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US4233207A
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Hydrolytically stable ortho-alkylated phenyl phosphonites and stabilized compositions
Assignee: BASF Corp
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Filing: 1979-07-09
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Granted: 1980-11-11
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Expires: 1999-07-09
Abstract
Abstract Hydrolytically stable, ortho-alkylated phenyl phosphonites of the formula ##STR1## wherein R 1 and R 2 are alkyl or phenylalkyl, R 3 is hydrogen, alkyl or carboalkoxyalkyl, R 4 is alkyl, phenyl or phenyl substituted by alkyl, R 5 is halogen, --XH or XR 6 where X is O or S and R 6 is phenyl substituted by alkyl, phenylalkyl or carboalkoxyalkyl, are useful as stabilizers for organic polymers and lubricating oils, particularly as processing stabilizers for polyolefins.
Inventors
- 👤 John d. Spivack
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 17:10
CPC Classifications
C; C08; C08K; C08K5/00; C08K5/49; C08K5/51; C08K5/53; C08K5/5393; C09; C09K; C09K15/00; C09K15/04; C09K15/32; C09K15/322; C09K15/324; C10; C10M; C10M137/00; C10M137/12; C10M2223/00; C10M2223/06; C10M2223/065
Claims Analysis
Total Claims: 22
Claim 1
Independent Claim
241 words
A compound of the formula ##STR16## wherein R 1 is branched alkyl of 3 to 8 carbon atoms, benzyl, α-methylbenzyl or α,α-dimethylbenzyl, R 2 is alkyl of 1 to 18 carbon atoms, benzyl, α-methylbenzyl or α,α-dimethylbenzyl. R 3 is hydrogen, alkyl of 1 to 18 carbon atoms, carboalkoxy of 2 to 19 carbon atoms, carboalkoxyalkyl of 3 to 24 carbon atoms, carbophenoxy, carbophenoxyalkyl of 8 to 16 carbon atoms; or said carbophenoxy or said carbophenoxyalkyl with the phenoxy substituted with 1 to 3 alkyl groups with 1 to 8 carbon atoms in each alkyl group, R 4 is alkyl of 1 to 18 carbon atoms, phenyl or phenyl substituted by 1 to 3 alkyl groups with 1 to 8 carbon atoms in each alkyl group, R 5 is halogen, --XH or --XR 6 , X is O or S, R 6 is phenyl, substituted by alkyl, having the formula ##STR17## R 7 is hydrogen, branched alkyl of 3 to 18 carbon atoms, benzyl, α-methylbenzyl or α,α-dimethylbenzyl, R 8 is hydrogen, alkyl of 1 to 18 carbon atoms, benzyl, α-methylbenzyl or α,α-dimethylbenzyl, and R 9 is hydrogen, alkyl of 1 to 18 carbon atoms, carboalkoxy of 2 to 19 carbon atoms, carboalkoxyalkyl of 3 to 24 carbon atoms, carbophenoxy, carbophenoxyalkyl of 8 to 16 carbon atoms; or said carbophenoxy or said carbophenoxyalkyl with the phenoxy substituted with 1 to 3 alkyl groups with 1 to 8 carbon atoms in each alkyl group.
Claim 2
Dependent Claim
241 words
A compound of the formula ##STR16## wherein R 1 is branched alkyl of 3 to 8 carbon atoms, benzyl, α-methylbenzyl or α,α-dimethylbenzyl, R 2 is alkyl of 1 to 18 carbon atoms, benzyl, α-methylbenzyl or α,α-dimethylbenzyl. R 3 is hydrogen, alkyl of 1 to 18 carbon atoms, carboalkoxy of 2 to 19 carbon atoms, carboalkoxyalkyl of 3 to 24 carbon atoms, carbophenoxy, carbophenoxyalkyl of 8 to 16 carbon atoms; or said carbophenoxy or said carbophenoxyalkyl with the phenoxy substituted with 1 to 3 alkyl groups with 1 to 8 carbon atoms in each alkyl group, R 4 is alkyl of 1 to 18 carbon atoms, phenyl or phenyl substituted by 1 to 3 alkyl groups with 1 to 8 carbon atoms in each alkyl group, R 5 is halogen, --XH or --XR 6 , X is O or S, R 6 is phenyl, substituted by alkyl, having the formula ##STR17## R 7 is hydrogen, branched alkyl of 3 to 18 carbon atoms, benzyl, α-methylbenzyl or α,α-dimethylbenzyl, R 8 is hydrogen, alkyl of 1 to 18 carbon atoms, benzyl, α-methylbenzyl or α,α-dimethylbenzyl, and R 9 is hydrogen, alkyl of 1 to 18 carbon atoms, carboalkoxy of 2 to 19 carbon atoms, carboalkoxyalkyl of 3 to 24 carbon atoms, carbophenoxy, carbophenoxyalkyl of 8 to 16 carbon atoms; or said carbophenoxy or said carbophenoxyalkyl with the phenoxy substituted with 1 to 3 alkyl groups with 1 to 8 carbon atoms in each alkyl group.
Claim 3
Dependent Claim
220 words
A compound according to claim 1 wherein R 1 is branched alkyl of 4 to 12 carbon atoms, α-methyl-benzyl or α,α-dimethylbenzyl, R 2 is alkyl of 3 to 12 carbon atoms, α-methylbenzyl or α,α-dimethylbenzyl, R 3 is hydrogen, alkyl of 1 to 18 carbon atoms, carboalkoxy of 2 to 19 carbon atoms, carboalkoxyalkyl of 3 to 21 carbon atoms or carbophenoxy with the phenoxy substituted with 1 to 3 alkyl groups with 1 to 8 carbon atoms in each alkyl group, R 4 is alkyl of 1 to 18 carbon atoms, phenyl or phenyl substituted by 1 to 3 alkyl groups with 1 to 8 carbon atoms in each alkyl group, R 5 is chlorine or --XR 6 , X is O, R 7 is hydrogen, branched alkyl of 4 to 12 carbon atoms, α-methylbenzyl or α,α-dimethylbenzyl, R 8 is hydrogen, alkyl of 1 to 12 carbon atoms, α-methylbenzyl or α,αdimethylbenzyl, and R 9 is hydrogen, alkyl of 1 to 18 carbon atoms, carboalkoxy of 2 to 19 carbon atoms, carboalkoxyalkyl of 3 to 21 carbon atoms or carbophenoxy with the phenoxy substituted with 1 to 3 alkyl groups with 1 to 8 carbon atoms in each alkyl group, with the proviso that all of R 7 , R 8 and R 9 cannot be hydrogen at the same time.
Claim 4
Dependent Claim
181 words
A compound according to claim 1 wherein R 1 is tertiary alkyl of 4 to 8 carbon atoms, R 2 is branched alkyl of 4 to 8 carbon atoms, R 3 is hydrogen, alkyl of 1 to 9 carbon atoms, carboalkoxy of 2 to 9 carbon atoms, carboalkoxyalkyl of 3 to 11 carbon atoms or carbophenoxy with the phenoxy substituted with 1 to 3 alkyl groups with 1 to 4 carbon atoms in each alkyl group, R 4 is phenyl or phenyl substituted by 1 to 3 alkyl groups with 1 to 4 carbon atoms in each alkyl group, R 5 is chlorine or --XR 6 , X is O, R 7 is tertiary alkyl of 4 to 8 carbon atoms, R 8 is hydrogen or alkyl of 1 to 8 carbon atoms, and R 9 is hydrogen, alkyl of 1 to 9 carbon atoms, carboalkoxy of 2 to 9 carbon atoms, carboalkoxyalkyl of 3 to 11 carbon atoms or carbophenoxy with the phenoxy substituted with 1 to 3 alkyl groups with 1 to 4 carbon atoms in each alkyl group.
Claim 5
Dependent Claim
131 words
A compound according to claim 1 wherein R 1 is isopropyl or tert-butyl, R 2 is alkyl of 1 to 4 carbon atoms, R 3 is hydrogen, alkyl of 1 to 18 carbon atoms, --CH 2 CH 2 COOCH 3 ,--COOCH 3 ,--COOC 18 H 37 or ##STR18## R 4 is alkyl of 1 to 18 carbon atoms or phenyl, R 5 is chlorine, --XH or XR 6 , X is O, ##STR19## R 7 is hydrogen, isopropyl or tert-butyl, R 8 is hydrogen or alkyl of 1 to 4 carbon atoms, and R 9 is alkyl of 1 to 4 carbon atoms, --COOCH 3 , --CH 2 CH 2 COOCH 3 or ##STR20## with the proviso that both R 7 and R 8 cannot be hydrogen at the same time.
Claim 6
Dependent Claim
11 words
The compound according to claim 1 which is O-(2,6-di-tert-butyl-4-methylphenyl)-O'-2,4-di-tert-butylphenyl) phenylphosphonite .
Claim 7
Dependent Claim
10 words
The compound according to claim 1 which is O-(2,4-di-tert-butylphenyl)-O'-(2,4,6-tri-tert-butylphenyl) phenylphosphonite.
Claim 8
Dependent Claim
11 words
The compound according to claim 1 which is O-[2,6-di-tert-butylphenyl-4-(2-carbomethoxyethyl)phenyl]- O'-(4-tert-butylphenyl) phenylphosphonite.
Claim 9
Dependent Claim
11 words
The compound according to claim 1 which is O-( 2,6-di-tert-butyl-4-methylphenyl)-O'-(4-tert-butylphenyl) phenylphosphonite.
Claim 10
Dependent Claim
10 words
The compound according to claim 1 which is O,O'bis(2,6-di-tert-butyl-4-carbomethoxyphenyl) phenylphosphonite.
Claim 11
Dependent Claim
10 words
The compound according to claim 1 which is O,O'-bis-[2,6-di-tert-butyl-4-(carbo-2,4-di-tert-butylphenoxy)-phenyl] phenylphosphonite.
Claim 12
Dependent Claim
30 words
A composition of matter comprising an organic polymer subject to oxidative, thermal or actinic degradation stabilized with from 0.01 to 5% by weight of a compound according to claim 1.
Claim 13
Dependent Claim
15 words
A composition according to claim 11 wherein the polymer is a polyolefin homopolymer or copolymer.
Claim 14
Dependent Claim
17 words
A composition according to claim 12 stabilized with O-(2,6-di-tert-butyl-4-methylphenyl)-O'-(2,4-di-tert-butylphenyl) phenylphosphonite, O-(2,4- tert-butylphenyl)-O'-(2,4,6-tri-tert-butylphenyl) phenylphosphonite or O,O'-bis [2,6-di-tert-butyl-4-(carbo-2,4-di-tert-butylphenoxy)phenyl] phenylphosphonite.
Claim 15
Dependent Claim
152 words
A compound of the formula ##STR21## wherein R 4 is alkyl of 1 to 18 carbon atoms, phenyl or phenyl substituted by 1 to 3 alkyl groups with 1 to 8 carbon atoms in each alkyl group, X is O or S, R 7 is hydrogen, branched alkyl of 3 to 18 carbon atoms, benzyl, α-methylbenzyl or α,α-dimethylbenzyl, R 8 is hydrogen, alkyl of 1 to 18 carbon atoms, benzyl, α-methylbenzyl or α,α-dimethylbenzyl, and R 9 is hydrogen, alkyl of 1 to 18 carbon atoms, carboalkoxy of 2 to 19 carbon atoms, carboalkoxyalkyl of 3 to 24 carbon atoms, carbophenoxy, carbophenoxyalkyl of 8 to 16 carbon atoms; or carbophenoxy or carbophenoxyalkyl with the phenoxy substituted with 1 to 3 alkyl groups with 1 to 18 carbon atoms in each alkyl group, with the proviso that all of R 7 , R 8 and R 9 cannot be hydrogen at the same time.
Claim 16
Dependent Claim
152 words
A compound of the formula ##STR21## wherein R 4 is alkyl of 1 to 18 carbon atoms, phenyl or phenyl substituted by 1 to 3 alkyl groups with 1 to 8 carbon atoms in each alkyl group, X is O or S, R 7 is hydrogen, branched alkyl of 3 to 18 carbon atoms, benzyl, α-methylbenzyl or α,α-dimethylbenzyl, R 8 is hydrogen, alkyl of 1 to 18 carbon atoms, benzyl, α-methylbenzyl or α,α-dimethylbenzyl, and R 9 is hydrogen, alkyl of 1 to 18 carbon atoms, carboalkoxy of 2 to 19 carbon atoms, carboalkoxyalkyl of 3 to 24 carbon atoms, carbophenoxy, carbophenoxyalkyl of 8 to 16 carbon atoms; or carbophenoxy or carbophenoxyalkyl with the phenoxy substituted with 1 to 3 alkyl groups with 1 to 18 carbon atoms in each alkyl group, with the proviso that all of R 7 , R 8 and R 9 cannot be hydrogen at the same time.
Claim 17
Dependent Claim
139 words
A compound according to claim 14 wherein R 4 is alkyl of 1 to 8 carbon atoms, phenyl or phenyl substituted by 1 to 3 alkyl groups with 1 to 8 carbon atoms in each alkyl group, X is O, R 7 is hydrogen, branched alkyl of 4 to 12 carbon atoms , α-methylbenzyl or α,α-dimethylbenzyl, R 8 is hydrogen, alkyl of 1 to 12 carbon atoms, α-methylbenzyl or α,α-dimethylbenzyl, and R 9 is hydrogen, alkyl of 1 to 18 carbon atoms, carboalkoxy of 2 to 19 carbon atoms, carboalkoxyalkyl of 3 to 21 carbon atoms or carboxyphenoxy with the phenoxy substituted with 1 to 3 alkyl groups with 1 to 8 carbon atoms in each alkyl group, with the proviso that all of R 7 , R 8 and R 9 cannot be hydrogen at the same time.
Claim 18
Dependent Claim
104 words
A compound according to claim 14 wherein R 4 is phenyl or phenyl substituted by 1 to 3 alkyl groups with 1 to 4 carbon atoms in each alkyl group, X is O, R 7 is tertiary alkyl of 4 to 8 carbon atoms, R 8 is hydrogen or alkyl of 1 to 8 carbon atoms, and R 9 is hydrogen, alkyl of 1 to 9 carbon atoms, carboalkoxy of 2 to 9 carbon atoms, carboalkoxyalkyl of 3 to 11 carbon atoms, or carbophenoxy with the phenoxy substituted with 1 to 3 alkyl groups with 1 to 4 carbon atoms in each alkyl group.
Claim 19
Dependent Claim
10 words
The compound according to claim 14 which is O-(2,4-di-tert-butylphenyl) phenylphosphonochloridite.
Claim 20
Dependent Claim
10 words
The compound according to claim 1 which is O,O'-bis(2,6-di-tert-butyl-4-methylphenyl) phenylphosphonite.
Claim 21
Dependent Claim
10 words
The compound according to claim 1 which is O,O'-bis(2,4-tri-tert-butylphenyl) phenylphosphonite.
Claim 22
Dependent Claim
42 words
A composition according to claim 11 wherein the polymer is selected from the group consisting of polyethylene, polypropylene, polyisobutylene, poly(butene-1), poly(pentene-1), poly(3-methylbutene-1), poly(4-methylpentene-1), ethylene/propylene copolymer, polystyrene, ABS resin, SBR, polyisoprene, polyethylene terephthalate, polybutylene terephthalate, polyurethane, polycarbonate, nylon 6, nylon 6-6 and polysulfone.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1983-11-11 | 1984-05-12 | 1984-11-11 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-11-11 | 1988-05-12 | 1988-11-11 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-11-11 | 1992-05-12 | 1992-11-11 | $7700.00 | Window Closed / Lapsed |