US4874803A
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US
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Dianhydride coupled polymer stabilizers
Assignee: Arkema Inc
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Filing: 1987-09-21
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Granted: 1989-10-17
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Expires: 2007-09-21
Abstract
Abstract The present invention comprises reaction products resulting from the reaction of hydrazido-substituted or certain amino-substituted polymer stabilizers and cyclic dianhydrides, as well as the use of such products. The polymer stabilizers of the invention are useful for protecting a large variety of synthetic polymeric organic materials from the degradative effects of heat, light and oxygen. Some of the modifiers are flame retardants and many are metal deactivators in addition to their primary activity.
Inventors
- 👤 Arthur L. Baron
- 👤 Terry N. Myers
- 👤 Jerome Wicher
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 09:40
CPC Classifications
C; C07; C07D; C07D209/00; C07D209/02; C07D209/44; C07D209/48; C07D403/00; C07D403/02; C07D403/04; C07D487/00; C07D487/02; C07D487/04; C07D487/08; C08; C08K; C08K5/00; C08K5/0008; C08K5/005
Claims Analysis
Total Claims: 25
Claim 1
Independent Claim
228 words
A polymer stabilizer compound having a general formula ##STR13## D is divalent radical --C(═O)--N(G)--C(═O)--(CH 2 ) x --, where X is 0 or 1, E is monovalent radical --(CH 2 ) x --C(═O)NH--G, where x is 0 or 1, d is 0, 1 or 2, A is an organic tetravalent radical of 2 to 48 carbons, when A is a non-aromatic tetravalent radical, two groups of two valences on adjacent carbon atoms are present to accommodate the one or two D diradical or diradicals and/or the one or two E monovalent radical or radicals and/or the one or two COOH group or groups; and when A is an aromatic tetravalent radical, two groups of two valences in ortho or peri position are present to accommodate the one or two D diradical or diradicals and/or the E monovalent radical or radicals and/or the COOH group or groups, and G is a monovalent stabilizer radical selected from the group consisting of (a) hindered phenol-substituted amido, (b) hindered amine-substituted amido, (c) dialkyl sulfide-substituted amido, (d) a compound selected from the group consisting of 2-hydroxybenzophenone-substituted amido and 2-hydroxy-benzophenone-substituted alkyl, (e) a compound selected from the group consisting of 2-(2-hydroxyphenyl)-2H-henzotriazole-substituted amido and 2-(2-hydroxyphenyl)-2H-benzoptriazole-substituted alkyl, (f) secondary aromatic amine-substituted amido, (g) a compound selected from the group consisting of benzimidazole-substituted amido and benzothiazole-substiuted amido, (h) oxanilide-substituted amido, (i) halogenated aromatic-substituted amido, and mixtures thereof.
Claim 2
Dependent Claim
228 words
A polymer stabilizer compound having a general formula ##STR13## D is divalent radical --C(═O)--N(G)--C(═O)--(CH 2 ) x --, where X is 0 or 1, E is monovalent radical --(CH 2 ) x --C(═O)NH--G, where x is 0 or 1, d is 0, 1 or 2, A is an organic tetravalent radical of 2 to 48 carbons, when A is a non-aromatic tetravalent radical, two groups of two valences on adjacent carbon atoms are present to accommodate the one or two D diradical or diradicals and/or the one or two E monovalent radical or radicals and/or the one or two COOH group or groups; and when A is an aromatic tetravalent radical, two groups of two valences in ortho or peri position are present to accommodate the one or two D diradical or diradicals and/or the E monovalent radical or radicals and/or the COOH group or groups, and G is a monovalent stabilizer radical selected from the group consisting of (a) hindered phenol-substituted amido, (b) hindered amine-substituted amido, (c) dialkyl sulfide-substituted amido, (d) a compound selected from the group consisting of 2-hydroxybenzophenone-substituted amido and 2-hydroxy-benzophenone-substituted alkyl, (e) a compound selected from the group consisting of 2-(2-hydroxyphenyl)-2H-henzotriazole-substituted amido and 2-(2-hydroxyphenyl)-2H-benzoptriazole-substituted alkyl, (f) secondary aromatic amine-substituted amido, (g) a compound selected from the group consisting of benzimidazole-substituted amido and benzothiazole-substiuted amido, (h) oxanilide-substituted amido, (i) halogenated aromatic-substituted amido, and mixtures thereof.
Claim 3
Dependent Claim
1358 words
The compound of claim 1 in which the hindered phenol-substituted amido group (a) is ##STR14## wherein R 6 is t-alkyl to 4 to 8 carbons and must be adjacent to the hydroxy substituent, R 7 is selected from the group consisting of hydrogen, alkyl of 1 to 8 carbons including t-alkyl of 4 to 8 carbons, and alkoxy of 1 to 8 carbons, X 1 is a divalent radical selected from the group consisting of --N(R)--C(═O)--R 8 --C(═O)--NH--, --N(R)--C(═O)--O--R 9 --, --N(R)--C(═O)--R 9 --Z--R 10 --, and --N(R)--C(═O)--R 9 --, and ##STR15## Z is selected from the group consisting of --N(R)--, --S--, --O-- and --N(R)--R 11 --N(R)--, R is selected from the group consisting of hydrogen, primary or secondary alkyl of 1 to 8 carbons, aralkyl of 7 to 12 carbons, and cycloalkyl of 5 to 12 carbons, R 8 is selected from the group consisting of a direct bond, alkylene of 1 to 14 carbons, oxydialkylene of 4 to 10 carbons, thiodialkylene of 4 to 10 carbons, alkenylene or 2 to 10 carbons, and o-, m- and p-phenylene, R 9 and R 10 are independently selected from the group consisting of a direct bond and alkylene of 1 to 4 carbons, and R 11 is alkylene of 2 to 12 carbons; the hindered amine-substituted amido group (b) is ##STR16## wherein R 12 is selected from the group consisting of hydrogen and alkyl of 1 to 4 carbons, R 13 is selected from hydrogen, oxyl, hydroxy, alkyl of 1 to 20 carbons, alkenyl or alkynyl of 3 to 8 carbons, aralkyl of 7 to 12 carbons, aliphatic acyl of 1 to 10 carbons, aromatic acyl of 7 to 13 carbons, alkoxycarbonyl of 2 to 9 carbons, aryloxycarbonyl of 7 to 15 carbons, alkyl, aryl, cycloalkyl substituted carbamoyl of 2 to 13 carbons, aralkyl substituted carbamoyl of 2 to 13 carbons, hydroxyalkyl of 1 to 5 carbons, 2-cyanoethyl, epoxyalkyl of 3 to 10 carbons and polyalkylene oxide of 4 to 30 carbons, X 2 is a divalent radical selected from the group consisting of --N(R)--C(═O)--R 8 --C(═O)--W--, --N(R)--C(═O)--R 9 --Z--R 10 -- and --N(R)--C(═O)--R 9 --, and W is selected from the group consisting of --Z--, --N(CH 2 --CH 2 )--C.tbd.N)-- and a radical of formula ##STR17## the diakyl sulfide-substituted amido group (c) is --N(R)--C(═O)--R.sup.14 --S--R.sup.15 wherein R 14 is alkylene of 1 to 4 carbons, and R 15 is selected from the group consisting of aralkyl of 7 to 12 carbons, alkyl of 1 to 18 carbons and dialkylaminoalkyl of 3 to 12 carbons; the compound selected for the group consisting of the 2-hydroxybenzophenone-substituted amido and 2-hydroxy-benzophenone-substituted alkyl groups (d) is ##STR18## wherein R 16 and R 17 are independently selected from the group consisting of hydrogen, hydroxy, alkyl of 1 to 8 carbons, alkoxy of 1 to 8 carbons and a connecting group X 4 with the proviso that only one of either R 16 or R 17 is the connecting group X 4 , X 4 is a divalent radical selected from the group consisting of --N(R)--C(═O)--R 9 --Z--, --N(R)--C(═O)--O--R 9 --Z--, --R 10 --, --R 26 --O--, --N(R)--C(═O)-- and --N(R)--S(═O) 2 --, R 26 is alkylene of 1 to 4 carbons, and the aromatic nuclei have substituents selected from the group consisting of hydroxy, alkyl of 1 to 8 carbons and alkoxy of 1 to 8 carbons; the compound selected from the group consisting of 2-(2-hydroxyphenyl)-2H-benzotriazole-substituted amido and 2-(2-hydroxyphenyl)-2H-benzotriazole-substituted alkyl groups (e) is ##STR19## wherein R 18 is selected from the group consisting of hydrogen, alkyl of 1 to 4 carbons, alkoxy of 1 to 8 carbons, carboxy, alkoxycarbonyl of 2 to 11 carbons, carboxylic acid amide, chlorine, bromine, sulfonic acid, alkylsulfonyl and the connecting group X 5 , R 19 is selected from hydrogen, hydroxy, alkyl of 1 to 8 carbons including t-alkyl of 4 to 8 carbons, alkoxy of 1 to 8 carbons, aralkyl of 7 to 12 carbons, aryl of 6 to 14 carbons and the connecting group X 6 , the substitution being such that only one of the substituents R 18 and R 19 is the connecting group, X 5 is a divalent radical selected from --N(R)--C(═O)--, --N(R)--S(═O) 2 -- and X 6 is selected from the group consisting of a direct bond and a divalent radical selected from the group consisting of --N(R)--C(═O)--R 8 --C(═O)--NH--R 9 --, --N(R)--C(═O)--R 9 --Z--R 10 --, --N(R)--C(═O)--O--R 9 , --N(R)--C(═O)--R 9 --, --R 10 --, --R 26 --O--, and --N(R)--C(═O)--, and the aromatic rings A and B have substituents selected from the group consisting of hydrogen, alkyl of 1 to 8 carbons, alkoxy of 1 to 8 carbons, chlorine and bromine; the secondary aromatic amine-substituted amido group (f) is ##STR20## wherein R 20 is selected from the group consisting of aryl of 6 to 14 carbons, alkyl of 1 to 12 carbons and cycloalkyl of 5 to 12 carbons, and X 7 is a divalent radical selected from --N(R)--C(═O)--R 8 --C(═O)--NH-- and --N(R)--C(═O)--R 9 --NH--; the compound selected from the group consisting of benzimidazole-substituted amido and benzothiazole-substituted amido groups (g) is ##STR21## wherein X 8 is a divalent radical selected from the group consisting of --N(R)--C(═O)--R 9 --Z-- and --N(R)--C(═O)--R 8 --C(═O)--NH--, Y is selected from --NH-- and --S--, and the aromatic nucleus has substituents selected from the group consisting of hydrogen, hydroxy, alkyl of 1 to 8 carbons, and alkoxy of 1 to 8 carbons; ##STR22## wherein the aromatic nuclei have substituents selected from the group consisting of hydrogen, alkyl of 1 to 8 carbons, alkoxy of 1 to 4 carbons and halogen; ##STR23## wherein R 21 , R 22 , R 23 , R 24 , and R 25 are independently selected from the group consisting of hydrogen, chlorine, bromine, hydroxy, alkoxy or alkylthio of 1 to 12 carbons, acyloxy of 6 to 12 carbons, acylthio of 6 to 12 carbons, aryl of 6 to 12 carbons, alkyl of 1 to 8 carbons, aralkyl of 7 to 13 carbons, and alkoxycarbonyl of 1 to 8 carbons, with the proviso that at least one of R 21 , R 22 , R 23 , R 24 , and R 25 must be chlorine or bromine; A is selected from the group consisting of a linear saturated aliphatic tetravalent radical of 2 to 20 carbons, branched saturated aliphatic tetravalent radical of 2 to 20 carbons, linear unsaturated aliphatic tetravalent radical of 2 to 20 carbons, branched unsaturated aliphatic tetravalent radical of 2 to 20 carbons, saturated alicyclic tetravalent radical of 4 to 12 carbons, unsaturated alicyclic tetravalent radical of 4 to 12 carbons, aralkyl tetravalent radical of 7 to 48 carbons, aralkenyl tetravalent radical of 9 to 48 carbons, aromatic homocyclic tetravalent radical formed of one ring or two or more fused or linked rings each of which contains to 7 carbons, and aromatic heterocyclic tetravalent radical formed of one ring or two or more fused or linked rings each of which contains 4 to 6 carbons and optionally containing heteroatom ring members selected from the group consisting of oxygen, sulfur and nitrogen atoms; and when A contains several interlinked cycles, the linking members are selected from the group consisting of a direct bond and a divalent radical selected from --O--, --S--, --SO--, --SO 2 --, --CO--, --NR 1 --, --COO--, --CHOR 1 --, --CF 2 --, --N═N--, ##STR24## --CO--(R 1 )N--R 5 --N(R 2 )--CO--, --O--CO--R 5 --CO--O--, --CO--O--R 5 --O--CO--, --(R 1 )N--CO--N(R 2 )--, --(R 1 )N--COCO--N(R 2 )--, --CO--N(R 1 )-- and --O--R 5 --O--, where R 1 and R 2 are independently selected from the group consisting of hydrogen, alkyl of 1 to 4 carbons, cycloalkyl of 4 to 7 carbons and phenyl, R 3 and R 4 are independently selected from the group consisting of alkyl of 1 to 4 carbons, cycloalkyl of 4 to 7 carbons and phenyl, and R 5 is selected for the group consisting of linear alkylene of 1 to 12 carbons, branched alkylene of 1 to 12 carbons, cycloalkylene of 5 to 12 carbons, arylene of 5 to 20 carbons, diphenylsulfonyl-4,4'-diyl, diphenylsulfonyl-3,4'-diyl, 4,4'-alkylidenediphenyl-1,1'-diyl and 4,3'-alkylidenediphenyl-1,1'-diyl, and n is an integer of 1-4.
Claim 4
Dependent Claim
203 words
The compound of claim 1 in which the hindered phenol group (a) is ##STR25## wherein R 6 is t-alkyl of 4 to 8 carbons and must be adjacent to the hydroxy substituent, R 7 is selected from the group consisting of hydrogen, alkyl of 1 to 8 carbons, and alkoxy of 1 to 8 carbons, X 1 is a divalent radical selected from the group consisting of --N(R)--C(═O)--R 8 --C(═O)--NH--, --N(R)--C(═O)--O--R 9 --, --N(R)--C(═O)--R 9 --Z--R 10 --, and --N(R)--C(═O)--R 9 --, and ##STR26## Z is selected from the group consisting of --N(R)--, --S--, --O-- and --N(R)--R 11 --N(R)--, R is selected from the group consisting of hydrogen, primary or secondary alkyl of 1 to 8 carbons, aralkyl of 7 to 12 carbons, and cycloalkyl of 5 to 12 carbons, R 8 is selected from the group consisting of a direct bond, alkylene of 1 to 14 carbons, oxydialkylene of 4 to 10 carbons, thiodialkylene of to 10 carbons, alkenylene of 2 to 10 carbons, and o-, m-, and p-phenylene, R 9 and R 10 are independently selected from the group consisting of a direct bond and alkylene of 1 to 4 carbons, and R 11 is alkylene of 2 to 12 carbons.
Claim 5
Dependent Claim
281 words
The compound of claim 1 in which the hindered amine light stabilizer group (b) is ##STR27## wherein R 12 is selected from the group consisting of hydrogen and alkyl of 1 to 4 carbons, R 13 is selected from hydrogen, oxyl, hydroxy, alkyl of 1 to 20 carbons, alkenyl or alkynyl of 3 to 8 carbons, aralkyl of 7 to 12 carbons, aliphatic acyl of 1 to 10 carbons, aromatic acyl of 7 to 13 carbons, alkoxycarbonyl of to 9 carbons, aryloxycarbonyl of 7 to 15 carbons, alkyl, aryl, cycloalkyl substituted carbamoyl of 2 to 13 carbons, aralkyl substituted carbamoyl of 2 2-cyanoethyl, epoxyalkyl of 3 to 10 carbons and polyalkylene oxide of 4 to 30 carbons, X 2 is a divalent radical selected from the group consisting of --N(R)--C(═O)--R 8 --C(═O)--W--, --N(R)--C(═O)--R 9 --Z--R 10 -- and --N(R)--C(═O)--R 9 --, R is selected from the group consisting of hydrogen, primary or secondary alkyl of 1 to 8 carbons, aralkyl of 7 to 12 carbons, and cycloalkyl of 5 to 12 carbons, R 8 is selected from the group consisting of a direct bond, alkylene of 1 to 14 carbons, oxydialkylene of 4 to 10 carbons, thiodialkylene of 4 to 10 carbons, alkenylene of 2 to 10 carbons, and o-, m-, and p-phenylene, R 9 and R 10 are independently selected from the group consisting of a direct bond and alkylene of 1 to 4 carbons, Z is selected from the group consisting of --N(R)--, --S--, --O-- and --N(R)--R 11 --N(R)--, R 11 is alkylene of 2 to 12 carbons, and W is selected from the group consisting of --Z--, --N(CH 2 --CH 2 --C.tbd.N)-- and a radical of formula ##STR28##
Claim 6
Dependent Claim
85 words
The compound of claim 1 in which the dialkyl sulfide group (c) is --N(R)--C(═O)--R.sup.14 --S--R.sup.15 wherein R is selected from the group consisting of hydrogen, primary or secondary alkyl of 1 to 8 carbons, aralkyl of 7 to 12 carbons, and cycloalkyl of 5 to 12 carbons, R 14 is alkylene of 1 to 4 carbons, and R 15 is selected from the group consisting of aralkyl of 7 to 12 carbons, alkyl of 1 to 18 carbons and dialkylaminoalkyl of 3 to 12 carbons.
Claim 7
Dependent Claim
206 words
The compound of claim 1 in which the hydroxybenzophenone group (d) is ##STR29## wherein R 16 and R 17 are independently selected from the group consisting of hydrogen, hydroxy, alkyl of 1 to 8 carbons, alkoxy of 1 to 8 carbons and a connecting group X 4 with the proviso that only one of either R 16 or R 17 is the connecting group X 4 , X 4 is a divalent radical selected from the group consisting of --N(R)--C(═O)--R 9 --Z--, --N(R)--C(═O)--O--R 9 --Z--, --R 26 --, --N(R)--C(═O)-- and --N(R)--S(═O) 2 --, R is selected from the group consisting of hydrogen, primary or secondary alkyl of 1 to 8 carbons, aralkyl of 7 to 12 carbons, and cycloalkyl of 5 to 12 carbons, R 9 and R 10 are independently selected from the group consisting of a direct bond and alkylene of 1 to 4 carbons, R 26 is alkylene of 1 to 4 carbons, Z is selected from the group consisting of --N(R)--, --S--, --O-- and --N(R)--R 11 --N(R)--, R 11 is alkylene of 2 to 12 carbons, and the aromatic nuclei have substituents selected from the group consisting of hydroxy, alkyl of 1 to 8 carbons and alkoxy of 1 to 8 carbons.
Claim 8
Dependent Claim
338 words
The compound of claim 1 in which the 2-(2-hydroxyphenyl)-2H-benzotriazole group (e) is ##STR30## wherein R 18 is selected from the group consisting of hydrogen, alkyl of 1 to 4 carbons, alkoxy of 1 to 8 carbons, carboxy, alkoxycarbonyl of 2 to 11 carbons, carboxylic acid amide, chlorine, bromine, sulfonic acid, alkylsulfonyl and the connecting group X 5 , R 19 is selected from hydrogen, hydroxy, alkyl of 1 to 8 carbons including t-alkyl of 4 to 8 carbons, alkoxy of 1 to 8 carbons, aralkyl of 7 to carbons, aryl of 6 to 14 carbons and the connecting group X 6 , the substitution being such that only one of the substituents R 18 and R 19 is the connecting X 5 is a divalent radical selected from --N(R)--C(═O)--, --N(R)--S(═O) 2 -- and X 6 is selected from the group consisting of a direct bond and a divalent radical selected from the group consisting of --N(R)--C(═O)--R 8 --C(═O)--NH--R 9 --, --N(R)--C(═O)--R 9 --Z--R 10 --, --N(R)--C(═O)--O--R 9 , --N(R)--C(═O)--R 9 --, --R 10 --, --R 26 --O--, and --N(R)--C(═O)--, R is selected from the group consisting of hydrogen, primary or secondary alkyl of 1 to 8 carbons, aralkyl of 7 to 12 carbons, and cycloalkyl of 5 to 12 carbons, R 8 is selected from the group consisting of a direct bond, alkylene of 1 to 14 carbons, oxydialkylene of 4 to 10 carbons, thiodialkylene of 4 to 10 carbons, alkenylene of 2 to 10 carbons, and o-, m-, and p-phenylene, R 9 and R 10 are independently selected from the group consisting of a direct bond and alkylene of 1 to 4 carbons, R 26 is alkylene of 1 to 4 carbons, Z is selected from the group consisting of --N(R)--, --S--, --O-- and --N(R)--R 11 --N(R)--, R 11 is alkylene of 2 to 12 carbons, and the aromatic rings A and B have substituents selected from the group consisting of hydrogen, alkyl of 1 to 8 carbons, alkoxy of 1 to 8 carbons, chlorine and bromine.
Claim 9
Dependent Claim
151 words
The compound of claim 1 in which the secondary aromatic amine group (f) is ##STR31## wherein R 20 is selected from the group consisting of aryl of 6 to 14 carbons, alkyl of 1 to 12 carbons and cycloalkyl of 5 to 12 carbons, X 7 is a divalent radical selected from --N(R)--C(═O)--R 8 --C(═O)--NH-- and --N(R)--C(═O)--R 9 --NH--, R is selected from the group consisting of hydrogen, primary or secondary alkyl of 1 to 8 carbons, aralkyl of 7 to 12 carbons, and cycloalkyl of 5 to 12 carbons, R 8 is selected from the group consisting of a direct bond, alkylene of 1 to 14 carbons, oxydialkylene of 4 to 10 carbons, thiodialkylene of 4 to 10 carbons, alkenylene of 2 to 10 carbons, and o-, m-, and p-phenylene, and R 9 is selected from the group consisting of a direct bond and alkylene of 1 to 4 carbons.
Claim 10
Dependent Claim
181 words
The compound of claim 1 in which the heterocyclic compound (g) is ##STR32## wherein X 8 is a divalent radical selected from the group consisting of --N(R)--C(═O)--R 9 --Z-- and --N(R)--C(═O)--R 8 --C(═O)--NH--, R is selected from the group consisting of hydrogen, primary or secondary alkyl of 1 to 8 carbons, aralkyl of 7 to 12 carbons, and cycloalkyl of 5 to 12 carbons, R 8 is selected from the group consisting of a direct bond, alkylene of 1 to 14 carbons, oxydialkylene of 4 to 10 carbons, thiodialkylene of to 10 carbons, alkenylene of 2 to 10 carbons, and o-, m-, and p-phenylene, R 9 is selected from the group consisting of a direct bond and alkylene of 1 to 4 carbons Z is selected from the group consisting of --N(R)--, --S--, --O-- and --N(R)--R 11 --N(R)--, R 11 is alkylene of 2 to 12 carbons, Y is selected from --NH-- and --S--, and the aromatic nucleus has substituents selected from the group consisting of hydrogen, hydroxy, alkyl of 1 to 8 carbons, and alkoxy of 1 to 8 carbons.
Claim 11
Dependent Claim
233 words
The compound of claim 1 in which the oxanilide derivative (h) is ##STR33## wherein X 1 is a divalent radical selected from the group consisting of --N(R)--C(═O)--R 8 --C(═O)--NH--, --N(R)--C(═O)--O--R 9 --, --N(R)--C(═O)--R 9 --Z--R 10 --, and --N(R)--C(═O)--R 9 --, and ##STR34## Z is selected from the group consisting of --N(R)--, --S--, --O-- and --N(R)--R 11 --N(R)--, R is selected from the group consisting of hydrogen, primary or secondary alkyl of 1 to 8 carbons, aralkyl of 7 to 12 carbons, and cycloalkyl of 5 to 12 carbons, R 6 is t-alkyl of 4 to 8 carbons and must be adjacent to the hydroxy substituent, R 7 is selected from the group consisting of hydrogen, alkyl of 1 to 8 carbons including t-alkyl of 4 to 8 carbons, and alkoxy of 1 to 8 carbons, R 8 is selected from the group consisting of a direct bond, alkylene of 1 to 14 carbons, oxydialkylene of 4 to 10 carbons, thiodialkylene of to 10 carbons, alkenylene of 2 to 10 carbons, and o-, m-, and p-phenylene, R 9 and are independently selected from the group consisting of a direct bond and alkylene of 1 to 4 carbons, R 11 is alkylene of 2 to 12 carbons, and the aromatic nuclei have substituents selected from the group consisting of hydrogen, alkyl of 1 to 8 carbons, alkoxy of 1 to 4 carbons and halogen.
Claim 12
Dependent Claim
188 words
The compound of claim 1 in which the halogen containing amide derivative (i) is ##STR35## wherein R is selected from the group consisting of hydrogen, primary or secondary alkyl of 1 to 8 carbons, aralkyl of 7 to 12 carbons, and cycloalkyl of 5 to 12 carbons, R 8 is selected from the group consisting of a direct bond, alkylene of 1 to 14 carbons, oxydialkylene of 4 to 10 carbons, thiodialkylene of 4 to 10 carbons, alkenylene of 2 to 10 carbons, and o-, m-, and p-phenylene, R 21 , R 22 , R 23 , R 24 , and R 25 are independently selected from the group consisting of hydrogen, chlorine, bromine, hydroxy, alkoxy or alkylthio of 1 to 12 carbons, acyloxy of 6 to 12 carbons, acylthio of 6 to 12 carbons, aryl of 6 to 12 carbons, alkyl of 1 to 8 carbons, aralkyl of 7 to 13 carbons, and alkoxycarbonyl of 1 to 8 carbons, with the proviso that at least one of R 21 , R 22 , R 23 , R 24 , and R 25 must be chlorine or bromine.
Claim 13
Dependent Claim
156 words
The compound of claim 1 in which A is selected from the group consisting of a linear saturated aliphatic tetravalent radical of 2 to 20 carbons, branched saturated aliphatic tetravalent radical of 2 to 20 carbons, linear unsaturated aliphatic tetravalent radical of 2 to 20 carbons, branched unsaturated aliphatic tetravalent radical of 2 to 20 carbons, saturated alicyclic tetravalent radical of 4 to 12 carbons, unsaturated alicyclic tetravalent radical of 4 to 12 carbons, aralkyl tetravalent radical of 7 to 48 carbons, aralkenyl tetravalent radical of 9 to 48 carbons, aromatic homocyclic tetravalent radical formed of one ring or two or more fused or linked rings each of which contains 5 to 7 carbons, and aromatic heterocyclic tetravalent radical formed of one ring or two or more fused or linked rings each of which contains 4 to 6 carbons and optionally containing heteroatom ring members selected from the group consisting of oxygen, sulfur and nitrogen atoms.
Claim 14
Dependent Claim
220 words
The compound of claim 12 wherein A is an aromatic tetravalent radical containing 6 to 24 carbons when aromatic homocyclic, and 4 to 24 carbons having substituents selected from the group consisting of 1 to 6 oxygen, sulfur and nitrogen atoms when heterocyclic, or containing several interlinked cycles, the linking members being selected from the group consisting of a direct bond and a divalent radical selected from --O--, --S--, --SO--, --SO 2 --, --CO--, --NR 1 --, --COO--, --CHOR 1 --, --CF 2 --, --N═N--, ##STR36## --CO--(R 1 )N--R 5 --N(R 2 )--CO--, --O--CO--R 5 --CO--O--, --CO--O--R 5 --O--CO--, --(R 1 )N--CO--N(R 2 )--, --(R 1 )N--COCO--N(R 2 )--, --CO--N(R 1 )-- and --O--R 5 --O--, where R 1 and R 2 are independently selected from the group consisting of hydrogen, alkyl of 1 to 4 carbons, cycloalkyl of 4 to 7 carbons and phenyl, R 3 and R 4 are independently selected from the group consisting of alkyl of 1 to 4 carbons, cycloalkyl of 4 to 7 carbons and phenyl, and R 5 is selected from the group consisting of linear alkylene of 1 to 12 carbons, branched alkylene of 1 to 12 carbons, cycloalkylene of 5 to 12 carbons, arylene of 5 to 20 carbons, diphenylsulfonyl-4,4'-diyl, diphenylsulfonyl-3,4'-diyl, 4,4'-alkylidenediphenyl-1,1'-diyl and 4,3'-alkylidenediphenyl-1,1'-diyl, and n is an integer of 1-4.
Claim 15
Dependent Claim
135 words
The compound of claim 13 wherein substituents for A, R 1 , R 2 , R 3 , R 4 and R 5 are selected from the group consisting of alkyl of 1 to 4 carbons, alkoxy of 1 to 4 carbons, acyl of 1 to 4 carbons, acyloxy of 1 to 4 carbons, alkoxycarbonyl of 2 to 5 carbons, arylcarbonyl of 7 to 11 carbons, acryloyloxy, methacryloyloxy, aryloxy of 6 to 10 carbons, aralkyl of 7 to 10 carbons, aryloxycarbonyl of 7 to 11 carbons, phenyl, hydroxy, carboxy, nitrile, chloro, bromo, epoxy, alkylmercapto of 1 to 6 carbons, arylmercapto of 6 to 10 carbons, alkylamino of 1 to 4 carbons, dialkylamino of 2 to 8 carbons, arylamino of 8 carbons, aryl alkylamino of 7 to 10 carbons and trialkoxysilyl of 4 to 9 carbons.
Claim 16
Dependent Claim
85 words
The compound of claim 14 in which A is selected from the group consisting of a tetravalent saturated alicyclic radical of 4 to 12 carbons, a tetravalent unsaturated alicyclic radical of 4 to 12 carbons, an aromatic homocyclic radical of one ring or two or more fused or linked rings each of which contains 6 carbons, wherein the linking members are a direct bond or divalent radical selected from the group consisting of --O--, --S--, --SO--, --CO--, --COO--, --CO--O--R 5 --O--CO-- or --O--R 5 --O--.
Claim 17
Dependent Claim
83 words
The compound of claim 15 in which A is selected from the group consisting of a tetravalent saturated alicyclic radical of 4 to 12 carbons, a tetravalent unsaturated alicyclic radical of 4 to 12 carbons, an aromatic homocyclic radical of one ring or two to six fused or linked rings each of which contains 6 carbons, wherein the linking members are a direct bond or divalent radical selected from the group consisting of --O--, --S--, --CO--, --CO--O--R 5 --O--CO-- and --O--R 5 --O--.
Claim 18
Dependent Claim
28 words
The compound of claim 16 selected from the group consisting of N,N'-bis[3-(3,5-di-t-butyl-4-hydroxyphenyl)propanamido]pyromellitimide, N,N'-bis[N'-(2,2,6,6-tetramethylpiperidin-4-yl)oxamido]pyromellitimide, N,N'-bis(3-n-hexylthiopropylamido)pyromellitimide, N,N'-bis[3-(3,5-di-t-butyl-4-hydroxyphenyl)propanamido]-3,3',4,4'-benzophenonenetetracarboxylic diimide, N,N'-bis[3-(3,5-di-t-butyl-4-hydroxyphenyl)propanamido]-1,4,5,8-naphthalenetetracarboxylic diimide, 2-[2-(2,4,6-tribromophenyl-amino)-2-oxoacetamido]-3a,4,5,7a-tetrahydro-7-methyl-5-[1-(2-[2,4,6-tribromophenylamino]-2-oxoacetamido)-2,5-dioxopyrrollidin-3-yl]-1H-isoindole-1,3(2H)-dione, N,N'-bis[3-(3,5-di-t-butyl-4-hydroxyphenyl)propanamido]-3,3',4,4'-biphenyltetracarboxylic diimide, 4,4'-(4-acetoxy-2,6-dioxa-1,7-dioxoheptane-1,7-diyl)-bis-[N-(3-[3,5-di-t-butyl-4-hydroxyphenyl]propanamido)phthalimide], 4,4'-(2,5-dioxa-1,6-dioxohexane-1,6-diyl)-bis-[N-(3-[3,5-di-t-butyl-4-hydroxyphenyl]propanamido)phthalimide], N,N'-bis[N'-(2,4,6-tribromophenyl)oxamido]pyromellitimide, N,N'-bis[N'-(3,5-di-t-butyl-4-hydroxyphenyl)oxamido]-3,3',4,4'-benzophenonetetracarboxylic diimide, and N,N'-bis[N'-(3,5-di-t-butyl-4-hydroxyphenyl)oxamido]pyromellitimide.
Claim 19
Dependent Claim
30 words
A polymer composition comprising a synthetic polymer which is subject to thermal, oxidative or actinic light degradation and an effective amount for stabilization of the stabilizer compound of claim 1.
Claim 20
Dependent Claim
25 words
The composition of claim 18 wherein the stabilizer compound is added in an amount of about 0.01% to about 10% by weight of the polymer.
Claim 21
Dependent Claim
25 words
The composition of claim 18 wherein the stabilizer compound is added in an amount of about 0.05% to about 2% by weight of the polymer.
Claim 22
Dependent Claim
34 words
The compound of claim 1 comprising a mixed bis N-(amido)imide stabilizer containing at least two different G groups wherein each G group is selected from any of the monovalent stabilizer radicals (a) through (i).
Claim 23
Dependent Claim
7 words
The compound of claim 21 comprising 2-[3-(3,5-di-t-butyl-4-hydroxyphenyl)propanamido]-3a,4,5,7a-tetrahydro-7-methyl-5-[1-(3-hexylthiopropylamido)-2,5-dioxopyrrolidin-3-yl]-1H-isoindole-1,3(2H)-dione.
Claim 24
Dependent Claim
7 words
The compound of claim 21 comprising 2-(3-hexylthiopropylamido)-3a,4,5,7a-tetrahydro-7-methyl-5-{1-[3-(3,5-di-t-butyl-4-hydroxyphenyl)propanamido]-2,5-dioxopyrrolidin-3-yl}-1H-isoindole-1,3(2H)-dione.
Claim 25
Dependent Claim
34 words
A multifunctional stabilized polymer composition comprising a synthetic polymer which is subject to thermal, oxidative or actinic light degradation and an effective amount for stabilization of more than one stabilizer compound of claim 1.
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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) | 1992-10-16 | 1993-04-17 | 1993-10-17 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1996-10-16 | 1997-04-17 | 1997-10-17 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2000-10-16 | 2001-04-17 | 2001-10-17 | $7700.00 | Window Closed / Lapsed |