US4980420A
Expired / Lapsed
US
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Benzotriazole and oxanilide UV absorber hydrazides
Assignee: Arkema Inc
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Filing: 1989-02-13
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Granted: 1990-12-25
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Expires: 2009-02-13
Abstract
Abstract Hydrazide functionalized benzotrialzole and oxanilide ultraviolet absorbers (Formulas I and II) useful for stabilizing coreactive or inert polymeric compositions and novel intermediates (Formula III used to make certain types of compounds of Formula I) are disclosed and have the general formulas: ##STR1## wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , X, Y, all substituents thereof, and n are set forth in the Summary of the Invention.
Inventors
- 👤 Ronald E. MacLeay
- 👤 Terry N. Myers
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 14:32
CPC Classifications
C; C08; C08F; C08F8/00; C08F8/30
Claims Analysis
Total Claims: 7
Claim 1
Independent Claim
173 words
A polymeric compound comprising the reaction product of a polymer containing (a) at least one ester, epoxide or anhydride functional group, or combinations thereof, in the polymer backbone, on grafted side chains, as a pendant unit or combinations thereof and (b) a compound of formula ##STR11## where R 1 is hydrogen, substituted or unsubstituted aliphatic of 1-8 carbons, substituted or unsubstituted alkoxy of 1-8 carbons, substituted or unsubstituted alkoxycarbonyl of 2-8 carbons, alkylaminocarbonyl of 2-5 carbons, dialkylaminocarbonyl of 3-9 carbons, substituted or unsubstituted N-(alkyl)-N-(aryl)aminocarbonyl of 8-15 carbons, alkoxysulfonyl of 1-4 carbons, --C(═O)--OH--, --C(═O)NH 2 , or --S(═O) 2 --OH; R 2 is hydrogen, substituted or unsubstituted aliphatic of 1-8 carbons, substituted or unsubstituted aryl of 6-14 carbons, substituted or unsubstituted araliphatic of 7-22 carbons, substituted or unsubstituted alkoxy of 1-8 carbons, alkylaminocarbonyl of 2-5 carbons, dialkylaminocarbonyl of 3-9 carbons, or substituted or unsubstituted N-(alkyl)-N-(aryl)aminocarbonyl of 8-15 carbons; R 3 is hydrogen, substituted or unsubstituted aliphatic of 1-20 carbons, substituted or unsubstituted araliphatic of 7-22 cartons, or substituted or unsubstituted alicyclic of 5-12 carbons;
Claim 2
Dependent Claim
173 words
A polymeric compound comprising the reaction product of a polymer containing (a) at least one ester, epoxide or anhydride functional group, or combinations thereof, in the polymer backbone, on grafted side chains, as a pendant unit or combinations thereof and (b) a compound of formula ##STR11## where R 1 is hydrogen, substituted or unsubstituted aliphatic of 1-8 carbons, substituted or unsubstituted alkoxy of 1-8 carbons, substituted or unsubstituted alkoxycarbonyl of 2-8 carbons, alkylaminocarbonyl of 2-5 carbons, dialkylaminocarbonyl of 3-9 carbons, substituted or unsubstituted N-(alkyl)-N-(aryl)aminocarbonyl of 8-15 carbons, alkoxysulfonyl of 1-4 carbons, --C(═O)--OH--, --C(═O)NH 2 , or --S(═O) 2 --OH; R 2 is hydrogen, substituted or unsubstituted aliphatic of 1-8 carbons, substituted or unsubstituted aryl of 6-14 carbons, substituted or unsubstituted araliphatic of 7-22 carbons, substituted or unsubstituted alkoxy of 1-8 carbons, alkylaminocarbonyl of 2-5 carbons, dialkylaminocarbonyl of 3-9 carbons, or substituted or unsubstituted N-(alkyl)-N-(aryl)aminocarbonyl of 8-15 carbons; R 3 is hydrogen, substituted or unsubstituted aliphatic of 1-20 carbons, substituted or unsubstituted araliphatic of 7-22 cartons, or substituted or unsubstituted alicyclic of 5-12 carbons;
Claim 3
Dependent Claim
506 words
R 4 , R 5 , R 6 and R 7 are independently hydrogen, hydroxy, substituted or unsubstituted aliphatic of 1-8 carbons, substituted or unsubstituted aryl of 6-14 carbons, substituted or unsubstituted araliphatic of 7-22 carbons, substituted or unsubstituted alkoxy of 1-12 carbons or substituted or unsubstituted alkylthio of 1-12 carbons, chloro, bromo, or substituted or unsubstituted alkoxycarbonyl or 2-8 carbons; X is X a when attached to ring A, X b when attached to ring B and X e when attached either ring E; X a is a direct bond; X b and X e are divalent radicals of formula --Z x --R 8 --{--N(R 9 )═O)] y --R 10 --) z --; Z is --O--, --N(R 11 )--, --S--, or --S(═O) 2 --; x and z are independently 1; y is independently 0 or 1; R 8 is a direct bond or substituted or unsubstituted alkylene diradical of 1-4 carbons; R 9 is hydrogen, substituted or unsubstituted aliphatic of 1-20 carbons, substituted or unsubstituted alicyclic of 5-12 carbons, substituted or unsubstituted aryl of 6-14 carbons, or substituted or unsubstituted araliphatic of 7-22 carbons; R 10 is a direct bond, substituted or unsubstituted aliphatic diradical of 1-20 carbons, substituted or unsubstituted aryl diradical of 6-12 carbons, substituted or unsubstituted alicyclic diradical of 5-12 carbons, or substituted or unsubstituted araliphatic diradical of 7-22 carbons; R 11 is hydrogen, substituted or unsubstituted aliphatic of 1-20 carbons, substituted or unsubstituted alicyclic of 5-12 carbons, substituted or unsubstituted aryl of 6-14 carbons, or substituted or unsubstituted araliphatic of 7-22 carbons; n is 1; Y is ##STR12## R 12 is hydrogen; R 13 is hydrogen, substituted or unsubstituted aliphatic of 1-20 carbons, substituted or unsubstituted alicyclic of 5-12 carbons, substituted or unsubstituted aryl of 6-14 carbons, or substituted or unsubstituted araliphatic of 7-22 carbons, and when alicyclic, R 13 may optionally contain 1-6 heteroatoms --O--, --S-- or --N(R 21 )--, with the proviso that multiple heteroatoms must be separated from each other and the chain ends by at least one carbon atom; Q is a direct bond between the nitrogen and R 13 ; R 21 is hydrogen, aliphatic of 1 to 8 carbons, aliphatic acyl of 2-6 carbons, or substituted or unsubstituted benzoyl; optional substituents for R 1 , R 2 , R 3 , R 8 , R 9 , R 10 , R 11 , R 13 and R 21 are independently one or more of the following: chloro, bromo, alkyl of 1-4 carbons, alkoxy of 1-8 carbons, phenoxy, cyano, hydroxy, epoxy, carboxy, alkyoxycarbonyl of 2-6 carbons, acyloxy of 1-4 carbons, acryloyl, acryloyoxy, methacryloyl, methacryloyoxy, hydroxymethyl, hydroxyethyl, alkylthio of 1-4 carbons or trialkoxysilyl of 3-12 carbons; and additional optional substituents for R 13 are aliphatic of 1-20 carbons, cycloaliphatic of 5-12 carbons, aryl of 6-14 carbons, aralkyl of 7-22 carbons, alkoxy of 1-20 carbons, cycloalkoxy of 5-12 carbons, aryloxy of 6-14 carbons, aralkoxy of 7-15 carbons, aliphatic acyloxy of 2-20 carbons, alicyclic acyloxy of 6-13 carbons, aryl acyloxy of 7-15 carbons, or araliphatic acyloxy of 8-16 carbons.
Claim 4
Dependent Claim
506 words
R 4 , R 5 , R 6 and R 7 are independently hydrogen, hydroxy, substituted or unsubstituted aliphatic of 1-8 carbons, substituted or unsubstituted aryl of 6-14 carbons, substituted or unsubstituted araliphatic of 7-22 carbons, substituted or unsubstituted alkoxy of 1-12 carbons or substituted or unsubstituted alkylthio of 1-12 carbons, chloro, bromo, or substituted or unsubstituted alkoxycarbonyl or 2-8 carbons; X is X a when attached to ring A, X b when attached to ring B and X e when attached either ring E; X a is a direct bond; X b and X e are divalent radicals of formula --Z x --R 8 --{--N(R 9 )═O)] y --R 10 --) z --; Z is --O--, --N(R 11 )--, --S--, or --S(═O) 2 --; x and z are independently 1; y is independently 0 or 1; R 8 is a direct bond or substituted or unsubstituted alkylene diradical of 1-4 carbons; R 9 is hydrogen, substituted or unsubstituted aliphatic of 1-20 carbons, substituted or unsubstituted alicyclic of 5-12 carbons, substituted or unsubstituted aryl of 6-14 carbons, or substituted or unsubstituted araliphatic of 7-22 carbons; R 10 is a direct bond, substituted or unsubstituted aliphatic diradical of 1-20 carbons, substituted or unsubstituted aryl diradical of 6-12 carbons, substituted or unsubstituted alicyclic diradical of 5-12 carbons, or substituted or unsubstituted araliphatic diradical of 7-22 carbons; R 11 is hydrogen, substituted or unsubstituted aliphatic of 1-20 carbons, substituted or unsubstituted alicyclic of 5-12 carbons, substituted or unsubstituted aryl of 6-14 carbons, or substituted or unsubstituted araliphatic of 7-22 carbons; n is 1; Y is ##STR12## R 12 is hydrogen; R 13 is hydrogen, substituted or unsubstituted aliphatic of 1-20 carbons, substituted or unsubstituted alicyclic of 5-12 carbons, substituted or unsubstituted aryl of 6-14 carbons, or substituted or unsubstituted araliphatic of 7-22 carbons, and when alicyclic, R 13 may optionally contain 1-6 heteroatoms --O--, --S-- or --N(R 21 )--, with the proviso that multiple heteroatoms must be separated from each other and the chain ends by at least one carbon atom; Q is a direct bond between the nitrogen and R 13 ; R 21 is hydrogen, aliphatic of 1 to 8 carbons, aliphatic acyl of 2-6 carbons, or substituted or unsubstituted benzoyl; optional substituents for R 1 , R 2 , R 3 , R 8 , R 9 , R 10 , R 11 , R 13 and R 21 are independently one or more of the following: chloro, bromo, alkyl of 1-4 carbons, alkoxy of 1-8 carbons, phenoxy, cyano, hydroxy, epoxy, carboxy, alkyoxycarbonyl of 2-6 carbons, acyloxy of 1-4 carbons, acryloyl, acryloyoxy, methacryloyl, methacryloyoxy, hydroxymethyl, hydroxyethyl, alkylthio of 1-4 carbons or trialkoxysilyl of 3-12 carbons; and additional optional substituents for R 13 are aliphatic of 1-20 carbons, cycloaliphatic of 5-12 carbons, aryl of 6-14 carbons, aralkyl of 7-22 carbons, alkoxy of 1-20 carbons, cycloalkoxy of 5-12 carbons, aryloxy of 6-14 carbons, aralkoxy of 7-15 carbons, aliphatic acyloxy of 2-20 carbons, alicyclic acyloxy of 6-13 carbons, aryl acyloxy of 7-15 carbons, or araliphatic acyloxy of 8-16 carbons.
Claim 5
Dependent Claim
17 words
The polymeric compound of claim 1 which is a reaction product of the polymer and (2-[(phenylamino)-2-oxoacetamido]phenoxy)acetyl hydrazide.
Claim 6
Dependent Claim
17 words
The polymeric compound of claim 1 which is a reaction product of the polymer and 2-([2-hydroxy-3-(2H-benzotriazol-2-yl)-5-methylphenyl]methylamini)-2-oxoacetyl hydrazide.
Claim 7
Dependent Claim
17 words
The polymeric compound of claim 1 which is a reaction product of the polymer and 4-([2-hydroxy-3-(2H-benzotriazol-2-yl)-5-methylphenyl]methylamino)-4-oxobutanoyl hydrazide.
References Cited (Backward Citations)
US3159646A
Cited
US3214436A
Cited
US3862087A
Cited
US3218332A
Cited
US3399173A
Cited
US3629192A
Cited
US3629191A
Cited
US3766205A
Cited
US3272891A
Cited
US3542573A
Cited
JPS4843658A
Cited
EP0057160B1
Cited
US4692486A
Cited
US4785063A
Cited
GB2188631A
Cited
GB2196966A
Cited
GB2197318A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1993-12-24 | 1994-06-25 | 1994-12-25 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1997-12-24 | 1998-06-25 | 1998-12-25 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2001-12-24 | 2002-06-25 | 2002-12-25 | $7700.00 | Window Closed / Lapsed |