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US4376836A
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Triazylaminotriazines, their preparation and their use for stabilizing synthetic polymers
Assignee: Hoechst AG
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Filing: 1981-07-13
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Granted: 1983-03-15
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Expires: 2001-07-13
Abstract
Abstract Triazinylaminotriazines of the general formula <IMAGE> which are used as stabilizers for polymers, are prepared by reacting a cyanuric halide with amines containing triazinyl and polyalkylpiperidylamino groups.
Inventors
- 👤 Hartmut Wiezer
- 👤 Gerhard Pfahler
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 16:59
CPC Classifications
C; C08; C08K; C08K5/00; C08K5/16; C08K5/34; C08K5/3467; C08K5/3477; C08K5/3492; C08K5/34926
Claims Analysis
Total Claims: 10
Claim 1
Independent Claim
327 words
Triazinylaminotriazines of the general formula (I) ##STR9## in which the radicals R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are identical or different and denote C 1 - to C 18 -alkyl, C 5 - to C 12 -cycloalkyl, C 7 - to C 14 -aralkyl or a group of the formula (II), (III) or (IV) ##STR10## but at least the radicals R 1 , R 3 and R 5 represent a group of the formula (III) or (IV), and, in the formulae (II), (III) and (IV), R 7 denotes hydrogen or C 1 - to C 5 -alkyl, R 8 and R 9 denote identical or different radicals, which can be hydrogen, C 1 - to C 18 -alkyl, C 5 - to C 12 -cycloalkyl, C 7 - to C 14 -aralkyl or a group of the formula (II), l, m and n denote identical or different integers from 2 to 6, p denotes an integer from 1 to 3 and X denotes a radical of the formula ##STR11## in which R 10 and R 11 represent identical or different radicals which can be hydrogen, C 1 - to C 18 -alkyl, which can be substituted by hydroxyl, C 1 - to C 18 -alkoxy or C 1 - to C 4 -dialkylamino, C 5 - to C 12 -cycloalkyl, phenyl, which can be substituted by C 1 - to C 18 -alkyl, or C 7 - to C 14 -aralkyl or a group of the formula (II), but, in said X, at least one radical R 10 or R 11 must be a C 2 - to C 5 -alkyl group which is substituted by C 1 - to C 4 -dialkylamino, and R 12 is hydrogen, C 1 - to C 18 -alkyl, C 5 - to C 12 -cycloalkyl, C 7 - to C 14 -aralkyl or a group of the formula (II).
Claim 2
Dependent Claim
327 words
Triazinylaminotriazines of the general formula (I) ##STR9## in which the radicals R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are identical or different and denote C 1 - to C 18 -alkyl, C 5 - to C 12 -cycloalkyl, C 7 - to C 14 -aralkyl or a group of the formula (II), (III) or (IV) ##STR10## but at least the radicals R 1 , R 3 and R 5 represent a group of the formula (III) or (IV), and, in the formulae (II), (III) and (IV), R 7 denotes hydrogen or C 1 - to C 5 -alkyl, R 8 and R 9 denote identical or different radicals, which can be hydrogen, C 1 - to C 18 -alkyl, C 5 - to C 12 -cycloalkyl, C 7 - to C 14 -aralkyl or a group of the formula (II), l, m and n denote identical or different integers from 2 to 6, p denotes an integer from 1 to 3 and X denotes a radical of the formula ##STR11## in which R 10 and R 11 represent identical or different radicals which can be hydrogen, C 1 - to C 18 -alkyl, which can be substituted by hydroxyl, C 1 - to C 18 -alkoxy or C 1 - to C 4 -dialkylamino, C 5 - to C 12 -cycloalkyl, phenyl, which can be substituted by C 1 - to C 18 -alkyl, or C 7 - to C 14 -aralkyl or a group of the formula (II), but, in said X, at least one radical R 10 or R 11 must be a C 2 - to C 5 -alkyl group which is substituted by C 1 - to C 4 -dialkylamino, and R 12 is hydrogen, C 1 - to C 18 -alkyl, C 5 - to C 12 -cycloalkyl, C 7 - to C 14 -aralkyl or a group of the formula (II).
Claim 3
Dependent Claim
41 words
A compound according to claim 1 wherein only one of the two radicals R 10 and R 11 of the radical denoted by X is a C 1 - to C 5 -alkyl group substituted by C 1 -C 4 dialkylamino.
Claim 4
Dependent Claim
35 words
A compound according to claim 1 wherein both R 10 and R 11 of the radical denoted by X are C 2 - to C 5 -alkyl groups substituted by C 1 -C 4 dialkylamino.
Claim 5
Dependent Claim
212 words
A process for the preparation of the triazinylaminotriazines as claimed in claim 1, which comprises A. reacting 1 mole of a cyanuric halide with 1.0 to 1.05 moles of an amine of the formula (V) ##STR12## at 0° to 10° C., and then B. reacting the compound obtained according to A with 1.0 to 1.05 moles of an amine of the formula (VI) ##STR13## at 20° to 50° C., each reaction being carried out in the presence of equivalent amounts of an inorganic base and in the presence of an organic solvent, to give a compound of the formula (VII) ##STR14## C. reacting (p+2) moles of this compound with 1 mole of a polyamine of the formula (VIII) ##STR15## at 80° to 180° C. in the presence of equivalent amounts of an inorganic base and of an organic solvent, and finally D. allowing the reaction product obtained according to C to react with the equivalent amount, relative to the remaining amino groups, of a cyanuric halide at 10° to 180° C., likewise in an organic solvent and in the presence of an inorganic base, the indices R 7 to R 12 , l, m, n and p used in the formulae having the meaning given in claim 1 and Hal representing halogen.
Claim 6
Dependent Claim
28 words
A process as claimed in claim 4, wherein the reaction steps A to D are carried out by a so-called "one-pot process" without isolation of the intermediate stages.
Claim 7
Dependent Claim
36 words
A process for stabilizing synthetic polymers against the harmful effect of light, which comprises adding 0.01 to 5 parts by weight, relative to the polymer, of a stabilizer as claimed in claim 1 to the polymers.
Claim 8
Dependent Claim
12 words
Process as claimed in claim 6, which comprises using as polymers polyolefins.
Claim 9
Dependent Claim
22 words
Process as claimed in claim 6, which comprises using as polymers halogen-containing polymers, polyacrylates or polymethacrylates or homopolymers or copolymers of styrene.
Claim 10
Dependent Claim
32 words
Synthetic polymers which have been stabilized against decomposition by UV light and which contain 0.01 to 5 parts by weight, relative to the polymer, of a stabilizer as claimed in claim 1.
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) | 1986-03-14 | 1986-09-13 | 1987-03-15 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-03-14 | 1990-09-13 | 1991-03-15 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-03-14 | 1994-09-13 | 1995-03-15 | $7700.00 | Window Closed / Lapsed |