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US4005094A Expired / Lapsed US ⏱️ 0.0 years remaining

Piperidine-spiro-hydantoin derivatives

Assignee: Sankyo Co Ltd
•
Filing: 1975-01-10
•
Granted: 1977-01-25
•
Expires: 1995-01-10
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Abstract

Abstract Piperidine-spiro-hydrantoin derivatives having the formula ##STR1## 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 acryloxyalkyl group, an alkylthioalkyl group, an acyloxyalkyl group, an epoxyalkyl group, an N-alkyl-substituted aminoalkyl group, an alkoxycarbonylalkyl group, an aryloxycarbonylalkyl group, an aliphatic acyl group, an alkoxycarbonyl group, a phosphino group which is substituted with phenoxy or alkoxy or a phosphinyl group which is substituted with phenoxy or alkoxy, When n is 2, an alkenylene group of 4 to 18 carbon atoms, a dialkyleneether group, an aralkylene group, a bis(acyloxyalkylene) group or an alkylene-bis(oxycarbonylalkyl) group, When n is 3, a tris(acyloxyalkylene) group, an alkane-tris(oxycarbonylalkyl) group or a group of the formula ##STR2## 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, a tetrakis (acyloxyalkylene) group. These compounds (I) are useful as stabilizers against photo-and thermal-deteriorations 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 above and X 1 is a halogen atom.

Inventors

  • 👤 Keisuku Murayama
  • 👤 Syoji Moriyama
  • 👤 Takao Yoshioka
  • 👤 Toshimasa Toda
  • 👤 Eiko Mori
  • 👤 Hideo Horiuchi
  • 👤 Susumu Higashida
  • 👤 Katsuaki Matsui
  • 👤 Tomoyuki Kurumada
  • 👤 Noriyuki Ohata
  • 👤 Hisayou Ohsawa

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-29 14:26
CPC Classifications
C; C08; C08K; C08K5/00; C08K5/16; C08K5/34; C08K5/3442; C08K5/3445

Claims Analysis

Total Claims: 17
Claim 1
Independent Claim 189 words
A compound having the formula ##STR15##wherein X represents oxygen atom or sulfur atom; n is an integer of 1 to 4 inclusive; and R represents, when n is 1: alkenyl of 3 or 4 carbon atoms which may be substituted by halogen; 2-propynyl which may be substituted by phenyl; benzyl or phenethyl which may be substituted by halogen, alkyl of 1 to 4 carbon atoms or halomethyl; hydroxyalkyl of 2 to 4 carbon atoms; methoxyalkyl or ethoxyalkyl with 1 to 8 carbon atoms in the alkyl moiety; 2-vinyloxyethyl; 2-phenoxyethyl; 2-methylthioethyl; 2-acetoxyethyl, 4-decanoyloxybutyl; 2-acryloyloxyethyl, 2-methacryloyloxyethyl; 2-benzoyloxyethyl, 2-m-toluoyloxyethyl; 2,3-epoxypropyl; 2-dimethylaminoethyl; ethoxycarbonylalkyl having 1 to 8 carbon atoms in the alkyl moiety; phenoxycarbonylmethyl; acetyl, propionyl, butyryl; ethoxycarbonyl; ##STR16## when n is 2: an alkenylene group of 4 to 18 carbon atoms; --(CH 2 ) 2 --O--(CH 2 ) 2 --; ##STR17## --(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 --; ##STR18## or --CH 2 --CO--O--(CH 2 ) 2 --O--CO--CH 2 --; when n is 3: ##STR19##
Claim 2
Dependent Claim 189 words
A compound having the formula ##STR15##wherein X represents oxygen atom or sulfur atom; n is an integer of 1 to 4 inclusive; and R represents, when n is 1: alkenyl of 3 or 4 carbon atoms which may be substituted by halogen; 2-propynyl which may be substituted by phenyl; benzyl or phenethyl which may be substituted by halogen, alkyl of 1 to 4 carbon atoms or halomethyl; hydroxyalkyl of 2 to 4 carbon atoms; methoxyalkyl or ethoxyalkyl with 1 to 8 carbon atoms in the alkyl moiety; 2-vinyloxyethyl; 2-phenoxyethyl; 2-methylthioethyl; 2-acetoxyethyl, 4-decanoyloxybutyl; 2-acryloyloxyethyl, 2-methacryloyloxyethyl; 2-benzoyloxyethyl, 2-m-toluoyloxyethyl; 2,3-epoxypropyl; 2-dimethylaminoethyl; ethoxycarbonylalkyl having 1 to 8 carbon atoms in the alkyl moiety; phenoxycarbonylmethyl; acetyl, propionyl, butyryl; ethoxycarbonyl; ##STR16## when n is 2: an alkenylene group of 4 to 18 carbon atoms; --(CH 2 ) 2 --O--(CH 2 ) 2 --; ##STR17## --(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 --; ##STR18## or --CH 2 --CO--O--(CH 2 ) 2 --O--CO--CH 2 --; when n is 3: ##STR19##
Claim 3
Dependent Claim 29 words
A compound as claimed in claim 1, wherein n is 1, R is alkyl, 2,3-epoxypropyl, methoxymethyl, ethoxymethyl, acetoxyethyl, 4-decanoyloxybutyl, 2-acryloyloxethyl, ethoxy carbonylmethyl or 2-methacryloyloxyethyl, and X is oxygen atom.
Claim 4
Dependent Claim 17 words
A compound having the formula ##STR20##wherein X represents oxygen atom or sulfur atom; and R represents, ##STR21##
Claim 5
Dependent Claim 17 words
A compound having the formula ##STR20##wherein X represents oxygen atom or sulfur atom; and R represents, ##STR21##
Claim 6
Dependent Claim 1 words
3-Allyl-1,3,8-triaza-7,7,9,9-tetramethyl-spiro[4.5]decane-2,4-dione.
Claim 7
Dependent Claim 1 words
3-Allyl-1,3,8-triaza-7,7,9,9-tetramethyl-spiro[4.5]decane-2,4-dione.
Claim 8
Dependent Claim 1 words
1,3,8-Triaza-3-ethoxymethyl-7,7,9,9-tetramethyl-spiro[4.5]decane-2,4-dione.
Claim 9
Dependent Claim 1 words
1,3,8-Triaza-3-ethoxymethyl-7,7,9,9-tetramethyl-spiro[4.5]decane-2,4-dione.
Claim 10
Dependent Claim 1 words
3-(2-Acetoxyethyl)-1,3,8-triaza-7,7,9,9-tetramethyl-spiro[4.5]decane-2,4-dione.
Claim 11
Dependent Claim 1 words
3-(2-Acetoxyethyl)-1,3,8-triaza-7,7,9,9-tetramethyl-spiro[4.5]decane-2,4-dione.
Claim 12
Dependent Claim 1 words
1,3,8-Triaza-3-(4-decanoyloxybutyl)-7,7,9,9-tetramethyl-spiro[4.5]decane-2,4-dione.
Claim 13
Dependent Claim 1 words
1,3,8-Triaza-3-(4-decanoyloxybutyl)-7,7,9,9-tetramethyl-spiro[4.5]decane-2,4-dione.
Claim 14
Dependent Claim 1 words
3-(2-Acryloyloxyethyl)-1,3,8-triaza-7,7,9,9-tetramethyl-spiro[4.5]decane-2,4-dione
Claim 15
Dependent Claim 1 words
3-(2-Acryloyloxyethyl)-1,3,8-triaza-7,7,9,9-tetramethyl-spiro[4.5]decane-2,4-dione
Claim 16
Dependent Claim 1 words
1,3,8-Triaza-3-(2,3-epoxypropyl)-7,7,9,9-tetramethyl-spiro[4.5]decane-2,4-dione.
Claim 17
Dependent Claim 1 words
1,3,8-Triaza-3-(2,3-epoxypropyl)-7,7,9,9-tetramethyl-spiro[4.5]decane-2,4-dione.

References Cited (Backward Citations)

No citation records indexed.

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1980-01-25 1980-07-26 1981-01-25 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1984-01-25 1984-07-26 1985-01-25 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1988-01-25 1988-07-26 1989-01-25 $7700.00 Window Closed / Lapsed

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