EP0172413A2
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EP
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Process for producing piperidine derivatives
Assignee: Sumitomo Chemical Co Ltd
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Filing: 1985-07-17
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Granted: —
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Expires: 2005-07-17
Abstract
Abstract wherein R, is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms; R 2 is a hydrogen atom or an alkyl group having 1 to 2 carbon atoms; and R 3 and R 4 is each independently an alkyl group having 1 to 12 carbon atoms, which process comprises reacting a piperidine represented by the general formula (I) wherein R 1 and R 2 are as defined above, with a ketone represented by the general formula (II) wherein R 3 and R 4 are as defined above, in the presence of chloroform and alkali and in the presence or absence of a phase transfer catalyst, and a stabilized resin composition comprising a resin, said piperidine derivative, a phenol-type antioxidant and a sulfur-containing antioxidant.
Inventors
- 👤 Takeo Fujii
- 👤 Tamaki Ishii
- 👤 Shinichi Yachigo
- 👤 Tatsuo Kaneoya
- 👤 Yukoh Takahashi
- 👤 Yuzo Maegawa
- 👤 Haruki Okamura
- 👤 Eizo Okino
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-10-27 16:40
CPC Classifications
C; C08; C08K; C08K5/00; C08K5/04; C08K5/13; C07; C07D; C07D211/00; C07D211/04; C07D211/06; C07D211/36; C07D211/56; C07D211/58; C08K5/16; C08K5/34; C08K5/3412; C08K5/3432; C08K5/3435; C08K5/36; C08K5/37; C08K5/375
Claims Analysis
Total Claims: 24
Claim 1
Independent Claim
123 words
A process for producing a piperidine derivative represented by the general formula (III) wherein R 1 is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms; R 2 is a hydrogen atom or an alkyl group having 1 to 12 carbon atoms; and R 3 and R 4 are each independently an alkyl group having 1 to 12 carbon atoms, which process comprises reacting a piperidine represented by the general formula (I) wherein R 1 and R 2 are as defined above, with a ketone represented by the general formula (II) wherein R 3 and R 4 are as defined above, in the presence of chloroform and alkali and in the presence or absence of a phase transfer catalyst.
Claim 2
Dependent Claim
123 words
A process for producing a piperidine derivative represented by the general formula (III) wherein R 1 is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms; R 2 is a hydrogen atom or an alkyl group having 1 to 12 carbon atoms; and R 3 and R 4 are each independently an alkyl group having 1 to 12 carbon atoms, which process comprises reacting a piperidine represented by the general formula (I) wherein R 1 and R 2 are as defined above, with a ketone represented by the general formula (II) wherein R 3 and R 4 are as defined above, in the presence of chloroform and alkali and in the presence or absence of a phase transfer catalyst.
Claim 3
Dependent Claim
56 words
A process according to Claim 1, wherein in the general formula (III), R 1 is a hydrogen atom or a methyl group, R 2 is a hydrogen atom or a hydrocarbon group having 1 to 4 carbon atoms; and R 3 and R 4 are each independently a hydrocarbon group having 1 to 7 carbon atoms.
Claim 4
Dependent Claim
19 words
A process according to Claim 1, wherein the alkali is a hydroxide of alkali metals or alkaline earth metals.
Claim 5
Dependent Claim
15 words
A process according to Claim 3, wherein the alkali is sodium hydroxide or potassium hydroxide.
Claim 6
Dependent Claim
25 words
A process according to Claim 1, wherein the phase transfer catalyst is benzyltrimethylammonium chloride, benzyltriethylammonium chloride, tetrabutylammonium bromide, tetrabutylphosphonium chloride, trioctylmethylammonium chloride or tetraphenylphosphonium bromide.
Claim 7
Dependent Claim
27 words
A process according to Claim 1, wherein the piperidine represented by the general formula (I) is 4-amino-2,2,6,6-tetramethylpiperidine, 4-amino-1,2,2,6,6-pentamethylpiperidine, 4-amino-l-ethyl-2,2,6,6-tetramethylpiperidine, 4-N-butylamino-2,2,6,6-tetramethylpiperidine, 4-N-butylamino-l,2,2,6,6-pentamethyl- piperidine, 4-N-octylamino-2,2,6,6-tetramethylpiperidine, 4-N-octylamino-l,2,2,6,6-pentamethylpiperidine, 4-N-laurylamino-2,2,6,6-tetramethylpiperidine or 4-N-laurylamino-l,2,2,6,6-pentamethylpiperidine.
Claim 8
Dependent Claim
28 words
A process according to Claim 1, wherein the ketone represented by the general formula (II) is acetone, methyl ethyl ketone, methyl isopropyl ketone, methyl isobutyl ketone or 2-nonanone.
Claim 9
Dependent Claim
26 words
A process according to Claim 1, wherein the ratio of the piperidine represented by the general formula (I) to chloroform is 1 to 0.5-4 by mole.
Claim 10
Dependent Claim
33 words
A process according to Claim 1, wherein the ratio of the piperidine represented by the general formula (I) to the ketone represented by the general formula (II) is 1 to 0.5-2 by mole.
Claim 11
Dependent Claim
34 words
A process according to Claim 1, wherein the ratio of the piperidine represented by the general formula (I) to chloroform is 1 to 0.5-4 by mole in the absence of a phase transfer catalyst.
Claim 12
Dependent Claim
41 words
A process according to Claim 1, wherein the ratio of the piperidine represented by the general formula (I) to the ketone represented by the general formula (II) is 1 to 0.5-2 by mole in the absence of a phase transfer catalyst.
Claim 13
Dependent Claim
27 words
A process according to Claim 1, wherein the ratio of the piperidine represented by the general formula (I) to the alkali is 1 to 1-4 by mole.
Claim 14
Dependent Claim
29 words
A process according to Claim 1, wherein the ratio of the piperidine represented by the general formula (I) to the phase transfer catalyst is 1 to 0.0001-0.01 by mole.
Claim 15
Dependent Claim
33 words
A process according to Claim 1, wherein the reaction between the piperidine represented by the general formula (I) and the ketone represented by the general formula (II) is conducted at -30° to 60°C.
Claim 16
Dependent Claim
73 words
A stabilized resin composition comprising a resin, a piperidine derivative represented by the general formula (III) wherein R l is a hydrogen atom or an.alkyl group having 1 to 3 carbon atoms; R 2 is a hydrogen atom or an alkyl group having 1 to 12 carbon atoms; and R 3 and R 4 are each independently an alkyl group having 1 to 12 carbon atoms, a phenol-type antioxidant and a sulfur-containing antioxidant.
Claim 17
Dependent Claim
73 words
A stabilized resin composition comprising a resin, a piperidine derivative represented by the general formula (III) wherein R l is a hydrogen atom or an.alkyl group having 1 to 3 carbon atoms; R 2 is a hydrogen atom or an alkyl group having 1 to 12 carbon atoms; and R 3 and R 4 are each independently an alkyl group having 1 to 12 carbon atoms, a phenol-type antioxidant and a sulfur-containing antioxidant.
Claim 18
Dependent Claim
58 words
A stabilized resin composition according to Claim 15, wherein in the general formula (III), R 1 is a hydrogen atom or a methyl group, R 2 is a hydrogen atom or a hydrocarbon group having 1 to 4 carbon atoms, and R 3 and R 4 are each independently a hydrocarbon group having 1 to 7 carbon atoms.
Claim 19
Dependent Claim
42 words
A stabilized resin composition according to Claim 15, wherein the phenol-type antioxidant is one member selected from the group consisting of 2,6-di-t-butyl-4-methylphenol, n-octadecyl 3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate, 2,2'-methylenebis-(4-methyl-6-t-butylphenol), 4,4'-butylidenebis(3-methyl-6-t-butylphenol), 4,4'-thiobis(3-methyl-6-t-butylphenol), 2-t-butyl-6-(3-t-butyl-5-methyl-2-hydroxybenzyl)-4-methylphenyl acrylate, 1,1,3-tris(2-methyl-4-hydroxy-5-t-butylphenyl)butane, 1,3,5-trimethyl-2,4,6-tris(3-alkyl-5-t-butyl-4-hydroxybenzyl)benzene, l,3,5-tris(3-alkyl-5-t-butyl-4-hydroxybenzyl) isocyanurate, l,3,5-tris(3-(3-alkyl-5-t-butyl-4-hydroxyphenyl)propionyloxyethyl) isocyanurate, ethylene glycol bis(3,3-bis(4-hydroxy-3-t-butylphenyl)butanate, and pentaerythritol tetrakis(3-(3-alkyl-5-t-butyl-4-hydroxyphenyl) propionate).
Claim 20
Dependent Claim
31 words
A stabilized resin composition according to Claim 15, wherein the sulfur-containing antioxidant is one member selected from the group consisting of dilauryl thiodipropionate, dimyristyl thiodipropionate, distearyl thiodipropionate, pentaerythritol tetrakis(3-dodecylthiopropionate), and 3,9-bis(2-dodecylthioethyl)-2,4,8,10-tetraoxaspiro[5.5]undecane.
Claim 21
Dependent Claim
73 words
A stabilized resin composition according to Claim 15, wherein said resin is poly-a-olefins, a-olefin copolymers, copolymers of poly-a-olefin with a vinyl monomer, chlorinated polyethylene, EVA resin, polyvinyl chloride, methacrylic resin, polystyrene, high impact polystyrene, ABS resin, AES resin, MBS resin, polyethylene terephthalate, polybutylene terephthalate, polyamide, polyimide, polycarbonate, polyacetal, polyurethane, unsaturated polyester resin, or blended products of these resins with isoprene rubber, butadiene rubber, acrylonitrile-butadiene copolymer rubber, styrene-butadiene copolymer rubber or ethylene propylene rubber.
Claim 22
Dependent Claim
63 words
A stabilized resin composition according to Claim 15, wherein the amount of the piperidine derivative represented by the general formula (III) is 0.01 to 5 parts by weight based on 100 parts by weight of the resin and the ratio of said piperidine derivative to the phenol-type antioxidant and the sulfur-containing antioxidant in this order is 1-20 : 1 : 1-15 by weight.
Claim 23
Dependent Claim
15 words
A stabilized resin composition according to Claim 15, wherein a phosphite-type antioxidant has been incorporated.
Claim 24
Dependent Claim
26 words
A stabilized resin composition according to Claim 15, wherein a light stabilizer other than the piperidine derivative represented by the general formula (III) has been incorporated.
References Cited (Backward Citations)
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