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2,2,6,6-Tetramethyl-4-piperidyl carboxylic acid esters and amides of mono and poly alcohols, phenols and amines as stabilizers for synthetic polymers

Assignee: Adeka Corp
•
Filing: 1980-08-14
•
Granted: 1982-06-22
•
Expires: 2000-08-14
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Abstract

Abstract 2,2,6,6-Tetramethyl-4-piperidyl carboxylic acid esters and amides of mono and poly alcohols, phenols and amines are provided, useful as stabilizers for organic polymeric materials, and having the general formula: <IMAGE>

Inventors

  • 👤 Yutaka Nakahara
  • 👤 Toshihiro Shibata
  • 👤 Naohiro Kubota

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-08 23:17
CPC Classifications
C; C07; C07D; C07D491/00; C07D491/02; C07D491/10; C08; C08K; C08K5/00; C08K5/16; C08K5/34; C08K5/3412; C08K5/3432; C08K5/3435

Claims Analysis

Total Claims: 34
Claim 1
Independent Claim 483 words
2,2,6,6-Tetramethyl-4-piperidyl carboxylic acid esters and amides having the general formula: ##STR148## wherein: R 1 , R 2 and R 3 are selected from the group consisting of hydrogen and alkyl having from one to about eighteen carbon atoms; X is oxygen or imino>NH; m is zero, 1 or 2; n is zero, 1 or 2; m+n is 1 or 2; p is zero or 1; q is 1 to 6; ##STR149## is linked to carbon in place of one R 2 or R 3 group; and Z is selected from the group consisting of: (a) OR 5 where R 5 is alkyl, aryl or cycloalkyl having one to twenty-four carbon atoms and hydroxy-, carboxy- and oxy-substituted such groups having from one to five OH or O groups; and 2,2,6,6-tetramethyl-4-piperidyl; (b) OR 6 O where R 6 is alkylene, arylene or cycloalkylene having one to twenty-four carbon atoms and hydroxy-substituted such groups having one to four OH groups; R 6 alkylene, arylene or cycloalkylene can include oxyether --O-- and thioether --S-- linking groups attached to alkylene, arylene or cycloalkylene groups as in polyoxyalkylene and polythioalkylene groups and polyoxyalkylene arylene groups having from one to about five oxy or thio groups and from two to about six alkylene groups having from two to about six carbon atoms; (c) ##STR150## where R 6 is alkylene, arylene or cycloalkylene having one to twenty-four carbon atoms and hydroxy-substituted such groups having one to four OH groups; R 6 alkylene, arylene or cycloalkylene can include oxyether --O-- and thioether --S-- linking groups attached to alkylene, arylene or cycloalkylene groups as in polyoxyalkylene and polythioalkylene groups and polyoxyalkylene arylene groups having from one to about five oxy or thio groups and from two to about six alkylene groups having from two to about six carbon atoms; R 7 is alkyl, aryl or cycloalkyl having one to twenty-four carbon atoms and hydroxy-substituted such groups having from one to five OH groups; (d) NHR 5 where R 5 is alkyl, aryl or cycloalkyl having one to twenty-four carbon atoms and amino-substituted such groups having from one to five amino groups; (e) ##STR151## where R 6 is alkylene, arylene or cycloalkylene having one to twenty-four carbon atoms and amino-substituted such groups having one to four amino groups; R 7 is alkyl, aryl or cycloalkyl having one to twenty-four carbon atoms and amino-substituted such groups having one to five amino groups; (f) --NHNH 2 ; --NHNH--; --NHNHCOCONHNH 2 ; --NHNHCOR 7 ; --NHNHCOR 6 CONHNH 2 ; --NHNHCOR 6 CONHNH--; --NHNHCOCONHNH-- 1 ; --NHR 6 NH 2 --; --NHR 6 NH--; NHR 6 NHCOR 6 CONHR 6 NH; ##STR152## where R 6 is alkylene, arylene or cycloalkylene having one to twenty-four carbon atoms and amino-substituted such groups having one to four amino groups; and such groups including oxyether and thioether linking groups as in (b) above, and R 7 is as in (c) above.
Claim 2
Dependent Claim 483 words
2,2,6,6-Tetramethyl-4-piperidyl carboxylic acid esters and amides having the general formula: ##STR148## wherein: R 1 , R 2 and R 3 are selected from the group consisting of hydrogen and alkyl having from one to about eighteen carbon atoms; X is oxygen or imino>NH; m is zero, 1 or 2; n is zero, 1 or 2; m+n is 1 or 2; p is zero or 1; q is 1 to 6; ##STR149## is linked to carbon in place of one R 2 or R 3 group; and Z is selected from the group consisting of: (a) OR 5 where R 5 is alkyl, aryl or cycloalkyl having one to twenty-four carbon atoms and hydroxy-, carboxy- and oxy-substituted such groups having from one to five OH or O groups; and 2,2,6,6-tetramethyl-4-piperidyl; (b) OR 6 O where R 6 is alkylene, arylene or cycloalkylene having one to twenty-four carbon atoms and hydroxy-substituted such groups having one to four OH groups; R 6 alkylene, arylene or cycloalkylene can include oxyether --O-- and thioether --S-- linking groups attached to alkylene, arylene or cycloalkylene groups as in polyoxyalkylene and polythioalkylene groups and polyoxyalkylene arylene groups having from one to about five oxy or thio groups and from two to about six alkylene groups having from two to about six carbon atoms; (c) ##STR150## where R 6 is alkylene, arylene or cycloalkylene having one to twenty-four carbon atoms and hydroxy-substituted such groups having one to four OH groups; R 6 alkylene, arylene or cycloalkylene can include oxyether --O-- and thioether --S-- linking groups attached to alkylene, arylene or cycloalkylene groups as in polyoxyalkylene and polythioalkylene groups and polyoxyalkylene arylene groups having from one to about five oxy or thio groups and from two to about six alkylene groups having from two to about six carbon atoms; R 7 is alkyl, aryl or cycloalkyl having one to twenty-four carbon atoms and hydroxy-substituted such groups having from one to five OH groups; (d) NHR 5 where R 5 is alkyl, aryl or cycloalkyl having one to twenty-four carbon atoms and amino-substituted such groups having from one to five amino groups; (e) ##STR151## where R 6 is alkylene, arylene or cycloalkylene having one to twenty-four carbon atoms and amino-substituted such groups having one to four amino groups; R 7 is alkyl, aryl or cycloalkyl having one to twenty-four carbon atoms and amino-substituted such groups having one to five amino groups; (f) --NHNH 2 ; --NHNH--; --NHNHCOCONHNH 2 ; --NHNHCOR 7 ; --NHNHCOR 6 CONHNH 2 ; --NHNHCOR 6 CONHNH--; --NHNHCOCONHNH-- 1 ; --NHR 6 NH 2 --; --NHR 6 NH--; NHR 6 NHCOR 6 CONHR 6 NH; ##STR152## where R 6 is alkylene, arylene or cycloalkylene having one to twenty-four carbon atoms and amino-substituted such groups having one to four amino groups; and such groups including oxyether and thioether linking groups as in (b) above, and R 7 is as in (c) above.
Claim 3
Dependent Claim 18 words
A compound according to claim 1 having the general formula: ##STR153## wherein Z is as in claim 1.
Claim 4
Dependent Claim 18 words
A compound according to claim 1 having the general formula: ##STR154## wherein Z is as in claim 1.
Claim 5
Dependent Claim 18 words
A compound according to claim 1 having the general formula: ##STR155## wherein Z is as in claim 1.
Claim 6
Dependent Claim 18 words
A compound according to claim 1 in which R 1 , R 2 and R 3 are hydrogen.
Claim 7
Dependent Claim 11 words
A compound according to claim 1 in which X is NH.
Claim 8
Dependent Claim 32 words
A compound according to claim 1 having the general formula: ##STR156## wherein R 1 , R 2 and R 3 , X, m, n, p and Z are as in claim 1.
Claim 9
Dependent Claim 45 words
A compound according to claim 1 in which Z is OR 5 , where R 5 is selected from the group consisting of alkyl, aryl and cycloalkyl having from one to twenty-four carbon atoms and hydroxy-substituted such groups having from one to five OH groups.
Claim 10
Dependent Claim 95 words
A compound according to claim 1 in which Z is ##STR157## where R 6 is selected from the group consisting of alkylene, arylene, and cycloalkylene having one to twenty-four carbon atoms and hydroxy-substituted such groups having one to four OH groups; polyoxyalkylene and polythioalkylene having from one to about five oxy or thio groups and from two to about six alkylene groups having from two to about six carbon atoms; and R 7 is alkyl, aryl or cycloalkyl having one to twenty-four carbon atoms and hydroxy-substituted such groups having from one to five OH groups.
Claim 11
Dependent Claim 43 words
A compound according to claim 1 in which Z is NHR 5 where R 5 is selected from the group consisting of alkyl, aryl and cycloalkyl having one to twenty-four carbon atoms and amino-substituted such groups having from one to five amino groups.
Claim 12
Dependent Claim 71 words
A compound according to claim 1 in which Z is ##STR158## where R 6 is selected from the group consisting of alkylene, arylene and cycloalkylene having one to twenty-four carbon atoms and amino-substituted such groups having one to four amino groups; and R 7 is selected from the group consisting of alkyl, aryl and cycloalkyl having one to twenty-four carbon atoms and amino-substituted such groups having one to five amino groups.
Claim 13
Dependent Claim 11 words
A compound according to claim 1 in which q is 1.
Claim 14
Dependent Claim 11 words
A compound according to claim 1 in which q is 2.
Claim 15
Dependent Claim 15 words
A compound according to claim 1 in which q is 2 and Z is --NHNH--.
Claim 16
Dependent Claim 17 words
A compound according to claim 1 in which q is 1 and Z is NHNH 2 .
Claim 17
Dependent Claim 15 words
A compound according to claim 1 in which q is 3 and Z is ##STR159##
Claim 18
Dependent Claim 15 words
A compound according to claim 1 in which q is 2 and Z is NHNHCOCONHNH.
Claim 19
Dependent Claim 15 words
A compound according to claim 17 in which q is 3 and Z is ##STR160##
Claim 20
Dependent Claim 10 words
A compound according to claim 1 having the formula: ##STR161##
Claim 21
Dependent Claim 10 words
A compound according to claim 1 having the formula: ##STR162##
Claim 22
Dependent Claim 10 words
A compound according to claim 1 having the formula: ##STR163##
Claim 23
Dependent Claim 10 words
A compound according to claim 1 having the formula: ##STR164##
Claim 24
Dependent Claim 10 words
A compound according to claim 1 having the formula: ##STR165##
Claim 25
Dependent Claim 28 words
A polyvinyl chloride resin composition having improved resistance to deterioration when heated at 350° F., comprising a polyvinyl chloride resin and a compound in accordance with claim 1.
Claim 26
Dependent Claim 20 words
A polyvinyl chloride resin composition in accordance with claim 24, in which the polyvinyl chloride resin is polyvinyl chloride homopolymer.
Claim 27
Dependent Claim 25 words
A polyvinyl chloride resin composition in accordance with claim 24, in which the polyvinyl chloride resin is a copolymer of vinyl chloride and vinyl acetate.
Claim 28
Dependent Claim 39 words
An olefin polymer composition having improved resistance to deterioration comprising an olefin polymer selected from the group consisting of polymers of alpha-olefins having from two to six carbon atoms and polystyrene, and a compound in accordance with claim 1.
Claim 29
Dependent Claim 14 words
An olefin polymer composition in accordance with claim 24 wherein the polyolefin is polypropylene.
Claim 30
Dependent Claim 14 words
An olefin polymer composition in accordance with claim 24 wherein the polyolefin is polyethylene.
Claim 31
Dependent Claim 24 words
An acrylonitrile-butadiene-styrene polymer having its resistance to deterioration when heated at 300° F. and above enhanced by a compound in accordance with claim 1.
Claim 32
Dependent Claim 21 words
A polyester polymer composition having improved resistance to deterioration comprising a polyester polymer and a compound in accordance with claim 1.
Claim 33
Dependent Claim 21 words
A polyurethane resin composition having improved resistance to deterioration comprising a polyurethane resin and a compound in accordance with claim 1.
Claim 34
Dependent Claim 23 words
An ethylene-vinyl acetate copolymer composition having improved resistance to deterioration comprising an ethylene-vinyl acetate copolymer and a compound in accordance with claim 1.

References Cited (Backward Citations)

US3431233A Cited
US3692778A Cited
US4007158A Cited
US4105625A Cited
US4128608A Cited
US4237294A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1985-06-21 1985-12-21 1986-06-22 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1989-06-21 1989-12-21 1990-06-22 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1993-06-21 1993-12-21 1994-06-22 $7700.00 Window Closed / Lapsed

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