US4578472A
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2,2,6,6-Tetramethylpiperidine and its production
Assignee: Sumitomo Chemical Co Ltd
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Filing: 1984-05-15
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Granted: 1986-03-25
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Expires: 2004-05-15
Abstract
Abstract There is provided a 2,2,6,6-tetramethylpiperidine derivative represented by the formula (I), ##STR1## wherein R 1 and R 2 independently represent a hydrogen atom or methyl group, and R 3 represents an alkylene group having one to four carbon atoms. A method for producing said derivatives is also provided.
Inventors
- 👤 Masakatsu Yoshimura
- 👤 Takeo Fujii
- 👤 Shinichi Yachigo
- 👤 Tamaki Ishii
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 12:13
CPC Classifications
C; C07; C07D; C07D211/00; C07D211/04; C07D211/06; C07D211/36; C07D211/56; C07D211/58; C08; C08K; C08K5/00; C08K5/16; C08K5/34; C08K5/3412; C08K5/3432; C08K5/3435
Claims Analysis
Total Claims: 20
Claim 1
Independent Claim
36 words
A 2,2,6,6-tetramethylpiperidine derivative represented by the formula (I), ##STR7## wherein R 1 and R 2 independently represent a hydrogen atom or methyl group, and R 3 represents an alkylene group having one to four carbon atoms.
Claim 2
Dependent Claim
36 words
A 2,2,6,6-tetramethylpiperidine derivative represented by the formula (I), ##STR7## wherein R 1 and R 2 independently represent a hydrogen atom or methyl group, and R 3 represents an alkylene group having one to four carbon atoms.
Claim 3
Dependent Claim
18 words
The 2,2,6,6-tetramethylpiperidine derivative as described in claim 1, wherein R 1 and R 2 are a hydrogen atom.
Claim 4
Dependent Claim
39 words
The 2,2,6,6-tetramethylpiperidine derivative as described in claim 1, wherein the substituent R 3 is --CH 2 --, --CH 2 CH 2 --, --CH 2 CH 2 CH 2 -- or --CH 2 CH 2 CH 2 CH 2 --.
Claim 5
Dependent Claim
18 words
The 2,2,6,6-tetramethylpiperidine derivative as described in claim 3, wherein R 1 and R 2 are a hydrogen atom.
Claim 6
Dependent Claim
17 words
The 2,2,6,6-tetramethylpiperidine derivative as described in claim 1, wherein the substituent R 3 is --CH 2 --.
Claim 7
Dependent Claim
17 words
The 2,2,6,6-tetramethylpiperidine derivative as described in claim 2, wherein the substituent R 3 is --CH 2 --.
Claim 8
Independent Claim
176 words
A method for producing a 2,2,6,6-tetramethylpiperidine derivative represented by the formula (I), ##STR8## wherein R 1 and R 2 independently represent a hydrogen atom or methyl group, and R 3 represents an alkylene group having one to four carbon atoms, wherein a 4-amino-2,2,6,6-tetramethylpiperidine compound represented by the formula (II), ##STR9## wherein R 1 has the same meaning as above, is reacted with a halogenated carboxylic acid or ester represented by the formula (III), ##STR10## wherein X represents a halogen atom, R 3 has the same meaning as above, and R 4 represents a hydrogen atom or lower alkyl group, and then the resulting reaction product is reacted with a 4-hydroxy-2,2,6,6-tetramethylpiperidine compound represented by the formula (IV), ##STR11## wherein R 2 has the same meaning as above, in the presence of a basic catalyst, wherein the molar ratio of the compound of formula (II) to the acid of formula (III) is 1 to 2.5 and wherein the molar ratio of the compound of formula (IV) is 2 to 2.5 times amount of the compound of formula (II).
Claim 9
Independent Claim
176 words
A method for producing a 2,2,6,6-tetramethylpiperidine derivative represented by the formula (I), ##STR8## wherein R 1 and R 2 independently represent a hydrogen atom or methyl group, and R 3 represents an alkylene group having one to four carbon atoms, wherein a 4-amino-2,2,6,6-tetramethylpiperidine compound represented by the formula (II), ##STR9## wherein R 1 has the same meaning as above, is reacted with a halogenated carboxylic acid or ester represented by the formula (III), ##STR10## wherein X represents a halogen atom, R 3 has the same meaning as above, and R 4 represents a hydrogen atom or lower alkyl group, and then the resulting reaction product is reacted with a 4-hydroxy-2,2,6,6-tetramethylpiperidine compound represented by the formula (IV), ##STR11## wherein R 2 has the same meaning as above, in the presence of a basic catalyst, wherein the molar ratio of the compound of formula (II) to the acid of formula (III) is 1 to 2.5 and wherein the molar ratio of the compound of formula (IV) is 2 to 2.5 times amount of the compound of formula (II).
Claim 10
Dependent Claim
18 words
The method as described in claim 7, wherein in the first-step reaction, an inert organic solvent is used.
Claim 11
Dependent Claim
16 words
The method as claimed in claim 8, wherein the inert organic solvent is toluene or xylene.
Claim 12
Dependent Claim
20 words
The method as described in claim 7, wherein in the first-step reaction, the reaction temperature is 10° to 100° C.
Claim 13
Dependent Claim
41 words
The method as described in claim 7, wherein the halogenated carboxylic acid or ester represented by the formula (III) is monochloroacetic acid, monobromoacetic acid, 3-chloropropionic acid, 3-bromopropionic acid, 4-chlorobutyric acid, 4-bromobutyric acid, 5-chlorovaleric acid, 5-bromovaleric acid or lower alkyl esters thereof.
Claim 14
Dependent Claim
20 words
The method as claimed in claim 11, wherein the lower alkyl ester is the methyl, ethyl, propyl or butyl ester.
Claim 15
Dependent Claim
54 words
The method as described in claim 7, wherein in the second-step reaction to react the reaction product resulting from said first-step reaction with a 4-hydroxy-2,2,6,6-tetramethylpiperidine compound represented by the formula (IV) in the presence of a basic catalyst, the reaction product is used after separated from the reaction solution or without being separated therefrom.
Claim 16
Dependent Claim
52 words
The method as described in claim 13, wherein the basic catalyst used in the second-step reaction is sodium hydroxide, potassium hydroxide, lithium hydroxide, lithium aluminum hydride, sodium boron hydride, sodium hydride, lithium hydride, sodium amide, sodium tert-butoxide, potassium tert-butoxide, sodium methoxide, potassium methoxide, sodium phenoxide, potassium phenoxide, metallic sodium or metallic potassium.
Claim 17
Dependent Claim
31 words
The method as described in claim 14, wherein the amount of the catalyst used is 0.1 to 0.5 time by mole based on the 4-amino-2,2,6,6-tetramethylpiperidine compound represented by the formula (II).
Claim 18
Dependent Claim
16 words
The method as described in claim 13, wherein the reaction temperature is 10° to 50° C.
Claim 19
Dependent Claim
18 words
The method as described in claim 7, wherein in the second-step reaction, an inert organic solvent is used.
Claim 20
Dependent Claim
17 words
The method as claimed in claim 17, wherein the inert organic solvent is methanol, toluene or xylene.
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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) | 1989-03-24 | 1989-09-23 | 1990-03-25 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1993-03-24 | 1993-09-23 | 1994-03-25 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1997-03-24 | 1997-09-23 | 1998-03-25 | $7700.00 | Window Closed / Lapsed |