US4097587A
Expired / Lapsed
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1,3,8-Triazaspiro 4.5!decane-2,4-dione polymer stabilizers
Assignee: Sankyo Co Ltd
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Filing: 1976-05-19
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Granted: 1978-06-27
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Expires: 1996-05-19
Abstract
Abstract Novel 7,7,9,9-tetra-substituted-1,3,8-triazaspiro[4.5]decane-2,4-diones having an alkyl or allyl group at either the 6- or the 10- position are useful for the stabilization of polymers against photo- and thermal- deterioration.
Inventors
- 👤 Nobuo Soma
- 👤 Tomoyuki Kurumada
- 👤 Heimo Brunetti
- 👤 Jean Rody
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 10:07
CPC Classifications
C; C07; C07D; C07D221/00; C07D221/02; C07D221/20; C07D211/00; C07D211/04; C07D211/68; C07D211/72; C07D211/74; C08; C08K; C08K5/00; C08K5/16; C08K5/34; C08K5/3442; C08K5/3445
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
229 words
A piperidine compound having the formula (I): ##STR25## wherein R a represents methyl group; R b represents ethyl group; R c represents an alkyl group of 1 to 5 carbons; R d represents ethyl group; or R c and R d , together with the carbon atom to which they are attached, represent a cycloalkyl group of 5 to 7 carbons; one of R e and R e' represents hydrogen atom and the other of R e and R e' represents a lower alkyl group of 1 to 4 carbons or an allyl group; n is 1 or 2; Y represents hydrogen atom or, when neither X nor Z represents hydrogen atom, Y represents hydrogen methyl group, ethyl group, allyl group or benzyl group; X represents hydrogen atom, or an alkyl group of 1 to 4 carbons; when n = 1: Z represents hydrogen atom, an alkyl group of 1 to 18 carbons 2,3-epoxypropyl group, or phenyl group when n = 2: X represents an alkylene group of 1 to 10 carbons and acid addition salts thereof wherein the acids are selected from the group consisting of sulphuric acid, hydrochloric acid or phosphoric acid; formic acid, acetic acid, valeric acid, stearic acid, oxalic acid, adipic acid, sebacic acid, maleic acid, benzoic acid, p-t-butylbenzoic acid, 4-hydroxy-3,5-di-t-butylbenzoic acid, salicylic acid or terephthalic acid; methanesulphonic acid or p-toluene-sulphonic acid; or phenylphosphonic acid.
Claim 2
Dependent Claim
229 words
A piperidine compound having the formula (I): ##STR25## wherein R a represents methyl group; R b represents ethyl group; R c represents an alkyl group of 1 to 5 carbons; R d represents ethyl group; or R c and R d , together with the carbon atom to which they are attached, represent a cycloalkyl group of 5 to 7 carbons; one of R e and R e' represents hydrogen atom and the other of R e and R e' represents a lower alkyl group of 1 to 4 carbons or an allyl group; n is 1 or 2; Y represents hydrogen atom or, when neither X nor Z represents hydrogen atom, Y represents hydrogen methyl group, ethyl group, allyl group or benzyl group; X represents hydrogen atom, or an alkyl group of 1 to 4 carbons; when n = 1: Z represents hydrogen atom, an alkyl group of 1 to 18 carbons 2,3-epoxypropyl group, or phenyl group when n = 2: X represents an alkylene group of 1 to 10 carbons and acid addition salts thereof wherein the acids are selected from the group consisting of sulphuric acid, hydrochloric acid or phosphoric acid; formic acid, acetic acid, valeric acid, stearic acid, oxalic acid, adipic acid, sebacic acid, maleic acid, benzoic acid, p-t-butylbenzoic acid, 4-hydroxy-3,5-di-t-butylbenzoic acid, salicylic acid or terephthalic acid; methanesulphonic acid or p-toluene-sulphonic acid; or phenylphosphonic acid.
Claim 3
Dependent Claim
142 words
A compound of claim 1 wherein R a is methyl group; R b and R d are each ethyl group; R c is an alkyl group of 1 to 5 carbon atoms; or R c and R d , together with the carbon atom to which they are attached, form a cycloalkyl group having from 5 to 7 carbon atoms; one of R e and R e' is hydrogen atom and the other of R e and R e' is an alkyl group having from 1 to 4 carbon atoms or allyl group; X is hydrogen or an alkyl group having 1 to 4 carbon atoms; when n is 1: Z is hydrogen, an alkyl group of 1 to 18 carbon atoms, 2,3-epoxypropyl group or phenyl group; when n is 2: Z is an alkylene group of 1 to 10 carbon atoms.
Claim 4
Dependent Claim
57 words
A piperidine compound according to claim 2, wherein X represents hydrogen atom or methyl group; Y represents hydrogen atom; Z represents hydrogen atom, an alkyl group having from 1 to 8 carbon atoms, 2,3-epoxypropyl group, phenyl group; or when n = 2: Z represents an alkylene group having from 2 to 6 carbon atoms or p-xylylene group.
Claim 5
Dependent Claim
26 words
A polymer composition stabilized against photo- and thermal-deterioration thereof wherein there is incorporated, in an amount sufficient to prevent said deterioration, a piperidine of claim 1.
Claim 6
Dependent Claim
26 words
A polymer composition stabilized against photo- and thermal-deterioration thereof wherein there is incorporated, in an amount sufficient to prevent said deterioration, a piperidine of claim 2.
Claim 7
Dependent Claim
26 words
A polymer composition stabilized against photo- and thermal-deterioration thereof wherein there is incorporated, in an amount sufficient to prevent said deterioration, a piperidine of claim 3.
Claim 8
Dependent Claim
32 words
A polymer composition according to claim 4, wherein said piperidine derivative is selected from the group consisting of: 7,9-diethyl-3,6,7,9-tetramethyl-1,3,8-triazaspiro 4.5!decane-2,4-dione 3-butyl-7,9-diethyl-6,7,9-trimethyl-1,3,8-triazaspiro 4.5!decane-2,4-dione 7,9-diethyl-6,7,9-trimethyl-3-octyl-1,3,8-triazaspiro 4.5!decane-2,4-dione 7,9-diethyl-6,7,9-trimethyl-3-phenyl-1,3,8-triazaspiro 4.5!decane-2,4-dione 3-(2,3-epoxypropyl)-7,9-diethyl-6,7,9-trimethyl-1,3,8-triazaspiro 4.5!decane-2,4-dione 1,4-bis(7,9-diethyl-6,7,9-trimethyl-2,4-dioxo-1,3,8-triazaspiro 4.5!dec-3-yl)butane 1,6-bis(7,9-diethyl-6,7,9-trimethyl-2,4-dioxo-1,3,8-triazaspiro 4.5!dec-3-yl)hexane
Claim 9
Dependent Claim
10 words
2-bis(7,9-diethyl-6,7,9-trimethyl-2,4-dioxo-1,3,8-triazaspiro 4.5!dec-3-ylacetoxy)ethane 7,9-diethyl-6,7,8,9-tetramethyl-1,3,8-triazaspiro 4.5!decane-2,4-dione 7,9-diethyl-3,6,7,8,9-pentamethyl-1,3,8-triazaspiro 4.5!decane-2,4-dione 1,6-bis(7,9-diethyl-6,7,8,9-tetramethyl-2,4-dioxo-1,3,8-triazaspiro 4.5!dec-3-yl)hexane 7,9-diethyl-1,3,6,7,8,9-hexamethyl-1,3,8-triazaspiro 4.5!decane-2,4-dione.
Claim 10
Dependent Claim
10 words
2-bis(7,9-diethyl-6,7,9-trimethyl-2,4-dioxo-1,3,8-triazaspiro 4.5!dec-3-ylacetoxy)ethane 7,9-diethyl-6,7,8,9-tetramethyl-1,3,8-triazaspiro 4.5!decane-2,4-dione 7,9-diethyl-3,6,7,8,9-pentamethyl-1,3,8-triazaspiro 4.5!decane-2,4-dione 1,6-bis(7,9-diethyl-6,7,8,9-tetramethyl-2,4-dioxo-1,3,8-triazaspiro 4.5!dec-3-yl)hexane 7,9-diethyl-1,3,6,7,8,9-hexamethyl-1,3,8-triazaspiro 4.5!decane-2,4-dione.
Claim 11
Dependent Claim
30 words
A polymer composition according to claim 4, wherein said piperidine derivative is incorporated in an amount of from 0.01 to 5.0% by weight based upon the weight of the polymer.
Claim 12
Dependent Claim
30 words
A polymer composition according to claim 7, wherein said piperidine derivative is incorporated in an amount of from 0.01 to 5.0% by weight based upon the weight of the polymer.
Claim 13
Dependent Claim
13 words
A polymer composition according to claim 4, wherein said polymer is polyvinyl chloride.
Claim 14
Dependent Claim
13 words
A polymer composition according to claim 4, wherein said polymer is a polyolefin.
Claim 15
Dependent Claim
13 words
A polymer composition according to claim 4, wherein said polymer is a polyurethane.
Claim 16
Dependent Claim
13 words
A polymer composition according to claim 4, wherein said polymer is a polyamide.
Claim 17
Dependent Claim
13 words
A polymer composition according to claim 4, wherein said polymer is a polypropylene.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-06-26 | 1981-12-26 | 1982-06-27 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-06-26 | 1985-12-26 | 1986-06-27 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-06-26 | 1989-12-26 | 1990-06-27 | $7700.00 | Window Closed / Lapsed |