US4981915A
Expired / Lapsed
US
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Multipurpose polymer bound stabilizers
Assignee: Arkema Inc
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Filing: 1989-06-23
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Granted: 1991-01-01
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Expires: 2009-06-23
Abstract
Abstract Polymer bound stabilizer compounds are provided in which two or more different classes of stabilizers are chemically bound to anhydride containing polymers or copolymers. Polymeric stabilizers are prepared by the reaction of primary amino or hydrazido substituted stabilizers (i.e., antioxidants, light stabilizers, etc.) with some or all of the anhydride groups of the polymer or copolymer to form pendant stabilizer substituted imide or amic acid groups. The polymer bound stabilizers are not lost from the polymer system by volatilization, migration or extraction, even at high temperatures. The polymer bound stabilizer compounds may be used as concentrates to stabilize other polymer systems.
Inventors
- 👤 Ronald E. MacLeay
- 👤 Terry N. Myers
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 12:10
CPC Classifications
C; C08; C08F; C08F8/00; C08F8/30; C08F2800/00; C08F2800/20
Claims Analysis
Total Claims: 26
Claim 1
Independent Claim
126 words
A polymer with recurring units having a formula ##STR16## or both in which the units occur either in the polymer backbone, on grafted side chains, as pendant units, or as combinations thereof and wherein x is 0 or 1, R 1 and R 2 are independently hydrogen, alkyl of 1-6 carbons, cycloalkyl of 5-7 carbons, phenyl, chlorine or bromine and each ##STR17## is the residue of a primary amino substituted stabilizer group selected from (a) hindered phenols, (b) hindered amine light stabilizers, (c) 2-hydroxybenzophenones, (d) 2-(2-hydroxyphenyl)-2H-benzotriazoles, (e) secondary aromatic amines, (f) mercaptobenzothiazoles or mercaptobenzimidazoles, (g) aryl salicylates, (h) salicylic acid derivatives, (i) oxamide derivatives or (j) dialkyl sulfides, with the proviso that at least two different groups from (a) through (j) are attached to the polymer.
Claim 2
Dependent Claim
126 words
A polymer with recurring units having a formula ##STR16## or both in which the units occur either in the polymer backbone, on grafted side chains, as pendant units, or as combinations thereof and wherein x is 0 or 1, R 1 and R 2 are independently hydrogen, alkyl of 1-6 carbons, cycloalkyl of 5-7 carbons, phenyl, chlorine or bromine and each ##STR17## is the residue of a primary amino substituted stabilizer group selected from (a) hindered phenols, (b) hindered amine light stabilizers, (c) 2-hydroxybenzophenones, (d) 2-(2-hydroxyphenyl)-2H-benzotriazoles, (e) secondary aromatic amines, (f) mercaptobenzothiazoles or mercaptobenzimidazoles, (g) aryl salicylates, (h) salicylic acid derivatives, (i) oxamide derivatives or (j) dialkyl sulfides, with the proviso that at least two different groups from (a) through (j) are attached to the polymer.
Claim 3
Dependent Claim
62 words
The composition of claim 1 in which (a) is ##STR18## wherein R 3 is t-alkyl of 4-8 carbons, R 4 is hydrogen, hydroxyl, alkyl of 1-8 carbons or alkoxy of 1-8 carbons and X 1 is a direct bond or a divalent radical --(CH 2 ) y -- or --CH 2 --CH 2 --O-- in which y is 1, 2 or 3.
Claim 4
Dependent Claim
156 words
The composition of claim 1 in which (b) is ##STR19## wherein R 5 is hydrogen or alkyl of 1-4 carbons, R 6 hydrogen, oxyl, hydroxyl, alkyl of 1-20 carbons, alkenyl of 3-8 carbons, alkynyl of 3-8 carbons, aralkyl of 7-12 carbons, aliphatic acyl of 1-10 carbons, aromatic acyl of 7-13 carbons, alkoxycarbonyl of 2-9 carbons, aryloxycarbonyl of 7-15 carbons, alkyl, aryl, cycloalkyl or aralkyl substituted carbamoyl of 2-13 carbons, hydroxyalkyl of 1-5 carbons, 2-cyanoethyl, epoxyalkyl of 3-10 carbons or a polyalkylene oxide group of 4-20 carbons, and X 9 is a direct bond or a divalent radical --(CH 2 ) y --, --CH 2 --CH 2 --O-- or --R 7 --N(R 23 )--, where y is 1, 2 or 3, R 7 is alkylene of 2-12 carbons and R 23 is hydrogen, alkyl of 1-10 carbons, aryl of 6-12 carbons, aralkyl of 7-12 carbons, cycloalkyl of 5-12 carbons, 2-cyanoethyl or a radical of the formula ##STR20##
Claim 5
Dependent Claim
162 words
The composition of claim 1 in which (j) is --X 2 --C(═O)--(CH 2 ) z --S--R 8 wherein R 8 is aralkyl of 7-12 carbons, alkyl of 1-18 carbons or dialkylaminoalkyl of 3-12 carbons, z is 1 or 2 and X 2 is a divalent radical --CH 2 --CH 2 --O-- or --R 7 --N(R 23 )--, wherein R 7 is alkylene of 2-12 carbons, R 23 is hydrogen, alkyl of 1-10 carbons, aryl of 6-12 carbons, aralkyl of 7-12 carbons, cycloalkyl of 5-12 carbons or 2-cyanoethyl, R 5 is hydrogen or alkyl of 1-4 carbons and R 6 is hydrogen, oxyl, hydroxyl, alkyl of 1-20 carbons, alkenyl or alkynyl of 3-8 carbons, aralkyl of 7-12 carbons, aliphatic acyl of 1-10 carbons, aromatic acyl of 7-13 carbons, alkoxycarbonyl of 2-9 carbons, aryloxycarbonyl of 7-15 carbons, alkyl, aryl, cycloalkyl or aralkyl substituted carbamoyl of 2-13 carbons, hydroxyalkyl of 1-5 carbons, 2-cyanoethyl, epoxyalkyl of 3-10 carbons or a polyalkylene oxide group of 4-20 carbons.
Claim 6
Dependent Claim
213 words
The composition of claim 1 in which (c) is ##STR21## wherein R 9 and R 10 are independently hydrogen, hydroxyl, alkyl of 1-8 carbons, alkoxy of 1-4 carbons or a connecting group X 3 , with the proviso that only one of either R 9 or R 10 can be the connecting group X 3 , and X 3 is a direct bond or a divalent radical --CH 2 --CH 2 --O--, --R 7 --N(R 23 )--C(═O)-- or --R 7 --N(R 23 )--S(═O) 2 , in which R 7 is alkylene of 2-12 carbons, R 23 is hydrogen, alkyl of 1-10 carbons, aryl of 6-12 carbons, aralkyl of 7-12 carbons, cycloalkyl of 5-12 carbons or 2-cyanoethyl, R 5 is hydrogen or alkyl of 1-4 carbons and R 6 is hydrogen, oxyl, hydroxyl, alkyl of 1-20 carbons, alkenyl or alkynyl of 3-8 carbons, aralkyl of 7-12 carbons, aliphatic acyl of 1-10 carbons, aromatic acyl of 7-13 carbons, alkoxycarbonyl of 2-9 carbons, aryloxycarbonyl of 7-15 carbons, alkyl, aryl, cycloalkyl or aralkyl substituted carbamoyl of 2-13 carbons, hydroxyalkyl of 1-5 carbons, 2-cyanoethyl, epoxyalkyl of 3-10 carbons or a polyalkylene oxide group of 4-20 carbons and optional substituents for the aromatic nuclei are one or more of hydroxyl, alkyl of 1-8 carbons or alkoxy of 1-4 carbons.
Claim 7
Dependent Claim
257 words
The composition of claim 1 in which (d) is ##STR22## where R 11 is hydrogen, alkyl of 1-4 carbons, alkoxy of 1-4 carbons, carboxyl, alkoxycarbonyl of 2-11 carbons, carboxamide, chlorine, bromine, sulfonic acid, alkylsulfonyl, or the connecting group X 4 , R 12 is hydrogen, alkyl of 1-8 carbons, aralkyl of 7-12 carbons, aryl of 6-14 carbons or the connecting group X 5 , with the proviso that when R 12 is X 5 , R 11 cannot be X 4 , X 4 is a divalent radical --R 7 --N(R 23 )--S(═O) 2 -- or --R 7 --N(R 23 )--C(═O)--, in which R 7 is alkylene of 2-12 carbons, R 23 is hydrogen, alkyl of 1-10 carbons, aryl of 6-12 carbons, aralkyl of 7-12 carbons, cycloalkyl of 5-12 carbons or 2-cyanoethyl, X 5 is a direct bond or a divalent radical --(CH 2 ) y -- or --CH 2 --CH 2 --O--, R 5 is hydrogen or alkyl of 1-4 carbons, R 6 is hydrogen, oxyl, hydroxyl, alkyl of 1-20 carbons, alkenyl or alkynyl of 3-8 carbons, aralkyl of 7-12 carbons, aliphatic acyl of 1-10 carbons, aromatic acyl of 7-13 carbons, alkoxycarbonyl of 2-9 carbons, aryloxycarbonyl of 7-15 carbons, alkyl, aryl, cycloalkyl or aralkyl substituted carbamoyl of 2-13 carbons, hydroxyalkyl of 1-5 carbons, 2-cyanoethyl, epoxyalkyl of 3-10 carbons or a polyalkylene oxide group of 4-20 carbons, y is 1, 2 or 3 and optional substituents for rings A and B are one or more of alkyl or 1-8 carbons, alkoxy of 1-8 carbons, chlorine or bromine.
Claim 8
Dependent Claim
34 words
The composition of claim 1 in which (e) is ##STR23## where R 13 is aryl of 6-14 carbons, alkyl of 1-12 carbons or cycloalkyl of 5-12 carbons and X 6 is a direct bond.
Claim 9
Dependent Claim
45 words
The composition of claim 1 in which (f) is ##STR24## where Q is --NH--, --S-- or --O--, X 7 is a direct bond and the aromatic nucleus is optionally substituted with one or more of hydroxy, alkyl of 1-8 carbons or alkoxy of 1-8 carbons.
Claim 10
Dependent Claim
80 words
The composition of claim 1 in which (h) is ##STR25## where X 2 is a divalent radical --CH 2 --CH 2 --O-- or --R 7 --N(R 23 )-- wherein R 7 is alkylene of 2-12 carbons, R 23 is hydrogen, alkyl of 1-10 carbons, aryl of 6-12 carbons, aralkyl of 7-12 carbons, cycloalkyl of 5-12 carbons or 2-cyanoethyl, and the aromatic nucleus is optionally substituted with one or more of hydroxy, alkyl of 1-8 carbons or alkoxy of 1-8 carbons.
Claim 11
Dependent Claim
43 words
The composition of claim 1 in which (g) is ##STR26## where R 14 is aryl of 6-10 carbons, optionally substituted with one or more of alkyl of 1-8 carbons, alkoxy of 1-8 carbons, chlorine or bromine and X 7 is a direct bond.
Claim 12
Dependent Claim
89 words
The composition of claim 1 in which (i) is ##STR27## wherein R 15 , R 16 , R 17 , R 18 and R 19 are independently hydrogen, hydroxyl, alkoxy of 1-12 carbons, alkylthio of 1-12 carbons, acyloxy of 2-12 carbons, acylthio of 2-12 carbons, alkyl of 1-8 carbons, aryl of 6-12 carbons, chlorine, bromine, aralkyl of 7-13 carbons, alkaryl of 7-13 carbons or alkoxycarbonyl of 2-8 carbons and X 8 is alkylene of 2-12 carbons, arylene of 6-12 carbons, aralkylene of 7-13 carbons or alkenylene of 2-13 carbons.
Claim 13
Dependent Claim
74 words
The composition of claim 3 in which at least one of the groups attached to the polymer is (b) in which R 5 is hydrogen or methyl, R 6 is hydrogen, methyl, acetyl, benzoyl, 2-hydroxyethyl or benzyl and X 9 is a direct bond, --(CH 2 ) y -- or --R 7 --N(R 23 )--, where R 7 is alkylene of 2-10 carbons and R 23 is hydrogen, alkyl of 1-4 carbons or 2,2,6,6-tetramethyl-4-piperidinyl.
Claim 14
Dependent Claim
61 words
The composition of claim 12 in which one of the other groups attached to the polymer is (d) having a structure ##STR28## in which R 11 is hydrogen or chlorine, R 12 is X 5 and X 5 is --(CH 2 ) y -- or --CH 2 --CH 2 --O--, an optional substituent for Ring B being alkyl of 1-8 carbons.
Claim 15
Dependent Claim
53 words
The composition of claim 12 in which one of the other groups attached to the polymer is (c) having a structure ##STR29## in which R 9 is hydrogen, hydroxyl or alkoxy of 1 to 4 carbons, R 10 is the connecting group X 3 and X 3 is --CH 2 --CH 2 --O--.
Claim 16
Dependent Claim
86 words
The composition of claim 12 in which one of the other groups attached to the polymer is (a) having a structure ##STR30## in which the hydroxyl group is in the 4 position, R 3 and R 4 are independently t-butyl or t-amyl where at least one of the t-alkyl groups is ortho to the hydroxyl group and X 1 is a direct bond or a divalent radical --(CH 2 ) y -- or --CH 2 --CH 2 --O-- in which y is 1, 2 or 3.
Claim 17
Dependent Claim
51 words
The composition of claim 12 in which one of the other groups attached to the polymer is (g) having a structure ##STR31## where R 14 is aryl of 6-10 carbons optionally substituted with one or more of alkyl of 1-8 carbons, chlorine or bromine and X 7 is a direct bond.
Claim 18
Dependent Claim
71 words
The composition of claim 12 in which one of the other groups attached to the polymer is (i) having a structure ##STR32## wherein R 15 , R 16 , R 17 , R 18 and R 19 are independently hydrogen, hydroxyl, alkyl of 1-4 carbons or alkoxy of 1-4 carbons, and X 8 is alkylene of 2-12 carbons, arylene of 6-12 carbons, aralkylene of 7-13 carbons, or alkenylene of 2-13 carbons.
Claim 19
Dependent Claim
81 words
The composition of claim 2 in which at least one of the groups attached to the polymer is (a) in which the hydroxyl group is in the 4 position, R 3 and R 4 are independently t-butyl or t-amyl where at least one of the t-alkyl groups is ortho to the hydroxyl group, X 1 is a direct bond or a divalent radical --(CH 2 ) y -- or --CH 2 --CH 2 --O-- and y is 1, 2 or 3.
Claim 20
Dependent Claim
56 words
The composition of claim 18 in which one of the other groups attached to the polymer is (j) having a structure --X.sup.2 --C(═O)--(CH.sub.2).sub.z --S--R.sup.8 in which R 8 is alkyl of 6-18 carbons, benzyl or dimethylaminoethyl, X 2 is --R 7 --N(R 23 )--, R 7 is alkylene of 2-6 carbons and R 23 is hydrogen.
Claim 21
Dependent Claim
53 words
The composition of claim 18 in which one of the other groups attached to the polymer is (c) having a structure ##STR33## in which R 9 is hydrogen, hydroxyl or alkoxy of 1-4 carbons, R 10 is the connecting group X 3 and X 3 is the diradical --CH 2 --CH 2 --O--.
Claim 22
Dependent Claim
67 words
The composition of claim 18 in which one of the other groups attached to the polymer is (d) having a structure ##STR34## in which R 11 is hydrogen or chlorine, R 12 is X 5 , X 5 is --(CH 2 ) y -- or --CH 2 --CH 2 --O-- and y is 1 or 2, an optional substituent for Ring B being alkyl of 1-8 carbons.
Claim 23
Dependent Claim
43 words
The composition of claim 18 in which one of the other groups attached to the polymer is (e) having a structure ##STR35## in which R 13 is aryl of 6-10 carbons or alkyl of 1-12 carbons and X 6 is a direct bond.
Claim 24
Dependent Claim
50 words
The composition of claim 5 in which at least one of the groups attached to the polymer is (c) in which R 9 is hydrogen, hydroxyl or alkoxy of 1 to 4 carbons, R 10 is the connecting group X 3 and X 3 is --CH 2 --CH 2 --O--.
Claim 25
Dependent Claim
62 words
The composition of claim 23 in which one of the other groups attached to the polymer is (h) having a structure ##STR36## in which X 2 is --R 7 --N(R 23 )--, wherein R 7 is alkylene of 2-12 carbons, R 23 is hydrogen, alkyl of 1-10 carbons, aryl of 6-12 carbons, aralkyl of 7-12 carbons, cycloalkyl of 5-12 carbons or 2-cyanoethyl.
Claim 26
Dependent Claim
37 words
The composition of claim 23 in which one of the other groups attached to the polymer is (f) having a structure ##STR37## in which Q is --NH--, --S-- or --O-- and X 7 is a direct bond.
References Cited (Backward Citations)
US2971939A
Cited
US3336267A
Cited
US3257354A
Cited
US3629192A
Cited
US3488311A
Cited
US3509110A
Cited
US3560456A
Cited
US3560457A
Cited
US3560455A
Cited
US3553177A
Cited
US3555001A
Cited
US3723375A
Cited
US3998907A
Cited
US3919354B1
Cited
US3919354A
Cited
US3884882A
Cited
US4108943A
Cited
US4153596A
Cited
US4097551A
Cited
US4276401A
Cited
US4381373A
Cited
US4413096A
Cited
CA1180497A
Cited
GB2145100A
Cited
EP0076691A1
Cited
US4692486A
Cited
US4591619A
Cited
US4486570A
Cited
EP0084882A1
Cited
US4522983A
Cited
JPS59221314A
Cited
JPS59221315A
Cited
US4522992A
Cited
US4523008A
Cited
GB2174093A
Cited
US4730017A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1993-12-31 | 1994-07-02 | 1995-01-01 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1997-12-31 | 1998-07-02 | 1999-01-01 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2001-12-31 | 2002-07-02 | 2003-01-01 | $7700.00 | Window Closed / Lapsed |