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US4351759A Expired / Lapsed US ⏱️ 0.0 years remaining

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
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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).

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

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