an effective stabilizing amount of a phenolic antioxidant.
- 7. A composition according to claim 6 wherein the phenolic antioxidant is selected from the group consisting of n-octadecyl 3,5-di-tert-butyl-4-hydroxyhydrocinnamate, neopentanetetrayl tetrakis(3,5-di-tert-butyl-4-hydroxyhydrocinammate), 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-trimethyl-2,4,6-tris(3,5-di-tert-butyl-4-hydroxybenzyl)benzene, 3,6-dioxaoctamethylene 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-hydroxyanilino)-3,5-di-(octylthio)-s-triazine, N,N'-hexamethylene-bis(3,5-di-tert-butyl-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-di-tert-butyl-4-hydroxyhydrocinnamoyloxy)-ethyl]-oxamide.
- 8. A composition according to claim 7 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).
- 9. A composition according to claim 1 which additionally contains an effective stabilizing amount of a hindered amine compound.
- 10. A composition according to claim 9 wherein the hindered amine compound is 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,
- 4-benzoyl-2,2,6,6-tetramethylpiperidine, 4-stearyloxy-2,2,6,6-tetramethylpiperidine,
- 3-n-octyl-7,7,9,9-tetramethyl-1,3,8-triaza-spiro[4.5]decane-2,4-dione,
- 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'-hexamethylenebis-(amino-2,2,6,6-tetramethylpiperidine) and 1,2-dibromoethane,
- tetrakis(2,2,6,6-tetramethylpiperidin-4-yl) 1,2,3,4-butanetetracarboxylate,
- tetrakis(1,2,2,6,6-pentamethylpiperidin-4-yl) 1,2,3,4-butanetetracarboxylate,
- polycondensation product of 2,4-dichloro-6-morpholino-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-tetramethyl-piperidin-4-yl)-amino-s-triazine-2-yl]-1,10-diamino-4,7-diazadecane,
- mixed [2,2,6,6-tetramethylpiperidin-4-yl/.beta.,.beta.,.beta.',.beta.'-tetramethyl-3,9-(2,4,8,10-tetraoxaspiro[5.5]undecane) diethyl]1,2,3,4-butanetetracarboxylate,
- mixed [1,2,2,6,6-pentamethylpiperidin-4-yl/.beta.,.beta.,.beta.',.beta.'-tetramethyl-3,9-(2,4,8,10-tetraoxaspiro[5.5]undecane)diethyl]1,2,3,4-butanetetracarboxylate, octamethylene bis(2,2,6,6-tetramethylpiperidin-4-carboxylate) and
- 4,4'-ethylenebis(2,2,6,6-tetramethylpiperazin-3-one).
- 11. A composition according to claim 10 wherein the hindered amine compound is bis(2,2,6,6-tetramethylpiperidin-4-yl) sebacate, the polycondensation product of 1-(2-hydroxyethyl)-2,2,6,6-tetramethyl-4-hydroxypiperdine and succinic acid, the polycondensation product of 2,4-dichloro-6-tetra-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-tetramethyl-piperidin-4-yl)amino)-s-triazine-2-yl]-1,10-diamino-4,7-diazadecane.
Parent Case Info
This is a divisional of Ser. No. 572,729 filed Aug. 23, 1990, now U.S. Pat. No. 5,075,481.
US Referenced Citations (3)
Number |
Name |
Date |
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4751319 |
Odorisio et al. |
Jun 1988 |
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4812501 |
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4831178 |
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Foreign Referenced Citations (1)
Number |
Date |
Country |
3047443 |
Jul 1982 |
DEX |
Non-Patent Literature Citations (2)
Entry |
S. D. Pastor et al., J. Am. Chem. Soc., 110, 6547 (1988). |
Abstract for German 3,047,443. |
Divisions (1)
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Number |
Date |
Country |
Parent |
572729 |
Aug 1990 |
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