US5981073A
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US
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Compounds based on dibenzoylresorcinol, and related compositions and articles
Assignee: General Electric Co
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Filing: 1997-01-16
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Granted: 1999-11-09
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Expires: 2017-01-16
Abstract
Abstract Novel dibenzoylresorcinol-based compounds are disclosed wherein the dibenzoylresorcinol is bonded to the residue of either an alcohol or a carboxylic acid group, via a methylene carboxylate linking group; and wherein the dibenzoylresorcinol is bonded directly to a substituted or unsubstituted aryl group which does not include a pendent hydroxyl group. The groups attached to the dibenzoylresorcinol may contain a wide variety of functional sites which permit further reaction, e.g., copolymerization. The described compounds are very useful as UV light absorbers and may be used to form improved coating compositions which usually include a transparent, polymeric matrix material. The coating compositions may be applied to various substrates, e.g., thermoplastics, to afford a selection of enhanced properties, such as UV light resistance and abrasion resistance.
Inventors
- 👤 James Edward Pickett
- 👤 Wen P Liao
- 👤 Amy Kathleen Simonian
- 👤 Gregory Ronald Gillette
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 10:51
CPC Classifications
C; C08; C08K; C08K5/00; C08K5/04; C08K5/13; C08K5/132; C07; C07C; C07C45/00; C07C45/61; C07C45/67; C07C45/68; C07C45/70; C07C45/71; C07C49/00; C07C49/76; C07C49/82; C07C49/83; C07C49/835; C07C49/84; C07C69/00; C07C69/007; C07D; C07D211/00; C07D211/04; C07D211/06; C07D211/36; C07D211/40; C07D211/44; C07D211/46; C09; C09D; C09D7/00; C09D7/40; C09D7/48; Y; Y10; Y10T; Y10T428/00; Y10T428/31504; Y10T428/31507; Y10T428/31551; Y10T428/31855; Y10T428/31935; Y10T428/31942
Claims Analysis
Total Claims: 47
Claim 1
Independent Claim
72 words
A compound having the formula ##STR9## wherein Ar 1 and Ar 2 are independently substituted or unsubstituted monocyclic or polycyclic aryl groups; R is hydrogen, an aryl group, or a linear or branched alkyl chain having less than about 10 carbon atoms, and A is (a) a radical deriving from an alcohol or a carboxylic acid, or (b) a substituted or unsubstituted aryl group which does not include a pendent hydroxyl group.
Claim 2
Dependent Claim
72 words
A compound having the formula ##STR9## wherein Ar 1 and Ar 2 are independently substituted or unsubstituted monocyclic or polycyclic aryl groups; R is hydrogen, an aryl group, or a linear or branched alkyl chain having less than about 10 carbon atoms, and A is (a) a radical deriving from an alcohol or a carboxylic acid, or (b) a substituted or unsubstituted aryl group which does not include a pendent hydroxyl group.
Claim 3
Dependent Claim
18 words
The compound of claim 1, wherein the alcohol of element (a) is a linear or branched aliphatic group.
Claim 4
Dependent Claim
34 words
The compound of claim 2, wherein the linear or branched aliphatic group is selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, amyl, isoamyl, hexyl, octyl, decyl, and dodecyl.
Claim 5
Dependent Claim
19 words
The compound of claim 1, wherein the alcohol of element (a) is a carbocyclic alcohol or a heterocyclic alcohol.
Claim 6
Dependent Claim
25 words
The compound of claim 4, wherein the alcohol contains at least one aliphatic or aromatic branch comprising from about 1 to about 20 carbon atoms.
Claim 7
Dependent Claim
39 words
The compound of claim 4, wherein the carbocyclic alcohol is selected from the group consisting of cyclohexanol, cyclopentanol, cyclooctanol, cyclodecanol, cyclododecanol, exonorborneol, and derivatives of any of the foregoing which contain at least one aliphatic or aromatic carbon branch.
Claim 8
Dependent Claim
30 words
The compound of claim 4, wherein the heterocyclic alcohol includes at least one atom selected from the group consisting of nitrogen, sulfur, and oxygen, in at least one cyclic chain.
Claim 9
Dependent Claim
15 words
The compound of claim 7, wherein the heterocyclic alcohol is piperidinol or a substituted piperidinol.
Claim 10
Dependent Claim
11 words
The compound of claim 8, wherein the substituted piperidinol is 2,2,6,6-tetramethyl-4-piperidinol.
Claim 11
Dependent Claim
29 words
The compound of claim 1, wherein the alcohol of element (a) is a diol, a derivative of a diol, a polymerized diol, or a derivative of a polymerized diol.
Claim 12
Dependent Claim
24 words
The compound of claim 10, wherein the diol is an alkane-diol, and the alkane group contains from about 2 to about 20 carbon atoms.
Claim 13
Dependent Claim
20 words
The compound of claim 11, wherein the alkane-diol is selected from the group consisting of propanediol, butanediol, pentanediol, and hexanediol.
Claim 14
Dependent Claim
26 words
The compound of claim 10, wherein the alcohol is selected from the group consisting of ethylene glycol, propylene glycol, neopentyl glycol, polyethylene glycol, and polypropylene glycol.
Claim 15
Dependent Claim
18 words
The compound of claim 10, wherein the derivative of the diol or the polymerized diol is an ester.
Claim 16
Dependent Claim
14 words
The compound of claim 1, wherein the alcohol of element (a) is a polyol.
Claim 17
Dependent Claim
19 words
The compound of claim 15, wherein the polyol is selected from the group consisting of pentaerythritol, dipentaerythritol, and glycerol.
Claim 18
Dependent Claim
11 words
The compound of claim 15, wherein the polyol is partially esterified.
Claim 19
Dependent Claim
13 words
The compound of claim 1, wherein the alcohol of element (a) is polyfunctional.
Claim 20
Dependent Claim
22 words
The compound of claim 18, wherein the functional moieties include at least one hydroxy group or at least one carboxylic acid group.
Claim 21
Dependent Claim
41 words
The compound of claim 1, wherein the carboxylic acid is selected from the group consisting of polycarboxylic acids, branched derivatives of monocarboxylic acids or polycarboxylic acids; cyclic derivatives of mono- or polycarboxylic acids, and functional derivatives of mono- or polycarboxylic acids.
Claim 22
Dependent Claim
39 words
The compound of claim 20, wherein the polycarboxylic acid is selected from the group consisting of succinic acid, glutaric acid, adipic acid, suberic acid, palmitic acid, azelaic acid, malonic acid, oxalic acid, maleic acid, fumaric acid, and phthalic acid.
Claim 23
Dependent Claim
9 words
A diester derivative of the compound of claim 21.
Claim 24
Dependent Claim
20 words
The compound of claim 20, wherein the polycarboxylic acid includes at least one polyether linkage within a carbon atom chain.
Claim 25
Dependent Claim
19 words
The compound of claim 23, wherein the polyether linkage includes at least one pendent cyclic chain or heterocyclic chain.
Claim 26
Dependent Claim
14 words
The compound of claim 24, wherein at least one of the chains is acid-functionalized.
Claim 27
Dependent Claim
20 words
The compound of claim 20, wherein the polycarboxylic acid includes at least one hydroxy group within a carbon atom chain.
Claim 28
Dependent Claim
24 words
The compound of claim 20, wherein the functional derivative of the mono- or polycarboxylic acid includes at least one vinyl group or allyl group.
Claim 29
Dependent Claim
24 words
The compound of claim 27, wherein the functional derivative of the mono- or polycarboxylic acid comprises at least one acrylic group or methacrylic group.
Claim 30
Dependent Claim
16 words
A copolymer prepared by the reaction of the compound of claim 27 with a copolymerizable monomer.
Claim 31
Dependent Claim
27 words
The copolymer of claim 29, wherein the copolymerizable monomer is selected from the group consisting of acrylates, methacrylates, styrenes, and substituted derivatives of any of the foregoing.
Claim 32
Dependent Claim
30 words
The compound of claim 1, wherein the aryl group of element (b) is selected from the class consisting of phenyl, alkyl-substituted phenyl groups, halogen-substituted phenyl groups, and alkoxy-substituted phenyl groups.
Claim 33
Dependent Claim
18 words
The compound of claim 1, wherein the aryl group of element (b) has a vinyl group attached thereto.
Claim 34
Dependent Claim
41 words
The compound of claim 32, wherein the vinyl group is attached to the 3-position or the 4-position on the aryl ring, relative to the attachment site of A, or is present as a mixture of isomers in the 3-position and 4-position.
Claim 35
Dependent Claim
16 words
A copolymer prepared by the reaction of the compound of claim 32 with a copolymerizable monomer.
Claim 36
Dependent Claim
16 words
A copolymer prepared by the reaction of the compound of claim 33 with a copolymerizable monomer.
Claim 37
Dependent Claim
63 words
The compound of claim 1, in which A is an alcohol selected from component (a), prepared in an etherification reaction by combining a compound of the formula ##STR10## with an alcohol in a reaction medium, wherein R, Ar 1 and Ar 2 are as described above, and R 2 is a linear or branched alkyl chain containing less than about 10 carbon atoms.
Claim 38
Dependent Claim
50 words
The compound of claim 1, in which A is selected from component (b), said compound being prepared in a process which comprises reacting a 4,6-dibenzoylresorcinol with a benzyl halide compound, an aqueous base, and a compatible phase transfer catalyst under conditions suitable for obtaining a substantial yield of the compound.
Claim 39
Dependent Claim
34 words
The compound of claim 37, wherein the benzyl halide compound is selected from the group consisting of benzyl bromide, benzyl chloride, 3-vinyl benzyl chloride, 3-vinyl benzyl bromide, 4-vinyl benzyl chloride, and 4-vinyl benzyl bromide.
Claim 40
Dependent Claim
86 words
A coating composition, comprising: I) an ultraviolet light-absorbing compound having the formula ##STR11## wherein Ar 1 and Ar 2 are independently substituted or unsubstituted monocyclic or polycyclic aryl groups; R is hydrogen, an aryl group, or a linear or branched alkyl chain having less than about 10 carbon atoms, and A is (a) a radical deriving from an alcohol or a carboxylic acid, or (b) a substituted or unsubstituted aryl group which does not include a pendent hydroxyl group; and II) a substantially transparent matrix composition.
Claim 41
Dependent Claim
86 words
A coating composition, comprising: I) an ultraviolet light-absorbing compound having the formula ##STR11## wherein Ar 1 and Ar 2 are independently substituted or unsubstituted monocyclic or polycyclic aryl groups; R is hydrogen, an aryl group, or a linear or branched alkyl chain having less than about 10 carbon atoms, and A is (a) a radical deriving from an alcohol or a carboxylic acid, or (b) a substituted or unsubstituted aryl group which does not include a pendent hydroxyl group; and II) a substantially transparent matrix composition.
Claim 42
Dependent Claim
24 words
The coating of claim 39, wherein the transparent matrix comprises a polymer selected from the group consisting of acrylics, urethanes, melamines, and mixtures thereof.
Claim 43
Dependent Claim
19 words
The coating of claim 39, wherein there is at least one polymer linkage between component (I) and component (II).
Claim 44
Dependent Claim
96 words
A solid substrate with a coating composition applied thereon, wherein the coating composition comprises: I) an ultraviolet light-absorbing compound having the formula ##STR12## wherein Ar 1 and Ar 2 are independently substituted or unsubstituted monocyclic or polycyclic aryl groups; R is hydrogen, an aryl group, or a linear or branched alkyl chain having less than about 10 carbon atoms, and A is (a) a radical deriving from an alcohol or a carboxylic acid, or (b) a substituted or unsubstituted aryl group which does not include a pendent hydroxyl group; and II) a substantially transparent matrix composition.
Claim 45
Dependent Claim
96 words
A solid substrate with a coating composition applied thereon, wherein the coating composition comprises: I) an ultraviolet light-absorbing compound having the formula ##STR12## wherein Ar 1 and Ar 2 are independently substituted or unsubstituted monocyclic or polycyclic aryl groups; R is hydrogen, an aryl group, or a linear or branched alkyl chain having less than about 10 carbon atoms, and A is (a) a radical deriving from an alcohol or a carboxylic acid, or (b) a substituted or unsubstituted aryl group which does not include a pendent hydroxyl group; and II) a substantially transparent matrix composition.
Claim 46
Dependent Claim
12 words
The invention of claim 42, wherein the substrate comprises a thermoplastic material.
Claim 47
Dependent Claim
21 words
The invention of claim 43, wherein the thermoplastic material is a polycarbonate or a copolymer based in part on a polycarbonate.
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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) | 2002-11-08 | 2003-05-10 | 2003-11-09 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2006-11-08 | 2007-05-10 | 2007-11-09 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2010-11-08 | 2011-05-10 | 2011-11-09 | $7700.00 | Window Closed / Lapsed |