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US3975462A Expired / Lapsed US ⏱️ 0.0 years remaining

Piperidine-spiro-hydantoin derivatives and their use as stabilizers

Assignee: Sankyo Co Ltd
•
Filing: 1974-10-22
•
Granted: 1976-08-17
•
Expires: 1994-10-22
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Abstract

Abstract Piperidine-spiro-hydantoin derivatives having the formula ##SPC1## Wherein X represents oxygen atom or sulfur atom; n is an integer of 1 to 4 inclusive, and R represents various aliphatic or aromatic groups depending on the value of n. These compounds (I) are useful as stabilizers against photo and thermal deterioration of various synthetic polymers and can be prepared, for example, by reacting the corresponding 3-unsubstituted piperidine-spiro-hydantoin compound with the halide R-(X 1 ) n in which R and n are as defined herein and X 1 is a halogen atom.

Inventors

  • 👤 Keisuke Murayama
  • 👤 Syoji Morimura
  • 👤 Takao Yoshioka
  • 👤 Toshimasa Toda
  • 👤 Eiko Mori
  • 👤 Hideo Horiuchi
  • 👤 Susumu Higashida
  • 👤 Katsuaki Matsui
  • 👤 Tomoyuki Kurumada
  • 👤 Noriyuki Ohta
  • 👤 Hisayou Ohsawa

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-28 17:32
CPC Classifications
C; C08; C08K; C08K5/00; C08K5/16; C08K5/34; C08K5/3442; C08K5/3445; C07; C07F; C07F9/00; C07F9/02; C07F9/547; C07F9/6561; C09; C09K; C09K15/00; C09K15/04; C09K15/30; C09K15/32; C09K15/322

Claims Analysis

Total Claims: 17
Claim 1
Independent Claim 234 words
A synthetic polymer composition stabilized against photo and thermal deterioration wherein there is incorporated, in a sufficient amount to prevent said deterioration, a compound having the formula ##SPC11## wherein X represents oxygen atom or sulfur atom; n is an integer of 1 to 4 inclusive; and R represents, when n is 1, an alkenyl group which may be substituted with halogen, an alkynyl group which may be substituted with phenyl, an aralkyl group which may be substituted with halogen, alkyl of 1 to 4 carbon atoms or halomethyl, a hydroxyalkyl group, an alkoxyalkyl group, an alkenyloxyalkyl group, an aryloxyalkyl group, an alkylthioalkyl group, and acyloxyalkyl group, an epoxyalkyl group, an N-alkyl-substituted aminoalkyl group, an alkoxycarbonylalkyl group, an aryloxycarbonylalkyl group, an alkoxycarbonyl group, (C 2 H 5 O) 2 --P--, ##SPC12## when n is 2, an alkenylene group of 4 to 18 carbon atoms, a dialkyleneether group, an aralkylene group, --(CH 2 ) 2 --O--CO--CO--O--(CH 2 ) 2 --, --(CH 2 ) 2 --O--CO--(CH 2 ) 2 --CO--O-- (CH 2 ) 2 --, --(CH 2 ) 2 --O--CO--(CH 2 ) 4 --CO--O--(CH 2 ) 2 --, ##SPC13## --ch 2 --co--o--(ch 2 ) 2 --o--co--ch 2 --; when n is 3, ##EQU1## ##SPC14## ##EQU2## or a group of the formula ##EQU3## in which p is an integer of 1 to 8 inclusive and p's may be the same or different, and, when n is 4, ##SPC15##2.
Claim 2
Dependent Claim 234 words
A synthetic polymer composition stabilized against photo and thermal deterioration wherein there is incorporated, in a sufficient amount to prevent said deterioration, a compound having the formula ##SPC11## wherein X represents oxygen atom or sulfur atom; n is an integer of 1 to 4 inclusive; and R represents, when n is 1, an alkenyl group which may be substituted with halogen, an alkynyl group which may be substituted with phenyl, an aralkyl group which may be substituted with halogen, alkyl of 1 to 4 carbon atoms or halomethyl, a hydroxyalkyl group, an alkoxyalkyl group, an alkenyloxyalkyl group, an aryloxyalkyl group, an alkylthioalkyl group, and acyloxyalkyl group, an epoxyalkyl group, an N-alkyl-substituted aminoalkyl group, an alkoxycarbonylalkyl group, an aryloxycarbonylalkyl group, an alkoxycarbonyl group, (C 2 H 5 O) 2 --P--, ##SPC12## when n is 2, an alkenylene group of 4 to 18 carbon atoms, a dialkyleneether group, an aralkylene group, --(CH 2 ) 2 --O--CO--CO--O--(CH 2 ) 2 --, --(CH 2 ) 2 --O--CO--(CH 2 ) 2 --CO--O-- (CH 2 ) 2 --, --(CH 2 ) 2 --O--CO--(CH 2 ) 4 --CO--O--(CH 2 ) 2 --, ##SPC13## --ch 2 --co--o--(ch 2 ) 2 --o--co--ch 2 --; when n is 3, ##EQU1## ##SPC14## ##EQU2## or a group of the formula ##EQU3## in which p is an integer of 1 to 8 inclusive and p's may be the same or different, and, when n is 4, ##SPC15##2.
Claim 3
Dependent Claim 15 words
The synthetic polymer composition of claim 1 wherein n is 3 and R is ##STR5##
Claim 4
Dependent Claim 73 words
The synthetic polymer composition according to claim 1 wherein said compound (I) is a member selected from the compounds (I) in which n is 1 and R is an alkenyl group; an alkoxyalkyl group, an acyloxyalkyl group, an epoxyalkyl group or an alkoxycarbonylalkyl group, provided that the alkyl moiety attached directly to the N atom of a piperidinespiro-hydantoin structure has 1 to 8 carbon atoms in the substituted alkyl groups; or diphenoxyphosphinyl group.
Claim 5
Dependent Claim 73 words
The synthetic polymer composition according to claim 1 wherein said compound (I) is a member selected from the compounds (I) in which n is 1, R is allyl group; 2,3-epoxypropyl group; or an alkoxyalkyl group, an alkanoyloxyalkyl group or an alkenoyloxyalkyl group, provided that the alkyl moiety attached directly to the N atom of a piperidinespiro-hydantoin structure has 1 to 4 carbon atoms in the substituted alkyl groups and X is oxygen atom.
Claim 6
Dependent Claim 31 words
The synthetic polymer composition according to claim 1 wherein said compound (I) is incorporated in an amount of 0.01 - 5.0% by weight based upon the amount of said synthetic polymer.
Claim 7
Dependent Claim 17 words
The synthetic polymer composition according to claim 1 wherein said polymer is a homopolymer of an olefin.
Claim 8
Dependent Claim 15 words
The synthetic polymer composition according to claim 1 wherein said polymer is polypropylene or polystyrene.
Claim 9
Dependent Claim 22 words
The synthetic polymer composition according to claim 1 wherein said polymer is a copolymer of an olefin with other ethylenically unsaturated monomer.
Claim 10
Dependent Claim 15 words
The synthetic polymer composition according to claim 1 wherein said polymer is an acrylonitrile-butadiene-styrene copolymer.
Claim 11
Dependent Claim 26 words
The synthetic polymer composition according to claim 1 wherein said polymer is a polyamide having recurring amide groups as integral parts of the main polymer chain.
Claim 12
Dependent Claim 13 words
The synthetic polymer composition according to claim 1 wherein said polymer is 6-nylon.
Claim 13
Dependent Claim 14 words
The synthetic polymer composition according to claim 1 wherein said polymer is a polyurethane.
Claim 14
Dependent Claim 15 words
The synthetic polymer composition according to claim 1 wherein said polymer is a polyvinyl chloride.
Claim 15
Dependent Claim 14 words
The synthetic polymer composition according to claim 1 wherein said polymer is a polyester.
Claim 16
Dependent Claim 14 words
The synthetic polymer composition according to claim 1 wherein said polymer is a polyacetal.
Claim 17
Dependent Claim 27 words
The synthetic polymer composition according to claim 1 wherein said compound (I) is selected from the group consisting of, 3-allyl-1,3,8-triaza-7,7,9,9-tetramethyl-spiro[4.5] decane-2,4-dione, 1,3,8-triaza-3-ethoxymethyl-7,7,9,9-tetramethylspiro[4.5]decane-2,4-dione, 3-(2-acetoxyethyl)-1,3,8-triaza-7,7,9,9-tetramethylspiro[4.5]decane-2,4-dione, 1,3,8-triaza-3-(4-decanoyloxybutyl)-7,7,9,9-tetramethylspiro[4.5]decane-2,4-dione, 3-(2-acryloyloxyethyl)-1,3,8-triaza-7,7,9,9-tetramethylspiro[4.5]decane-2,4-dione and 1,3,8-triaza-3-(2,3-epoxypropyl)-7,7,9,9-tetramethylspiro[4.5]decane-2,4-dione.

References Cited (Backward Citations)

US2225384A Cited
US2687416A Cited
US3213104A Cited
US2143816A Cited
US2551134A Cited
US2778825A Cited
US2928841A Cited
US3542729A Cited
US3705126A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1979-08-17 1980-02-16 1980-08-17 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1983-08-17 1984-02-16 1984-08-17 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1987-08-17 1988-02-16 1988-08-17 $7700.00 Window Closed / Lapsed

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