US4351759A
Expired / Lapsed
US
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Alkylated 2,2'-biphenylene phosphites and stabilized compositions
Assignee: BASF Corp
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Filing: 1981-03-23
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Granted: 1982-09-28
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Expires: 2001-03-23
Abstract
Abstract Alkylated 1,1'-biphenyl-2,2'diyl phosphites are prepared by reacting alkylated 2,2'-biphenol with phosphorus trichloride in an organic solvent and then reacting the intermediate with an alcohol or thiol. Said phosphites are useful as stabilizers of organic polymers and lubricating oils, especially as process stabilizers for polyolefins, elastomers, polyesters and polycarbonates.
Inventors
- 👤 John d. Spivack
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 14:56
CPC Classifications
C; C08; C08K; C08K5/00; C08K5/49; C08K5/5398; C08K5/51; C08K5/52; C08K5/527
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
288 words
A composition of matter comprising an organic material subject to oxidative, thermal and actinic degradation stabilized with from about 0.01 to about 5% by weight, of the total composition, of a 1,1'-biphenyl-2,2'-diyl phosphite of the formula ##STR9## wherein R is an alkyl group of 1 to 18 carbon atoms, R 1 is hydrogen or alkyl group of 1 to 18 carbon atoms, and R 2 is an alkyl group of 1 to 20 carbon atoms, phenyl, phenyl substituted by 1 to 3 alkyl groups each having 1 to 8 carbon atoms, or by two alkyl groups each having 1 to 8 carbon atoms and by --COOR 4 where R 4 is alkyl of 1 to 18 carbon atoms, R 3 is an n-valent radical selected from the group consisting of a straight- or branched-chain alkylene of 2 to 12 carbon atoms, a straight- or branched chain alkane-triyl, -tetrayl, -pentayl or -hexayl of 3 to 6 carbon atoms, alkenylene of 4 to 6 carbon atoms, cycloalkylene of 6 to 12 carbon atoms, 1,4-cyclohexanedimethylene, arylene or arenetriyl of 6 to 10 carbon atoms, p-xylylene, phenylene-E-phenylene where E is a direct bond, --O--, --S--, --NR 5 --, where R 5 is alkyl of 1 to 18 carbon atoms; a straight- or branched chain alkylene or alkylidene of 1 to 12 carbon atoms or cycloalkylidene of 5 to 6 carbon atoms, said arylene or said phenylene-E-phenylene substituted by 1 to 4 alkyl groups each having 1 to 8 carbon atoms, --(CH 2 ) x X(CH 2 ) x -- where x is 2 to 6, dipentaerythrityl, and ##STR10## where Y is hydrogen, methyl or ethyl and z is 1 to 10, X is oxygen or sulfur, and n is 2 to 6.
Claim 2
Dependent Claim
288 words
A composition of matter comprising an organic material subject to oxidative, thermal and actinic degradation stabilized with from about 0.01 to about 5% by weight, of the total composition, of a 1,1'-biphenyl-2,2'-diyl phosphite of the formula ##STR9## wherein R is an alkyl group of 1 to 18 carbon atoms, R 1 is hydrogen or alkyl group of 1 to 18 carbon atoms, and R 2 is an alkyl group of 1 to 20 carbon atoms, phenyl, phenyl substituted by 1 to 3 alkyl groups each having 1 to 8 carbon atoms, or by two alkyl groups each having 1 to 8 carbon atoms and by --COOR 4 where R 4 is alkyl of 1 to 18 carbon atoms, R 3 is an n-valent radical selected from the group consisting of a straight- or branched-chain alkylene of 2 to 12 carbon atoms, a straight- or branched chain alkane-triyl, -tetrayl, -pentayl or -hexayl of 3 to 6 carbon atoms, alkenylene of 4 to 6 carbon atoms, cycloalkylene of 6 to 12 carbon atoms, 1,4-cyclohexanedimethylene, arylene or arenetriyl of 6 to 10 carbon atoms, p-xylylene, phenylene-E-phenylene where E is a direct bond, --O--, --S--, --NR 5 --, where R 5 is alkyl of 1 to 18 carbon atoms; a straight- or branched chain alkylene or alkylidene of 1 to 12 carbon atoms or cycloalkylidene of 5 to 6 carbon atoms, said arylene or said phenylene-E-phenylene substituted by 1 to 4 alkyl groups each having 1 to 8 carbon atoms, --(CH 2 ) x X(CH 2 ) x -- where x is 2 to 6, dipentaerythrityl, and ##STR10## where Y is hydrogen, methyl or ethyl and z is 1 to 10, X is oxygen or sulfur, and n is 2 to 6.
Claim 3
Dependent Claim
30 words
A composition of claim 1 wherein R is an α-branched alkyl radical of 3 to 8 carbon atoms, and R 1 is an alkyl of 1 to 8 carbon atoms.
Claim 4
Dependent Claim
16 words
A composition of claim 2 wherein R 1 is in the meta position to R group.
Claim 5
Dependent Claim
61 words
A composition of claim 3 wherein R is tert-butyl or tert-octyl, R 1 is a tert-alkyl group of 4 to 8 carbon atoms, R 2 is phenyl substituted in the ortho positions by two alkyl groups each having 3 to 8 carbon atoms and in the parapositions by --COOR 4 where R 4 is alkyl of 1 to 12 carbon atoms.
Claim 6
Dependent Claim
25 words
A composition of claim 4 wherein R 2 is substituted in the ortho positions by two tert-butyl groups and in the para position by carbomethoxy.
Claim 7
Dependent Claim
45 words
A composition of claim 1 wherein R 3 is alkylene of 2 to 6 carbon atoms, 1,2,3-propanetriyl, 2,2-dimethyl-1,2,2-propanetriyl, pentaerythrityl, 1,4-cyclohexylene, 1,4-cyclohexanedimethylene, 1,4-phenylene, phenylene-E-phenylene where E is methylene, 2,2-propylidene or 1,1-butylidene, 3-thiapentamethylene or ##STR11## where Y is hydrogen or methyl and z is 1 to 3.
Claim 8
Dependent Claim
14 words
A composition of claim 1 wherein the phosphite is O,O'-hexa-methylene-bis[O 1 ,O 2 -(3,3',5,5'-tetra-tert-butyl-1,1'-biphenyl-2,2'-diyl)phosphite].
Claim 9
Dependent Claim
15 words
A composition of claim 1 wherein the phosphite is O,O'-neopentanediyl-bis[O 1 , O 2 -(3,3',5,5'-tetra-tert-butyl-1,1'-biphenyl-2,2'-diyl)phosphite].
Claim 10
Dependent Claim
13 words
A composition of claim 1 wherein the organic material is a synthetic polymer.
Claim 11
Dependent Claim
14 words
A composition of claim 9 wherein the polymer is a polyolefin homopolymer or copolymer.
Claim 12
Dependent Claim
24 words
A composition of claim 10 which additionally contains from about 0.01 to about 5% by weight, of the total composition, of a phenolic antioxidant.
Claim 13
Dependent Claim
31 words
A composition of claim 11 wherein the phenolic antioxidant is selected from the group consisting of 2,6-di-tert-butyl-4-methylphenol 4,4'-thio-bis(6-tert-butyl-3-methylphenol), 2,2'-methylene-bis(6-tert-butyl-4-methylphenol), 4,4'-methylene-bis-(2,6-di-tert-butylphenol), 1,1,3-tris-(5-tert-butyl-4-hydroxy-2-methylphenyl)butane, 1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)-2,4,6-trimethylbenzene, 2-octylthio-4,6-bis(3,5-di-tert-butyl-4-hydroxyanilino)-s-triazine, n-octadecyl 3,5-di-tert-butyl-4-hydroxyhydrocinnamate, neopentanetetrayl tetrakis(3,5-di-tert-butyl-4-hydroxyhydrocinnamate), 1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)isocyanurate; and thiodiethylene bis(3,5-di-tert-butyl-4-hydroxyhydrocinnamate).
References Cited (Backward Citations)
US3476699A
Cited
US3415906A
Cited
US3297631A
Cited
US3558554A
Cited
US3796684A
Cited
SU378389A1
Cited
SU429070A1
Cited
SU440390A1
Cited
US4094855A
Cited
US4276232A
Cited
US4137201A
Cited
US4143028A
Cited
US4196117A
Cited
US4259492A
Cited
US4185006A
Cited
US4252750A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1985-09-27 | 1986-03-29 | 1986-09-28 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-09-27 | 1990-03-29 | 1990-09-28 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-09-27 | 1994-03-29 | 1994-09-28 | $7700.00 | Window Closed / Lapsed |