Patent US4762872A successfully refreshed from Google Patents.
US4762872A
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Oligomeric light stabilizers with substituted piperidine ends
Assignee: Goodrich Corp
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Filing: 1987-07-17
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Granted: 1988-08-09
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Expires: 2007-07-17
Abstract
Abstract A poly(α-aminoacetamide) ("poly(AAMID)" for brevity) main chain having terminal polysubstituted piperidinyl chain ends are novel compounds which have highly desirable UV-light stabilizing (UV-S) activity coupled with unexpectedly good thermal stability. These compounds, referred to as "piperidinyl-chain ended poly(AAMID)s", are oligomers which contain from 2 to about 18 AAMID repeating units, for use in polymer recipes to formulate a stabilized polymeric composition comprising a UV-light-degradable organic polymer containing an effective amount of the poly(AAMID) sufficient to stabilize the polymer. A poly(AAMID) is especially effective in a polyolefin in which there is from about 0.1 percent by weight (% by wt), to about 5% by wt of the oligomer, and is also effective in a wide variety of pastel colored and/or transparent commercially significant polymers.
Inventors
- 👤 John T. Lai
- 👤 Pyong Nae-Son
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 01:25
CPC Classifications
C; C08; C08K; C08K5/00; C08K5/16; C08K5/34; C08K5/3412; C08K5/3432; C08K5/3435; C07; C07D; C07D211/00; C07D211/04; C07D211/06; C07D211/36; C07D211/56; C07D211/58
Claims Analysis
Total Claims: 31
Claim 1
Independent Claim
51 words
A poly(α-aminoacetamide) ("poly(AAMID") oligomer represented by the following structure: ##STR8## wherein, R represents C 2 -C 18 alkylene, C 6 -C 18 aryl, C 7 -C 18 alkaryl or aralkyl, methylene-bis-C 6 -C 18 aryl, piperazinediyl or aryl substituted with Cl or Br, C 1 -C 6 alkoxy, monocyano, or mononitro;
Claim 2
Dependent Claim
51 words
A poly(α-aminoacetamide) ("poly(AAMID") oligomer represented by the following structure: ##STR8## wherein, R represents C 2 -C 18 alkylene, C 6 -C 18 aryl, C 7 -C 18 alkaryl or aralkyl, methylene-bis-C 6 -C 18 aryl, piperazinediyl or aryl substituted with Cl or Br, C 1 -C 6 alkoxy, monocyano, or mononitro;
Claim 3
Dependent Claim
52 words
R 1 , R 4 and R 5 represent a substituent selected from the group consisting of C 1 -C 20 alkyl, hydroxyalkyl, and N-alkylaminoalkyl, with R 4 and R 5 in combination being cyclizable to form a 5- to 8-membered alicyclic ring; and, in addition, only R 1 may be H;
Claim 4
Dependent Claim
52 words
R 1 , R 4 and R 5 represent a substituent selected from the group consisting of C 1 -C 20 alkyl, hydroxyalkyl, and N-alkylaminoalkyl, with R 4 and R 5 in combination being cyclizable to form a 5- to 8-membered alicyclic ring; and, in addition, only R 1 may be H;
Claim 5
Dependent Claim
13 words
R 2 and R 3 represent H or C 1 -C 18 alkyl;
Claim 6
Dependent Claim
13 words
R 2 and R 3 represent H or C 1 -C 18 alkyl;
Claim 7
Dependent Claim
54 words
R 6 , R 7 , R 8 , and R 9 independently represent C 1 -C 24 alkyl, and C 4 -C 7 polymethylene which are cyclizable forming a spiro cycloalkylene substituent with the C atom of the piperidine ring; and, n is an integer in the range from 2 to about 18.
Claim 8
Dependent Claim
54 words
R 6 , R 7 , R 8 , and R 9 independently represent C 1 -C 24 alkyl, and C 4 -C 7 polymethylene which are cyclizable forming a spiro cycloalkylene substituent with the C atom of the piperidine ring; and, n is an integer in the range from 2 to about 18.
Claim 9
Dependent Claim
17 words
The poly(AAMID) oligomer of claim 1 wherein said R represents one or more of the following: ##STR9##
Claim 10
Dependent Claim
33 words
The poly(AAMID) oligomer of claim 2 wherein R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 independently represent C 1 -C 5 lower alkyl.
Claim 11
Dependent Claim
34 words
The poly(AAMID) oligomer of claim 2 having a number average molecular weight in the range from about 1500 to about 20,000, and n is an integer in the range from 2 to about 10.
Claim 12
Dependent Claim
86 words
A stabilized composition of matter which comprises a UV light sensitive synthetic resinous material subject to the deleterious effects of oxygen and heat, and from about 0.01 percent to about 10 percent by weight of a poly(α-aminoacetamide) ("poly(AAMID")) oligomer represented by the following structure: ##STR10## wherein, R represents C 2 -C 18 alkylene, C 6 -C 18 aryl, C 7 -C 18 alkaryl or aralkyl, methylene-bis-C 6 -C 18 aryl, piperazinediyl or aryl substituted with Cl or Br, C 1 -C 6 alkoxy, monocyano, or mononitro;
Claim 13
Dependent Claim
86 words
A stabilized composition of matter which comprises a UV light sensitive synthetic resinous material subject to the deleterious effects of oxygen and heat, and from about 0.01 percent to about 10 percent by weight of a poly(α-aminoacetamide) ("poly(AAMID")) oligomer represented by the following structure: ##STR10## wherein, R represents C 2 -C 18 alkylene, C 6 -C 18 aryl, C 7 -C 18 alkaryl or aralkyl, methylene-bis-C 6 -C 18 aryl, piperazinediyl or aryl substituted with Cl or Br, C 1 -C 6 alkoxy, monocyano, or mononitro;
Claim 14
Dependent Claim
56 words
R 1 , R 4 and R 5 represent a substituent selected from the group consisting of C 1 -C 20 alkyl, hydroxyalkyl, and N-alkylaminoalkyl, with R 4 and R 5 in combination being cyclizable to form a 5- to 8-membered alicyclic ring, typically cyclohexyl or cycloheptyl; and, in addition, only R 1 may be H;
Claim 15
Dependent Claim
56 words
R 1 , R 4 and R 5 represent a substituent selected from the group consisting of C 1 -C 20 alkyl, hydroxyalkyl, and N-alkylaminoalkyl, with R 4 and R 5 in combination being cyclizable to form a 5- to 8-membered alicyclic ring, typically cyclohexyl or cycloheptyl; and, in addition, only R 1 may be H;
Claim 16
Dependent Claim
13 words
R 2 and R 3 represent H or C 1 -C 18 alkyl;
Claim 17
Dependent Claim
13 words
R 2 and R 3 represent H or C 1 -C 18 alkyl;
Claim 18
Dependent Claim
54 words
R 6 , R 7 , R 8 , and R 9 independently represent C 1 -C 24 alkyl, and C 4 -C 7 polymethylene which are cyclizable forming a spiro cycloalkylene substituent with the carbon atom of the piperidine ring; and, n is an integer in the range from 2 to about 18.
Claim 19
Dependent Claim
54 words
R 6 , R 7 , R 8 , and R 9 independently represent C 1 -C 24 alkyl, and C 4 -C 7 polymethylene which are cyclizable forming a spiro cycloalkylene substituent with the carbon atom of the piperidine ring; and, n is an integer in the range from 2 to about 18.
Claim 20
Dependent Claim
20 words
The composition of claim 5 wherein said material is a polyolefin selected from the group consisting of polyethylene and polypropylene.
Claim 21
Independent Claim
55 words
A method for preparing a poly(α-aminoacetamide) ("poly(AAMID") oligomer represented by the following structure: ##STR11## wherein, R represents C 2 -C 18 alkylene, C 6 -C 18 aryl, C 7 -C 18 alkaryl or aralkyl, methylene-bis-C 6 -C 18 aryl, piperazinediyl or aryl substituted with Cl or Br, C 1 -C 6 alkoxy monocyano, or mononitro;
Claim 22
Independent Claim
55 words
A method for preparing a poly(α-aminoacetamide) ("poly(AAMID") oligomer represented by the following structure: ##STR11## wherein, R represents C 2 -C 18 alkylene, C 6 -C 18 aryl, C 7 -C 18 alkaryl or aralkyl, methylene-bis-C 6 -C 18 aryl, piperazinediyl or aryl substituted with Cl or Br, C 1 -C 6 alkoxy monocyano, or mononitro;
Claim 23
Dependent Claim
56 words
R 1 , R 4 and R 5 represent a substituent selected from the group consisting of C 1 -C 20 alkyl, hydroxyalkyl, and N-alkylaminoalkyl, with R 4 and R 5 in combination being cyclizable to form a 5- to 8-membered alicyclic ring, typically cyclohexyl or cycloheptyl; and, in addition, only R 1 may be H;
Claim 24
Dependent Claim
56 words
R 1 , R 4 and R 5 represent a substituent selected from the group consisting of C 1 -C 20 alkyl, hydroxyalkyl, and N-alkylaminoalkyl, with R 4 and R 5 in combination being cyclizable to form a 5- to 8-membered alicyclic ring, typically cyclohexyl or cycloheptyl; and, in addition, only R 1 may be H;
Claim 25
Dependent Claim
13 words
R 2 and R 3 represent H or C 1 -C 18 alkyl;
Claim 26
Dependent Claim
13 words
R 2 and R 3 represent H or C 1 -C 18 alkyl;
Claim 27
Dependent Claim
145 words
R 6 , R 7 , R 8 , and R 9 independently represent C 1 -C 24 alkyl, and C 4 -C 7 polymethylene which are cyclizable forming a spiro cycloalkylene substituent with the C atom of the piperidine ring; and, n is an integer in the range from 2 to about 18, which process comprises, (a) reacting (i) a primary diamine wherein said R is intermediate the primary amine groups, and (ii) a monoketone with a 4-alkylamino polysubstituted piperazine, in the presence of a base and sufficient haloform to provide said oligomer having the designated repeating unit, said monoketone being present in an amount from about 2 to about 25 times greater than the molar amount required to react with said diamine; (b) maintaining the temperature during reaction below that which degrades said diamine; and, (c) recovering said oligomer having piperidyl chain ends.
Claim 28
Dependent Claim
145 words
R 6 , R 7 , R 8 , and R 9 independently represent C 1 -C 24 alkyl, and C 4 -C 7 polymethylene which are cyclizable forming a spiro cycloalkylene substituent with the C atom of the piperidine ring; and, n is an integer in the range from 2 to about 18, which process comprises, (a) reacting (i) a primary diamine wherein said R is intermediate the primary amine groups, and (ii) a monoketone with a 4-alkylamino polysubstituted piperazine, in the presence of a base and sufficient haloform to provide said oligomer having the designated repeating unit, said monoketone being present in an amount from about 2 to about 25 times greater than the molar amount required to react with said diamine; (b) maintaining the temperature during reaction below that which degrades said diamine; and, (c) recovering said oligomer having piperidyl chain ends.
Claim 29
Dependent Claim
19 words
The process of claim 7 wherein said monoketone is selected from the group consisting of acetone, 2-butanone, and cyclohexanone.
Claim 30
Dependent Claim
10 words
The process of claim 7 wherein said haloform is chloroform.
Claim 31
Dependent Claim
14 words
The process of claim 7 wherein said base is an aqueous alkali metal hydroxide.
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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) | 1991-08-09 | 1992-02-08 | 1992-08-09 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1995-08-09 | 1996-02-08 | 1996-08-09 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1999-08-09 | 2000-02-08 | 2000-08-09 | $7700.00 | Window Closed / Lapsed |