Patent US4692487A successfully refreshed from Google Patents.
US4692487A
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1,2-ethanediyl-bis-2-piperazinone esters, oligomers thereof, and compositions stabilized thereby
Assignee: Goodrich Corp
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Filing: 1986-09-02
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Granted: 1987-09-08
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Expires: 2006-09-02
Abstract
Abstract A bis-polysubstituted piperazinone ("bis-PSP") in which two PSP moieties are closely coupled through an ethylene linkage, may be esterified so as to incorporate particular moieties in a macromolecule which may have only one bis-PSP unit, or may be esterified to form an oligomer having plural esterified bis-PSP repeating units. The macromolecule not only exhibits excellent UV-stabilization and antioxidant properties in synthetic resinous materials thus performing a highly effective dual function, but also is resistant to extraction with solvents, particularly polar solvents.
Inventors
- 👤 Pyong-Nae Son
- 👤 John T. Lai
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 23:22
CPC Classifications
C; C07; C07D; C07D403/00; C07D403/14; C07D241/00; C07D241/02; C07D241/06; C07D241/08; C08; C08G; C08G73/00; C08G73/06; C08G73/0622; C08G73/0633; C08K; C08K5/00; C08K5/16; C08K5/34; C08K5/3442; C08K5/3462; C08K5/3467; C08K5/3477; C08K5/3492; C08K5/34926
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
148 words
An esterified bis-polysubstituted piperazinone ("bis-PSP") represented by the structure ##STR9## wherein, A' represents CH 3 --(CH 2 ) x -- wherein x is an integer in the range from 6 to about 20; and, hydroxyphenyl having C 1 -C 10 alkyl substituents; R 1 -R 4 each independently represent C 1 -C 12 alkyl; C 5 -C 14 cycloalkyl or hydroxycycloalkyl having from 5 to 8 ring C atoms, C 7 -C 14 alkenyl or aralkyl; C 2 -C 7 alkylene; R 1 and R 2 , or R 3 and R 4 together with the ring C atom of the piperazinone ring represent cycloalkyl having from 5 to about 8 ring C atoms; and, R 5 and R 6 are the same as R 1 -R 4 defined above, and additionally may be H; and, R 7 represents lower alkyl C 1 -C 6 , and H.
Claim 2
Dependent Claim
148 words
An esterified bis-polysubstituted piperazinone ("bis-PSP") represented by the structure ##STR9## wherein, A' represents CH 3 --(CH 2 ) x -- wherein x is an integer in the range from 6 to about 20; and, hydroxyphenyl having C 1 -C 10 alkyl substituents; R 1 -R 4 each independently represent C 1 -C 12 alkyl; C 5 -C 14 cycloalkyl or hydroxycycloalkyl having from 5 to 8 ring C atoms, C 7 -C 14 alkenyl or aralkyl; C 2 -C 7 alkylene; R 1 and R 2 , or R 3 and R 4 together with the ring C atom of the piperazinone ring represent cycloalkyl having from 5 to about 8 ring C atoms; and, R 5 and R 6 are the same as R 1 -R 4 defined above, and additionally may be H; and, R 7 represents lower alkyl C 1 -C 6 , and H.
Claim 3
Dependent Claim
149 words
An esterified bis-polysubstituted piperazinone oligomer ("bis-PSP oligomer") having the structure ##STR10## wherein, A" represents --(CH 2 ) n' --, alkylene, wherein n' is an integer in the range from 2 to about 20; and, cycloalkylene having 5 to about 8 ring carbon atoms; R 1 -R 4 each independently represent C 1 -C 12 alkyl; C 5 -C 14 cycloalkyl or hydroxycycloalkyl having from 5 to 8 ring C atoms, C 7 -C 14 alkenyl or aralkyl; C 2 -C 7 alkylene; R 1 and R 2 , or R 3 and R 4 together with the ring C atom of the piperazinone ring represent cycloalkyl having from 5 to about 8 ring C atoms; and, R 5 and R 6 are the same as R 1 -R 4 defined above, and additionally may be H; and, R 7 represents lower alkyl C 1 -C 6 , and H.
Claim 4
Dependent Claim
149 words
An esterified bis-polysubstituted piperazinone oligomer ("bis-PSP oligomer") having the structure ##STR10## wherein, A" represents --(CH 2 ) n' --, alkylene, wherein n' is an integer in the range from 2 to about 20; and, cycloalkylene having 5 to about 8 ring carbon atoms; R 1 -R 4 each independently represent C 1 -C 12 alkyl; C 5 -C 14 cycloalkyl or hydroxycycloalkyl having from 5 to 8 ring C atoms, C 7 -C 14 alkenyl or aralkyl; C 2 -C 7 alkylene; R 1 and R 2 , or R 3 and R 4 together with the ring C atom of the piperazinone ring represent cycloalkyl having from 5 to about 8 ring C atoms; and, R 5 and R 6 are the same as R 1 -R 4 defined above, and additionally may be H; and, R 7 represents lower alkyl C 1 -C 6 , and H.
Claim 5
Dependent Claim
20 words
The esterified bis-PSP of claim 1 represented by the structure ##STR11## and identified as the 1,2-ethanediylbis[2,2,6,6-tetramethyl-2-oxo-4,1-piperazinediyl)-1-methyl-2,1-ethanediyl] ester of 3,5-bis(1,1-dimethylethyl)-4-hydroxybenzene-propanoic acid.
Claim 6
Dependent Claim
20 words
The esterified bis-PSP of claim 1 represented by the structure ##STR12## and identified as the 1,2-ethanediylbis[2,2,6,6-tetramethyl-2-oxo-4,1-piperazinediyl)-2,1-ethanediyl] ester of stearic acid.
Claim 7
Dependent Claim
17 words
The esterified bis-PSP oligomer of claim 2 represented by the structure ##STR13## and identfied as (ii) poly[oxycarbonyl-1,8-octanediylcarbonyloxy-1,2-ethanediyl(2,2,6,6-tetramethyl-3-oxo-1,4-piperazinediyl)-1,2-ethanediyl(3,3,5,5-tetramethyl-2-oxo-1,4-piperazinediyl)1,2-ethanediyl].
Claim 8
Dependent Claim
16 words
The esterified bis-PSP oligomer of claim 2 represented by the structure ##STR14## and identified as poly[oxycarbonyl-1,3-propanediylcarbonyloxy-1,2-ethanediyl(2,2,6,6-tetramethyl-3-oxo-1,4-piperazinediyl)-1,2-ethanediyl(3,3,5,5-tetramethyl-2-oxo-1,4-piperazinediyl)1,2-ethanediyl].
Claim 9
Dependent Claim
239 words
A stabilized composition of matter comprising an organic material subject to degradation by ultravilet light or ooxidation, having dispersed therein from about 0.02 part to about 5 parts by weight per 100 parts by weight of said organic material, a stabilizer selected from the group consisting of an esterified bis-polysubstituted piperazinone ("bis-PSP") represented by the structure ##STR15## and, an esterified bis-polysubstituted piperazinone oligomer ("bis-PSP oligomer") represented by the structure ##STR16## wherein, A' represents CH 3 --(CH 2 ) x -- wherein x is an integer in the range from 6 to about 20; and, hydroxyphenyl having C 1 -C 10 alkyl substituents; A" represents --(CH 2 ) n' --, alkylene, wherein n' is an integer in the range from 2 to about 20; and, cycloalkylene having 5 to about 8 ring carbon atoms; R 1 -R 4 each independently represent C 1 -C 12 alkyl; C 5 -C 14 cycloalkyl or hydroxycycloalkyl having from 5 to 8 ring C atoms, C 7 -C 14 alkenyl or aralkyl; C 2 -C 7 alkylene; R 1 and R 2 , or R 3 and R 4 together with the ring C atom of the piperazinone ring represent cycloalkyl having from 5 to about 8 ring C atoms; and, R 5 and R 6 are the same as R 1 -R 4 defined above, and additionally may be H; and, R 7 represents lower alkyl C 1 -C 6 , and H.
Claim 10
Dependent Claim
239 words
A stabilized composition of matter comprising an organic material subject to degradation by ultravilet light or ooxidation, having dispersed therein from about 0.02 part to about 5 parts by weight per 100 parts by weight of said organic material, a stabilizer selected from the group consisting of an esterified bis-polysubstituted piperazinone ("bis-PSP") represented by the structure ##STR15## and, an esterified bis-polysubstituted piperazinone oligomer ("bis-PSP oligomer") represented by the structure ##STR16## wherein, A' represents CH 3 --(CH 2 ) x -- wherein x is an integer in the range from 6 to about 20; and, hydroxyphenyl having C 1 -C 10 alkyl substituents; A" represents --(CH 2 ) n' --, alkylene, wherein n' is an integer in the range from 2 to about 20; and, cycloalkylene having 5 to about 8 ring carbon atoms; R 1 -R 4 each independently represent C 1 -C 12 alkyl; C 5 -C 14 cycloalkyl or hydroxycycloalkyl having from 5 to 8 ring C atoms, C 7 -C 14 alkenyl or aralkyl; C 2 -C 7 alkylene; R 1 and R 2 , or R 3 and R 4 together with the ring C atom of the piperazinone ring represent cycloalkyl having from 5 to about 8 ring C atoms; and, R 5 and R 6 are the same as R 1 -R 4 defined above, and additionally may be H; and, R 7 represents lower alkyl C 1 -C 6 , and H.
Claim 11
Dependent Claim
61 words
The stabilized composition of claim 7 wherein said esterified bis-PSP is selected from the group consisting of (i) 1,2-ethanediylbis[2,2,6,6-tetramethyl-2-oxo-4,1-piperazinediyl)-2,1-ethanediyl] ester of 3,5-bis(1,1-dimethylethyl)-4-hydroxybenzenepropanoic acid; (ii) 1,2-ethanediylbis[2,2,6,6-tetramethyl-2-oxo-4,1-piperazinediyl)-2,1-ethanediyl] ester of stearic acid; (iii) 1,2-ethanediylbis[2,2,6,6-tetramethyl-2-oxo-4,1-piperazinediyl)-1-methyl-2,1-ethanediyl] ester of 3,5-bis(1,1-dimethylethyl)-4-hydroxybenzene-propanoic acid; and, (iv) 1,2-ethanediylbis[2,2,6,6-tetramethyl-2-oxo-4,1-piperazinediyl)-1-methyl-2,1-ethanediyl] ester of stearic acid; and, said esterified bis-PSP oligomer is selected from the group consisting of (i) poly[oxycarbonyl-1,2-ethanediylcarbonyloxy-1,2-ethanediyl(2,2,6,6-tetramethyl-3-oxo-1,4-piperazinediyl)-1,2-ethanediyl(3,3,5,5-tetramethyl-2-oxo-1,4-piperazinediyl)1,2-ethanediyl]; (ii) poly[oxycarbonyl-1,8-octanediylcarbonyloxy-1,2-ethanediyl(2,2,6,6-tetramethyl-3-oxo-1,4-piperazinediyl)-1,2-ethanediyl(3,3,5,5-tetramethyl-2-oxo-1,4-piperazinediyl)1,2-ethanediyl]; and, (iii) poly[oxycarbonyl-1,3-propanediylcarbonyloxy-1,2-ethanediyl(2,2,6,6-tetramethyl-3-oxo-1,4-piperazinediyl)-1,2-ethanediyl(3,3,5,5-tetramethyl-2-oxo-1,4-piperazinediyl)1,2-ethanediyl].
References Cited (Backward Citations)
US3899491A
Cited
US4097452A
Cited
US4190571A
Cited
US4240961A
Cited
US4466916A
Cited
US4477665A
Cited
US4455401A
Cited
US4536564A
Cited
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| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1990-09-07 | 1991-03-09 | 1991-09-08 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1994-09-07 | 1995-03-09 | 1995-09-08 | $3760.00 | Window Closed / Lapsed |
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