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US4351915A Expired / Lapsed US ⏱️ 0.0 years remaining

2,2,6,6-Tetramethyl-4-piperidyl spiro aliphatic ethers as stabilizers for synthetic polymers

Assignee: Adeka Corp
•
Filing: 1981-05-26
•
Granted: 1982-09-28
•
Expires: 2001-05-26
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Abstract

Abstract 2,2,6,6-Tetramethyl-4-piperidyl spiro aliphatic ethers which are useful as stabilizers for organic polymeric materials, and have the general formula are disclosed: <IMAGE> (I) wherein: Y1 is <IMAGE> A1, A2, A3, A4, A5, and A6 are groups which are defined in the specification, at least one pair of A1 and A2; A3 and A4; and A5 and A6 being taken together to form the group <IMAGE> the groups R1, R2, R3 and Z as well as X, p, and m being as defined in the specification.

Inventors

  • 👤 Naohiro Kubota
  • 👤 Toshihiro Shibata
  • 👤 Kazuo Sugibuchi
  • 👤 Motonubu Minagawa

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-27 04:53
CPC Classifications
C; C07; C07D; C07D491/00; C07D491/02; C07D491/10; C07F; C07F9/00; C07F9/02; C07F9/547; C07F9/6561; C08; C08K; C08K5/00; C08K5/16; C08K5/34; C08K5/3412; C08K5/3432; C08K5/3435

Claims Analysis

Total Claims: 44
Claim 1
Independent Claim 559 words
2,2,6,6-Tetramethyl-4-piperidyl spiro aliphatic ethers having the general formula: ##STR117## wherein: Y 1 is ##STR118## A 1 , A 2 , A 3 , A 4 , A 5 , and A 6 each are selected from the group consisting of hydrogen; alkyl and hydroxyalkyl having from one to about eighteen carbon atoms; cycloalkyl having from three to about eight carbon atoms; aryl having from about six to about eighteen carbon atoms; acyl having from one to about eighteen carbon atoms ##STR119## wherein R 4 is selected from the group consisting of aliphatic having from one to about eighteen carbon atoms; cycloaliphatic having from three to about eight carbon atoms; heterocyclic having from six to about eighteen carbon atoms; and aromatic having from six to about eighteen carbon atoms; carbamoyl ##STR120## wherein R 5 is selected from the group consisting of aliphatic having from one to about eighteen carbon atoms; cycloaliphatic hving from three to about eight carbon atoms; heterocyclic having from six to about eighteen carbon atoms; and aromatic having from six to about eighteen carbon atoms; ##STR121## and monovalent oxyacid groups; at least one pair of A 1 and A 2 ; A 3 and A 4 ; and A 5 and A 6 being taken together to form the group: ##STR122## wherein: Z is selected from the group consisting of hydrogen; oxyl O.; alkyl and hydroxyalkyl having from one to about twenty carbon atoms; and aryl and hydroxyaryl having from six to about twenty carbon atoms; X is selected from the group consisting of alkylene having from one to about eighteen carbon atoms; cycloalkylene having from three to about eight carbon atoms; arylene having from about six to about eighteen carbon atoms; polyacyl ##STR123## wherein R 4 is as above and n 1 is a number from 2 to 4; polycarbamoyl ##STR124## wherein R 5 is as above and n 2 is a number from 2 to 4; ##STR125## and di- and trivalent oxyacid groups; R 1 and R 2 each are selected from the group consisting of hydrogen; alkyl having from one to about eighteen carbon atoms; cycloalkyl having from three to about eight carbon atoms; aryl having from about six to about eighteen carbon atoms; carbamoyl ##STR126## wherein R 5 is selected from the group consisting of aliphatic having from one to about eighteen carbon atoms; cycloaliphatic having from three to about eight carbon atoms; heterocyclic having from six to about eighteen carbon atoms; and aromatic having from six to about eighteen carbon atoms; ##STR127## and monovalent oxyacid groups; R 3 is selected from the group consisting of alkyl having from one to about eighteen carbon atoms; cycloalkyl having from three to about eight carbon atoms; aryl having from about six to about eighteen carbon atoms; and --X--O--R 1 ; R 7 is selected from the group consisting of the residues of monohydric alcohols having from one to about eighteen carbon atoms and phenols having from six to about fifty carbon atoms; R 11 is selected from the group consisting of alkylene and oxyalkylene having from two to about ten carbon atoms and from zero to about five oxyether groups; cycloalkylene having from three to about eight carbon atoms; and arylene having from six to about fifty carbon atoms; and isocyanurate; m is a number from zero to 10; and p is zero or 1.
Claim 2
Dependent Claim 559 words
2,2,6,6-Tetramethyl-4-piperidyl spiro aliphatic ethers having the general formula: ##STR117## wherein: Y 1 is ##STR118## A 1 , A 2 , A 3 , A 4 , A 5 , and A 6 each are selected from the group consisting of hydrogen; alkyl and hydroxyalkyl having from one to about eighteen carbon atoms; cycloalkyl having from three to about eight carbon atoms; aryl having from about six to about eighteen carbon atoms; acyl having from one to about eighteen carbon atoms ##STR119## wherein R 4 is selected from the group consisting of aliphatic having from one to about eighteen carbon atoms; cycloaliphatic having from three to about eight carbon atoms; heterocyclic having from six to about eighteen carbon atoms; and aromatic having from six to about eighteen carbon atoms; carbamoyl ##STR120## wherein R 5 is selected from the group consisting of aliphatic having from one to about eighteen carbon atoms; cycloaliphatic hving from three to about eight carbon atoms; heterocyclic having from six to about eighteen carbon atoms; and aromatic having from six to about eighteen carbon atoms; ##STR121## and monovalent oxyacid groups; at least one pair of A 1 and A 2 ; A 3 and A 4 ; and A 5 and A 6 being taken together to form the group: ##STR122## wherein: Z is selected from the group consisting of hydrogen; oxyl O.; alkyl and hydroxyalkyl having from one to about twenty carbon atoms; and aryl and hydroxyaryl having from six to about twenty carbon atoms; X is selected from the group consisting of alkylene having from one to about eighteen carbon atoms; cycloalkylene having from three to about eight carbon atoms; arylene having from about six to about eighteen carbon atoms; polyacyl ##STR123## wherein R 4 is as above and n 1 is a number from 2 to 4; polycarbamoyl ##STR124## wherein R 5 is as above and n 2 is a number from 2 to 4; ##STR125## and di- and trivalent oxyacid groups; R 1 and R 2 each are selected from the group consisting of hydrogen; alkyl having from one to about eighteen carbon atoms; cycloalkyl having from three to about eight carbon atoms; aryl having from about six to about eighteen carbon atoms; carbamoyl ##STR126## wherein R 5 is selected from the group consisting of aliphatic having from one to about eighteen carbon atoms; cycloaliphatic having from three to about eight carbon atoms; heterocyclic having from six to about eighteen carbon atoms; and aromatic having from six to about eighteen carbon atoms; ##STR127## and monovalent oxyacid groups; R 3 is selected from the group consisting of alkyl having from one to about eighteen carbon atoms; cycloalkyl having from three to about eight carbon atoms; aryl having from about six to about eighteen carbon atoms; and --X--O--R 1 ; R 7 is selected from the group consisting of the residues of monohydric alcohols having from one to about eighteen carbon atoms and phenols having from six to about fifty carbon atoms; R 11 is selected from the group consisting of alkylene and oxyalkylene having from two to about ten carbon atoms and from zero to about five oxyether groups; cycloalkylene having from three to about eight carbon atoms; and arylene having from six to about fifty carbon atoms; and isocyanurate; m is a number from zero to 10; and p is zero or 1.
Claim 3
Dependent Claim 39 words
2,2,6,6-Tetramethyl-4-piperidyl spiro aliphatic ethers according to claim 1 in which each pair of A 1 and A 2 ; A 3 and A 4 ; and A 5 and A 6 are taken together to form the group: ##STR128##
Claim 4
Dependent Claim 33 words
2,2,6,6-Tetramethyl-4-piperidyl spiro aliphatic ethers according to claim 1 in which at least one of A 1 , A 2 , A 3 , A 4 , A 5 and A 6 is hydrogen.
Claim 5
Dependent Claim 13 words
2,2,6,6-Tetramethyl-4-piperidyl spiro aliphatic ethers according to claim 1 in which Z is O.
Claim 6
Dependent Claim 13 words
2,2,6,6-Tetramethyl-4-piperidyl spiro aliphatic ethers according to claim 1 in which Z is hydroxyalkyl.
Claim 7
Dependent Claim 13 words
2,2,6,6-Tetramethyl-4-piperidyl spiro aliphatic ethers according to claim 1 in which Z is hydroxyaryl.
Claim 8
Dependent Claim 13 words
2,2,6,6-Tetramethyl-4-piperidyl spiro aliphatic ethers according to claim 1 in which X is alkylene.
Claim 9
Dependent Claim 13 words
2,2,6,6-Tetramethyl-4-piperidyl spiro aliphatic ethers according to claim 1 in which X is cycloalkylene.
Claim 10
Dependent Claim 13 words
2,2,6,6-Tetramethyl-4-piperidyl spiro aliphatic ethers according to claim 1 in which X is arylene.
Claim 11
Dependent Claim 72 words
2,2,6,6-Tetramethyl-4-piperidyl spiro aliphatic ethers according to claim 1 in which X is polyacyl ##STR129## wherein R 4 is selected from the group consisting of aliphatic having from one to about eighteen carbon atoms; cycloaliphatic having from three to about eight carbon atoms; heterocyclic having from six to about eighteen carbon atoms; and aromatic having from six to about eighteen carbon atoms; and n 1 is a a number from 2 to 4.
Claim 12
Dependent Claim 71 words
2,2,6,6-Tetramethyl-4-piperidyl spiro aliphatic ethers according to claim 1 in which X is polycarbamoyl ##STR130## wherein R 5 is selected from the group consisting of aliphatic having from one to about eighteen carbon atoms; cycloaliphatic having from three to about eight carbon atoms; heterocyclic having from six to about eighteen carbon atoms; and aromatic having from six to about eighteen carbon atoms; and n 2 is a number from 2 to 4.
Claim 13
Dependent Claim 12 words
2,2,6,6-Tetramethyl-4-piperidyl spiro aliphatic ethers according to claim 1 wherein X is ##STR131##
Claim 14
Dependent Claim 13 words
2,2,6,6-Tetramethyl-4-piperidyl spiro aliphatic ethers according to claim 1 in which X is ##STR132##
Claim 15
Dependent Claim 18 words
2,2,6,6-Tetramethyl-4-piperidyl spiro aliphatic ethers according to claim 1 in which X is a di- or trivalent oxyacid group.
Claim 16
Dependent Claim 17 words
2,2,6,6-Tetramethyl-4-piperidyl spiro aliphatic ethers according to claim 1 wherein R 1 and R 2 each are hydrogen.
Claim 17
Dependent Claim 17 words
2,2,6,6-Tetramethyl-4-piperidyl spiro aliphatic ethers according to claim 1 wherein R 1 and R 2 each are alkyl.
Claim 18
Dependent Claim 17 words
2,2,6,6-Tetramethyl-4-piperidyl spiro aliphatic ethers according to claim 1 wherein R 1 and R 2 each are aryl.
Claim 19
Dependent Claim 64 words
2,2,6,6-Tetramethyl-4-piperidyl spiro aliphatic ethers according to claim 1 wherein R 1 and R 2 each are ##STR133## wherein R 5 is selected from the group consisting of aliphatic having from one to about eighteen carbon atoms; cycloaliphatic having from three to about eight carbon atoms; heterocyclic having from six to about eighteen carbon atoms; and aromatic having from six to about eighteen carbon atoms.
Claim 20
Dependent Claim 50 words
2,2,6,6-Tetramethyl-4-piperidyl spiro aliphatic ethers according to claim 1 wherein R 1 and R 2 each are ##STR134## wherein R 7 is selected from the group consisting of the residues of monohydric alcohols having from one to about eighteen carbon atoms and phenols having from six to about fifty carbon atoms.
Claim 21
Dependent Claim 19 words
2,2,6,6-Tetramethyl-4-piperidyl spiro aliphatic ethers according to claim 1 wherein R 1 and R 2 each are monovalent oxyacid groups.
Claim 22
Dependent Claim 12 words
2,2,6,6-Tetramethyl-4-piperidyl spiro aliphatic ethers according to claim 1 wherein m is zero.
Claim 23
Dependent Claim 12 words
2,2,6,6-Tetramethyl-4-piperidyl spiro aliphatic ethers according to claim 1 wherein m is 1.
Claim 24
Dependent Claim 12 words
2,2,6,6-Tetramethyl-4-piperidyl spiro aliphatic ethers according to claim 1 wherein p is zero.
Claim 25
Dependent Claim 12 words
2,2,6,6-Tetramethyl-4-piperidyl spiro aliphatic ethers according to claim 1 wherein p is 1.
Claim 26
Dependent Claim 15 words
2,2,6,6-Tetramethyl-4-piperidyl spiro aliphatic ethers according to claim 23 wherein R 3 is --X--O--R 1 .
Claim 27
Dependent Claim 12 words
2,2,6,6-Tetramethyl-4-piperidyl spiro aliphatic ethers according to claim 1 having the structure: ##STR135##
Claim 28
Dependent Claim 12 words
2,2,6,6-Tetramethyl-4-piperidyl spiro aliphatic ethers according to claim 1 having the structure: ##STR136##
Claim 29
Dependent Claim 12 words
2,2,6,6-Tetramethyl-4-piperidyl spiro aliphatic ethers according to claim 1 having the structure: ##STR137##
Claim 30
Dependent Claim 12 words
2,2,6,6-Tetramethyl-4-piperidyl spiro aliphatic ethers according to claim 1 having the structure: ##STR138##
Claim 31
Dependent Claim 12 words
2,2,6,6-Tetramethyl-4-piperidyl spiro aliphatic ethers according to claim 1 having the structure: ##STR139##
Claim 32
Dependent Claim 12 words
2,2,6,6-Tetramethyl-4-piperidyl spiro aliphatic ethers according to claim 1 having the structure: ##STR140##
Claim 33
Dependent Claim 12 words
2,2,6,6-Tetramethyl-4-piperidyl spiro aliphatic ethers according to claim 1 having the structure: ##STR141##
Claim 34
Dependent Claim 12 words
2,2,6,6-Tetramethyl-4-piperidyl spiro aliphatic ethers according to claim 1 having the structure: ##STR142##
Claim 35
Dependent Claim 57 words
A polyvinyl chloride resin composition having improved resistance to deterioration when heated at 350° F., comprising a polyvinyl chloride resin formed at least in part of the recurring group ##STR143## and having a chlorine content in excess of 40%, where X is either hydrogen or chlorine; and a 2,2,6,6-tetramethyl-4-piperidyl spiro aliphatic ether in accordance with claim 1.
Claim 36
Dependent Claim 20 words
A polyvinyl chloride resin composition in accordance with claim 34 in which the polyvinyl chloride resin is polyvinyl chloride homopolymer.
Claim 37
Dependent Claim 25 words
A polyvinyl chloride resin composition in accordance with claim 34 in which the polyvinyl chloride resin is a copolymer of vinyl chloride and vinyl acetate.
Claim 38
Dependent Claim 42 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 2,2,6,6-tetramethyl-4-piperidyl spiro aliphatic ether in accordance with claim 1.
Claim 39
Dependent Claim 14 words
An olefin polymer composition in accordance with claim 37 wherein the polyolefin is polypropylene.
Claim 40
Dependent Claim 14 words
An olefin polymer composition in accordance with claim 37 wherein the polyolefin is polyethylene.
Claim 41
Dependent Claim 15 words
An olefin polymer composition in accordance with claim 37 wherein the polyolefin is ethylene-propylene copolymer.
Claim 42
Dependent Claim 22 words
An acrylonitrile-butadiene-styrene terpolymer having improved resistance to deterioration comprising acrylonitrile-butadiene-styrene terpolymer and a 2,2,6,6-tetramethyl-4-piperidyl spiro aliphatic ether in accordance with claim 1.
Claim 43
Dependent Claim 25 words
An ethylene-vinyl acetate copolymer composition having improved resistance to deterioration comprising ethylene-vinyl acetate copolymer and a 2,2,6,6-tetramethyl-4-piperidyl spiro aliphatic ether in accordance with claim 1.
Claim 44
Dependent Claim 24 words
A polyurethane resin composition having improved resistance to deterioration comprising a polyurethane resin and a 2,2,6,6-tetramethyl-4-piperidyl spiro aliphatic ether in accordance with claim 1.

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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) 1985-09-27 1986-03-29 1986-09-28 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1989-09-27 1990-03-29 1990-09-28 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1993-09-27 1994-03-29 1994-09-28 $7700.00 Window Closed / Lapsed

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