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US4110304A Expired / Lapsed US ⏱️ 0.0 years remaining

Stabilizer system and its use for stabilizing styrene polymers

Assignee: BASF Corp
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Filing: 1975-12-05
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Granted: 1978-08-29
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Expires: 1995-12-05
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Abstract

Abstract Stabilizer system consisting of (a) at least one sterically hindered cyclic amine of the formula I ##STR1## in which q is 1 or 2, X represents an organic grouping which complements the nitrogen-containing ring to give a 5-membered, 6-membered or 7-membered ring, R 1 and R 2 represent methyl or together represent --(CH 2 ) 5 --, R 3 represents methyl, R 4 represents alkyl with 1-5 carbon atoms or together with R 3 represents the radicals --(CH 2 ) 4 --, --(CH 2 ) 5 -- ##STR2## and, if q is 1, Y denotes hydrogen, --O·, hydroxyl alkyl, substituted alkyl, alkenyl, alkinyl, aralkyl, substituted aralkyl or acyl or, if q is 2, Y denotes alkylene, alkenylene, alkinylene, cycloalkylene or aralkylene, and (b) at least one co-stabilizer for stabilizing plastics.

Inventors

  • 👤 Bernard Gilg
  • 👤 Helmut Muller
  • 👤 Jean Rody

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-23 12:09
CPC Classifications
C; C08; C08K; C08K5/00; C08K5/16; C08K5/34; C08K5/3467; C08K5/3472; C08K5/3475; C08K5/04; C08K5/13; C08K5/132; C08K5/20; C08K5/3412; C08K5/3432; C08K5/3435

Claims Analysis

Total Claims: 8
Claim 1
Independent Claim 658 words
A stabilizer system consisting essentially of a) at least one sterically hindered cyclic amine selected from the group consisting of ##STR28## wherein Y 1 denotes hydrogen, --O·, is alkyl with 1-8 carbon atoms, halogenoalkyl with 1-5 carbon atoms, cyanoalkyl with 1-5 carbon atoms, epoxylalkyl with 3-4 carbon atoms, hydroxyaralkyl with 8-12 carbon atoms, acyloxyalkyl with 4-20 carbon atoms, aminoalkyl with 2-4 carbon atoms, acylamine with 2-18 carbon atoms, alkoxycarbonyalkyl with 3-21 carbon atoms, alkoxyalkyl with 3-20 carbon atoms, aralkyl with 7-20 carbon atoms, alkenyl with 3-6 carbon atoms or alkinyl with 3-6 carbon atoms, R 1 and R 2 represent methyl or together represent --(CH 2 ) 5 --, R 3 represents methyl, R 4 represents alkyl with 1-5 carbon atoms or together with R 3 represents the radicals --(CH 2 ) 4 --, --(CH 2 ) 5 , ##STR29## R 8 and R 9 independently of one another denote alkoxycarbonyl with 2-6 carbon atoms, benzoyl, nitrile or phenyl, R 16 denotes hydrogen or the radical of an acyl group which is derived from an aliphatic carboxylic acid with 2-18 carbon atoms, from an aromatic carboxylic acid with 7-10 carbon atoms or from a carbamic acid substituted at the nitrogen by alkyl with 1-12 carbon atoms, benzyl or phenyl, with the ring Z representing a benzene or cyclohexane ring which is not substituted further or is substituted further by 1-2 alkyl groups with 1-5 carbon atoms, R 23 denotes hydrogen, alkyl with 1-20 carbon atoms, benzyl, alkylene with 1-20 carbon atoms, or alkoxycarbonyalkyl with 2-26 carbon atoms, or an acyl group which is derived from an aliphatic carboxylic acid with 2-20 carbon atoms, from benzoic acid or from a carbamic acid substituted at the nitrogen by alkyl with 1-24 carbon atoms or phenyl, Y 2 denotes hydrogen, -- O· or methyl and p represents an integer of 1 to 3 and b) at least one co-stabilizer of the formulae ##STR30## in which L 1 denotes hydrogen alkyl with 1-18 carbon atoms, allyl, methallyl or benzyl, L 2 denotes hydrogen, L 3 denotes hydrogen or hydroxyl, L 4 denotes hydrogen, hydroxyl alkoxy with 1-20 carbon atoms, allyloxy, methallyloxy or benzyloxy, L 5 denotes hydrogen, alkyl with 1-12 carbon atoms, alkenyl with 3-12 carbon atoms, cyclohexyl, aralkyl with 7-11 carbon atoms, phenyl, acylamino with 2- 12 carbon atoms, acylaminomethyl with 3-13 carbon atoms, chlorine or bromine, L 6 denotes hydrogen, methyl, hydroxyl, alkoxy with 1-12 carbon atoms or acylamino with 2-12 carbon atoms, L 7 denotes hydrogen, alkyl with 1-12 carbon atoms, aralkyl with 7-11 carbon atoms, cyclohexyl, phenyl, alkoxycarbonylethyl with 4-15 carbon atoms, alkoxy with 1-12 carbon atoms, chlorine, bromine, carboxyl, alkoxycarbonyl with 2-13 carbon atoms or acylamino with 2-12 carbon atoms, L 8 denotes hydrogen, alkyl with 1-8 carbon atoms, alkoxy with 1-12 carbon atoms, chlorine, bromine, acylamino with 2-12 carbon atoms, carboxyl, alkoxycarbonyl with 2-13 carbon atoms, acyloxy with 2-12 carbon atoms, carbamoyl with 3-17 carbon atoms, alkoxysulphonyl with 1-12 carbon atoms, phenoxysulphonyl or sulphonamido with 2-16 carbon atoms, L 9 denotes hydrogen, methyl, chlorine or bromine, L 10 and L 12 independently of one another denote alkyl with 1-8 carbon atoms, alkoxy with 1-12 carbon atoms, allyloxy, methallyloxy, phenoxy, benzyloxy, chlorine, bromine or alkoxycarbonyl with 2-13 carbon atoms, L 11 and L 13 independently of one another denote hydrogen or alkyl with 1-8 carbon atoms, L 14 and L 15 independently of one another denote hydrogen or alkyl with 1-12 carbon atoms, L 16 denotes alkoxy with 1-12 carbon atoms, L 17 denotes alkyl with 1-3 carbon atoms or phenyl, L 18 denotes alkyl with 1-12 carbon atoms, L 19 denotes alkyl with 1-12 carbon atoms, L 20 denotes hydrogen, alkyl with 1-8 carbon atoms, alkoxy with 1-8 carbon atoms or chlorine, L 21 denotes nitrile or alkoxycarbonyl with 2-20 carbon atoms and L 22 denotes hydrogen or alkyl with 1-3 carbon atoms, the ratio of stabilizer (a) to co-stabilizer (b) being from 1:10 to 10:1.
Claim 2
Dependent Claim 658 words
A stabilizer system consisting essentially of a) at least one sterically hindered cyclic amine selected from the group consisting of ##STR28## wherein Y 1 denotes hydrogen, --O·, is alkyl with 1-8 carbon atoms, halogenoalkyl with 1-5 carbon atoms, cyanoalkyl with 1-5 carbon atoms, epoxylalkyl with 3-4 carbon atoms, hydroxyaralkyl with 8-12 carbon atoms, acyloxyalkyl with 4-20 carbon atoms, aminoalkyl with 2-4 carbon atoms, acylamine with 2-18 carbon atoms, alkoxycarbonyalkyl with 3-21 carbon atoms, alkoxyalkyl with 3-20 carbon atoms, aralkyl with 7-20 carbon atoms, alkenyl with 3-6 carbon atoms or alkinyl with 3-6 carbon atoms, R 1 and R 2 represent methyl or together represent --(CH 2 ) 5 --, R 3 represents methyl, R 4 represents alkyl with 1-5 carbon atoms or together with R 3 represents the radicals --(CH 2 ) 4 --, --(CH 2 ) 5 , ##STR29## R 8 and R 9 independently of one another denote alkoxycarbonyl with 2-6 carbon atoms, benzoyl, nitrile or phenyl, R 16 denotes hydrogen or the radical of an acyl group which is derived from an aliphatic carboxylic acid with 2-18 carbon atoms, from an aromatic carboxylic acid with 7-10 carbon atoms or from a carbamic acid substituted at the nitrogen by alkyl with 1-12 carbon atoms, benzyl or phenyl, with the ring Z representing a benzene or cyclohexane ring which is not substituted further or is substituted further by 1-2 alkyl groups with 1-5 carbon atoms, R 23 denotes hydrogen, alkyl with 1-20 carbon atoms, benzyl, alkylene with 1-20 carbon atoms, or alkoxycarbonyalkyl with 2-26 carbon atoms, or an acyl group which is derived from an aliphatic carboxylic acid with 2-20 carbon atoms, from benzoic acid or from a carbamic acid substituted at the nitrogen by alkyl with 1-24 carbon atoms or phenyl, Y 2 denotes hydrogen, -- O· or methyl and p represents an integer of 1 to 3 and b) at least one co-stabilizer of the formulae ##STR30## in which L 1 denotes hydrogen alkyl with 1-18 carbon atoms, allyl, methallyl or benzyl, L 2 denotes hydrogen, L 3 denotes hydrogen or hydroxyl, L 4 denotes hydrogen, hydroxyl alkoxy with 1-20 carbon atoms, allyloxy, methallyloxy or benzyloxy, L 5 denotes hydrogen, alkyl with 1-12 carbon atoms, alkenyl with 3-12 carbon atoms, cyclohexyl, aralkyl with 7-11 carbon atoms, phenyl, acylamino with 2- 12 carbon atoms, acylaminomethyl with 3-13 carbon atoms, chlorine or bromine, L 6 denotes hydrogen, methyl, hydroxyl, alkoxy with 1-12 carbon atoms or acylamino with 2-12 carbon atoms, L 7 denotes hydrogen, alkyl with 1-12 carbon atoms, aralkyl with 7-11 carbon atoms, cyclohexyl, phenyl, alkoxycarbonylethyl with 4-15 carbon atoms, alkoxy with 1-12 carbon atoms, chlorine, bromine, carboxyl, alkoxycarbonyl with 2-13 carbon atoms or acylamino with 2-12 carbon atoms, L 8 denotes hydrogen, alkyl with 1-8 carbon atoms, alkoxy with 1-12 carbon atoms, chlorine, bromine, acylamino with 2-12 carbon atoms, carboxyl, alkoxycarbonyl with 2-13 carbon atoms, acyloxy with 2-12 carbon atoms, carbamoyl with 3-17 carbon atoms, alkoxysulphonyl with 1-12 carbon atoms, phenoxysulphonyl or sulphonamido with 2-16 carbon atoms, L 9 denotes hydrogen, methyl, chlorine or bromine, L 10 and L 12 independently of one another denote alkyl with 1-8 carbon atoms, alkoxy with 1-12 carbon atoms, allyloxy, methallyloxy, phenoxy, benzyloxy, chlorine, bromine or alkoxycarbonyl with 2-13 carbon atoms, L 11 and L 13 independently of one another denote hydrogen or alkyl with 1-8 carbon atoms, L 14 and L 15 independently of one another denote hydrogen or alkyl with 1-12 carbon atoms, L 16 denotes alkoxy with 1-12 carbon atoms, L 17 denotes alkyl with 1-3 carbon atoms or phenyl, L 18 denotes alkyl with 1-12 carbon atoms, L 19 denotes alkyl with 1-12 carbon atoms, L 20 denotes hydrogen, alkyl with 1-8 carbon atoms, alkoxy with 1-8 carbon atoms or chlorine, L 21 denotes nitrile or alkoxycarbonyl with 2-20 carbon atoms and L 22 denotes hydrogen or alkyl with 1-3 carbon atoms, the ratio of stabilizer (a) to co-stabilizer (b) being from 1:10 to 10:1.
Claim 3
Dependent Claim 151 words
A stabilizer system according to claim 1, characterised in that Y 1 denotes hydrogen, --O· or methyl, R 1 , R 2 , R 3 , and R 4 denote methyl, s denotes 1, p denotes 1 R 8 denotes nitrile, R 9 denotes ethoxycarbonyl, phenyl or benzoyl, denotes hydrogen or the radical of an acyl group which is derived from an aliphatic carboxylic acid with 2-12 carbon atoms, from benzoic acid or from a N-alkyl-carbamic acid with 2-8 carbon atoms, with the ring Z representing a benzene ring which is substituted further by 1-2 methyl, isopropyl or tert.-butyl groups, and R 23 denotes hydrogen, alkyl with 6-18 carbon atoms or benzyl, or an acyl group which is derived from an aliphatic carboxylic acid with 3-18 carbon atoms, from benzoic acid or from a carbamic acid which is substituted at the nitrogen by alkyl with 1- 12 carbon atoms or phenyl.
Claim 4
Dependent Claim 201 words
A stabilizer system of claim of claim 2, wherein in the co-stabilizers of formulae II to VIII L 1 denotes hydrogen, alkyl with 1-12 carbon atoms or benzyl, L 2 denotes hydrogen, L 3 denotes hydrogen or hydroxyl, L 4 denotes hydrogen, hydroxyl or alkoxy with 1-12 carbon atoms, L 5 denotes hydrogen, alkyl with 1-8 carbon atoms, allyl, methallyl, phenyl, benzyl, α-phenethyl, α-phenylisopropyl, acylaminomethyl with 3-9 carbon atoms or chlorine, L 6 denotes hydrogen, methyl, hydroxyl or alkoxy with 1-8 carbon atoms, cyclohexyl, phenyl, benzyl, α-phenethyl, α-phenylisopropyl or chlorine, L 8 denotes hydrogen, methyl or chlorine, L 9 denotes hydrogen, L 10 and L 12 independently of one another denote alkyl with 1-4 carbon atoms, alkoxy with 1-8 carbon atoms or chlorine, L 11 and L 13 independently of one another denote hydrogen or alkyl with 1-4 carbon atoms, L 14 denotes hydrogen or alkyl with 1-8 carbon atoms, L 15 denotes hydrogen, L 16 denotes alkoxy with 1-4 carbon atoms, L 17 denotes methyl or phenyl, L 18 denotes alkyl with 1-8 carbon atoms, L 19 denotes alkyl with 1-4 carbon atoms, L 20 denotes hydrogen, L 21 denotes alkoxycarbonyl with 2-5 carbon atoms and L 22 denotes hydrogen.
Claim 5
Dependent Claim 153 words
Stabilizer system according to claim 2 characterised in that the co-stabilizers used are compounds of the formulae ##STR31## in which L 1 denotes hydrogen, alkyl with 1-12 carbon atoms or benzyl, L 2 denotes hydrogen, L 3 denotes hydrogen or hydroxyl, L 4 denotes hydrogen, hydroxyl or alkoxy with 1-12 carbon atoms, L 5 denotes hydrogen, alkyl with 1-8 carbon atoms, allyl, methallyl, phenyl, benzyl, α-phenethyl, α-phenylisopropyl, acylaminomethyl with 3-9 carbon atoms or chlorine, L 6 denotes hydrogen, methyl, hydroxyl or alkoxy with 1-8 carbon atoms, L 7 denotes hydrogen, alkyl with 1-8 carbon atoms, cyclohexyl, phenyl, benzyl, α-phenethyl, α-phenylisopropyl or chlorine, L 8 denotes hydrogen, methyl or chlorine, L 9 denotes hydrogen, L 10 and L 12 independently of one another denote alkyl with 1-4 carbon atoms, alkoxy with 1-8 carbon atoms or chlorine and L 11 and L 13 independently of one another denote hydrogen or alkyl with 1-4 carbon atoms.
Claim 6
Dependent Claim 20 words
Stabilizer system according to claim 2, characterised in that it contains, as the co-stabilizer, a compound of the formula III.
Claim 7
Dependent Claim 12 words
Polystyrene or styrene copolymers containing a stabilizer system according to claim 1.
Claim 8
Dependent Claim 19 words
A stabilizer system of claim 1 wherein the ratio of stabilizer (a) to co-stabilizer (b) is 2:1 to 1:2.

References Cited (Backward Citations)

US3847930A Cited
US3899491A Cited
US3939168A Cited
US3954779A Cited
US3960809A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1981-08-28 1982-02-27 1982-08-29 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1985-08-28 1986-02-27 1986-08-29 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1989-08-28 1990-02-27 1990-08-29 $7700.00 Window Closed / Lapsed

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