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US4125516A
Expired / Lapsed
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Alkylthioalkanoyloxyalkyl and alkylthioalkyl substituted bis-hydantoin compounds
Assignee: BASF Corp
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Filing: 1977-01-17
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Granted: 1978-11-14
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Expires: 1997-01-17
Abstract
Abstract Alkylthioalkanoyloxyalkyl and alkylthioalkyl derivatives of N-heterocyclic moieties are stabilizers for organic materials subject to oxidative, thermal and/or light induced deterioration. They are prepared by classical transesterification, oxirane ring opening and addition of mercaptan to olefin reactions. Typical embodiments are tris[2-(3-n-dodecythiopropionyloxy)ethyl isocyanurate] and 3-(3-n-dodecylthio-2-hydroxypropyl)-5,5-dimethylhydantoin. These compounds are used in conjunction with phenolic antioxidants to stabilize organic materials, particularly polyolefins and hydrocarbon compositions, against the deleterious effects of heat and oxygen and against discoloration.
Inventors
- 👤 Martin Dexter
- 👤 David H. Steinberg
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 13:42
CPC Classifications
C; C07; C07D; C07D233/00; C07D233/54; C07D233/66; C07D233/72; C07D251/00; C07D251/02; C07D251/12; C07D251/26; C07D251/30; C07D251/34; C08; C08K; C08K5/00; C08K5/36; C08K5/37; C08K5/378
Claims Analysis
Total Claims: 9
Claim 1
Independent Claim
159 words
A compound of the formula ##STR21## where m is an integer from 0 to 2 and n is an integer from 0 to 2, with the proviso that the sum of m + n must be 2 when T is a radical of the structure ##STR22## where m is an integer from 0 to 3 and n is an integer from 0 to 3, with the proviso that the sum of m + n must be 3 when T is a radical of the structure ##STR23## wherein R is alkyl of 1 to 30 carbon atoms or cycloalkyl of 5 to 12 carbon atoms, p is 0, 1 or 2, R 1 is hydrogen or methyl, R 2 is hydrogen, methyl or ethyl, R 3 and R 4 are independently alkyl of 1 to 6 carbon atoms or together R 3 and R 4 are pentamethylene, and R 5 is alkylene of 1 to 12 carbon atoms or 3-oxapentamethylene.
Claim 2
Dependent Claim
159 words
A compound of the formula ##STR21## where m is an integer from 0 to 2 and n is an integer from 0 to 2, with the proviso that the sum of m + n must be 2 when T is a radical of the structure ##STR22## where m is an integer from 0 to 3 and n is an integer from 0 to 3, with the proviso that the sum of m + n must be 3 when T is a radical of the structure ##STR23## wherein R is alkyl of 1 to 30 carbon atoms or cycloalkyl of 5 to 12 carbon atoms, p is 0, 1 or 2, R 1 is hydrogen or methyl, R 2 is hydrogen, methyl or ethyl, R 3 and R 4 are independently alkyl of 1 to 6 carbon atoms or together R 3 and R 4 are pentamethylene, and R 5 is alkylene of 1 to 12 carbon atoms or 3-oxapentamethylene.
Claim 3
Dependent Claim
59 words
A compound according to claim 1 which is ##STR24## where R is alkyl of 1 to 18 carbon atoms or cyclohexyl, p is 0 or 1, R 2 is hydrogen or methyl, R 3 and R 4 are independently alkyl of 1 to 4 carbon atoms, and R 5 is alkylene of 1 to 6 carbon atoms or 3-oxapentamethylene.
Claim 4
Dependent Claim
19 words
A compound according to claim 1 which is ##STR25## where R is alkyl of 12 to 18 carbon atoms.
Claim 5
Dependent Claim
9 words
The compound according to claim 1 which is 1,1'-methylene-bis[3-(3-n-dodecylthio-2-hydroxypropyl)-5,5-dimethylhydantoin].
Claim 6
Dependent Claim
9 words
The compound according to claim 1 which is 1,1'-methylene-bis[3-(3-n-dodecylthiopropionyloxy-2-hydroxypropyl)-5,5-dimethylhydantoin].
Claim 7
Dependent Claim
9 words
The compound according to claim 1 which is 3,3'-[2-(3-n-dodecylthiopropionyloxy-2-hydroxypropoxy)]trimethylene-bis-[1-(3-n-dodecylthiopropionyloxy-2-hydroxypropyl)-5,5-dimethylhydantoin].
Claim 8
Dependent Claim
37 words
A composition of matter stabilized against deterioration which comprises a polyolefin; from about 0.005 to 5% by weight of a phenolic antioxidant; and from about 0.005 to 5% by weight of a compound according to claim 1.
Claim 9
Dependent Claim
11 words
A composition according to claim 7 wherein the polyolefin is polypropylene.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-11-13 | 1982-05-15 | 1982-11-14 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-11-13 | 1986-05-15 | 1986-11-14 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-11-13 | 1990-05-15 | 1990-11-14 | $7700.00 | Window Closed / Lapsed |